Bevirimat

• CAT Number: I002271
• CAS Number: 174022-42-5
• Molecular Formula: C36H56O6
• Molecular Weight: 584.8
• Purity: ≥95%
• Target: HIV
• Solubility: CHCl3 < 10 mg/ml
• Storage: Store at -20C
• InChI: InChI=1S/C36H56O6/c1-21(2)22-12-17-36(30(40)41)19-18-34(8)23(28(22)36)10-11-25-33(7)15-14-26(42-27(37)20-31(3,4)29(38)39)32(5,6)24(33)13-16-35(25,34)9/h22-26,28H,1,10-20H2,2-9H3,(H,38,39)(H,40,41)/t22-,23+,24-,25+,26-,28+,33-,34+,35+,36-/m0/s1
• InChIKey: YJEJKUQEXFSVCJ-WRFMNRASSA-N
• SMILES: [H][C@]1([C@H](C(C)=C)CC2)[C@@]2(C(O)=O)CC[C@]3(C)[C@]1([H])CC[C@@]4([H])[C@@]3(C)CC[C@]5([H])[C@]4(C)CC[C@H](OC(CC(C)(C)C(O)=O)=O)C5(C)C

Bevirimat (CAT: I002271) is an investigational antiretroviral drug that was developed for the treatment of HIV-1 infection. It belongs to a class of compounds known as maturation inhibitors, which target the late stage of HIV replication by inhibiting the processing of the viral Gag polyprotein. Bevirimat specifically targets the cleavage site between the p24 and p2 subunits of the Gag protein, preventing the release of mature viral particles from infected cells. However, despite promising early results, further clinical development of bevirimat has been discontinued due to challenges in achieving consistent antiviral activity across different HIV-1 strains. Nonetheless, the research on maturation inhibitors like bevirimat has contributed to the understanding of HIV replication and the development of other antiretroviral drugs.

Reference

1: Yebra G, Holguín A. The maturation inhibitor bevirimat (PA-457) can be active
in patients carrying HIV type-1 non-B subtypes and recombinants. Antivir Ther.
2008;13(8):1083-5. PubMed PMID: 19195334.

2: Martin DE, Blum R, Wilton J, Doto J, Galbraith H, Burgess GL, Smith PC, Ballow
C. Safety and pharmacokinetics of Bevirimat (PA-457), a novel inhibitor of human
immunodeficiency virus maturation, in healthy volunteers. Antimicrob Agents
Chemother. 2007 Sep;51(9):3063-6. Epub 2007 Jun 18. PubMed PMID: 17576843; PubMed
Central PMCID: PMC2043192.

3: Adamson CS, Ablan SD, Boeras I, Goila-Gaur R, Soheilian F, Nagashima K, Li F,
Salzwedel K, Sakalian M, Wild CT, Freed EO. In vitro resistance to the human
immunodeficiency virus type 1 maturation inhibitor PA-457 (Bevirimat). J Virol.
2006 Nov;80(22):10957-71. Epub 2006 Sep 6. PubMed PMID: 16956950; PubMed Central
PMCID: PMC1642185.

4: Temesgen Z, Feinberg JE. Drug evaluation: bevirimat–HIV Gag protein and viral
maturation inhibitor. Curr Opin Investig Drugs. 2006 Aug;7(8):759-65. Review.
PubMed PMID: 16955688.