Human Liver Adverse Effects Database

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FDA/Center for Drug Evaluation and Research

FDA's Center for Drug Evaluation and Research, Office of Pharmaceutical Science, Informatics and Computational Safety Analysis Staff's Adverse Effects Database contains data for 631 unique pharmaceuticals listed in FDA/CDER's Spontaneous Reporting System Database. The ICSAS Adverse Effects Database includes adverse drug reaction (ADR) reports described using a standardized vocabulary of 1191 COSTAR terms linked to 22 organ systems which are based upon the anatomical COSTAR term nomenclature. For each of the 631 drugs in our database, we extracted the counts of ADR reports for all populated COSTAR terms for the time periods described below.

Pharmaceutical shipping unit data were used to estimate pharmaceutical usage and human exposure and were selected to match the time period of the ADR data. The data were obtained as “units” which refer to package shipping units. When available, we manually extracted and summed these data for the first five years of marketing, and integrated the information into our database for each pharmaceutical.

The adverse event data were obtained in three groups. Group 1 contained 356 pharmaceuticals that were approved as New Molecular Entities between January 1, 1978 and December 31, 1996. The shipping unit data for this group were summed for each pharmaceutical for the first five years after approval, except for pharmaceuticals approved after December 31, 1991 where shipping data were summed until December, 1996. In those cases where marketing of the pharmaceutical was delayed for several years after its approval, data for the first five years of marketing were used. Group 2 contained 253 pharmaceuticals that were approved prior to January 1, 1978. Since shipping unit data were not available to us prior to this date, shipping data were summed for the five year period from January 1, 1992 to December 31, 1996. Group 3 contained 22 pharmaceuticals from an additional set of drugs for which no shipping data were obtained. These 22 drugs were selected because they have 30 or more ADR reports associated with a single COSTAR term. These chemicals were classified as having a significant adverse effect and were included in the database only for modeling these specific endpoints.

The ADR report data and the pharmaceutical shipping values were used to estimate pharmaceutical usage and human exposure by calculating a Reporting Index (RI) for up to a five year period for each pharmaceutical in the study. The RI = (# ADR reports / # shipping units) × 1,000,000. Index values were calculated for all 631 generic pharmaceuticals in the database with available shipping data. Where less than five years of data were available, ADR and shipping data are from matching time periods.

Of the 631 compounds in the database, 490 have ADR data available for one or more of the 47 liver effects COSTAR term endpoints. The liver adverse effect data from the five liver enzyme increase endpoints, were used to optimize the database for identification of a significant adverse effect, as described in the following research article: Matthews, E.J., Kruhlak, N.L., Weaver, J.L., Benz, R.D., and Contrera, J.F. Assessment of the Health Effects of Chemicals in Humans: II. Construction of an Adverse Effects Database for QSAR Modeling, Current Drug Discovery Technologies, 2005, 1:243-254. The abstract for this article is as follows:

The FDA's Spontaneous Reporting System (SRS) database contains over 1.5 million adverse drug reaction (ADR) reports for 8620 drugs/biologics that are listed for 1191 COSTAR (Coding Symbols for Thesaurus of Adverse Reaction) terms of adverse effects. We have linked the trade names of the drugs to 1861 generic names and retrieved molecular structures for each chemical to obtain a set of 1515 organic chemicals that are suitable for modeling with commercially available QSAR software packages. ADR report data for 631 of these compounds were extracted and pooled for the first five years that each drug was marketed. Patient exposure was estimated during this period using pharmaceutical shipping units obtained from IMS Health. Significant drug effects were identified using a Reporting Index (RI), where RI = (# ADR reports / # shipping units) × 1,000,000. MCASE/MC4PC software was used to identify the optimal conditions for defining a significant adverse effect finding. Results suggest that a significant effect in our database is characterized by ≥4 ADR reports and ≥20,000 shipping units during five years of marketing, and a RI ≥4.0. Furthermore, for a test chemical to be evaluated as active it must contain a statistically significant molecular structural alert, called a decision alert, in two or more toxicologically related endpoints. We also report the use of a composite module, which pools observations from two or more toxicologically related COSTAR term endpoints to provide signal enhancement for detecting adverse effects.

The data presented here are for five liver enzyme COSTAR endpoints and a composite module which pools data from the five individual endpoints.

The database contains the following fields:

The generic name of each chemical
The chemical structure in Simplified Molecular Input Line Entry System (SMILES) code format (generated using MultiCASE Inc.'s MC4PC program)
For module A10 (liver enzyme composite module):
1. Overall activity category for each compound (A for active, M for marginally active, or I for inactive) based on the number of active and marginally active scores for each compound at the five individual endpoints (see research article for full description of method)
2. Number of endpoints at which each compound is marginally active (M)
3. Number of endpoints at which each compound is active (A)
For modules A11 to A15 (alkaline phosphatase increased, SGOT increased, SGPT increased, LDH increased, and GGT increased, respectively):
1. Overall activity category for each compound (A for active, M for marginally active, or I for inactive) based on the RI and ADR values (see the research article for full description of method)
2. Number of ADR reports for each compound, given as <4 or ≥4
3. Reporting Index value for each compound, except where no shipping units were available (NSU)

Group 1 comprises of compounds for which ADR data were available for the first five years of marketing, so when no ADR reports were listed during this period the compounds were evaluated as inactive. Group 2 comprises of compounds for which a "steady state" period of ADR data were available (1992-1996). In cases where no ADR reports were filed during this period, the compounds were scored as "NA" (data not available) since they may have had one or more ADR reports during their first five years of marketing which should not be negated by a lack of ADR reports during the steady-state period.

All data contained in this file are non-proprietary.

Comments or corrections of these data should be sent to: R.Daniel.Benz@fda.hhs.gov.

Human Liver Adverse Effects Database (490 pharmaceuticals)

(PDF version of this document)

A B C D E F-G H-K L M N O P Q-R S T U-Z

A10

A11

A12

A13

A14

A15

Composite
Activity

Alkalkine
Phosphatase
Increase

SGOT
Increase

SGPT
Increase

LDH
Increase

GGT
Increase

Generic Name

SMILES Code

Score

Mar-
ginal

Active

Actvty
Score

Num.
of
Rprts

Index
Value

Actvty
Score

Num.
of
Rprts

Index
Value

Actvty
Score

Num.
of
Rprts

Index
Value

Actvty
Score

Num.
of
Rprts

Index
Value

Actvty
Score

Num.
of
Rprts

Index
Value

Acarbose

C3=C(CO)C(O)C(O)C(O)C3NC2C(O)C(O)C(OC1C(O)C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC1CO)OC2C

0.0

≥4

5.2

≥4

5.2

2.6

≥4

4.3

Acebutolol

C1(C(=O)C)=CC(NC(=O)CCC)=CC=C1OCC(O)CNC(C)C

≥4

3.9

≥4

2.6

≥4

3.3

≥4

3.3

0.0

Acetaminophen

C1(O)=CC=C(NC(C)=O)C=C1

≥4

NSU

≥4

NSU

≥4

NSU

≥4

NSU

≥4

NSU

Acetohydroxamic acid

CC(=O)NO

0.0

Acetylcysteine

O=C(O)C(NC(C)=O)CS

≥4

4.8

Acyclovir

N1C(N)=NC2=C(C1=O)N=CN2COCCO

≥4

0.9

≥4

0.9

0.1

0.0

Adapalene

C6=C(OC)C(C13CC2CC(C1)CC(C2)C3)=CC(C4=CC5C(C=C4)=CC(C(O)=O)=CC=5)=C6

0.0

Adenosine

N1=CN=C3C(=C1N)N=CN3C2OC(CO)C(O)C2O

0.0

Albuterol

C1(CO)=C(O)C=CC(C(O)CNC(C)(C)C)=C1

0.0

0.1

0.0

Alclometasone

C1C(=O)C=C2C(C)(C=1)C3C(C(Cl)C2)C4C(C)(CC3O)C(O)(C(=O)CO)C(C)C4

0.0

Alclometasone dipropionate

C1C(=O)C=C2C(C)(C=1)C3C(C(Cl)C2)C4C(C)(CC3O)C(C(=O)COC(=O)CC)(OC(=O)CC)C(C)C4

0.0

Alendronic Acid

NCCCC(O)(P(O)(O)=O)P(O)(O)=O

≥4

2.5

≥4

1.4

≥4

1.4

≥4

1.5

≥4

0.8

Alfentanil

N3=NN(CC)C(=O)N3CCN2CCC(COC)(N(C1=CC=CC=C1)C(=O)CC)CC2

0.0

Allopurinol

N1C=NC2=C(C=1O)C=NN2

≥4

4.7

≥4

15.0

≥4

9.4

≥4

9.4

Alprazolam

C1=C(Cl)C=C3C(=C1)N4C(CN=C3C2=CC=CC=C2)=NN=C4C

≥4

0.4

≥4

0.7

≥4

0.9

≥4

0.5

0.0

Alprostadil

C1(C=CC(O)CCCCC)C(O)CC(=O)C1CCCCCCC(O)=O

0.0

Altretamine

N1=C(N(C)C)N=C(N(C)C)N=C1N(C)C

18.3

0.0

Amantadine

C1C2CC3CC1(N)CC(C2)C3

Amcinonide

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C5(C(=O)COC(C)=O)C(C4)OC6(O5)CCCC6

0.0

Amifostine

P(O)(=O)(O)SCCNCCCN

0.0

41.5

0.0

Aminocaproic acid

C(N)CCCCC(O)=O

Amino-
glutethimide

N2C(=O)CCC(C1=CC=C(N)C=C1)(CC)C2=O

0.0

Amiodarone

C1=CC=C3C(=C1)OC(CCCC)=C3C(=O)C2=CC(I)=C(OCCN(CC)CC)C(I)=C2

0.0

Amitriptyline

C1=CC=C2C(=C1)CCC3=C(C2=CCCN(C)C)C=CC=C3

Amlexanox

C1=C(C(C)C)C=C2C(=C1)OC3=C(C2=O)C=C(C(=O)O)C(N)=N3

0.0

Amlodipine

C2=C(Cl)C(C1C(C(=O)OC)=C(C)NC(COCCN)=C1C(=O)OCC)=CC=C2

≥4

1.0

≥4

1.3

≥4

1.2

≥4

0.7

≥4

0.8

Amoxapine

C1=C(Cl)C=C3C(=C1)OC4=C(N=C3N2CCNCC2)C=CC=C4

0.7

1.0

0.7

0.0

Amoxicillin

C3(O)=CC=C(C(N)C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O)C=C3

0.0

0.1

0.0

Amphotericin B

C2(O)C(C)C=CC=CC=CC=CC=CCCCCC(OC1OC(O)C(O)C(N)C1O)CC3C(C(=O)O)C(O)CC(O)(CC(O)CC(O)C(O)CCC(O)CC(O)CC(=O)OC(C)C2C)O3

Amrinone

C2(N)C(=O)NC=C(C1=CC=NC=C1)C=2

2.2

6.6

4.4

2.2

0.0

Anastrozole

C2=C(C(C)(C)C#N)C=C(C(C)(C)C#N)C=C2CN1N=CN=C1

6.4

≥4

16.1

≥4

12.8

6.4

0.0

Apraclonidine

C2=C(N)C=C(Cl)C(N=C1NCCN1)=C2Cl

0.0

Aspirin

C1=CC=CC(OC(=O)C)=C1C(=O)O

Astemizole

C1=CC=C5C(=C1)N(CC2=CC=C(F)C=C2)C(NC4CCN(CCC3=CC=C(OC)C=C3)CC4)=N5

≥4

1.2

≥4

2.6

≥4

2.8

0.4

≥4

1.4

Atenolol

C1=C(CC(N)=O)C=CC(OCC(O)CNC(C)C)=C1

0.1

≥4

0.5

≥4

0.3

0.1

0.0

Atorvastatin

C4(C1=CC=C(F)C=C1)=C(C2=CC=CC=C2)C(C(=O)NC3=CC=CC=C3)=C(C(C)C)N4CCC(O)CC(O)CC(O)=O

≥4

1.7

≥4

6.5

≥4

7.3

≥4

2.5

≥4

6.2

Atovaquone

C1=CC=C4C(=C1)C(=O)C(C3CCC(C2=CC=C(Cl)C=C2)CC3)=C(O)C4=O

0.0

18.2

9.1

0.0

Atracurium

C1(OC)=C(OC)C=C6C(=C1)CC[N+](C)(CCC(=O)OCCCCCOC(=O)CC[N+]3(C)C(CC2=CC(OC)=C(OC)C=C2)C4=C(CC3)C=C(OC)C(OC)=C4)C6C(C)C5=CC=C(OC)C(OC)=C5

