atazanavir   Click here for help

GtoPdb Ligand ID: 11138

Abbreviated name: ATV
Synonyms: BMS-232632 | CGP 73547 | latazanavir | Reyataz® | zrivada
Approved drug PDB Ligand
atazanavir is an approved drug (FDA (2003), EMA (2004))
Compound class: Synthetic organic
Comment: Atazanavir is a human immunodeficiency virus 1 (HIV-1) protease inhibitor (PI) [1].
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View more information in the IUPHAR Pharmacology Education Project: atazanavir

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 22
Topological polar surface area 171.22
Molecular weight 704.39
XLogP 4.55
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COC(=O)N[C@@H](C(C)(C)C)C(=O)NN(Cc1ccc(cc1)c1ccccn1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O
Isomeric SMILES COC(=O)N[C@@H](C(C)(C)C)C(=O)NN(Cc1ccc(cc1)c1ccccn1)C[C@@H]([C@H](Cc1ccccc1)NC(=O)[C@H](C(C)(C)C)NC(=O)OC)O
InChI InChI=1S/C38H52N6O7/c1-37(2,3)31(41-35(48)50-7)33(46)40-29(22-25-14-10-9-11-15-25)30(45)24-44(43-34(47)32(38(4,5)6)42-36(49)51-8)23-26-17-19-27(20-18-26)28-16-12-13-21-39-28/h9-21,29-32,45H,22-24H2,1-8H3,(H,40,46)(H,41,48)(H,42,49)(H,43,47)/t29-,30-,31+,32+/m0/s1
InChI Key AXRYRYVKAWYZBR-GASGPIRDSA-N
References
1. Bold G, Fässler A, Capraro HG, Cozens R, Klimkait T, Lazdins J, Mestan J, Poncioni B, Rösel J, Stover D et al.. (1998)
New aza-dipeptide analogues as potent and orally absorbed HIV-1 protease inhibitors: candidates for clinical development.
J. Med. Chem., 41 (18): 3387-401. [PMID:9719591]