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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:54 UTC
HMDB IDHMDB0015205
Secondary Accession Numbers
  • HMDB15205
Metabolite Identification
Common NameAtazanavir
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. [Wikipedia ]
Structure
Data?1582753270
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 Weight704.8555
Monoisotopic Molecular Weight704.389748048
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
CAS Registry Number198904-31-3
SMILES
COC(=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 Identifier
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 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0033 g/LNot Available
LogP4.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+254.84930932474
DeepCCS[M-H]-253.05630932474
DeepCCS[M-2H]-287.08930932474
DeepCCS[M+Na]+261.05230932474
AllCCS[M+H]+268.832859911
AllCCS[M+H-H2O]+268.132859911
AllCCS[M+NH4]+269.432859911
AllCCS[M+Na]+269.632859911
AllCCS[M-H]-266.932859911
AllCCS[M+Na-2H]-270.932859911
AllCCS[M+HCOO]-275.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AtazanavirCOC(=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)C5569.8Standard polar33892256
AtazanavirCOC(=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)C3664.8Standard non polar33892256
AtazanavirCOC(=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)C5051.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Atazanavir,2TMS,isomer #1COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)C(C)(C)C4814.7Semi standard non polar33892256
Atazanavir,2TMS,isomer #1COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)C(C)(C)C4367.1Standard non polar33892256
Atazanavir,2TMS,isomer #1COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)C(C)(C)C6420.2Standard polar33892256
Atazanavir,2TMS,isomer #10COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4793.2Semi standard non polar33892256
Atazanavir,2TMS,isomer #10COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4528.6Standard non polar33892256
Atazanavir,2TMS,isomer #10COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C6514.0Standard polar33892256
Atazanavir,2TMS,isomer #2COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4846.6Semi standard non polar33892256
Atazanavir,2TMS,isomer #2COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4377.1Standard non polar33892256
Atazanavir,2TMS,isomer #2COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)C(C)(C)C6495.9Standard polar33892256
Atazanavir,2TMS,isomer #3COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C)(C)C4828.8Semi standard non polar33892256
Atazanavir,2TMS,isomer #3COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C)(C)C4457.1Standard non polar33892256
Atazanavir,2TMS,isomer #3COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C(C)(C)C6534.5Standard polar33892256
Atazanavir,2TMS,isomer #4COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)O[Si](C)(C)C)C(C)(C)C4803.3Semi standard non polar33892256
Atazanavir,2TMS,isomer #4COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)O[Si](C)(C)C)C(C)(C)C4370.5Standard non polar33892256
Atazanavir,2TMS,isomer #4COC(=O)N[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@H](CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)O[Si](C)(C)C)C(C)(C)C6421.8Standard polar33892256
Atazanavir,2TMS,isomer #5COC(=O)N([C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)C(C)(C)C)[Si](C)(C)C4788.9Semi standard non polar33892256
Atazanavir,2TMS,isomer #5COC(=O)N([C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)C(C)(C)C)[Si](C)(C)C4444.8Standard non polar33892256
Atazanavir,2TMS,isomer #5COC(=O)N([C@H](C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)C(C)(C)C)[Si](C)(C)C6398.5Standard polar33892256
Atazanavir,2TMS,isomer #6COC(=O)N[C@H](C(=O)N(N(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4791.2Semi standard non polar33892256
Atazanavir,2TMS,isomer #6COC(=O)N[C@H](C(=O)N(N(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4536.5Standard non polar33892256
Atazanavir,2TMS,isomer #6COC(=O)N[C@H](C(=O)N(N(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C6506.5Standard polar33892256
Atazanavir,2TMS,isomer #7COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4762.5Semi standard non polar33892256
Atazanavir,2TMS,isomer #7COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4445.3Standard non polar33892256
Atazanavir,2TMS,isomer #7COC(=O)N[C@H](C(=O)NN(CC1=CC=C(C2=CC=CC=N2)C=C1)C[C@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C6476.1Standard polar33892256
Atazanavir,2TMS,isomer #8COC(=O)N[C@H](C(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4759.1Semi standard non polar33892256
Atazanavir,2TMS,isomer #8COC(=O)N[C@H](C(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C4451.2Standard non polar33892256
Atazanavir,2TMS,isomer #8COC(=O)N[C@H](C(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)NC(=O)[C@@H](N(C(=O)OC)[Si](C)(C)C)C(C)(C)C)[Si](C)(C)C)C(C)(C)C6463.2Standard polar33892256
Atazanavir,2TMS,isomer #9COC(=O)N[C@H](C(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(C)(C)C4796.9Semi standard non polar33892256
Atazanavir,2TMS,isomer #9COC(=O)N[C@H](C(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(C)(C)C4544.3Standard non polar33892256