0.0

Azathioprine

N2C=NC3=C(C=2SC1N(C)C=NC=1N(=O)=O)NC=N3

≥4

4.5

≥4

5.0

≥4

5.6

≥4

3.3

Azelaic acid

OC(=O)CCCCCCCC(O)=O

0.0

Azelastine

C1=CC=C4C(=C1)C(=O)N(C2CCCN(C)CC2)N=C4CC3=CC=C(Cl)C=C3

0.0

Azithromycin

C3(=O)C(C)C(OC1OC(C)C(O)C(C)(OC)C1)C(C)C(OC2OC(C)CC(N(C)C)C2O)C(O)(C)CC(C)CC(C)C(C)C(O)C(O)(C)C(CC)O3

≥4

1.0

≥4

2.9

≥4

2.3

≥4

0.8

≥4

1.0

Aztreonam

C2(C(=NOC(C)(C)C(O)=O)C(=O)NC1C(=O)N(S(O)(=O)=O)C1C)N=C(N)SC=2

≥4

6.9

≥4

3.2

≥4

3.8

0.6

Bacampicillin

N23C(C(NC(=O)C(N)C1=CC=CC=C1)C2=O)SC(C)(C)C3C(=O)OC(C)OC(=O)OCC

0.0

Baclofen

C(=O)(O)CC(C1=CC=C(Cl)C=C1)CN

≥4

5.4

≥4

5.4

Beclomethasone

C34(C)C(C2C(Cl)(C1(C)C(=CC(=O)C=C1)CC2)C(O)C3)CC(C)C4(O)C(=O)CO

0.0

Benazepril

C1=CC=C3C(=C1)N(CC(O)=O)C(=O)C(NC(C(=O)OCC)CCC2=CC=CC=C2)CC3

0.3

0.0

0.2

Benztropine

C3C4CCC(CC3OC(C1=CC=CC=C1)C2=CC=CC=C2)N4C

Bepridil

N(CC(N1CCCC1)COCC(C)C)(CC2=CC=CC=C2)C3C=CC=CC=3

0.0

27.1

0.0

Betamethasone

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)CO)C(C)C4

Betamethasone acetate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)COC(C)=O)C(C)C4

Betamethasone acibutate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(C(=O)COC(=O)C)(OC(=O)C(C)C)C(C)C4

Betamethasone benzoate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C5C(C)(CC3O)C(C(=O)CO)(OC(=O)C4=CC=CC=C4)C(C)C5

Betamethasone butyrate propionate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(C(=O)COC(=O)CC)(OC(=O)CCC)C(C)C4

Betamethasone dipropionate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(C(=O)COC(=O)CC)(OC(=O)CC)C(C)C4

Betamethasone valerate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(C(=O)CO)(OC(=O)CCCC)C(C)C4

