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
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 524534
Name: Brecanavir
CAS#: 313682-08-5
Chemical Formula: C33H41N3O10S2
Exact Mass: 703.22
Molecular Weight: 703.820
Elemental Analysis: C, 56.31; H, 5.87; N, 5.97; O, 22.73; S, 9.11

Price and Availability

Size Price Availability Quantity
1mg USD 150 Ready to ship
5mg USD 550 Ready to ship
10mg USD 950 Ready to ship
25mg USD 1650 Ready to ship
50mg USD 2950 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

More Info:

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

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
Formulation protocol: 1. 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 inhibitorresistant HIV. Antimicrob Agents Chemother. 2007 Sep;51(9):3147-54. doi: 10.1128/AAC.00401-07. Epub 2007 Jul 9. PMID: 17620375; PMCID: PMC2043237.
In vitro protocol: 1. 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 inhibitorresistant HIV. Antimicrob Agents Chemother. 2007 Sep;51(9):3147-54. doi: 10.1128/AAC.00401-07. Epub 2007 Jul 9. PMID: 17620375; PMCID: PMC2043237.
In vivo protocol: TBD

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1: Brecanavir's hopes dashed. AIDS Patient Care STDS. 2007 Feb;21(2):143. doi: 10.1089/apc.2007.9997. PMID: 17328663.


2: 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. PMID: 23474906.


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. doi: 10.1128/AAC.00401-07. Epub 2007 Jul 9. PMID: 17620375; PMCID: PMC2043237.


4: 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. doi: 10.1128/AAC.01490-05. PMID: 16723584; PMCID: PMC1479152.


5: 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. doi: 10.1128/AAC.01005-06. Epub 2007 Jan 29. PMID: 17261626; PMCID: PMC1855506.


6: Mabkhot YN, Alharbi MM, Al-Showiman SS, Ghabbour HA, Kheder NA, Soliman SM, Frey W. Stereoselective synthesis, X-ray analysis, computational studies and biological evaluation of new thiazole derivatives as potential anticancer agents. Chem Cent J. 2018 May 11;12(1):56. doi: 10.1186/s13065-018-0420-7. PMID: 29748782; PMCID: PMC5945573.


7: 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. PMID: 19373035.


8: 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. doi: 10.1093/jac/dkm122. Epub 2007 May 8. PMID: 17491001.


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


10: 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. PMID: 19372878.