Atazanavir (CED0003110)

Record Information
Version1.0
Creation Date2016-05-22 06:37:58 UTC
Update Date2026-08-22 12:10:03 UTC
Accession NumberCHEM019923
Identification
Common NameAtazanavir
ClassSmall Molecule
Description
Atazanavir belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 704.86 g/mol, Atazanavir is a heavy molecule. It has the chemical formula C38H52N6O7. Biologically, it serves as a protease inhibitor (PMC8533436). Its protein targets include acting as a modulator and causing the inhibition of synthesis of Pol polyprotein and Gag-Pol polyprotein (gag-pol). The compound is found in or released from seven recorded sources, including healthcare, pharmaceuticals & veterinary products (antivirals), food, food processing & cookware (processing meats), household cleaning & consumer products (non electric simulated smoking devices), and electrical & electronic equipment such as magnets, relays, television systems, and video games. The recorded route of exposure for this compound is oral.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03xs-5617198000-83a5e695710baf354772Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-a688edc7c86f0564ba20Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0905010000-c909027e64ed0c6bc4d8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000000900-0bb22caf4b863566bd9cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0400109000-e7d7d8600202d4603b49Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0903000000-3b9b3a8adea9bb1eb957Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0901000000-53416755c850b58d778cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0309021800-ea619882f4fe2c00b481Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000000900-12fe8f22e3abb6fcc9beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0901000000-cebaefef46a60a79f326Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000000900-2176c78cd40b45df512aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000000900-bc7d9bee134e63ae6552Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000000900-f123f82b3d344e90c694Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0309021800-9b965caf0be7610147e5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0905010000-b690776ff28fe5c6f7aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-2745c98fc68f31b0aaa1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0000000900-7e1de2ac8606722b93f7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-059i-0400009000-c82421a6236ad955ce10Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-54848dbe98136e86d7e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900103000-7e2d2a1d46db762c8c86Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-053i-0201059200-b81c365212b43bb09c94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-1701398000-2f76a00f3c27929b553cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-6903120000-8304658487ac35e7437bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kmu-1102009200-ca81976dd8359c5e3a13Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abl-1403129000-594995355b56a2f05946Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-7903112000-64d9d4a7da4cc1e44326Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-4401189800-5797711547d3647cc44eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1000191000-74910783b82bb236d6d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-054o-2028910000-1269652f7779ddb63cebNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-0300019100-73fbe3a4cc719c562df9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-5906571000-64ed60825e4281fd167fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-9411540000-c6d3542f4bc26c415d19Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
749.0Log mg/kg[420:1300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
351AntiviralsHealthcare, pharmaceuticals & veterinary productsNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Atazanavir Action Pathway
Atazanavir Action Pathway
Atazanavir Drug Metabolism Action Pathway
Atazanavir Drug Metabolism Action Pathway
Atazanavir Predicted Metabolism Pathway
Atazanavir Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureUDP-glucuronosyltransferase 1A1Q64550Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureUDP-glucuronosyltransferase 1A1P22309HumansPredicted (SEA)0.0778492
Click to view 3D structureProteaseQ9YQ12Human immunodeficiency virus 1Predicted (SEA)3.73676
Click to view 3D structurePol polyproteinQ72874Human immunodeficiency virus 1Predicted (SEA)3.42537
Cathepsin D structureClick to view 3D structureCathepsin DP07339HumansPredicted (SEA)12.1445
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)26.4687
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)219.846
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)206.768
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)159.98
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)104.863
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)116.54
Renin structureClick to view 3D structureReninP00797HumansPredicted (SEA)37.679
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)5.91654
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)18.2167
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)437.435
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)3.73676
Click to view 3D structureSolute carrier organic anion transporter family member 2B1O94956HumansPredicted (SEA)4.67095
Click to view 3D structurePepsin AP00791Sus scrofaPredicted (SEA)41.4936
Gamma-secretase subunit PEN-2 structureClick to view 3D structureGamma-secretase subunit PEN-2Q9NZ42HumansPredicted (SEA)45.3861
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)200.773
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)147.135
Cathepsin B structureClick to view 3D structureCathepsin BP07858HumansPredicted (SEA)221.17
Cathepsin S structureClick to view 3D structureCathepsin SP25774HumansPredicted (SEA)177.73
Plasmepsin II structureClick to view 3D structurePlasmepsin IIP46925Plasmodium falciparumPredicted (SEA)22.187
Gag-Pol polyprotein structureClick to view 3D structureGag-Pol polyproteinP03369HIV-1Predicted (SEA)19.2288
Concentrations
Not Available
External Links
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