Tìm theo
Brecanavir
Các tên gọi khác (1) :
  • BCV
Thuốc Gốc
Small Molecule
CAS: 313682-08-5
CTHH: C33H41N3O10S2
PTK: 703.823
Brecanavir (VX-385) an orally active aspartic protease inhibitor (PI), under investigation by Vertex and GlaxoSmithKline for the treatment of HIV. In July 2006, Vertex indicated that it expected GSK to initiate phase III trials of the drug in 2007. In December of 2006 GSK announced a decision to discontinue the development of brecanavir for the treatment of HIV. The decision was based on issues regarding the formulation of the drug.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C33H41N3O10S2
Phân tử khối
703.823
Monoisotopic mass
703.223335927
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
InChIKey=JORVRJNILJXMMG-OLNQLETPSA-N
IUPAC Name
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-1-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}-4-[N-(2-methylpropyl)2H-1,3-benzodioxole-5-sulfonamido]butan-2-yl]carbamate
Traditional IUPAC Name
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-1-{4-[(2-methyl-1,3-thiazol-4-yl)methoxy]phenyl}-4-[N-(2-methylpropyl)2H-1,3-benzodioxole-5-sulfonamido]butan-2-yl]carbamate
SMILES
[H][C@]12OCC[C@@]1([H])[C@H](CO2)OC(=O)N[C@@H](CC1=CC=C(OCC2=CSC(C)=N2)C=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC2=C(OCO2)C=C1
Độ hòa tan
1.77e-02 g/l
logP
3.7
logS
-4.6
pKa (strongest acidic)
13.18
pKa (Strongest Basic)
2.6
PSA
154.98 Å2
Refractivity
173.61 m3·mol-1
Polarizability
73.3 Å3
Rotatable Bond Count
14
H Bond Acceptor Count
10
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
6
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Brecanavir is an orally active aspartic protease inhibitor (PI) under investigation by Vertex and GlaxoSmithKline for the treatment of HIV. Test-tube data suggest that it has activity against virus with resistance to the currently available protease inhibitors, and that it is more powerful against wild-type HIV that existing protease inhibitors, being active at concentrations much lower than most existing protease inhibitors. Unlike some other protease inhibitors, brecanavir does not have a significant interaction with the nucleotide reverse transcriptase inhibitor (NtRTI) tenofovir (Viread). In December of 2006 GlaxoSmithKline announced their decision to discontinue the development of brecanavir for the treatment of HIV. The decision was based on issues regarding the formulation of the drug.
Cơ Chế Tác Dụng : Brecanavir (VX-385) an orally active aspartic protease inhibitor (PI), under investigation by Vertex and GlaxoSmithKline for the treatment of HIV. In July 2006, Vertex indicated that it expected GSK to initiate phase III trials of the drug in 2007. In December of 2006 GSK announced a decision to discontinue the development of brecanavir for the treatment of HIV. The decision was based on issues regarding the formulation of the drug. Brecanavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
Dược Động Học :
▧ Absorption :
Brecanavir, a CYP3A4 substrate, demonstrated low oral bioavailability in animals (0 to 30%), which increased to 60 to 100% following coadministration with oral ritonavir (a potent CYP3A inhibitor).
▧ Protein binding :
Estimated be 97 to 98%
▧ Metabolism :
Brecanavir is a known substrate of CYP450 3A4, the most important cytochrome P450 isoenzyme involved in metabolizing PIs and non-nucleoside reverse transcriptase inhibitors.
Chỉ Định : For the treatment of HIV-1 infection in combination with other antiretroviral agents.
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB04887
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5743186
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=10318428
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D03253
ChemSpider
http://www.chemspider.com/Chemical-Structure.4675192.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=4685
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