Bevirimat Chemical Properties

Melting point:

>263°C (dec.)

Boiling point:

662.7±40.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

Acetonitrile (Slightly), Methanol (Very Slightly, Heated, Sonicated)

pka

4.48±0.28(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

InChIKey

YJEJKUQEXFSVCJ-WRFMNRASSA-N

SMILES

CC([C@H]1[C@]2([H])[C@@]3([H])CC[C@@]4([H])[C@](CC[C@]5([H])[C@]4(C)CC[C@H](OC(CC(C)(C(O)=O)C)=O)C5(C)C)(C)[C@]3(C)CC[C@@]2(C(O)=O)CC1)=C

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

Bevirimat Usage And Synthesis

Description

PA-457 is an inhibitor of HIV-1 virion maturation. It inhibits the cleavage of the Gag capsid (CA) precursor CA-SP1 to the mature CA protein. PA-457 inhibits the replication of drug-sensitive and -resistant clinical isolates of HIV-1 in isolated human peripheral blood mononuclear cells (PBMCs; mean IC₅₀s = 10.3 and 7.8 nM, respectively). In vivo, it prevents replication of HIV-1 in SCID-hu Thy/Liv mice when administered at a dose of 100 mg/kg.

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.

Uses

Bevirimat is a HIV-1 maturation inhibitor, targetting the Gag CA-SP1 cleavage site. HIV Inhibitor.

Definition

ChEBI: A pentacyclic triterpenoid obtained by the formal condensation of 2,2-dimethylsuccinic acid with the 3-hydroxy group of betulinic acid. It is isolated from the Chinese herb Syzygium claviflorum. The first in the class of HIV-1 maturation inhib tors to be studied in humans, bevirimat was identified as a potent HIV drug candidate and several clinical trials were conducted, but development into a new drug was plagued by numerous resistance-related problems.

Enzyme inhibitor

This first-in-class, natural product-based antiviral (FW = 584.83 g/mol; CAS 174022-42-5; Abbreviation: BVM), also known as 3-O-(3',3'- dimethylsuccinyl)betulinate (DSB), 3β-(3-carboxy-3-methyl-butanoyloxy)- lup-20(29)-en-28-oic acid, PA-457, and MPC-4326, is a novel HIV-1 maturation inhibitor that blocks proteolytic processing of the Gag capsid precursor (CA-SP1) into mature capsid (CA) protein. Bevirimat binds to the Gag polypeptide at the CA/SP1 cleavage site. The net result of BVM treatment is the release of immature, noninfectious viral particles. Despite its promising mode of action, about half of all patients have viruses containing genetic polymorphisms in the Gag SP1 (at positions 6 to 8) protein do not respond to BVM treatment.

target

HIV

References

[1] DAVID E MARTIN  Graham P A  Karl Salzwedel. Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection.[J]. Antiviral Chemistry and Chemotherapy, 2008, 19 3: 107-113. DOI: 10.1177/095632020801900301
[2] DAN WANG  Feng L  Wuxun Lu. Pharmacological intervention of HIV-1 maturation[J]. Acta Pharmaceutica Sinica. B, 2015, 5 6: Pages 493-499. DOI: 10.1016/j.apsb.2015.05.004
[3] F LI. PA-457: a potent HIV inhibitor that disrupts core condensation by targeting a late step in Gag processing.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2003, 100 23: 13555-13560. DOI: 10.1073/pnas.2234683100
[4] CHERYL A STODDART. Potent activity of the HIV-1 maturation inhibitor bevirimat in SCID-hu Thy/Liv mice.[J]. PLoS ONE, 2007: e1251. DOI: 10.1371/journal.pone.0001251

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