Brecanavir
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MedKoo CAT#: 524534

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


Chemical Structure

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Brecanavir
CAS# 313682-08-5

Theoretical Analysis

MedKoo Cat#: 524534
Name: Brecanavir
CAS#: 313682-08-5
Chemical Formula: C33H41N3O10S2
Exact Mass: 703.22334
Molecular Weight: 703.82
Elemental Analysis: C, 56.31; H, 5.87; N, 5.97; O, 22.73; S, 9.11

Price and Availability

Size Price Availability Quantity
1.0mg USD 150.0 Ready to ship
5.0mg USD 550.0 Ready to ship
10.0mg USD 950.0 Ready to ship
25.0mg USD 1650.0 Ready to ship
50.0mg USD 2950.0 Ready to ship
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Synonym: Brecanavir; GW-0385; GW-0385; GW0385; GW-640385; GW 640385; GW640385; GW-640385X; VX-385; VX 385; VX385;

IUPAC/Chemical 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

InChi Key: JORVRJNILJXMMG-OLNQLETPSA-N

InChi Code: 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

SMILES Code: 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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: 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.

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

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 703.82 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Velthuisen EJ, Baughman TM, Johns BA, Temelkoff DP, Weatherhead JG. Synthesis and pharmacokinetic profile of highly deuterated brecanavir analogs. Eur J Med Chem. 2013 May;63:202-12. doi: 10.1016/j.ejmech.2013.02.001. Epub 2013 Feb 14. PubMed PMID: 23474906.

2: Gulnik SV, Eissenstat M. Approaches to the design of HIV protease inhibitors with improved resistance profiles. Curr Opin HIV AIDS. 2008 Nov;3(6):633-41. doi: 10.1097/COH.0b013e328313911d. PubMed PMID: 19373035.

3: Hazen R, Harvey R, Ferris R, Craig C, Yates P, Griffin P, Miller J, Kaldor I, Ray J, Samano V, Furfine E, Spaltenstein A, Hale M, Tung R, St Clair M, Hanlon M, Boone L. 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. Antimicrob Agents Chemother. 2007 Sep;51(9):3147-54. Epub 2007 Jul 9. PubMed PMID: 17620375; PubMed Central PMCID: PMC2043237.

4: Lalezari JP, Ward DJ, Tomkins SA, Garges HP. Preliminary safety and efficacy data of brecanavir, a novel HIV-1 protease inhibitor: 24 week data from study HPR10006. J Antimicrob Chemother. 2007 Jul;60(1):170-4. Epub 2007 May 8. PubMed PMID: 17491001.

5: Brecanavir's hopes dashed. AIDS Patient Care STDS. 2007 Feb;21(2):143. PubMed PMID: 17328663.

6: De Luca A. Resistance to newly approved and investigational protease inhibitors. Curr Opin HIV AIDS. 2007 Mar;2(2):130-6. doi: 10.1097/COH.0b013e3280287a38. PubMed PMID: 19372878.

7: Reddy YS, Ford SL, Anderson MT, Murray SC, Ng-Cashin J, Johnson MA. 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. Epub 2007 Jan 29. PubMed PMID: 17261626; PubMed Central PMCID: PMC1855506.

8: Drug interactions. Brecanavir--a new protease inhibitor. TreatmentUpdate. 2006 Jun-Jul;18(3):6-7. PubMed PMID: 17209240.

9: Ford SL, Reddy YS, Anderson MT, Murray SC, Fernandez P, Stein DS, Johnson MA. Single-dose safety and pharmacokinetics of brecanavir, a novel human immunodeficiency virus protease inhibitor. Antimicrob Agents Chemother. 2006 Jun;50(6):2201-6. PubMed PMID: 16723584; PubMed Central PMCID: PMC1479152.