Brecanavir

Category	HIV Protease
CAS	313682-08-5
Description	Brecanavir is a tyrosyl-based arylsulfonamide, high-affinity, protease inhibitor (PI) for the treatment of human immunodeficiency virus type-1. This compound potently inhibited HIV-1 in cell culture assays with 50% effective concentrations (EC(50)s) of 0.2 to 0.53 nM and was equally active against HIV strains utilizing either the CXCR4 or CCR5 coreceptor, as was found with other PIs. Brecanavir had a <5-fold increase in EC(50)s against 80% of patient isolates tested and had a greater mean in vitro potency than amprenavir, indinavir, lopinavir, atazanavir, tipranavir, and darunavir.

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Product Information

Synonyms	Brecanavir; UNII-E367I8C7FI; CHEMBL206031; GW-0385; GW-640385; GW-640385X; VX-385; GW0385; GW640385; GW640385X; VX385; GW 0385; GW 640385; GW 640385X; VX 385; [(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;
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
Molecular Weight	703.82
Molecular Formula	C33H41N3O10S2
Canonical SMILES	CC1=NC(=CS1)COC2=CC=C(C=C2)CC(C(CN(CC(C)C)S(=O)(=O)C3=CC4=C(C=C3)OCO4)O)NC(=O)OC5COC6C5CCO6
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+/
InChIKey	JORVRJNILJXMMG-OLNQLETPSA-N
Purity	≥98%
Density	1.43g/cm3
Solubility	Soluble in DMSO
Appearance	Solid powder
Application	HIV-1 Protease inhibitor
Shelf Life	As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly.
Storage	Store at -20 °C
Complexity	1150
Exact Mass	703.22333686
Index Of Refraction	1.641
In Vitro	This compound potently inhibited HIV-1 in cell culture assays with 50% effective concentrations (EC(50)s) of 0.2 to 0.53 nM and was equally active against HIV strains utilizing either the CXCR4 or CCR5 coreceptor, as was found with other PIs. Brecanavir had a <5-fold increase in EC(50)s against 80% of patient isolates tested and had a greater mean in vitro potency than amprenavir, indinavir, lopinavir, atazanavir, tipranavir, and darunavir. Brecanavir is by a substantial margin the most potent and broadly active antiviral agent among the PIs tested in vitro.
PSA	191.60000
Target	HIV Protease
XLogP3-AA	4.4