Betaxolol

C2CC2COCCC1=CC=C(OCC(O)CNC(C)C)C=C1

0.0

Bicalutamide

C2=CC(C#N)=C(C(F)(F)F)C=C2NC(=O)C(C)(O)CS(=O)(=O)C1=CC=C(F)C=C1

≥4

8.5

≥4

13.6

≥4

11.9

5.1

1.7

Bisoprolol

C1=CC(COCCOC(C)C)=CC=C1OCC(O)CNC(C)C

3.1

0.0

3.1

0.0

12.3

Bitolterol

C(=O)(OC2=C(OC(=O)C1=CC=C(C)C=C1)C=CC(C(O)CNC(C)(C)C)=C2)C3C=CC(C)=CC=3

0.0

Bretylium tosylate

C1=CC=C(Br)C(C[N+](C)(C)CC)=C1

0.0

Bretylium tosylate

C1=CC(C)=CC=C1S(O)(=O)=O

0.0

Brimonidine

C2=C(NC1=NCCN1)C(Br)=C3C(=C2)N=CC=N3

0.0

1.1

0.0

Bromocriptine

N56C(O)(OC(NC(=O)C4C=C3C2=C1C(=C(Br)NC1=CC=C2)CC3N(C)C4)(C(C)C)C5=O)C7N(C(=O)C6CC(C)C)CCC7

0.0

Budesonide

C1C(=O)C=C2C(C)(C=1)C3C(CC2)C4C(C)(CC3O)C5(C(=O)CO)C(C4)OC(CCC)O5

0.2

0.0

Bumetanide

S(=O)(=O)(N)C2=C(OC1=CC=CC=C1)C(NCCCC)=CC(C(=O)O)=C2

0.0

Buprenorphine

C1C=C(O)C(OC)=C2C=1CC6C34C2(CC(OC)(C(C(O)(C)C(C)(C)C)C3)CC4)CCN6CC5CC5

0.0

Bupropion

C1=CC(Cl)=CC(C(=O)C(C)NC(C)(C)C)=C1

0.0

Buspirone

C3C4(CC(=O)N(CCCCN2CCN(C1=NC=CC=N1)CC2)C3=O)CCCC4

≥4

0.9

≥4

2.4

≥4

3.1

0.4

0.6

Busulfan

S(=O)(=O)(C)OCCCCOS(=O)(=O)C

Butenafine

C2C3=C(C(CN(C)CC1=CC=C(C(C)(C)C)C=C1)=CC=2)C=CC=C3

0.0

Butoconazole

C3=CC(Cl)=CC=C3CCC(SC1=C(Cl)C=CC=C1Cl)CN2C=NC=C2

0.2

0.0

0.2

0.0

Butorphanol

C1=C(O)C=C2C(=C1)CC5C3(O)C2(CCCC3)CCN5CC4CCC4

0.0

Cabergoline

C1([H])(C(=O)N(C(=O)NCC)CCCN(C)C)CC2([H])C([H])(N(CC=C)C1)CC4C3=C2C=CC=C3NC=4

0.0

Calcipotriene

C4C(O)CC(=CC=C1CCCC3(C)C1CCC3C(C)C=CC(O)C2CC2)C(=C)C4O

0.0

0.3

0.0

Calcitriol

C3C(O)CC(=CC=C1CCCC2(C)C1CCC2C(C)CCCC(C)(C)O)C(=C)C3O

0.0

Captopril

N1(C(=O)C(C)([H])CS)C([H])(C(=O)O)CCC1

≥4

1.1

≥4

1.5

≥4

0.7

0.4

0.0

Carbamazepine

C1=CC=C2C(=C1)N(C(N)=O)C3=C(C=C2)C=CC=C3

≥4

3.3

≥4

4.4

Carmustine

N(C(=O)NCCCl)(N=O)CCCl

≥4

14.6

Carteolol

C1=CC(OCC(O)CNC(C)(C)C)=C2C(=C1)NC(=O)CC2

0.0

0.5

0.0

Carvedilol

C1C=CC2=C(C=1)C4=C(N2)C=CC=C4OCC(O)CNCCOC3=C(OC)C=CC=C3

0.0

Cefaclor

C3=CC=C(C(N)C(=O)NC1C(=O)N2C1SCC(Cl)=C2C(=O)O)C=C3

≥4

3.4

≥4

6.0

≥4

2.9

≥4

0.4

0.0

Cefadroxil

C3(O)=CC=C(C(N)C(=O)NC1C(=O)N2C1SCC(Cl)=C2C(=O)O)C=C3

0.0

Cefamandole

C4=CC=C(C(O)C(=O)NC1C(=O)N3C1SCC(CSC2N(C)N=NN=2)=C3C(=O)O)C=C4

0.0

Cefamandole naftate

C4=CC=C(C(C(=O)NC1C(=O)N3C1SCC(CSC2N(C)N=NN=2)=C3C(=O)O)OC=O)C=C4

0.0

Cefapirin

C3=NC=CC(SCC(=O)NC1C(=O)N2C1SCC(COC(C)=O)=C2C(=O)O)=C3

0.0

Cefazolin

C(C(=O)NC1C(=O)N3C1SCC(CSC2=NN=C(C)S2)=C3C(=O)O)N4C=NN=N4

Cefepime

N4=C(N)SC=C4C(C(=O)NC1C(=O)N3C1SCC(C[N+]2(C)CCCC2)=C3C(O)=O)=NOC

1.0

13.7

≥4

68.4

27.4

Cefixime

C(C(=O)NC1C(=O)N2C1SCC(C=C)=C2C(=O)O)(C3N=C(N)SC=3)=NOCC(=O)O

13.7

≥4

0.4

≥4

0.4

0.1

0.0

Cefmetazole

C(C(=O)NC1(OC)C(=O)N3C1SCC(CSC2=NN=NN2C)=C3C(=O)O)SCC#N

0.1

0.0

25.5

0.0

Cefonicid

C(O)(C(=O)NC1C(=O)N3C1SCC(CSC2=NN=NN2CS(O)(=O)=O)=C3C(=O)O)C4=CC=CC=C4

12.7

0.0

Cefoperazone

C(C(=O)NC1C(=O)N3C1SCC(CSC2=NN=NN2C)=C3C(=O)O)(C4=CC=C(O)C=C4)NC(=O)N5CCN(CC)C(=O)C5=O

0.0

≥4

0.4

0.2

0.1

0.0

Cefotaxime

C(C(=O)NC1C(=O)N2C1SCC(COC(C)=O)=C2C(=O)O)(=NCC)C3N=C(N)SC=3

0.3

≥4

4.7

2.0

0.0

Cefotetan

C(=O)(NC1(OC)C(=O)N3C1SCC(CSC2=NN=NN2C)=C3C(=O)O)C4SC(=C(C(=O)N)C(O)=O)S4

0.7

0.0

Cefoxitin

C(=O)(NC1(OC)C(=O)N2C1SCC(COC(N)=O)=C2C(=O)O)CC3=CC=CS3

0.0

Cefpodoxime

C(=O)(NC1C(=O)N2C1SCC(COC)=C2C(=O)OC(O)C)C(C3N=C(N)SC=3)=NOC

≥4

1.0

≥4

1.0

≥4

0.8

0.2

0.5

Cefpodoxime proxetil

C(=O)(NC1C(=O)N2C1SCC(COC)=C2C(=O)OC(C)OC(=O)OC(C)C)C(C3N=C(N)SC=3)=NOC

≥4

1.0

≥4

1.0

≥4

0.8

0.2

0.5

Cefprozil

C(=O)(NC1C(=O)N2C1SCC(C=CCC)=C2C(O)=O)C(N)C3=CC=C(O)C=C3

≥4

0.2

≥4

0.4

≥4

0.2

≥4

0.2

0.1

Ceftazidime

C(=O)(NC1C(=O)N3C1SCC(C[N+]2=CC=CC=C2)=C3C(O)=O)C(=NCC(C)(C)C(=O)O)C4N=C(N)SC=4

0.0

Ceftibuten

C2(NC(=O)C(C1N=C(N)SC=1)=CCC(O)=O)C(=O)N3C2SCC=C3C(O)=O

0.0

Ceftizoxime

C(=O)(NC1C(=O)N2C1SCC=C2C(O)=O)C(=NOC)C3NC(=N)SC=3

≥4

2.9

≥4

7.8

≥4

4.0

0.3

0.0

Ceftriaxone

C(=O)(NC1C(=O)N3C1SCC(CSC2N(C)NC(=O)C(=O)N=2)=C3C(O)=O)C(=NOC)C4N=C(N)SC=4

≥4

3.4

≥4

3.8

≥4

3.8

≥4

1.9

≥4

2.6

Cefuroxime

C(=O)(NC1C(=O)N2C1SCC(COC(N)=O)=C2C(O)=O)C(C3=CC=CO3)=NOC

0.0

0.2

0.0

Cefuroxime axetil

C(=O)(NC1C(=O)N2C1SCC(COC(N)=O)=C2C(=O)OC(C)OC(C)=O)C(C3=CC=CO3)=NOC

0.0

Cefuroxime pivoxetil

C(=O)(NC1C(=O)N2C1SCC(COC(N)=O)=C2C(=O)OC(C)OC(=O)C(C)(C)OC)C(C3=CC=CO3)=NOC

0.0

Cephalexin

C(=O)(NC1C(=O)N2C1SCC(C)=C2C(O)=O)C(N)C3=CC=CC=C3

Cetirizine

C(C1=CC=C(Cl)C=C1)(C2=CC=CC=C2)N3CCN(CCOCC(O)=O)CC3

0.0

1.0

≥4

1.3

1.0

0.6

Chenodiol

C1C(O)CC2C(C)(C1)C3C(C(O)C2)C4C(C)(CC3)C(C(C)CCC(O)=O)CC4

0.0

Chlormezanone

C2CC(=O)N(C)C(C1=CC=C(Cl)C=C1)S2(O)O

Ciclopirox

N2(O)C(C1CCCCC1)=CC(C)=CC2=O

0.0

Cidofovir

N1C(=O)N(CC(CO)OCP(O)(=O)O)C=CC=1N

92.2

46.1

0.0

46.1

0.0

Cinoxacin

C1C3=C(C=C2C=1C(=O)C(C(=O)O)=NN2CC)OCO3

0.0

≥4

16.9

≥4

15.1

0.0

Ciprofloxacin

C2(N1CCNCC1)=C(F)C=C4C(=C2)N(C3CC3)C=C(C(=O)O)C4=O

≥4

2.3

≥4

3.1

≥4

2.1

≥4

0.9

≥4

0.8

Cisapride

C3=CC(F)=CC=C3OCCCN2CCC(NC(=O)C1=CC(Cl)=C(N)C=C1OC)C(OC)C2

≥4

0.2

≥4

0.3

≥4

0.4

0.1

0.2

Cladribine

N1=C(Cl)N=C3C(=C1N)N=CN3C2CC(O)C(CO)O2

16.2

0.0

8.1

Clarithromycin

C3(O)(C)C(CC)OC(=O)C(C)C(CC1OC(C)C(O)C(C)(OC)C1)C(C)C(OC2OC(C)CC(N(C)C)C2O)C(C)(OC)CC(C)C(=O)C(C)C3O

≥4

3.1

≥4

3.8

≥4

3.3

≥4

1.4

≥4

1.5

Clobetasol

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(OC(=O)CC)(C(=O)CCl)C(C)C4

0.0

Clobetasol

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)CCl)C(C)C4

0.0

Clofazimine

C1=CC=C3C(=C1)N(C2=CC=C(Cl)C=C2)C5C(=N3)C=C(NC4=CC=C(Cl)C=C4)C(=NC(C)C)C=5

76.9

≥4

102.6

25.6

51.3

Clomiphene

C3=CC=CC(C(Cl)=C(C1=CC=CC=C1)C2=CC=C(OCCN(CC)CC)C=C2)=C3

≥4

18.8

≥4

25.0

≥4

15.6

Clomipramine

N2(CCCN(C)C)C1=CC(Cl)=CC=C1CCC3=C2C=CC=C3

0.0

Clonidine

C2=CC=C(Cl)C(N=C1NCCN1)=C2Cl

≥4

11.5

≥4

7.6

≥4

9.5

Clorazepic acid

C2(C1=CC=CC=C1)=NC(C(=O)O)C(=O)NC3=C2C=C(Cl)C=C3

Clozapine

C1(Cl)=CC=C3C(=C1)N=C(N2CCN(C)CC2)C4=C(N3)C=CC=C4

≥4

34.2

≥4

45.1

≥4

42.9

≥4

16.8

≥4

11.4

Cyclacillin

C2(NC(=O)C1(N)CCCCC1)C(=O)N3C2SC(C)(C)C3C(O)=O

0.0

Cyclobenzaprine

C1(=CCCN(C)C)C3=C(C=CC2C1=CC=CC=2)C=CC=C3

Cyclo-
phosphamide

P1(=O)(N(CCCl)CCCl)NCCCO1

≥4

4.6

≥4

8.5

≥4

8.5

≥4

8.5

Cytarabine

N2C(=O)N(C1C(O)C(O)C(CO)O1)C=CC=2N

≥4

4.1

≥4

6.1

≥4

4.1

Dactinomycin

C3(=O)C(N)=C(C(=O)NC1C(C)OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2N(C(=O)C(C)NC1=O)CCC2)C4C(=C3C)OC5C(N=4)=CC=CC=5C

≥4

29.6

≥4

23.7

Danazol

C1=C3C(C)(CC2=C1ON=C2)C4C(CC3)C5C(C)(CC4)C(O)(C#C)CC5

≥4

10.2

Dantrolene

C3(N(=O)=O)=CC=C(C2OC(C=NN1C(=O)NC(=O)C1)=CC=2)C=C3

Dapiprazole

N34C(CCN2CCN(C1=C(C)C=CC=C1)CC2)=NN=C3CCCC4

0.0

Daunorubicin

C13C(C(=O)C2=C(C1=O)C=CC=C2OC)=C(O)C5=C(C=3O)CC(O)(C(=O)C)CC5OC4OC(C)C(O)C(N)C4

0.0

Desflurane

C(F)(OC(F)F)C(F)(F)F

0.3

≥4

1.3

0.8

0.5

Dexamethasone

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)CO)C(C)C4

Dexamethasone acefurate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C5C(C)(CC3O)C(C(=O)COC(C)=O)(OC(=O)C4OC=CC=4)C(C)C5

Dexamethasone acetate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)COC(C)=O)C(C)C4

Dexamethasone dipropionate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(C(=O)COC(=O)CC)(OC(=O)CC)C(C)C4

Dexamethasone palmitate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)COC(=O)CCCCCCCCCCCCCC)C(C)C4

Dexamethasone valarate

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2)C4C(C)(CC3O)C(O)(C(=O)COC(=O)CCCC)C(C)C4

Dexfenfluramine

C1=CC=C(CC(C)NCC)C=C1C(F)(F)F

0.2

≥4

1.0

0.6

0.4

0.6

Dexrazoxane

C2(=O)NC(=O)CN(CC(C)N1CC(=O)NC(=O)C1)C2

0.0

Dezocine

C1=C(O)C=CC2=C1C3(C)CCCCCC(C2)C3N

0.0

Diazepam

C1=C(Cl)C=C3C(=C1)N(C)C(=O)CN=C3C2=CC=CC=C2

Diclofenac

C2(CC(O)=O)=CC=CC=C2NC1=C(Cl)C=CC=C1Cl

≥4

9.2

≥4

11.4

≥4

11.1

≥4

2.0

≥4

3.8

Didanosine

C3(N1C=NC2=C1N=CNC2=O)CCC(CO)O3

≥4

14.5

≥4

13.7

≥4

12.9

≥4

3.0

1.5

Diflunisal

C2(C(=O)O)C=C(C1=C(F)C=C(F)C=C1)C=CC=2O

0.0

0.3

0.5

0.0

Diltiazem

C1=CC3=C(C=C1)N(CCN(C)C)C(=O)C(OC(=O)C)C(C2=CC=C(OC)C=C2)S3

0.1

≥4

0.3

0.1

0.0

Dipivefrin

C1=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=CC(C(O)CNC)=C1

0.0

Dirithromycin

C3(C)(O)C(OC1OC(C)CC(N(C)C)C1O)C(C)C(OC2OC(C)C(O)C(C)(OC)C2)C(C)C(=O)OC(CC)C(C)(O)C4C(C)C(C(C)C3)NC(COCCOC)O4

0.0

5.4

0.0

2.7

Disopyramide

C(CCN(C(C)C)C(C)C)(C(N)=O)(C1=CC=CC=C1)C2=NC=CC=C2

Disulfiram

CCN(C(=S)SSC(=S)N(CC)CC)CC

≥4

26.0

≥4

58.6

≥4

45.6

≥4

26.0

19.5

Dobutamine

C2(O)=C(O)C=CC(CCNC(C)CCC1=CC=C(O)C=C1)=C2

0.0

Docetaxel

CC(C)(C)OC(=O)NC(C(O)C(=O)OC1CC5(O)C(C)(C)C(=C1C)C(O)C(=O)C3(C)C(O)CC2C(OC(C)=O)(CO2)C3C5OC(=O)C4=CC=CC=C4)C6=CC=CC=C6

13.1

0.0

13.1

6.6

Dorzolamide

C1(C)CC(NCC)C2=C(S1(=O)=O)SC(S(=O)(N)=O)=C2

0.0

0.2

0.1

0.0

Doxacurium chloride

C1(OC)=C(OC)C(OC)=C6C(=C1)CC[N+](C)(CCCOC(=O)CCC(=O)OCCC[N+]3(C)C(CC2=CC(OC)=C(OC)C(OC)=C2)C4=C(CC3)C=C(OC)C(OC)=C4OC)C6CC5=CC(OC)=C(OC)C(OC)=C5

