Details of the Drug

General Information of Drug (ID: DMRVH2S)

Drug Name

BRECANAVIR

Synonyms

Brecanavir; 313682-08-5; UNII-E367I8C7FI; GW64085X; GW640385; E367I8C7FI; CHEMBL206031; VX-385; GW0385; (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL [(1S,2R)-3-[(1,3-BENZODIOXOL-5-YLSULFONYL)(ISOBUTYL)AMINO]-2-HYDROXY-1-{4-[(2-METHYL-1,3-THIAZOL-4-YL)METHOXY]BENZYL}PROPYL]CARBAMATE; [3H]GW0385; Brecanavir [USAN:INN]; Proteinase inhibitor 640385; 2fde; 2fdd; Brecanavir (USAN); GSK 640385; GW 0385; AC1NX470; SCHEMBL1533991; BDBM4685; DTXSID10185296; JORVRJNILJXMMG-OLNQLETPSA-N; ZINC3994828; VX 385; AKOS005145761; DB04887; D03253

Indication

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

Human Immunodeficiency Virus

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

703.8

Logarithm of the Partition Coefficient (xlogp)

4.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C33H41N3O10S2
IUPAC Name: [(3aS,4R,6aR)-2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl] N-[(2S,3R)-4-[1,3-benzodioxol-5-ylsulfonyl(2-methylpropyl)amino]-3-hydroxy-1-[4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl]butan-2-yl]carbamate
Canonical SMILES: CC1=NC(=CS1)COC2=CC=C(C=C2)C[C@@H]([C@@H](CN(CC(C)C)S(=O)(=O)C3=CC4=C(C=C3)OCO4)O)NC(=O)O[C@H]5CO[C@@H]6[C@H]5CCO6
InChI: InChI=1S/C33H41N3O10S2/c1-20(2)14-36(48(39,40)25-8-9-29-30(13-25)45-19-44-29)15-28(37)27(35-33(38)46-31-17-43-32-26(31)10-11-41-32)12-22-4-6-24(7-5-22)42-16-23-18-47-21(3)34-23/h4-9,13,18,20,26-28,31-32,37H,10-12,14-17,19H2,1-3H3,(H,35,38)/t26-,27-,28+,31-,32+/m0/s1
InChIKey: JORVRJNILJXMMG-OLNQLETPSA-N

Cross-matching ID

PubChem CID: 5743186
CAS Number: 313682-08-5
UNII: E367I8C7FI
DrugBank ID: DB04887
TTD ID: D07FJM
VARIDT ID: DR00812

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Human immunodeficiency virus Protease (HIV PR)	TT5FNQT	POL_HV1B1	Modulator	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800016864)
2	Safety and pharmacokinetics of brecanavir, a novel human immunodeficiency virus type 1 protease inhibitor, following repeat administration with and without ritonavir in healthy adult subjects.Antimicrob Agents Chemother.2007 Apr;51(4):1202-8.