Bevirimat

Bevirimat
Clinical data
Other namesPA-457; 3-O-(3',3'-dimethylsuccinyl)-betulinic acid
Routes of
administration		Oral
ATC code
  • none
Pharmacokinetic data
MetabolismHepatic glucuronidation (UGT1A3-mediated)
Elimination half-life56.3 to 69.5 hours
ExcretionFecal[1]
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.125.475 Edit this at Wikidata
Chemical and physical data
FormulaC36H56O6
Molar mass584.838 g·mol−1
3D model (JSmol)
  • 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
  • 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 checkY
  • Key:YJEJKUQEXFSVCJ-WRFMNRASSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[2] 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.[3] On June 8, 2010 Myriad Genetics announced that it was abandoning there HIV portfolio to focus more on cancer drug development.[4]

  1. ^ Bullock P, Larsen D, Press R, Wehrman T, Martin DE (July 2008). "The absorption, distribution, metabolism and elimination of bevirimat in rats". Biopharm Drug Dispos. 29 (7): 396–405. doi:10.1002/bdd.625. PMID 18615840. S2CID 2987764.
  2. ^ Smith PF, Ogundele A, Forrest A, Wilton J, Salzwedel K, Doto J, Allaway GP, Martin DE (October 2007). "Phase I and II study of the safety, virologic effect, and pharmacokinetics/pharmacodynamics of single-dose 3-o-(3',3'-dimethylsuccinyl)betulinic acid (bevirimat) against human immunodeficiency virus infection". Antimicrob. Agents Chemother. 51 (10): 3574–81. doi:10.1128/AAC.00152-07. PMC 2043264. PMID 17638699.
  3. ^ "Myriad Pharmaceuticals Acquires Novel HIV Drug, Bevirimat". Press release. Myriad Genetics, Inc. 2009-01-21. Archived from the original on 2009-08-02. Retrieved 2009-01-22.
  4. ^ "Myriad Pharmaceuticals Announces Intent to Focus on Oncology Portfolio" (PDF). Press Release. Myriad Genetics, Inc. 2010-06-08. Archived from the original (PDF) on 2016-01-22. Retrieved 2012-02-14.