0.0

Doxazosin

C1(OC)=C(OC)C=C5C(=C1)N=C(N4CCN(C(=O)C2OC3=C(OC2)C=CC=C3)CC4)N=C5N

0.2

0.3

≥4

0.5

0.2

Doxepin

C1=CC=C2C(=C1)C(=CCCN(C)C)C3=C(CO2)C=CC=C3

434.8

Doxorubicin

C13C(C(=O)C2=C(C1=O)C=CC=C2OC)=C(O)C5=C(C=3O)CC(O)(C(=O)CO)CC5OC4OC(C)C(O)C(N)C4

Dronabinol

C1(C)CCC2C(C=1)C3=C(OC2(C)C)C=C(CCCCC)C=C3O

0.0

Droperidol

C1=CC=C4C(=C1)N(C3CCN(CCCC(=O)C2=CC=C(F)C=C2)CC=3)C(=O)N4

Econazole

C3=C(Cl)C=C(Cl)C(C(CN1C=NC=C1)OCC2=CC=C(Cl)C=C2)=C3

0.0

Enalapril

C2=CC=CC(CCC(NC(C)C(=O)N1C(C(O)=O)CCC1)C(=O)OCC)=C2

≥4

0.9

≥4

1.0

≥4

0.8

≥4

0.6

≥4

0.2

Encainide

C3=C(OC)C=CC(C(=O)NC2=CC=C(CCN1C(C)CCCC1)C=C2)=C3

≥4

3.6

≥4

12.4

≥4

7.7

≥4

4.1

0.0

Enflurane

C(F)(F)OC(F)(F)C(Cl)F

Enoxacin

C2(F)=C(N1CCNCC1)N=C3C(=C2)C(=O)C(C(O)=O)=CN3CC

0.0

Epoprostenol

C1(O)CC2C(C1C=CC(O)CCCCC)CC(=CCCCC(O)=O)O2

0.0

Erythromycin

C3(C)C(=O)C(C)CC(C)(O)C(OC1C(O)C(N(C)C)CC(C)O1)C(C)C(OC2OC(C)C(O)C(C)(OC)C2)C(C)C(=O)OC(CC)C(C)(O)C3O

≥4

7.3

≥4

7.9

≥4

8.5

Erythromycin acistrate

C3(C)C(=O)C(C)CC(C)(O)C(OC1C(OC(C)=O)C(N(C)C)CC(C)O1)C(C)C(OC2OC(C)C(O)C(C)(OC)C2)C(C)C(=O)OC(CC)C(C)(O)C3O

≥4

7.3

≥4

7.9

≥4

8.5

Erythromycin ethylsuccinate

C3(C)C(=O)C(C)CC(C)(O)C(OC1C(OC(=O)CCC(=O)OCC)C(N(C)C)CC(C)O1)C(C)C(OC2OC(C)C(O)C(C)(OC)C2)C(C)C(=O)OC(CC)C(C)(O)C3O

≥4

7.3

≥4

7.9

≥4

8.5

Erythromycin propionate

C3(C)C(=O)C(C)CC(C)(O)C(OC1C(OC(=O)CC)C(N(C)C)CC(C)O1)C(C)C(OC2OC(C)C(O)C(C)(OC)C2)C(C)C(=O)OC(CC)C(C)(O)C3O

≥4

7.3

≥4

7.9

≥4

8.5

Esmolol

C1=C(CCC(=O)OC)C=CC(OCC(O)CNC(C)C)=C1

0.0

4.6

0.0

4.6

0.0

Estazolam

C1=C(Cl)C=C3C(=C1)N4C(CN=C3C2=CC=CC=C2)=NN=C4

0.0

0.8

0.0

0.8

Estradiol

C1=C(O)C=C2C(=C1)C3C(CC2)C4C(C)(CC3)C(O)CC4

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estradiol benzoate

C2=C(OC(=O)C1=CC=CC=C1)C=C3C(=C2)C4C(CC3)C5C(C)(CC4)C(O)CC5

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estradiol cypionate

C1=C(O)C=C2C(=C1)C3C(CC2)C5C(C)(CC3)C(OC(=O)CCC4CCCCC4)CC5

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estradiol dipropionate

C1=C(OC(=O)CC)C=C2C(=C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CC)CC4

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estradiol enanthate

C1=C(O)C=C2C(=C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CCCCCC)CC4

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estradiol mustard

C1CC6(C)C(C2C1C4=C(CC2)C=C(OC(=O)C3=CC=C(N(CCCl)CCCl)C=C3)C=C4)CCC6OC(=O)C5=CC=C(N(CCCl)CCCl)C=C5

0.0

Estradiol undecylate

C1=C(O)C=C2C(=C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CCCCCCCCCC)CC4

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estradiol valerate

C1=C(O)C=C2C(=C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CCC)CC4

≥4

1.5

≥4

2.8

≥4

2.1

≥4

1.2

0.3

Estramustine

C34(C)C(C2C(C1=C(C=C(OC(=O)N(CCCl)CCCl)C=C1)CC2)CC3)CCC4O

43.7

0.0

Ethambutol

CCC(NCCNC(CC)CO)CO

Ethionamide

C1=CC(C(=S)N)=CC(CC)=N1

Etidronic acid

C(O)(C)(P(O)(=O)O)P(O)(=O)O

≥4

8.6

Etodolac

C12NC3C(C=1CCOC2(CC(=O)O)CC)=CC=CC=3CC

≥4

0.8

≥4

1.1

≥4

1.4

≥4

0.6

≥4

0.8

Etomidate

N2C=C(C(=O)OCC)N(C(C)C1=CC=CC=C1)C=2

0.0

Etoposide

C7=C(OC)C(O)=C(OC)C=C7C3C5=C(C(OC1C(O)C(O)C2C(O1)COC(C)O2)C4C3C(=O)OC4)C=C6C(=C5)OCO6

0.8

0.4

0.0

0.4

0.0

Etretinate

C1(C)=C(OC)C=C(C)C(C=CC(C)=CC=CC(C)=CC(=O)OCC)=C1C

≥4

5.3

≥4

5.3

≥4

3.2

≥4

2.9

0.6

Famciclovir

C12N=C(N)N=CC=1N=CN2CCC(COC(=O)C)COC(=O)C

0.0

Famotidine

C1SC(N=C(N)N)=NC=1CSCCC(N)=NS(N)(=O)=O

≥4

0.8

≥4

0.8

≥4

0.7

≥4

0.4

≥4

0.4

Felbamate

C1=CC=CC=C1C(COC(N)=O)COC(N)=O

≥4

15.0

≥4

11.7

≥4

11.7

≥4

8.3

≥4

15.8

Felodipine

C2(C)=C(C(=O)OCC)C(C1=CC=CC(Cl)=C1Cl)C(C(=O)OC)=C(C)N2

0.6

0.3

Fenfluramine

C1=CC=C(C(F)(F)F)C=C1CC(C)NCC

Fentanyl

C3=CC=CC=C3N(C(=O)CC)C2CCN(CCC1=CC=CC=C1)CC2

0.2

0.4

0.2

Fexofenadine

C4=CC=CC(C(O)(C1=CC=CC=C1)C3CCN(CCCC(O)C2=CC=C(C(C)(C)C(=O)O)C=C2)CC3)=C4

0.0

Finasteride

C1C(=O)NC2C(C)(C=1)C3C(CC2)C4C(C)(CC3)C(C(=O)NC(C)(C)C)CC4

≥4

2.5

≥4

2.7

≥4

2.7

≥4

1.1

≥4

1.0

Flecainide

C2=C(OCC(F)(F)F)C=CC(OCC(F)(F)F)=C2C(=O)NCC1CCCCN1

≥4

8.3

≥4

9.6

≥4

8.3

≥4

3.2

0.0

Flosequinan

C1(F)=CC=C2C(=C1)N(C)C=C(S(=O)C)C2=O

14.1

28.3

≥4

56.6

0.0

Floxuridine

N2C(=O)N(C1CC(O)C(CO)O1)C=C(F)C2=O

Fluconazole

C3=CC(F)=CC(F)=C3C(O)(CN1C=NC=N1)CN2N=CN=C2

≥4

8.4

≥4

9.8

≥4

9.1

≥4

3.0

≥4

4.2

Flucytosine

C1=C(F)C(N)=NC(=O)N1

Fludarabine

N1=C(F)N=C3C(=C1N)N=CN3C2C(O)C(O)C(COP(O)(O)=O)O2

≥4

9.2

≥4

9.2

≥4

10.7

≥4

18.3

0.0

Flumazenil

C1=C(F)C=C2C(=C1)N3C(CN(C)C2=O)=C(C(=O)OCC)N=C3

0.0

2.5

0.0

Flunisolide

C1C(=O)C=C2C(C)(C=1)C3C(CC2F)C4C(C)(CC3O)C5(C(=O)CO)C(C4)OC(C)(C)O5

0.0

Fluorouracil, 5-

C1=C(F)C(=O)NC(=O)N1

≥4

5.5

≥4

3.6

Fluoxetine

C2(C(F)(F)F)=CC=C(OC(CCNC)C1=CC=CC=C1)C=C2

≥4

4.7

≥4

9.6

≥4

8.7

≥4

3.2

≥4

3.3

Fluphenazine

C1=CC=C3C(=C1)N(CCCN2CCN(CCO)CC2)C4=C(S3)C=CC(C(F)(F)F)=C4

Fluphenazine decanoate

C1=CC=C3C(=C1)N(CCCN2CCN(CCOC(=O)CCCCCCCCC)CC2)C4=C(S3)C=CC(C(F)(F)F)=C4

Fluphenazine enanthate

C1=CC=C3C(=C1)N(CCCN2CCN(CCOC(=O)CCCCC)CC2)C4=C(S3)C=CC(C(F)(F)F)=C4

Flurbiprofen

C2(F)=C(C1=CC=CC=C1)C=CC(C(C)C(=O)O)=C2

≥4

0.9

≥4

0.9

≥4

0.9

0.2

≥4

0.9

Flutamide

C1(C(F)(F)F)=C(N(=O)=O)C=CC(NC(=O)C(C)C)=C1

≥4

16.8

≥4

22.4

≥4

20.2

≥4

8.4

≥4

6.7

Fluticasone

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2F)C4C(C)(CC3O)C(C(=O)SCF)(OC(=O)CC)C(C)C4

0.0

0.8

0.0

Fluvastatin

C2(C=CC(O)CC(O)CC(O)=O)N(C(C)C)C3=C(C=2C1=CC=C(F)C=C1)C=CC=C3

≥4

0.5

≥4

1.0

≥4

1.0

0.0

≥4

0.7

Fluvoxamine

C1=CC(C(F)(F)F)=CC=C1C(=NOCCN)CCCCOC

≥4

2.7

≥4

8.9

≥4

8.9

2.1

1.4

Foscarnet

P(=O)(O)(O)C(O)=O

≥4

181.6

≥4

121.1

≥4

72.6

≥4

48.4

36.3

Fosfomycin

C1(P(O)(=O)O)C(C)O1

0.0

Fosinopril

P(=O)(CC(=O)N2CC(C1CCCCC1)CC2C(=O)O)(CCCCC3=CC=CC=C3)OC(OC(=O)CC)C(C)C

0.3

≥4

1.5

≥4

1.5

0.6

Fosphenytoin

C2=CC=C(C(C1=CC=CC=C1)(NC(C)=O)C(=O)NCOP(O)(=O)O)C=C2

0.0

Furosemide

C2(C(O)=O)=CC(S(N)(=O)=O)=C(Cl)C=C2NCC1OC=CC=1

Gabapentin

C(=O)(O)CC1(CN)CCCCC1

≥4

0.7

≥4

0.8

≥4

0.8

0.4

≥4

0.7

Ganciclovir

N1C(N)=NC2=C(C1=O)N=CN2COC(CO)CO

≥4

4.2

≥4

2.7

≥4

2.3

≥4

1.9

0.8

Gemcitabine

N2C(=O)N(C1C(F)(F)C(O)C(CO)O1)C=CC=2N

4.3

1.4

Gemfibrozil

C1=C(C)C=C(OCCCC(C)(C)C(O)=O)C(C)=C1

0.0

Glimepiride

C3(=O)C(CC)=C(C)CN3C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)NC1CCC(C)CC1)C=C2

1.2

0.0

1.2

Glipizide

C3=C(C)N=CC(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)NC1CCCCC1)C=C2)=N3

≥4

0.8

≥4

0.7

≥4

0.6

0.4

0.0

Glyburide

C3(Cl)=CC=C(OC)C(C(=O)NCCC2=CC=C(S(=O)(=O)NC(=O)NC1CCCCC1)C=C2)=C3

≥4

3.4

≥4

1.8

≥4

2.2

≥4

0.8

0.0

Granisetron

C34C(C(=O)NC1CC2N(C)C(C1)CCC2)=NN(C)C=3C=CC=C4

≥4

1.0

0.6

0.2

Griseofulvin

C13(C(=O)C2=C(O1)C(Cl)=C(OC)C=C2OC)C(OC)=CC(=O)CC3C

≥4

5.5

≥4

5.5

≥4

6.9

5.5

Guanabenz

C1=CC=C(Cl)C(C=NNC(N)=N)=C1Cl

0.0

0.9

0.6

0.3

0.0

Guanadrel

C1CCCC2(C1)OC(CNC(N)=N)CO2

0.0

Guanfacine

N(C(=N)N)C(=O)CC1=C(Cl)C=CC=C1Cl

1.0

≥4

1.3

0.3

0.6

0.0

Halazepam

C1=C(Cl)C=C3C(=C1)N(CC(F)(F)F)C(=O)CN=C3C2=CC=CC=C2

0.0

Halobetasol

C1C(=O)C=C2C(C)(C=1)C3(F)C(CC2F)C4C(C)(CC3O)C(C(=O)CCl)(OC(=O)CC)C(C)C4

0.0

Haloperidol

C3=C(Cl)C=CC(C2(O)CCN(CCCC(=O)C1=CC=C(F)C=C1)CC2)=C3

Halothane

C(F)(F)(F)C(Cl)Br

≥4

16.5

Hydrochloro-
thiazide

C1(S(N)(=O)=O)=C(Cl)C=C2C(=C1)S(=O)(=O)NCN2

Hydromorphone

C1C=C(O)C4=C2C=1CC5C3C2(C(C(=O)CC3)O4)CN5C

0.0

Hydroxyurea

NC(=O)NO

Hydroxyzine

C3(Cl)=CC=C(C(C1=CC=CC=C1)N2CCN(CCOCCO)CC2)C=C3

Ibuprofen

C1(CC(C)C)=CC=C(C(C)C(O)=O)C=C1

≥4

NSU

≥4

NSU

≥4

NSU

Ibutilide

C1=C(NS(=O)(C)=O)C=CC(C(O)CCCN(CCCCCCC)CC)=C1

0.0

Idarubicin

C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(O)=C5C(=C3O)CC(O)(C(C)=O)CC5OC4OC(C)C(O)C(N)C4

0.0

Ifosfamide

C1CCN(CCCl)P(=O)(NCCCl)O1

5.0

≥4

17.5

7.5

0.0

Indapamide

S(=O)(=O)(N)C3C=C(C(=O)NN1C2=C(CC1C)C=CC=C2)C=CC=3Cl

0.5

1.0

0.5

0.0

Indinavir

C5=CN=CC(CN4CC(C(=O)NC(C)(C)C)N(CC(O)CC(C(=O)NC1C(O)CC2=C1C=CC=C2)CC3=CC=CC=C3)CC4)=C5

≥4

54.8

≥4

137.0

≥4

116.4

≥4

44.5

13.7

Indomethacin

N2(C(=O)C1=CC=C(Cl)C=C1)C(C)=C(CC(=O)O)C3=C2C=CC(OC)=C3

≥4

3.1

≥4

3.8

Iodixanol

C2(I)=C(C(=O)NCC(O)CO)C(I)=C(N(CC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I)C(=O)C)C(I)=C2C(=O)NCC(O)CO

