Structure via PubChem · Public domain (PubChem)
bevirimat
Sign in to saveAlso known as PA-457, YK-FH312, 3-O-(3',3'-dimethylsuccinyl) betulinic acid, BVM, MPC-4326
Bevirimat (research code MPC-4326) is an anti-HIV drug derived from a betulinic acid-like compound, first isolated from Syzygium claviflorum, a Chinese herb. It is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition. It is not currently U.S. Food and Drug Administration (FDA) approved. It was originally developed by the pharmaceutical company Panacos and reached Phase IIb clinical trials. Myriad Genetics announced on January 21, 2009 the acquisition of all rights to bevirimat for $7M USD. On June 8, 2010 Myriad Genetics announced that it was abandoning their HIV portf
In the Vinony graph
Vinony's link graph records 129 inbound references to bevirimat, and connects out to tenofovir alafenamide, clinical trial and biological half-life.
It is catalogued under topics including Carboxylic acids, Chemical pages without DrugBank identifier and Cyclopentanes.
Vinony links it to 5 Wikipedia language editions.
Chemical data
- Formula
- C36H56O6
- Molecular weight
- 584.8 g/mol
- IUPAC name
- (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
- SMILES
- CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
- InChIKey
- YJEJKUQEXFSVCJ-WRFMNRASSA-N
- XLogP
- 9.1
- Polar surface area
- 101 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- HIV-1 infection, HIV infection
via ChEMBL · EBI
Wikidata facts
- Subclass of
- carboxylic acid
- Mass
- 584.40769
Show 4 more facts
- chemical formula
- C₃₆H₅₆O₆
- canonical SMILES
- CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
- isomeric SMILES
- CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)CC(C)(C)C(=O)O)C)C(=O)O
- World Health Organisation international non-proprietary name
- bevirimat
Sources (2)
via Wikidata · CC0
~8 min read
Encyclopedic overview
9 sectionsContents
- Pharmacokinetics
- Mechanism of action
- Metabolism
- Toxicity and side effects
- Resistance
- Clinical trials
- See also
- References
- External links
Bevirimat (research code MPC-4326) is an anti-HIV drug derived from a betulinic acid-like compound, first isolated from Syzygium claviflorum, a Chinese herb. It is believed to inhibit HIV by a novel mechanism, so-called maturation inhibition. It is not currently U.S. Food and Drug Administration (FDA) approved. It was originally developed by the pharmaceutical company Panacos and reached Phase IIb clinical trials. Myriad Genetics announced on January 21, 2009 the acquisition of all rights to bevirimat for $7M USD. On June 8, 2010 Myriad Genetics announced that it was abandoning their HIV portfolio to focus more on cancer drug development.
==Pharmacokinetics== According to the only currently available study, "the mean terminal elimination half-life of bevirimat ranged from 56.3 to 69.5 hours, and the mean clearance ranged from 173.9 to 185.8 mL/hour."
Excerpted from Wikipedia’s “bevirimat” article, available under the CC BY-SA 4.0 licence.