Details of the Drug

General Information of Drug (ID: DML2D8Q)

Drug Name

Bevirimat

Synonyms

DSB; Bevirimat dimeglumine; DSB 2NMG; MPC-4326; PA-457; PA-103001-01; PA-103001-04; PA-457 di-NMG; Viral maturation inhibitor (HIV), Myrexis; Viral maturation inhibitor (HIV), Myriad; Viral maturation inhibitor (HIV), Panacos; YK-FH-312; 3-O-(3' 3'-dimethylsuccinyl)-betulinic acid

Indication

Disease Entry	ICD 11	Status	REF
Human immunodeficiency virus infection	1C62	Phase 2	[1]

Affected Organisms

Human Immunodeficiency Virus

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

584.8

Logarithm of the Partition Coefficient (xlogp)

9.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 56.3 - 69.5 hours [2]
Metabolism: The drug is metabolized via the hepatic []

Chemical Identifiers

Formula: C36H56O6
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
Canonical 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
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
InChIKey: YJEJKUQEXFSVCJ-WRFMNRASSA-N

Cross-matching ID

PubChem CID: 457928
ChEBI ID: CHEMBL65484
CAS Number: 174022-42-5
UNII: S125DW66N8
DrugBank ID: DB06581
TTD ID: D04MPB
INTEDE ID: DR1856

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus GAG protein (HIV gag)	TTFGZB6	GAG_HV1H2	Inhibitor	[3]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 2B7 (UGT2B7)	DEB3CV1	UD2B7_HUMAN	Substrate	[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3)	DEF2WXN	UD13_HUMAN	Substrate	[4]
UDP-glucuronosyltransferase 1A4 (UGT1A4)	DELOY3P	UD14_HUMAN	Substrate	[4]

Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	ClinicalTrials.gov (NCT00967187) Safety and Efficacy Study of MPC-4326 for Treatment of Patients With HIV-1 Infection.. U.S. National Institutes of Health.
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	Synthesis and biological evaluation of a new derivative of bevirimat that targets the Gag CA-SP1 cleavage site. Eur J Med Chem. 2013 Apr;62:453-65.
4	Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13.