0.0

Iohexol

C1(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(C)=O)CC(O)CO

144.9

0.0

144.9

0.0

Iopamidol

C1(I)=C(NC(=O)C(C)O)C(I)=C(C(=O)NC(CO)CO)C(I)=C1C(=O)NC(CO)CO

0.0

526.3

0.0

1579.0

0.0

Iopromide

C1(NC(=O)COC)=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I

0.0

Ioversal

C1(I)=C(N(C(=O)CO)CCO)C(I)=C(C(=O)NCC(O)CO)C(I)=C1C(=O)NCC(O)CO

0.0

400.0

0.0

Ipratropium bromide

[N+]2(C)(C(C)C)C3CC(OC(=O)C(C1=CC=CC=C1)CO)CC2CC3

0.1

0.0

Irinotecan

C3(OC(=O)N2CCC(N1CCCCC1)CC2)=CC=C4C(=C3)C(CC)=C5C(=N4)C6N(C5)C(=O)C7=C(C=6)C(O)(CC)C(=O)OC7

4.1

6.1

4.1

2.0

Isoflurane

C(F)(F)(F)C(Cl)OC(F)F

0.6

≥4

1.0

0.4

0.0

Isoniazid

C1=NC=CC(C(=O)NN)=C1

≥4

12.7

≥4

38.7

≥4

34.7

≥4

10.0

≥4

8.0

Isosorbide mononitrate

O1CC(O)C2C1C(ON(=O)=O)CO2

0.0

0.2

0.5

0.2

0.0

Isotretinoin

C1(C=CC(C)=CC=CC(C)=CC(=O)O)=C(C)CCCC1(C)C

≥4

45.7

≥4

98.4

≥4

63.7

≥4

54.0

0.0

Isradipine

C2C=C(C1C(C(=O)OC)=C(C)NC(C)=C1C(=O)OC(C)C)C3C(C=2)=NON=3

0.5

≥4

0.8

≥4

0.7

0.3

0.2

Itraconazole

C7=NN(C(C)CC)C(=O)N7C6=CC=C(N5CCN(C4=CC=C(OCC3COC(CN1C=NC=N1)(C2=CC=C(Cl)C=C2Cl)O3)C=C4)CC5)C=C6

≥4

12.4

≥4

19.6

≥4

19.8

≥4

5.8

≥4

14.1

Ketoconazole

C5(C1=C(Cl)C=C(Cl)C=C1)(CN2C=NC=C2)OC([H])(COC4C=CC(N3CCN(C(=O)C)CC3)=CC=4)CO5

≥4

5.4

≥4

14.7

≥4

10.7

2.7

0.0

Ketoprofen

C2=CC=CC(C(=O)C1=CC=CC(C(C)C(=O)O)=C1)=C2

0.6

0.4

0.0

Ketorolac

C3=CC=CC=C3C(=O)C1=CC=C2N1CCC2C(=O)O

≥4

1.4

≥4

0.9

≥4

0.6

≥4

0.5

Labetalol

C2=CC=CC(CCC(C)NCC(O)C1=CC=C(O)C(C(N)=O)=C1)=C2

≥4

0.9

≥4

3.0

≥4

1.1

0.4

0.0

Lamivudine

N2C(=O)N(C1CSC(CO)O1)C=CC=2N

≥4

2.1

≥4

8.7

≥4

9.0

≥4

2.1

≥4

1.7

Lamotrigine

C2=CC=C(C1=C(N)N=C(N)N=N1)C(Cl)=C2Cl

0.5

≥4

4.0

≥4

4.0

≥4

3.0

2.0

Lansoprazole

C1=CC=C3C(=C1)N=C(S(=O)CC2=NC=CC(OCC(F)(F)F)=C2C)N3

0.5

≥4

0.9

≥4

1.2

0.5

≥4

1.1

Latanoprost

C2=CC=CC(CCC(O)CCC1C(O)CC(O)C1CC=CCCCC(=O)OC(C)C)=C2

0.2

0.0

Levamisole

C3=CC=CC(C1N=C2N(C1)CCS2)=C3

≥4

38.3

≥4

26.5

8.8

≥4

29.4

5.9

Levobunolol

C12=C(C=CC=C1OCC(O)CNC(C)(C)C)C(=O)CCC2

0.0

Levocabastine

C4(C(=O)O)(C1=CC=CC=C1)C(C)CN(C3CCC(C#N)(C2=CC=C(F)C=C2)CC3)CC4

0.0

Levocarnitine

C[N+](C)(C)CC(O)CC(=O)O

0.0

Levofloxacin

C3(N1CCN(C)CC1)=C(F)C=C2C(=O)C(C(=O)O)=CN4C2=C3OCC4C

0.0

Levonorgestrel

C34(CC)C([H])(C2C([H])(C1([H])C(=CC(=O)CC1)CC2)CC3)CCC4(O)C#C

≥4

34.0

≥4

39.7

≥4

22.7

≥4

28.3

≥4

34.0

Lisinopril

C2=CC=CC(CCC(NC(C(=O)N1C(C(=O)O)CCC1)CCCCN)C(=O)O)=C2

≥4

2.0

≥4

1.5

≥4

1.4

≥4

1.2

≥4

1.0

Lodoxamide

C1(NC(=O)C(=O)O)=C(Cl)C(NC(=O)C(=O)O)=CC(C#N)=C1

0.0

Lomefloxacin

C1(C(=O)O)C(=O)C3=C(N(CC)C=1)C(F)=C(N2CC(C)NCC2)C(F)=C3

1.6

3.2

1.6

3.2

Loracarbef

C3=CC=C(C(N)C(=O)NC1C(=O)N2C1CCC(Cl)=C2C(O)=O)C=C3

0.2

0.0

0.1

Loratadine

C4(=C1C3=C(CCC2=C1C=CC(Cl)=C2)C=CC=N3)CCN(C(=O)OCC)CC4

≥4

0.7

≥4

0.9

≥4

0.6

0.2

≥4

0.5

Losartan

N4(CC3C=CC(C2C(C1NN=NN=1)=CC=CC=2)=CC=3)C(CO)=C(Cl)N=C4CCCC

0.4

≥4

0.8

≥4

1.0

0.4

0.6

Lovastatin

C1C(C)C=C3C(C1OC(=O)C(C)CC)C(CCC2OC(=O)CC(O)C2)C(C)C=C3

≥4

9.1

≥4

14.4

≥4

12.1

≥4

6.1

≥4

5.8

Loxapine

C1=CC=C3C(=C1)N=C(N2CCN(C)CC2)C4=C(O3)C=CC(Cl)=C4

≥4

9.9

≥4

9.9

Maprotiline

C1=CC=C2C(=C1)C3(CCCNC)C4=C(C2CC3)C=CC=C4

0.5

0.3

0.0

Masoprocol

C2(O)=C(O)C=CC(CC(C)C(C)CC1=CC=C(O)C(O)=C1)=C2

0.0

Mebendazole

C1(NC(=O)OC)=NC3=C(N1)C=CC(C(=O)C2=CC=CC=C2)=C3

Meclocycline

C1=CC(Cl)=C2C(=C1O)C(=O)C3C(C2=C)C(O)C4C(O)(C=3O)C(=O)C(C(N)=O)=C(O)C4N(C)C

0.0

Meclofenamic acid

C2(NC1=C(C(=O)O)C=CC=C1)=C(Cl)C(C)=CC=C2Cl

0.0

Medroxy-
progesterone

C12(C)C(=CC(=O)CC1)C(C)CC4C2CCC3(C)C(O)(C(=O)C)CCC34

Medroxy-
progesterone acetate

C12(C)C(=CC(=O)CC1)C(C)CC4C2CCC3(C)C(C(=O)C)(OC(=O)C)CCC34

Mefenamic acid

C2=CC=CC(NC1=CC=CC(C)=C1C)=C2C(=O)O

≥4

26.0

19.5

Mefloquine

C23=NC(C(F)(F)F)=CC(C(O)C1NCCCC1)=C2C=CC=C3C(F)(F)F

7.2

≥4

25.3

≥4

32.5

0.0

≥4

18.0

Megestrol

C14C(C)(C3C(C=C1C)C2C(C)(C(O)(C(=O)C)CC2)CC3)CCC(=O)C=4

Melphalan

C1=C(N(CCCl)CCCl)C=CC(CC(N)C(O)=O)=C1

Mercaptopurine, 6-

N1C=NC2=C(C=1S)NC=N2

≥4

4.4

≥4

5.2

Meropenem

C1(C(O)C)C(=O)N3C1C(C)C(SC2CC(C(=O)N(C)C)NC2)=C3C(O)=O

0.0

50.8

33.8

0.0

Mesalamine

C1=C(N)C=CC(O)=C1C(O)=O

≥4

1.3

≥4

2.2

≥4

1.8

≥4

1.1

≥4

1.5

Mesna

SCCS(=O)(=O)O

0.0

5.0

0.0

5.0

0.0

Mestranol

C1C(OC)=CC2=C(C=1)C3C(CC2)C4C(C)(CC3)C(O)(C#C)CC4

Metformin

CN(C)C(=N)NC(N)=N

0.0

Methohexital

C1(=O)N(C)C(=O)NC(=O)C1(C(C)C#CCC)CC=C

Methotrexate

N1C(N)=C3C(=NC=1N)N=CC(CN(C)C2=CC=C(C(=O)NC(C(=O)O)CCC(=O)O)C=C2)=N3

≥4

5.3

≥4

6.4

≥4

3.5

Methyldopa

C1(O)=C(O)C=CC(CC(C)(N)C(O)=O)=C1

Methyl-
prednisolone

C1C(=O)C=C2C(C)(C=1)C3C(CC2C)C4C(C)(CC3O)C(O)(C(=O)CO)CC4

Methyl-
prednisolone aceponate

C1C(=O)C=C2C(C)(C=1)C3C(CC2C)C4C(C)(CC3O)C(C(=O)COC(=O)C)(OC(=O)CC)CC4

Methyl-
prednisolone acetate

C1C(=O)C=C2C(C)(C=1)C3C(CC2C)C4C(C)(CC3O)C(O)(C(=O)COC(=O)C)CC4

Methyl-
prednisolone succinate

C1C(=O)C=C2C(C)(C=1)C3C(CC2C)C4C(C)(CC3O)C(O)(C(=O)COC(=O)CCC(O)=O)CC4

Methyl-
prednisolone suleptanate

C1C(=O)C=C2C(C)(C=1)C3C(CC2C)C4C(C)(CC3O)C(O)(C(=O)COC(=O)CCCCCCC(=O)N(C)CCS(=O)(=O)O)CC4

Metipranolol

C1(OC(C)=O)=C(C)C(C)=C(OCC(O)CNC(C)C)C=C1C

0.0

Metoclopramide

C1(Cl)=C(N)C=C(OC)C(C(=O)NCCN(CC)CC)=C1

NSU

0.0

Metoprolol

C1(CCOC)=CC=C(OCC(O)CNC(C)C)C=C1

≥4

0.4

≥4

0.5

≥4

0.5

0.3

0.0

Metronidazole

N1C=C(N(=O)=O)N(CCO)C=1C

≥4

6.2

Metyrosine

C1=C(O)C=CC(CC(C)(N)C(O)=O)=C1

0.0

Mexiletine

C1=CC=C(C)C(OCC(C)N)=C1C

≥4

3.1

≥4

6.7

≥4

3.6

≥4

2.0

0.0

Mezlocillin

C4=CC=C(C(NC(=O)N1C(=O)N(S(=O)(C)=O)CC1)C(=O)NC2C(=O)N3C2SC(C)(C)C3C(=O)O)C=C4

1.9

0.0

Midazolam

C1=C(Cl)C=C3C(=C1)N4C(CN=C3C2=CC=CC=C2F)=CN=C4C

0.2

0.0

Midodrine

C1(OC)=CC=C(OC)C(C(O)CNC(=O)CN)=C1

0.0

Minocycline

C1=CC(N(C)C)=C2C(=C1O)C(=O)C3C(C2)CC4C(O)(C=3O)C(=O)C(C(N)=O)=C(O)C4N(C)C

≥4

NSU

≥4

NSU

Minoxidil

C2(N1CCCCC1)=CC(N)=N(=O)C(N)=N2

≥4

0.7

≥4

0.9

≥4

1.1

0.0

0.3

Mirtazapine

C1=CC=C2C(=C1)C4N(C3=C(C2)C=CC=N3)CCN(C)C4

0.9

≥4

3.6

≥4

6.4

0.9

3.6

Misoprostol

C1(C=CCC(O)(C)CCCC)C(O)CC(=O)C1CCCCCCC(=O)OC

≥4

0.8

≥4

0.8

0.2

0.5

Mitoxantrone

C1=CC(O)=C2C(=C1O)C(=O)C3=C(C2=O)C(NCCNCCO)=CC=C3NCCNCCO

4.5

13.5

4.5

0.0

Mivacurium chloride

C6(OC)=CC(CC4C[N+](C)(CCCOC(=O)CCC=CCCC(=O)OCCC[N+]2(C)CCC3=C(C2CC1=CC(OC)=C(OC)C(OC)=C1)C=C(OC)C(OC)=C3)CC5=C4C=C(OC)C(OC)=C5)=CC(OC)=C6OC

