Bevirimat information

Bevirimat
Clinical data
Other names	PA-457; 3-O-(3',3'-dimethylsuccinyl)-betulinic acid
Routes of; administration	Oral
ATC code	none;
Pharmacokinetic data
Metabolism	Hepatic glucuronidation (UGT1A3-mediated)
Elimination half-life	56.3 to 69.5 hours
Excretion	Fecal
Identifiers
	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;
CAS Number	174022-42-5 ;
PubChem CID	457928;
ChemSpider	403003 ;
UNII	S125DW66N8;
ChEMBL	ChEMBL404519 ;
NIAID ChemDB	028530;
CompTox Dashboard (EPA)	DTXSID20169749 ;
ECHA InfoCard	100.125.475
Chemical and physical data
Formula	C36H56O6
Molar mass	584.838 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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 ; Key:YJEJKUQEXFSVCJ-WRFMNRASSA-N ;
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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 halting the development of maturation inhibitors, including bevirimat, to focus more on their oncology portfolio.^[4]

^ 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.
^ 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.
^ "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.
^ "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.

[pmid18615840-1] 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.

[pmid17638699-2] 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.

[url_Myriad_PR-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.

[urlfiles.shareholder.com-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.

Bevirimat information

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Clinical data

Other names	PA-457; 3-O-(3',3'-dimethylsuccinyl)-betulinic acid
Routes of administration	Oral
ATC code	none
Pharmacokinetic data
Metabolism	Hepatic glucuronidation (UGT1A3-mediated)
Elimination half-life	56.3 to 69.5 hours
Excretion	Fecal^[1]
Identifiers
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
CAS Number	174022-42-5^N
PubChem CID	457928
ChemSpider	403003^Y
UNII	S125DW66N8
ChEMBL	ChEMBL404519^Y
NIAID ChemDB	028530
CompTox Dashboard (EPA)	DTXSID20169749
ECHA InfoCard	100.125.475
Chemical and physical data
Formula	C₃₆H₅₆O₆
Molar mass	584.838 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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^Y Key:YJEJKUQEXFSVCJ-WRFMNRASSA-N^Y
^NY (what is this?) (verify)