Bevirimat
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Basic information
- CAS
174022-42-5- Standard SMILES
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)CC(C)(C)C(=O)O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12- InChIKey
YJEJKUQEXFSVCJ-WRFMNRASSA-N- Molecular formula
- C36H56O6
- Average molar mass
- 584.8 g/mol
- Monoisotopic mass
- 584.4076895
Names & identifiers
- Preferred name
- Bevirimat
- IUPAC
- (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
- English name
- Bevirimat
- Molecular formula
- C36H56O6
- Molecular weight
- 584.83
Names & synonyms
Bevirimat174022-42-5PA-457YK-FH312bevirimatumS125DW66N83-O-(3',3'-Dimethylsuccinyl)betulinic acid3-O-(3',3'-dimethylsuccinyl) betulinic acidPA-103001CHEBI:65484DTXSID20169749(3beta)-3-[(3-carboxy-3-methylbutanoyl)oxy]lup-20(29)-en-28-oic acid
Show more names
BVMCS-1322FH 11327MPC-4326Bevirimat, >99%Bevirimat(PA-457)BVMMPC-4326Bevirimat 174022-42-5
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid(3beta)-3-((3-carboxy-3-methylbutanoyl)oxy)lup-20(29)-en-28-oic aciddsb-2nmgMPC4326(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(3-carboxy-3-methylbutanoyl)oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta(a)chrysene-3a-carboxylic acidRefChem:119575DTXCID5092240YK-FH 312
Database identifiers
Properties
Computed structural propertiesFilling in
- XLogP
- 9.1
- Topological polar surface area
- 101 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 1,170
Physicochemical properties
- Melting point
- 263 °C · >263°C (dec.)
- Boiling point
- 662.7 · 662.7±40.0 °C(Predicted)
- Density
- 1.13 · 1.13±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- Acetonitrile (Slightly), Methanol (Very Slightly, Heated, Sonicated)
- pka
- 4.48 · 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
- FDA UNII
- 125 DW66N8 · S125DW66N8
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
- WGK Germany
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Mechanism of Action
Bevirimat has a novel mechanism of action, specifically inhibiting cleavage of spacer peptide 1 (SP1) from the C-terminus of capsid which results in defective core condensation. Specifically, bevirimat binds at the SP1/capsid junction, preventing cleavage by HIV protease.
Biological Half-Life56.3 to 69.5 hours
Metabolism/MetabolitesHepatic glucuronidation (UGT1A3-mediated)
Applications
DescriptionPA-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.
UsesBevirimat is a HIV-1 maturation inhibitor, targetting the Gag CA-SP1 cleavage site. HIV Inhibitor.
Additional notes
DefinitionChEBI: 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.
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Compound notes
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