0.0

Moexipril

N2(C(=O)C(C)NC(C(=O)OCC)CCC1=CC=CC=C1)C(C(=O)O)CC3=C(C2)C=C(OC)C(OC)=C3

0.0

1.3

0.0

Mometasone

C1C(=O)C=C2C(C)(C=1)C3(Cl)C(CC2)C5C(C)(CC3O)C(C(=O)CCl)(OC(=O)C4OC=CC=4)C(C)C5

0.0

Moricizine

C1=CC=C3C(=C1)SC4=C(N3C(=O)CCN2CCOCC2)C=C(NC(=O)OCC)C=C4

3.4

≥4

13.7

3.4

0.0

Mupirocin

C2C(CC1OC1C(C)C(C)O)C(O)C(O)C(CC(C)=CC(=O)OCCCCCCCCC(=O)O)O2

0.0

Mycophenolic Acid

C2(C)=C(OC)C(CC=C(C)CCC(=O)OCCN1CCOCC1)=C(O)C3=C2COC3=O

5.7

3.8

≥4

9.6

1.9

3.8

Nabilone

C1(O)C=C(C(C)(C)CCCCCC)C=C2C=1C3C(C(C)(C)O2)CCC(=O)C3

0.0

Nabumetone

C12C(C=C(CCC(=O)C)C=C1)=CC=C(OC)C=2

≥4

0.8

≥4

0.6

≥4

0.6

≥4

0.3

≥4

0.5

Nadolol

C1C=CC(OCC(O)CNC(C)(C)C)=C2C=1CC(O)C(O)C2

0.3

≥4

0.7

≥4

0.7

0.0

Nafcillin

C1=CC=C4C(=C1)C(C(=O)NC2C(=O)N3C2SC(C)(C)C3C(O)=O)=C(OCC)C=C4

≥4

10.9

Naftifine

C1C=CC3=C(C=1)C(CN(C)CC=CC2=CC=CC=C2)=CC=C3

0.0

Nalbuphine

C1=CC(O)=C5C3=C1CC(N(CC2CCC2)CC)C4(O)C3(C)C(C(O)CC4)O5

0.0

Nalmefene

C1=CC(O)=C5C3=C1CC(N(CC2CC2)CC)C4(O)C3(C)C(C(=C)CC4)O5

0.0

Naltrexone

C234C5(O)C(N(CC1CC1)CC2)CC6=C3C(OC4C(=O)CC5)=C(O)C=C6

0.0

23.3

0.0

Naproxen

C1=C(OC)C=C2C(=C1)C=C(C(C)C(=O)O)C=C2

0.1

≥4

0.1

0.0

0.1

Nedocromil

C1=C(C(=O)O)OC2=C(C1=O)C=C3C(=C2CCC)N(CC)C(C(O)=O)=CC3=O

0.0

0.5

0.3

0.0

Nefazodone

N4(CCOC1=CC=CC=C1)C(=O)N(CCCN3CCN(C2=CC(Cl)=CC=C2)CC3)N=C4CC

≥4

1.1

≥4

3.6

≥4

3.3

≥4

1.1

≥4

1.1

Netilmicin

C3(OC1C(O)C(NC)C(O)(C)CO1)C(O)C(OC2OC(CN)=CCC2N)C(N)CC3NCC

0.0

Nevirapine

C1=CC=C3C(=N1)N(C2CC2)C4=C(NC3=O)C(C)=CC=N4

≥4

27.5

≥4

68.7

≥4

55.0

≥4

34.4

≥4

41.2

Nicardipine

C3(C)=C(C(=O)OC)C(C1=CC=CC(N(=O)=O)=C1)C(C(=O)OCCN(C)CC2=CC=CC=C2)=C(C)N3

≥4

2.0

≥4

3.0

≥4

2.5

≥4

0.9

0.4

Nicotine

N2(C)C(C1C=NC=CC=1)CCC2

0.0

0.6

0.9

0.3

Nifedipine

C2(C(=O)OC)C(C1=C(N(=O)=O)C=CC=C1)C(C(=O)OC)=C(C)NC=2C

≥4

0.3

≥4

0.6

≥4

0.4

0.1

0.0

Nilutamide

C2(N1C(=O)C(C)(C)NC1=O)=CC=C(N(=O)=O)C(C(F)(F)F)=C2

0.0

19.5

0.0

Nimodipine

C2=CC(C1C(C(=O)OC(C)C)=C(C)NC(C)=C1C(=O)OCCOC)=CC(N(=O)=O)=C2

17.6

≥4

23.4

≥4

29.3

≥4

23.4

17.6

Nisoldipine

C2(C)=C(C(=O)OC)C(C1=CC=CC=C1N(=O)=O)C(C(=O)OCC(C)C)=C(C)N2

0.0

3.2

1.6

0.0

Nitrofurantoin

C2C=C(N(=O)=O)OC=2C=NN1C(=O)NC(=O)C1

≥4

32.8

≥4

52.0

≥4

27.4

≥4

35.6

≥4

16.4

Nizatidine

C1(CN(C)C)=NC(CSCCNC(NC)=CN(=O)=O)=CS1

≥4

1.4

≥4

3.0

≥4

2.4

≥4

0.5

≥4

0.8

Norfloxacin

C1(C(=O)O)C(=O)C3=C(N(CC)C=1)C=C(N2CCNCC2)C(F)=C3

≥4

6.3

≥4

5.6

≥4

3.0

≥4

3.7

0.0

Nortriptyline

C1C=CC2=C(C=1)CCC3=C(C2=CCCNC)C=CC=C3

≥4

15.4

11.6

Nystatin

C2(O)C(C)C(C)OC(=O)CC(O)CC(O)CC(O)CCC(O)C(O)CC(=O)CC(O)C(C(O)=O)C(O)CC(OC1C(O)C(N)C(O)C(C)O1)C=CC=CC=CC=CCCC=CC=CC2C

0.3

0.0

Ofloxacin

C2(F)C(N1CCN(C)CC1)=C4C3=C(C=2)C(=O)C(C(O)=O)=CN3C(C)CO4

≥4

1.2

≥4

1.9

≥4

2.1

≥4

1.2

0.5

Olanzapine

C2(N1CCN(C)CC1)=NC4=C(NC3=C2C=C(C)S3)C=CC=C4

≥4

3.7

≥4

16.5

≥4

15.5

≥4

2.1

≥4

9.1

Olopatadine

O1CC3=C(C(=CCCN(C)C)C2=C1C=CC(CC(O)=O)=C2)C=CC=C3

0.0

Olsalazine

C2=C(C(O)=O)C(O)=CC=C2N=NC1=CC(C(=O)O)=C(O)C=C1

0.7

2.2

1.5

0.7

0.0

Omeprazole

C1=C(OC)C=C3C(=C1)NC(S(=O)CC2=C(C)C(OC)=C(C)C=N2)=N3

≥4

1.8

≥4

1.2

≥4

0.9

≥4

0.5

≥4

0.8

Ondansetron

C1=CC=C2C(=C1)C4=C(N2C)CCC(CN3C(C)=NC=C3)C4=O

≥4

0.5

≥4

1.1

≥4

1.3

≥4

0.9

0.0

Oxaprocin

N3C(C1=CC=CC=C1)=C(C2=CC=CC=C2)OC=3CCC(O)=O

0.2

≥4

0.9

≥4

0.8

≥4

0.4

Oxiconazole

C3=C(Cl)C=C(Cl)C(C(=NOCC1=C(Cl)C=C(Cl)C=C1)CN2C=CN=C2)=C3

0.0

Oxtriphylline

C12=C(C(=O)C(C)C(=O)C1C)NC=N2

0.0

Paclitaxel

C3(C)C(OC(=O)C(O)C(NC(=O)C1=CC=CC=C1)C2=CC=CC=C2)CC4(O)C(C)(C)C=3C(CC(C)=O)C(=O)C5(C)C(C4)C6(OC(=O)C)C(CC5O)OC6

≥4

3.7

≥4

2.5

0.8

≥4

2.2

≥4

1.2

Pamidronic acid

NCCC(O)(P(O)(=O)O)P(O)(=O)O

≥4

16.6

4.1

12.4

Paroxetine

FC4C=CC(C3CCNCC3COC1=CC=C2C(=C1)OCO2)=CC=4

≥4

0.7

≥4

1.2

≥4

1.0

≥4

0.4

≥4

0.5

Pemoline

N2C(=O)C(C1=CC=CC=C1)OC=2N

≥4

14.0

≥4

22.7

≥4

23.5

≥4

6.2

Penbutolol

C2=CC=CC(OCC(O)CNC(C)(C)C)=C2C1CCCC1

0.0

Penciclovir

N1C(N)=NC2=C(C1=O)N=CN2CCC(CO)CO

0.0

Penicillamine

C(N)(C(=O)O)C(S)(C)C

Pentamidine

C2=C(C(N)=N)C=CC(OCCCCCOC1=CC=C(C(=N)N)C=C1)=C2

11.5

5.7

0.0

Pentostatin

N1=CNCC(O)C3=C1N(C2CC(O)C(CO)O2)C=N3

0.0

Pentoxifylline

N1(CCCCC(C)=O)C(=O)N(C)C2=C(C1=O)N(C)C=N2

≥4

1.0

≥4

0.9

0.3

≥4

0.6

0.0

Pergolide

C1=CC3=C2C(=C1)C4C(CC2=CN3)N(CCC)CC(CSC)C4

1.3

3.9

0.0

Permethrin

C3(C=C(Cl)Cl)C(C(=O)OCC2=CC(OC1=CC=CC=C1)=CC=C2)C3(C)C

0.0

Perphenazine

C1=CC=C3C(=C1)N(CCCN2CCN(CCO)CC2)C4=C(S3)C=CC(Cl)=C4

Phenelzine

C1=CC=CC(CCNN)=C1

≥4

4.9

≥4

4.9

≥4

4.9

Phenytoin

C3=CC=C(C2(C1=CC=CC=C1)NC(=O)NC2=O)C=C3

Pilocarpine

C2N=CN(C)C=2CC1C(CC)C(=O)OC1

0.0

4.6

0.0

Pimozide

C1=CC5=C(C=C1)N(C4CCN(CCCC(C2=CC=C(F)C=C2)C3=CC=C(F)C=C3)CC4)C(=O)N5

17.6

0.0

17.6

0.0

17.6

Pindolol

C1C=CC(OCC(O)CNC(C)C)=C2C=1NC=C2

1.0

≥4

2.6

≥4

2.6

0.7

0.0

Pipecuronium bromide

C2(N1CC[N+](C)(C)CC1)C(OC(C)=O)CC3C(C)(C2)C4C(CC3)C6C(C)(CC4)C(OC(C)=O)C(N5CC[N+](C)(C)CC5)C6

0.0

Piperacillin

N4(CC)C(=O)C(=O)N(C(=O)NC(C(=O)NC1C(=O)N2C1SC(C)(C)C2C(=O)O)C3=CC=CC=C3)CC4

0.3

0.0

Pirbuterol

N1=C(CO)C(O)=CC=C1C(O)CNC(C)(C)C

0.0

0.3

0.0

Piroxicam

C1=CC=C3C(=C1)S(=O)(=O)N(C)C(C(=O)NC2=NC=CC=C2)=C3O

≥4

2.6

≥4

1.7

≥4

0.9

0.5

0.0

Podofilox

C25C(C(C1C=C(OC)C(OC)=C(OC)C=1)C3=C(C2O)C=C4C(=C3)OCO4)C(=O)OC5

0.0

Pravastatin

C1C(O)C=C2C(C1OC(=O)C(C)CC)C(CCC(O)CC(O)CC(O)=O)C(C)C=C2

≥4

4.5

≥4

6.2

≥4

6.3

≥4

3.1

≥4

5.3

Prazepam

C1=C(Cl)C=C4C(=C1)N(CC2CC2)C(=O)CN=C4C3=CC=CC=C3

0.3

0.0

Praziquantel

N2(C(=O)C1CCCCC1)CC3N(C(=O)C2)CCC4=C3C=CC=C4

0.0

Prazosin

C3(N2CCN(C(=O)C1OC=CC=1)CC2)=NC(N)=C4C(=N3)C=C(OC)C(OC)=C4

Prednisone

C1C(=O)C=C2C(C)(C=1)C3C(CC2)C4C(C)(CC3=O)C(O)(C(=O)CO)CC4

Primidone

C2(=O)C(C1=CC=CC=C1)(CC)C(=O)NCN2

Probenecid

CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1

Procainamide

C1=C(N)C=CC(C(=O)NCCN(CC)CC)=C1

0.0

Procarbazine

C1=C(C(=O)NC(C)C)C=CC(CNNC)=C1

Propafenone

C2=CC=C(C(=O)CCC1=CC=CC=C1)C(OCC(O)CNCCC)=C2

≥4

7.6

≥4

5.7

≥4

4.7

1.9

2.9

Propofol

C1(C(C)C)=CC=CC(C(C)C)=C1O

≥4

0.4

≥4

0.7

≥4

0.5

≥4

0.5

0.1

Propylthiouracil

C1(CCC)=CC(=O)NC(=S)N1

Quazepam

N2=C(C1=CC=CC=C1F)C3=C(N(CC(F)(F)F)C(=S)C2)C=CC(Cl)=C3

0.0

Quinapril

C1=CC=C3C(=C1)CN(C(=O)C(C)NC(CCC2=CC=CC=C2)C(=O)OCC)C(C(O)=O)C3

≥4

1.4

≥4

1.1

≥4

1.2

0.4

≥4

1.4

Quinidine

C1(OC)=CC=C4C(=C1)C(C(O)C2CC3C(C=C)CN2CCC3)=CC=N4

Ramipril

C3=CC=CC(CCC(NC(C)C(=O)N1C(C(=O)O)CC2C1CCC2)C(=O)OCC)=C3

≥4

1.1

0.8

0.5

≥4

1.4

Ranitidine

C1C=C(CSCCNC(NC)=CN(=O)=O)OC=1CN(C)C

≥4

1.1

≥4

1.2

≥4

1.0

≥4

0.3

0.0

Remifentanil

C2=CC=CC=C2N(C(=O)CC)C1(C(=O)OC)CCN(CCC(=O)OC)CC1

0.0

Ribavirin

N2(C1C(O)C(O)C(CO)O1)N=C(C(=O)N)N=C2

0.0

Rifabutin

C6(O)C(C)C(O)C(C)C=CC=C(C)C(=O)NC2C(=O)C1C(O)=C(C)C5=C(C=1C3C=2NC4(N=3)CCN(CC(C)C)CC4)C(=O)C(C)(O5)OC=CC(OC)C(C)C(OC(C)=O)C6C

≥4

15.9

≥4

31.8

≥4

31.8

5.3

≥4

18.5

Rifampin

C2(C)C(O)C(C)C=CC=C(C)C(=O)NC5=C(C=NN1CCN(C)CC1)C(O)=C4C3C(=O)C(C)(OC=CC(OC)C(C)C(OC(C)=O)C(C)C2O)OC=3C(C)=C(O)C4=C5O

≥4

NSU

≥4

NSU

≥4

NSU

≥4

NSU

Riluzole

C1=C(OC(F)(F)F)C=C2C(=C1)N=C(N)S2

45.2

22.6

Rimantadine

C1C2CC3CC1CC(C(N)C)(C2)C3

1.7

3.3

1.7

0.0

Rimexolone

C1C(=O)C=C2C(C)(C=1)C3C(CC2)C4C(C)(CC3O)C(C)(C(=O)CC)C(C)C4

0.0

Risperidone

C4(CCN3CCC(C1=NOC2=C1C=CC(F)=C2)CC3)C(=O)N5C(=NC=4C)CCCC5

≥4

1.6

≥4

4.8

≥4

4.9

≥4

0.9

≥4

1.6

Ritodrine

C2=C(O)C=CC(C(O)C(C)NCCC1=CC=C(O)C=C1)=C2

1.1

≥4

4.2

≥4

4.2

0.0

Ritonavir

C4SC(C(C)C)=NC=4CNC(=O)NC(C(=O)NC(CC(O)C(NC(=O)OCC1SC=NC=1)CC2=CC=CC=C2)CC3=CC=CC=C3)C(C)C

≥4

30.8

≥4

95.9

≥4

95.9

≥4

32.5

≥4

49.7

Rocuronium bromide

C2(N1CCOCC1)C(O)CC3C(C)(C2)C4C(CC3)C6C(C)(CC4)C(OC(C)=O)C([N+]5(CC=C)CCCC5)C6

0.0

Ropivacaine

C2CCCC(C(=O)NC1=C(C)C=CC=C1C)N2CCC

0.0

Salmeterol

C2(CO)=C(O)C=CC(C(O)CNCCCCCCOCCCCC1=CC=CC=C1)=C2

0.0

0.1

0.0

0.1

Saquinavir

C1=CC5C(C=C1)=NC(C(=O)NC(C(=O)NC(C(O)CN2CC3C(CC2C(=O)NC(C)(C)C)CCCC3)CC4=CC=CC=C4)C(C)C(N)=O)=CC=5

0.0

Selegiline

C1=CC=CC(CC(C)N(C)CC#C)=C1

≥4

2.2

0.4

≥4

1.5

0.0

≥4

1.8

Sertraline

C1=CC=C3C(=C1)C(NC)CCC3C2=CC=C(Cl)C(Cl)=C2

≥4

2.0

≥4

2.7

≥4

2.1

≥4

0.9

≥4

2.0

Sevoflurane

C(F)(F)(F)C(C(F)(F)F)OCF

3.1

4.6

0.0

1.6

0.0

Simvastatin

C1C(C)C=C3C(C1OC(=O)C(C)(C)CC)C(CCC2OC(=O)CC(O)C2)C(C)C=C3

≥4

2.6

≥4

2.5

≥4

2.7

≥4

1.1

≥4

3.1

Sotalol

S(=O)(C)(=O)NC1=CC=C(C(O)CNC(C)C)C=C1

1.0

3.0

0.0

1.0

Sparfloxacin

C2(N1CC(C)NC(C)C1)=C(F)C(N)=C4C(=C2F)N(C3CC3)C=C(C(=O)O)C4=O

0.0

Spironolactone

C1C(=O)C=C2C(C)(C1)C3C(C(SC(=O)C)C2)C4C(C)(CC3)C5(CC4)CCC(=O)O5

Stavudine

N2(C1OC(CO)C=C1)C(=O)NC(=O)C(C)=C2

≥4

2.4

≥4

9.1

≥4

9.7

1.8

≥4

3.6

Streptozocin

C1([H])(NC(=O)N(C)N=O)C(O)([H])C(O)([H])C([H])(CO)OC1(O)[H]

