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].
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: atazanavir

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2003), EMA (2004))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
methyl N-[(2S)-1-[[(2S,3S)-3-hydroxy-4-[[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-[(4-pyridin-2-ylphenyl)methyl]amino]-1-phenylbutan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
International Nonproprietary Names Click here for help
INN number INN
8181 atazanavir
Synonyms Click here for help
BMS-232632 | CGP 73547 | latazanavir | Reyataz® | zrivada
Database Links Click here for help
CAS Registry No. 198904-31-3 (source: Scifinder)
ChEBI CHEBI:37924
ChEMBL Ligand CHEMBL1163
DrugCentral Ligand 254
GtoPdb PubChem SID 434122198
PubChem CID 148192
RCSB PDB Ligand DR7
Search Google for chemical match using the InChIKey AXRYRYVKAWYZBR-GASGPIRDSA-N
Search Google for chemicals with the same backbone AXRYRYVKAWYZBR
Search PubMed clinical trials atazanavir
Search PubMed titles atazanavir
Search PubMed titles/abstracts atazanavir
UniChem Compound Search for chemical match using the InChIKey AXRYRYVKAWYZBR-GASGPIRDSA-N
UniChem Connectivity Search for chemical match using the InChIKey AXRYRYVKAWYZBR-GASGPIRDSA-N
Wikipedia Atazanavir