Brecanavir

CAS

313682-08-5

Catalog Number

ACM313682085-1

Category

Inhibitors

Molecular Weight

703.82

Molecular Formula

C33H41N3O10S2

MSDS COA Spec Sheet

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Specification

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. Brecanavir is by a substantial margin the most potent and broadly active antiviral agent among the PIs tested in vitro.

Synonyms

Brecanavir; GW-0385; GW-0385; GW0385; GW-640385; GW 640385; GW640385; GW-640385X; VX-385; VX 385; VX385

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

Cc1nc(cs1)COc2ccc(cc2)C[C@@H]([C@@H](CN(CC(C)C)S(=O)(=O)c3ccc4c(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

InChI Key

JORVRJNILJXMMG-OLNQLETPSA-N

Solubility

Soluble in DMSO, not in water

Appearance

Solid powder

Shelf Life

>2 years if stored properly

Storage

Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).

Biological Target

Brecanavir (GW640385) is a novel, potent HIV protease inhibitor.

Drug Formulation

This drug may be formulated in DMSO

Elemental Analysis

C, 56.31; H, 5.87; N, 5.97; O, 22.73; S, 9.11

Exact Mass

703.22334

HS Tariff Code

2934.99.9001

In Vitro Activity

BCV (brecanavir) inhibited HIV-1 strain IIIB and the strain Ba-L, with subnanomolar activities of 0.2 and 0.42 nM, respectively. The
cell culture 50% inhibitory concentration values (CCIC50s) for BCV were determined with a small panel of uninfected B and T cells.
Reference: Antimicrob Agents Chemother. 2007 Sep;51(9):3147-54. https://pubmed.ncbi.nlm.nih.gov/17620375/

In Vivo Activity

TBD

Shipping

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Stock Solution Storage

0-4 °C for short term (days to weeks), or -20 °C for long term (months).