11.8

0.0

Succimer

OC(=O)C(S)C(S)C(O)=O

≥4

175.4

≥4

175.4

131.6

43.9

87.7

Sufentanil

C3=CC=CC(N(C(=O)CC)C2(COC)CCN(CCC1SC=CC=1)CC2)=C3

0.0

Sulconazole

C3=C(Cl)C=CC(C(SCC1=CC=C(Cl)C=C1)CN2C=NC=C2)=C3Cl

0.0

Sulfadiazine

C2=CC(N)=CC=C2S(=O)(=O)NC1=NC=CC=N1

Sulfasalazine

N3=CC=CC=C3NS(=O)(=O)C2=CC=C(N=NC1=CC=C(O)C(C(O)=O)=C1)C=C2

≥4

4.0

Sulindac

C3=C(S(C)=O)C=CC(C=C1C(C)=C(CC(O)=O)C2=C1C=CC(F)=C2)=C3

0.0

Sumatriptan

C1=C(CS(=O)(=O)NC)C=C2C(=C1)NC=C2CCN(C)C

≥4

0.1

≥4

0.3

≥4

0.3

≥4

0.1

Suprofen

C2(C(=O)C1=CC=C(C(C)C(=O)O)C=C1)SC=CC=2

6.1

0.0

Tacrine

C1(N)=C3C(=NC2C1=CC=CC=2)CCCC3

≥4

14.1

≥4

58.1

≥4

170.0

≥4

19.0

≥4

17.4

Tamoxifen

C(=C(C1C=CC=CC=1)CC)(C2=CC=C(OCCN(C)C)C=C2)C3C=CC=CC=3

≥4

4.8

≥4

3.4

Tazarotene

C1CSC3=C(C1(C)C)C=C(C#CC2=NC=C(C(=O)OCC)C=C2)C=C3

0.0

Temazepam

C1=C(Cl)C=C3C(=C1)N(C)C(=O)C(O)N=C3C2=CC=CC=C2

0.0

Teniposide

C4(C1=CC(OC)=C(O)C(OC)=C1)C6=C(C(OC3OC(C)C(OC(O)C2=CC=CS2)C(O)C3O)C5C4C(=O)OC5)C=C7C(=C6)OCO7

0.0

Terazosin

C1(OC)=C(OC)C=C4C(=C1)C(N)=NC(N3CCN(C(=O)C2CCCO2)CC3)=N4

0.5

≥4

1.6

≥4

1.3

0.5

0.8

Terbinafine

C1=CC=C2C(=C1)C(CN(C)CC=CC#CC(C)(C)C)=CC=C2

≥4

1.1

≥4

3.1

≥4

2.8

≥4

1.1

≥4

2.6

Terconazole

N5(C4=CC=C(OCC3OC(C1=CC=C(Cl)C=C1Cl)(CN2C=NC=N2)OC3)C=C4)CCN(C(C)C)CC5

0.0

Terfenadine

C4=CC=CC(C(O)(C1=CC=CC=C1)C3CCN(CCCC(O)C2=CC=C(C(C)(C)C)C=C2)CC3)=C4

≥4

0.6

≥4

0.7

≥4

0.7

0.2

0.1

Testosterone

C1C(=O)C=C2C(C)(C1)C3C(CC2)C4C(C)(CC3)C(O)CC4

0.0

4.8

7.2

2.4

4.8

Testosterone cypionate

C1C(=O)C=C2C(C)(C1)C3C(CC2)C5C(C)(CC3)C(OC(=O)CCC4CCCC4)CC5

0.0

4.8

7.2

2.4

4.8

Testosterone enanthate

C1C(=O)C=C2C(C)(C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CCCCCC)CC4

0.0

4.8

7.2

2.4

4.8

Testosterone ketolaurate

C1C(=O)C=C2C(C)(C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CC(=O)CCCCCCCCC)CC4

0.0

4.8

7.2

2.4

4.8

Testosterone phenylacetate

C1C(=O)C=C2C(C)(C1)C3C(CC2)C5C(C)(CC3)C(OC(=O)CC4=CC=CC=C4)CC5

0.0

4.8

7.2

2.4

4.8

Testosterone propionate

C1C(=O)C=C2C(C)(C1)C3C(CC2)C4C(C)(CC3)C(OC(=O)CC)CC4

0.0

4.8

7.2

2.4

4.8

Tetracycline

C1(C)(O)C4=C(C(=O)C2C1CC3C(O)(C=2O)C(=O)C(C(N)=O)=C(O)C3N(C)C)C(O)=CC=C4

Theophylline

N1(C)C(=O)N(C)C2=C(C1=O)NC=N2

0.0

Thioguanine

N1=C(N)N=C2C(=C1S)NC=N2

42.1

Thioridazine

C1=CC=C3C(=C1)N(CCC2CCCCN2C)C4=C(S3)C=CC(SC)=C4

≥4

3.2

Thio-tepa

P(=S)(N1CC1)(N2CC2)N3CC3

Thiothixene

C1=CC=C3C(=C1)C(=CCCN2CCN(C)CC2)C4=C(S3)C=CC(S(=O)(=O)N(C)C)=C4

Ticlopidine

C3=CC=C(CN1CC2=C(CC1)SC=C2)C(Cl)=C3

0.0

Timolol

C2(OCC(O)CNC(C)(C)C)C(N1CCOCC1)=NSN=2

0.1

0.0

Tioconazole

C3=C(Cl)C(C(OCC1C=CSC=1Cl)CN2C=NC=C2)=CC=C3Cl

0.0

Tiopronin

CC(S)C(=O)NCC(O)=O

0.0

Tizanidine

C2C(Cl)=C(NC1=NCCN1)C3C(C=2)=NSN=3

8.3

16.5

24.8

8.3

Tobramycin

C3C(N)C(OC1C(N)CC(O)C(CN)O1)C(O)C(OC2C(O)C(N)C(O)C(CO)O2)C3N

Tocainide

C1=CC=C(C)C(NC(=O)C(N)C)=C1C

≥4

1.7

≥4

3.5

≥4

2.2

≥4

1.7

0.0

Topiramate

C23(COS(=O)(=O)N)C(C1C(OC(C)(C)O1)CO2)OC(C)(C)O3

3.5

0.0

Topotecan

C1(O)=CC=C2C(=C1CN(C)C)C=C3C(=N2)C4N(C3)C(=O)C5=C(C=4)C(O)(CC)C(=O)OC5

0.0

11.6

Torsemide

C2=CC=C(C)C=C2NC1=C(S(=O)(=O)NC(=O)NC(C)C)C=NC=C1

0.0

0.5

0.0

Tramadol

C2=CC=C(OC)C=C2C1(O)CCCCC1CN(C)C

0.1

≥4

0.5

≥4

0.8

≥4

0.6

0.2

Trandolapril

C3=CC=CC(CCC(NC(C)C(=O)N1C(C(O)=O)CC2C1CCCC2)C(=O)OCC)=C3

0.0

7.0

10.5

0.0

Tranylcypromine

C2(C1=CC=CC=C1)CC2N

Trazodone

C1C=CN4C(C=1)=NN(CCCN3CCN(C2=CC(Cl)=CC=C2)CC3)C4=O

0.2

0.3

0.0

0.3

0.0

Tretinoin

C1CCC(C)=C(C=CC(C)=CC=CC(C)=CC(O)=O)C1(C)C

1.0

0.0

1.0

Triazolam

C1=C(Cl)C=C3C(=C1)N4C(CN=C3C2=CC=CC=C2Cl)=NN=C4C

0.4

0.3

0.0

Trientine

NCCNCCNCCN

0.0

69.4

0.0

Trifluoperazine

C1=CC=C3C(=C1)N(CCCN2CCN(C)CC2)C4=C(S3)C=C(C(F)(F)F)C=C4

Trifluridine

N2C(=O)N(C1CC(O)C(CO)O1)C=C(C(F)(F)F)C2=O

0.0

Trimethadione

N1(C)C(=O)C(C)(C)OC1=O

≥4

NSU

≥4

NSU

≥4

NSU

≥4

NSU

≥4

NSU

Trimetrexate

C2=C(CNC1=CC(OC)=C(OC)C(OC)=C1)C(C)=C3C(=C2)N=C(N)N=C3N

38.8

77.5

38.8

0.0

Trimipramine

N1(CC(C)CN(C)C)C3=C(CCC2=C1C=CC=C2)C=CC=C3

0.0

Ursodiol

C1C(O)CC2C(C)(C1)C3C(C(O)C2)C4C(C)(CC3)C(C(C)CCC(=O)O)CC4

≥4

14.5

≥4

9.7

4.8

Valacyclovir

N1C(N)=NC2C(C1=O)N=CN2COCCOC(=O)C(N)C(C)C

NSU

0.0

Valproic acid

C(=O)(O)C(CCC)CCC

≥4

6.5

≥4

10.4

≥4

4.8

≥4

3.5

0.0

Valsartan

C3(C1=CC=C(CN(C(C(=O)O)C(C)C)C(=O)CCCC)C=C1)=CC=CC=C3C2NN=NN=2

0.0

5.0

7.6

0.0

2.5

Vecuronium bromide

C2(N1CCCCC1)C(OC(C)=O)CC3C(C)(C2)C4C(CC3)C6C(C)(CC4)C(OC(C)=O)C([N+]5(C)CCCCC5)C6

0.0

1.0

0.0

Venlafaxine

C(C1(O)CCCCC1)(C2C=CC(OC)=CC=2)CN(C)C

≥4

1.3

≥4

2.7

≥4

2.3

≥4

0.7

≥4

0.9

Verapamil

C2(OC)=C(OC)C=CC(CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C=C1)=C2

≥4

0.7

0.3

0.1

0.0

Vincristine

C8(C5C=C4C12C([H])(C(O)(C(=O)OC)C(OC(=O)C)C3(CC)C1([H])N(CC2)CC=C3)N(C=O)C4=CC=5OC)(C(=O)OC)C6=C(C7=C(N6)C=CC=C7)CCN9CC(O)(CC)CC(C8)C9

Vinorelbine

C1=CC=C2C(=C1)C9=C(N2)C(C(=O)OC)(C3=C(OC)C=C4C(=C3)C57C(N4C)C(O)(C(=O)OC)C(OC(C)=O)C6(CC)C5N(CC=C6)CC7)CC8CN(CC(CC)=C8)C9

2.8

0.9

1.9

≥4

4.7

0.9

Warfarin

C1=CC=C3C(=C1)OC(=O)C(C(CC(C)=O)C2=CC=CC=C2)=C3O

≥4

NSU

≥4

NSU

≥4

NSU

Zafirlukast

C5=CC=CC(C)=C5S(=O)(=O)NC(=O)C4=CC=C(CC1=CN(C)C3=C1C=C(NC(=O)OC2CCCC2)C=C3)C(OC)=C4

≥4

2.6

≥4

10.1

≥4

9.5

≥4

3.7

0.5

Zalcitabine

N2C(=O)N(C1CCC(CO)O1)C=CC=2N

2.9

≥4

5.7

2.9

1.4

Zidovudine

N2C(=O)N(C1CC(N=N#N)C(CO)O1)C=C(C)C2=O

≥4

5.1

≥4

12.7

≥4

4.8

≥4

5.7

0.9

Zileuton

C1(C(C)N(O)C(=O)N)SC2=C(C=1)C=CC=C2

≥4

29.7

≥4

47.5

≥4

65.3

11.9

5.9

Zolpidem

C1C(C)=CN3C(C=1)=NC(C2=CC=C(C)C=C2)=C3CC(=O)N(C)C

≥4

3.0

≥4

3.8

≥4

3.9

≥4

0.7

≥4

3.0

Zomepirac

C2=C(Cl)C=CC(C(=O)C1N(C)C(CC(O)=O)=CC=1C)=C2

≥4

1.1

≥4

1.1

≥4

0.7

≥4

0.7

0.0

Date created: 1/11/2005