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Cyanovirin-N
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Drug Class: Microbicides

Drug Description
Cyanovirin-N, also known as CV-N, is a protein from the cyanobacterium Nostoc ellipsosporum (blue-green algae). The protein exists as either a quasi-symmetric, two-domain monomer or a domain-swapped dimer.[1]

HIV/AIDS-Related Uses
Cyanovirin-N is a potent HIV fusion inhibitor with activity against both HIV-1 and HIV-2 in vitro and in animal models.[2] It is in preclinical development as a microbicide for the prevention of sexual transmission of HIV.[3]

Non HIV/AIDS-Related Uses
Cyanovirin-N has potent in vitro activity against almost all strains of influenza A and B virus. Cyanovirin-N is moderately active in vitro against some herpes viruses and is potentially active against hepatitis C virus.[4][5]

In studies in vitro and in mouse models, cyanovirin-N was active against the Zaire strain of the Ebola virus.[6]

Dosing Information

Mode of Delivery
Intravaginal.[7]

Dosage Form
Topical gel. Preclinical studies are evaluating 0.5%, 1%, and 2% preparations in aqueous gel with hydroxyethyl cellulose.[8]

Pharmacology
Cyanovirin-N is a protein derived from cultures of the cyanobacterium, (blue-green algae) Nostoc ellipsosporum.[9]

Cyanovirin-N binds to certain high-mannose oligosaccharides (oligomannose-8 and oligomannose-9) on viral surface envelope glycoprotein gp120, blocking its interaction with cellular receptors. This unique and effectively irreversible interaction renders gp120 incapable of mediating virus-to-cell or cell-to-cell fusion.[10][11] Cyanovirin interacts with one sugar at a primary binding site with high affinity and to another sugar (a secondary binding site) with low affinity. In addition, cyanovirin-N appears to bind to viral oligosaccharides with high affinity and to mammalian oligosaccharides with low affinity, potentially providing potent inactivation of HIV-1 and -2 without potent adverse effects to the body.[12]

Cyanovirin-N's anti-HIV effects are expressed during the initial binding or fusion process. These effects may occur after the initial virus-to-cell attachment phase, but prior to the completion of viral entry and replication.[13]

Clinical Trials
Click here to search ClinicalTrials.gov for trials that use Cyanovirin-N.

Chemistry

CAS Number
184539-38-6[14]

Molecular Weight
11 kDa[15]

Other Names
CV-N[16]

Further Reading
PMID/12678493 Botos I, Wlodawer A. Cyanovirin-N: a sugar-binding antiviral protein with a new twist. Cell Mol Life Sci. 2003 Feb;60(2):277-87. Review. PMID: 12678493

PMID/15000694 Tsai CC, Emau P, Jiang Y, Agy MB, Shattock RJ, Schmidt A, Morton WR, Gustafson KR, Boyd MR. Cyanovirin-N inhibits AIDS virus infections in vaginal transmission models. AIDS Res Hum Retroviruses. 2004 Jan;20(1):11-18. PMID: 15000694

PMID/14529524 Tziveleka LA, Vagias C, Roussis V. Natural products with anti-HIV activity from marine organisms. Curr Top Med Chem. 2003;3(13):1512-35. PMID: 14529524

Manufacturer Information
Cyanovirin-N
  Cellegy Pharmaceuticals, Inc
  3490 Oyster Point Boulevard
  Suite 200
  South San Francisco,  CA  94080
  (650) 616-2200
    

References
[1] Cell Mol Life Sci - 2003 Feb;60(2):277-87
[2] National Synchrotron Light Source - Newsroom: Publications-Structures of the Complexes of a Potent Anti-HIV Protein Cyanovirin-N and High-Mannose Oligosaccharides. Available at: http://www.nsls.bnl.gov/newsroom/publications/activityreport/2003/pdf/sh_life_sci_1.pdf. Accessed 2/12/08.
[3] CONRAD - New Licensing Agreement to Maximize AIDS Drug Development [Press Release], February 1, 2006. Available at: http://www.conrad.org/press/02012006.htm. Accessed 2/12/08.
[4] Antimicrob Agents Chemother - 2003 Aug;47(8):2518-25
[5] J Biol Chem - 2006 Sep 1;281(35):25177-83
[6] Mini Rev Med Chem - 2005 Jan;5(1):21-31
[7] Expert Opin Investig Drugs - 2002 Aug;11(3):1077-97
[8] AIDS Res Hum Retroviruses - 2004;20(1):11-18
[9] ChemIDplus - Cyanovirin-N. Available at: http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp. Accessed 2/12/08.
[10] Antimicrob Agents Chemother - 2003 Aug;47(8):2518-25
[11] Peptide - 2004;25(4):551-61
[12] National Synchrotron Light Source - Newsroom: Publications-Structures of the Complexes of a Potent Anti-HIV Protein Cyanovirin-N and High-Mannose Oligosaccharides. Available at: http://www.nsls.bnl.gov/newsroom/publications/activityreport/2003/pdf/sh_life_sci_1.pdf. Accessed 2/12/08.
[13] Antimicrob Agents Chemother - 1997 Jul;41(7):1521-30
[14] ChemIDplus - Available at: http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp. Accessed 2/12/08.
[15] Cell Mol Life Sci - 2003 Feb;60(2):277-87
[16] ChemIDplus - Available at: http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp. Accessed 2/12/08.
Updated February 12, 2008