Atazanavir (CHEM019923)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:37:58 UTC
Update Date2016-11-09 01:16:06 UTC
Accession NumberCHEM019923
Identification
Common NameAtazanavir
ClassSmall Molecule
DescriptionAtazanavir (formerly known as BMS-232632) is an antiretroviral drug of the protease inhibitor (PI) class. Like other antiretrovirals, it is used to treat infection of human immunodeficiency virus (HIV). Atazanavir is distinguished from other PIs in that it can be given once-daily (rather than requiring multiple doses per day) and has lesser effects on the patient's lipid profile (the amounts of cholesterol and other fatty substances in the blood). Like other protease inhibitors, it is used only in combination with other HIV medications. The U.S. Food and Drug Administration (FDA) approved atazanavir on June 20, 2003.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AtazanavirumChEBI
ATZChEBI
LatazanavirChEBI
ZrivadaChEBI
ReyatazKegg
Atazanavir sulfateHMDB
Atazanavir sulphateHMDB
ATVHMDB
BMS-232632HMDB
Sulfate, atazanavirHMDB
3,12-Bis(1,1-dimethylethyl)-8-hydroxy-4,11-dioxo-9-(phenylmethyl)-6-((4-(2-pyridinyl)phenyl)methyl)-2,5,6,10,13-pentaazatetradecanedioic acid dimethyl esterHMDB
Chemical FormulaC38H52N6O7
Average Molecular Mass704.856 g/mol
Monoisotopic Mass704.390 g/mol
CAS Registry Number198904-31-3
IUPAC Namemethyl N-[(1S)-1-{[(2S,3S)-3-hydroxy-4-[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-N'-{[4-(pyridin-2-yl)phenyl]methyl}butanehydrazido]-1-phenylbutan-2-yl]carbamoyl}-2,2-dimethylpropyl]carbamate
Traditional Nameatazanavir
SMILESCOC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C=C1)C1=CC=CC=N1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C(C)(C)C
InChI IdentifierInChI=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 KeyAXRYRYVKAWYZBR-GASGPIRDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Alpha-amino acid amide
  • 2-phenylpyridine
  • Phenylbutylamine
  • Amphetamine or derivatives
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Pyridine
  • Methylcarbamate
  • Heteroaromatic compound
  • Carbamic acid ester
  • Carboxamide group
  • Carboxylic acid hydrazide
  • Carbonic acid derivative
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP4.08ALOGPS
logP4.54ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)11.92ChemAxon
pKa (Strongest Basic)4.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area171.22 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity191.8 m³·mol⁻¹ChemAxon
Polarizability76.83 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xs-5617198000-83a5e695710baf354772Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0900000000-a688edc7c86f0564ba20Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014r-0905010000-c909027e64ed0c6bc4d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4i-0000000900-0bb22caf4b863566bd9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-052r-0400109000-e7d7d8600202d4603b49Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0903000000-3b9b3a8adea9bb1eb957Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-0901000000-53416755c850b58d778cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-052r-0309021800-ea619882f4fe2c00b481Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-12fe8f22e3abb6fcc9beSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-0901000000-cebaefef46a60a79f326Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000900-2176c78cd40b45df512aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000900-bc7d9bee134e63ae6552Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-f123f82b3d344e90c694Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-052r-0309021800-9b965caf0be7610147e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014r-0905010000-b690776ff28fe5c6f7aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a4i-0900000000-2745c98fc68f31b0aaa1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-7e1de2ac8606722b93f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-059i-0400009000-c82421a6236ad955ce10Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-54848dbe98136e86d7e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0900103000-7e2d2a1d46db762c8c86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053i-0201059200-b81c365212b43bb09c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-1701398000-2f76a00f3c27929b553cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6903120000-8304658487ac35e7437bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kmu-1102009200-ca81976dd8359c5e3a13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abl-1403129000-594995355b56a2f05946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7903112000-64d9d4a7da4cc1e44326Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01072
HMDB IDHMDB0015205
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAtazanavir
Chemspider ID130642
ChEBI ID37924
PubChem Compound ID148192
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47.
2. Le Tiec C, Barrail A, Goujard C, Taburet AM: Clinical pharmacokinetics and summary of efficacy and tolerability of atazanavir. Clin Pharmacokinet. 2005;44(10):1035-50.
3. Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36.
4. von Hentig N: Atazanavir/ritonavir: a review of its use in HIV therapy. Drugs Today (Barc). 2008 Feb;44(2):103-32. doi: 10.1358/dot.2008.44.2.1137107.
5. Croom KF, Dhillon S, Keam SJ: Atazanavir: a review of its use in the management of HIV-1 infection. Drugs. 2009 May 29;69(8):1107-40. doi: 10.2165/00003495-200969080-00009.
6. Lopez-Cortes LF: [Pharmacology, pharmacokinetic features and interactions of atazanavir]. Enferm Infecc Microbiol Clin. 2008 Dec;26 Suppl 17:2-8. doi: 10.1016/S0213-005X(08)76613-8.
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15156449
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15353575
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15645003
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15737947
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17376023
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17619250
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18389089
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24108452
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24314017
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682