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]
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) 15
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 13
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
ChEBI ID
CHEMBL206031
CAS Number
313682-08-5
UNII
E367I8C7FI
DrugBank ID
DB04887
TTD ID
D07FJM
VARIDT ID
DR00812
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]
Molecular Interaction Atlas (MIA) 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.