Brecanavir

Brecanavir (INN; codenamed GW640385) is a protease inhibitor which has been studied for the treatment of HIV.[1]

Brecanavir
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • [(3R,3aS,6aR)-2,3,3a,4,5,6a-Hexahydrofuro[5,4-b]furan-3-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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC33H41N3O10S2
Molar mass703.82 g·mol−1
3D model (JSmol)
SMILES
  • O=S(=O)(c2ccc1OCOc1c2)N(CC(C)C)C[C@@H](O)[C@@H](NC(=O)O[C@@H]3[C@@H]4CCO[C@@H]4OC3)Cc6ccc(OCc5nc(sc5)C)cc6
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 Y
  • Key:JORVRJNILJXMMG-OLNQLETPSA-N Y
 NY (what is this?)  (verify)

In December 2006, its developer, GlaxoSmithKline discontinued further development because of insurmountable issues regarding formulation.[2]

See also

References
  1. Hazen R, Harvey R, Ferris R, et al. (September 2007). "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. 51 (9): 3147–54. doi:10.1128/AAC.00401-07. PMC 2043237. PMID 17620375.
  2. "GlaxoSmithKline discontinues clinical development of investigational protease inhibitor brecanavir (640385)" (Press release). GlaxoSmithKline. 2006-12-18. Archived from the original on 2008-12-03. Retrieved 2008-06-11.


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