Atazanavir,2TMS,isomer #9COC(=O)N[C@H](C(=O)N([C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC1=CC=C(C2=CC=CC=N2)C=C1)N(C(=O)[C@@H](NC(=O)OC)C(C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C(C)(C)C6565.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xs-5617198000-83a5e695710baf3547722017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Atazanavir GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 30V, Negative-QTOFsplash10-0a4i-0900000000-a688edc7c86f0564ba202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 40V, Positive-QTOFsplash10-014r-0905010000-c909027e64ed0c6bc4d82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 15V, Positive-QTOFsplash10-0a4i-0000000900-0bb22caf4b863566bd9c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 15V, Negative-QTOFsplash10-052r-0400109000-e7d7d8600202d4603b492021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 30V, Positive-QTOFsplash10-014i-0903000000-3b9b3a8adea9bb1eb9572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 50V, Positive-QTOFsplash10-014i-0901000000-53416755c850b58d778c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 30V, Positive-QTOFsplash10-052r-0309021800-ea619882f4fe2c00b4812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 10V, Positive-QTOFsplash10-0a4i-0000000900-12fe8f22e3abb6fcc9be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 50V, Positive-QTOFsplash10-014i-0901000000-cebaefef46a60a79f3262021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 20V, Positive-QTOFsplash10-0a4i-0000000900-2176c78cd40b45df512a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 20V, Positive-QTOFsplash10-0a4i-0000000900-bc7d9bee134e63ae65522021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 10V, Positive-QTOFsplash10-0a4i-0000000900-f123f82b3d344e90c6942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 30V, Positive-QTOFsplash10-052r-0309021800-9b965caf0be7610147e52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 40V, Positive-QTOFsplash10-014r-0905010000-b690776ff28fe5c6f7ae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 50V, Negative-QTOFsplash10-0a4i-0900000000-2745c98fc68f31b0aaa12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 10V, Negative-QTOFsplash10-0udi-0000000900-7e1de2ac8606722b93f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 20V, Negative-QTOFsplash10-059i-0400009000-c82421a6236ad955ce102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 40V, Negative-QTOFsplash10-0a4i-0900000000-54848dbe98136e86d7e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Atazanavir 30V, Negative-QTOFsplash10-0a4i-0900103000-7e2d2a1d46db762c8c862021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atazanavir 10V, Positive-QTOFsplash10-053i-0201059200-b81c365212b43bb09c942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atazanavir 20V, Positive-QTOFsplash10-000x-1701398000-2f76a00f3c27929b553c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atazanavir 40V, Positive-QTOFsplash10-0006-6903120000-8304658487ac35e7437b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atazanavir 10V, Negative-QTOFsplash10-0kmu-1102009200-ca81976dd8359c5e3a132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atazanavir 20V, Negative-QTOFsplash10-0abl-1403129000-594995355b56a2f059462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Atazanavir 40V, Negative-QTOFsplash10-0a4i-7903112000-64d9d4a7da4cc1e443262016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01072 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01072 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01072
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID130642
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAtazanavir
METLIN IDNot Available
PubChem Compound148192
PDB IDNot Available
ChEBI ID37924
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16176117 ]
  2. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]
  3. Swainston Harrison T, Scott LJ: Atazanavir: a review of its use in the management of HIV infection. Drugs. 2005;65(16):2309-36. [PubMed:16266202 ]
  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. [PubMed:18389089 ]
  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. [PubMed:19496633 ]
  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. [PubMed:20116610 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. 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. [PubMed:16176117 ]
  2. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Busti AJ, Hall RG, Margolis DM: Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47. [PubMed:15585441 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5
References
  1. Janneh O, Anwar T, Jungbauer C, Kopp S, Khoo SH, Back DJ, Chiba P: P-glycoprotein, multidrug resistance-associated proteins and human organic anion transporting polypeptide influence the intracellular accumulation of atazanavir. Antivir Ther. 2009;14(7):965-74. doi: 10.3851/IMP1399. [PubMed:19918100 ]
  2. Lucia MB, Golotta C, Rutella S, Rastrelli E, Savarino A, Cauda R: Atazanavir inhibits P-glycoprotein and multidrug resistance-associated protein efflux activity. J Acquir Immune Defic Syndr. 2005 Aug 15;39(5):635-7. [PubMed:16044020 ]
General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Perloff ES, Duan SX, Skolnik PR, Greenblatt DJ, von Moltke LL: Atazanavir: effects on P-glycoprotein transport and CYP3A metabolism in vitro. Drug Metab Dispos. 2005 Jun;33(6):764-70. Epub 2005 Mar 11. [PubMed:15764714 ]
  2. Lucia MB, Golotta C, Rutella S, Rastrelli E, Savarino A, Cauda R: Atazanavir inhibits P-glycoprotein and multidrug resistance-associated protein efflux activity. J Acquir Immune Defic Syndr. 2005 Aug 15;39(5):635-7. [PubMed:16044020 ]
  3. Chinn LW, Gow JM, Tse MM, Becker SL, Kroetz DL: Interindividual variability in the effect of atazanavir and saquinavir on the expression of lymphocyte P-glycoprotein. J Antimicrob Chemother. 2007 Jul;60(1):61-7. Epub 2007 May 17. [PubMed:17510066 ]
  4. Wood R: Atazanavir: its role in HIV treatment. Expert Rev Anti Infect Ther. 2008 Dec;6(6):785-96. doi: 10.1586/14787210.6.6.785. [PubMed:19053892 ]
  5. Janneh O, Anwar T, Jungbauer C, Kopp S, Khoo SH, Back DJ, Chiba P: P-glycoprotein, multidrug resistance-associated proteins and human organic anion transporting polypeptide influence the intracellular accumulation of atazanavir. Antivir Ther. 2009;14(7):965-74. doi: 10.3851/IMP1399. [PubMed:19918100 ]
  6. Storch CH, Theile D, Lindenmaier H, Haefeli WE, Weiss J: Comparison of the inhibitory activity of anti-HIV drugs on P-glycoprotein. Biochem Pharmacol. 2007 May 15;73(10):1573-81. Epub 2007 Jan 24. [PubMed:17328866 ]