Brecanavir

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Brecanavir

Systematic (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
Clinical data
Legal status	?
Identifiers
CAS number	313682-08-5^N
ATC code	None
PubChem	CID 5743186
ChemSpider	4675192^Y
UNII	E367I8C7FI^Y
ChEMBL	CHEMBL206031^Y
Chemical data
Formula	C₃₃H₄₁N₃O₁₀S₂
Mol. mass	703.82
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
N (what is this?) (verify)

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

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

References

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Entry/fusion inhibitors
(Discovery & development)

Nucleoside & nucleotide (NRTI)	Nucleoside analogues/NARTIs: Abacavir (ABC)°^# Emtricitabine (FTC)°^# Lamivudine (3TC)°^# Didanosine (ddI)^# Zidovudine (AZT)^# Apricitabine^† Stampidine^† Elvucitabine^† Racivir^† Amdoxovir^† Stavudine (d4T)^# Zalcitabine (ddC)^◊ Festinavir^† Nucleotide analogues/NtRTIs: Tenofovir disoproxil fumarate (TDF)°^# Tenofovir alafenamide fumarate (TAF)^†

Non-nucleoside (NNRTI) (Discovery & development)	(1st generation) Efavirenz (EFV)°^# Nevirapine (NVP)^# Loviride^◊ Delavirdine (DLV)^◊ (2nd generation) diarylpyrimidines (Etravirine Rilpivirine) Lersivirine^†

Protease Inhibitors (PI)
(Discovery and development)

1st generation	Fosamprenavir° Lopinavir°^# Nelfinavir^# Ritonavir^# Saquinavir^# Amprenavir^◊ Indinavir^◊^#

2nd generation	Atazanavir° Darunavir° Tipranavir

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)

Transcription inhibitors	Tat antagonists

Translation inhibitors	Trichosanthin

Other	Abzyme Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Griffithsin Hydroxycarbamide Miltefosine Portmanteau inhibitors Seliciclib^† Synergistic enhancers Tre recombinase Zinc finger protein transcription factor KP-1461^† Cobicistat^†

Failed agents	Dexelvucitabine Capravirine Emivirine Lodenosine Atevirdine Brecanavir Aplaviroc

°DHHS preferred first-line agent. ^◊Formerly or rarely used agent.

virs(prot)/clss

cutn/syst (hppv/hiva, infl/zost/zoon)/epon

drug (dnaa, rnaa, rtva, vacc)

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