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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H41N3O10S2
Molecular Weight 703.823
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BRECANAVIR

SMILES

[H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](CC3=CC=C(OCC4=CSC(C)=N4)C=C3)[C@H](O)CN(CC(C)C)S(=O)(=O)C5=CC=C6OCOC6=C5

InChI

InChIKey=JORVRJNILJXMMG-OLNQLETPSA-N
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

HIDE SMILES / InChI

Molecular Formula C33H41N3O10S2
Molecular Weight 703.823
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Brecanavir (previously known as VX-385), a HIV aspartyl protease inhibitor was developed for the treatment of HIV. The inhibition of HIV viral proteinase enzyme prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles. Brecanavir reached Phase II development. However, GlaxoSmithKline announced to discontinue development brecanavir. Because of the inability to develop a viable oral dosage formulation capable of delivering the desired brecanavir levels in patients with multi-drug resistant HIV.

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of wild-type and mutant human immunodeficiency virus type 1 proteases by GW0385 and other arylsulfonamides.
2004 Nov 16
Ultra-potent P1 modified arylsulfonamide HIV protease inhibitors: the discovery of GW0385.
2006 Apr 1
In vitro development of resistance to human immunodeficiency virus protease inhibitor GW640385.
2006 Mar
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.
2007 Apr
Preliminary safety and efficacy data of brecanavir, a novel HIV-1 protease inhibitor: 24 week data from study HPR10006.
2007 Jul
In vitro antiviral activity of the novel, tyrosyl-based human immunodeficiency virus (HIV) type 1 protease inhibitor brecanavir (GW640385) in combination with other antiretrovirals and against a panel of protease inhibitor-resistant HIV.
2007 Sep
Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization.
2007 Sep 28
Recent developments of peptidomimetic HIV-1 protease inhibitors.
2011
GS-8374, a prototype phosphonate-containing inhibitor of HIV-1 protease, effectively inhibits protease mutants with amino acid insertions.
2014 Mar

Sample Use Guides

In part 1 of the study, single oral doses of Brecanavir (BCV) ranged from 25 mg to 800 mg. In part 2, single oral doses of BCV ranged from 10 mg to 300 mg and were coadministered with 100-mg oral ritonavir (RTV) soft gel capsules. Single doses of BCV and BCV/RTV were generally well tolerated. There were no severe adverse events (SAEs), and no subject was withdrawn due to BCV.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:08:48 UTC 2023
Edited
by admin
on Fri Dec 15 16:08:48 UTC 2023
Record UNII
E367I8C7FI
Record Status Validated (UNII)
Record Version
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Name Type Language
BRECANAVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
GW64085X
Code English
BRECANAVIR [USAN]
Common Name English
GW-640385
Code English
GW-640385X
Code English
GW640385
Code English
Brecanavir [WHO-DD]
Common Name English
brecanavir [INN]
Common Name English
(3R,3AS,6AR)-HEXAHYDROFURO(2,3-B)FURAN-3-YL((1S,2R)-3-((1,3,BENZODIOXOL-5-YLSULFONYL)2-METHYLPROPYL)AMINO)-2-HYDROXY-1-(4-((2-METHYLTHIOZOL-5-YL)METHOXY)BENZYL)PROPYL)CARBAMATE
Common Name English
CARBAMIC ACID, ((1S,2R)-3-((1,3-BENZODIOXOL-5-YLSULFONYL)(2-METHYLPROPYL)AMINO)-2-HYDROXY-1-((4-((2-METHYL-4-THIAZOLYL)METHOXY)PHENYL)METHYL)PROPYL)-, (3R,3AS,6AR)-HEXAHYDROFURO(2,3-B)FURAN-3-YL ESTER
Common Name English
GW-64085X
Code English
Classification Tree Code System Code
NCI_THESAURUS C97366
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
Code System Code Type Description
CAS
313682-08-5
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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FDA UNII
E367I8C7FI
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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NCI_THESAURUS
C76908
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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MESH
C512121
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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ChEMBL
CHEMBL206031
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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USAN
RR-60
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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EVMPD
SUB33558
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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DRUG BANK
DB04887
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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SMS_ID
100000127502
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
PRIMARY
PUBCHEM
5743186
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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EPA CompTox
DTXSID10185296
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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INN
8705
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
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WIKIPEDIA
BRECANAVIR
Created by admin on Fri Dec 15 16:08:48 UTC 2023 , Edited by admin on Fri Dec 15 16:08:48 UTC 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY