Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0150)
Drug Name
Atazanavir
Synonyms
Atazanavir; Atazanavir Base; Atazanavir [INN:BAN]; Latazanavir; QZU4H47A3S; Reyataz; Reyataz (TN); Zrivada; atazanavirum; (3S,8S,9S,12S)-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 ESTER; 198904-31-3; ATV; BMS 232632; BMS-232632; CGP 73547; CGP-73547; CHEBI:37924; CHEMBL1163; DR7; DSSTox_CID_28617; DSSTox_GSID_48691; DSSTox_RID_82887; HSDB 7339; NCGC00182552-01; UNII-QZU4H47A3S
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 704.9 Topological Polar Surface Area 171
Heavy Atom Count 51 Rotatable Bond Count 18
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
148192
PubChem SID
621982 ; 10249838 ; 14715932 ; 14766361 ; 14790731 ; 15047322 ; 17436380 ; 24276961 ; 46225140 ; 46393831 ; 46508504 ; 46512956 ; 49831615 ; 50067727 ; 50070909 ; 50780515 ; 51091799 ; 53801241 ; 57346722 ; 85177037 ; 85177040 ; 85177051 ; 85177056 ; 87225781 ; 92308998 ; 92729699 ; 99437162 ; 103338831 ; 104418454 ; 124757264 ; 124894049 ; 125164068 ; 125267482 ; 126649083 ; 126665840 ; 126731250 ; 127338999 ; 127339000 ; 127474087 ; 134337995 ; 134339780 ; 135105507 ; 135692446 ; 137004575 ; 142410398 ; 143496681 ; 144206632 ; 152234924 ; 152344127 ; 160647610
ChEBI ID
ChEBI:37924
CAS Number
198904-31-3
TTD Drug ID
D07IQS
Formula
C38H52N6O7
Canonical SMILES
CC(C)(C)C(C(=O)NC(CC1=CC=CC=C1)C(CN(CC2=CC=C(C=C2)C3=CC=CC=N3)NC(=O)C(C(C)(C)C)NC(=O)OC)O)NC(=O)OC
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
InChIKey
AXRYRYVKAWYZBR-GASGPIRDSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Atazanavir metabolite M1 DM001783
71474000
Unclear 1 [5]
Atazanavir metabolite M1 DM001783
71474000
Oxidation - Dealkylation 1 [5]
Atazanavir metabolite M13 DM001787
72710767
Hydrolysis - Hydrolysis 1 [5]
Atazanavir metabolite M14 DM001788 N. A. Hydrolysis - Hydrolysis 1 [5]
Atazanavir metabolite M15 DM001789 N. A. Unclear 1 [5]
Atazanavir metabolite M15' DM001790 N. A. Oxidation - Dealkylation 1 [5]
Atazanavir metabolite M2 DM001776 N. A. Oxidation - Monohydroxylation 1 [5]
Atazanavir metabolite M3 DM001784 N. A. Oxidation - Monohydroxylation 1 [5]
Atazanavir metabolite M4 DM001785 N. A. Oxidation - Monohydroxylation 1 [5]
Atazanavir metabolite M5 DM001786
118753152
Oxidation - Monohydroxylation 1 [5]
Atazanavir metabolite M10 DM001779 N. A. Oxidation - Dihydroxylation 2 [5]
Atazanavir metabolite M12 DM019975 N. A. Unclear 2 [5]
Atazanavir metabolite M16 DM019976 N. A. Unclear 2 [5]
Atazanavir metabolite M6 DM001781
118753151
Other reaction - Monodehydrogenation 2 [5]
Atazanavir metabolite M7 DM001782
72710762
Other reaction - Monodehydrogenation 2 [5]
Atazanavir metabolite M8 DM001777 N. A. Unclear 2 [5]
Atazanavir metabolite M11 DM001780 N. A. Unclear 3 [5]
Atazanavir metabolite M9 DM001778 N. A. Unclear 3 [5]
⏷ Show the Full List of 18  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003047 Atazanavir Atazanavir metabolite M2 Oxidation - Monohydroxylation Unclear [5]
MR003055 Atazanavir Atazanavir metabolite M1 Oxidation - Dealkylation Unclear [5]
MR003057 Atazanavir Atazanavir metabolite M3 Oxidation - Monohydroxylation Unclear [5]
MR003058 Atazanavir Atazanavir metabolite M4 Oxidation - Monohydroxylation Unclear [5]
MR003059 Atazanavir Atazanavir metabolite M5 Oxidation - Monohydroxylation Unclear [5]
MR003060 Atazanavir Atazanavir metabolite M13 Hydrolysis - Hydrolysis Unclear [5]
MR003061 Atazanavir Atazanavir metabolite M14 Hydrolysis - Hydrolysis Unclear [5]
MR003062 Atazanavir Atazanavir metabolite M15 Unclear CYP3A4 [5]
MR003063 Atazanavir Atazanavir metabolite M15' Oxidation - Dealkylation Unclear [5]
MR003056 Atazanavir metabolite M1 Atazanavir metabolite M16 Unclear Unclear [5]
MR003048 Atazanavir metabolite M2 Atazanavir metabolite M8 Unclear Unclear [5]
MR003050 Atazanavir metabolite M2 Atazanavir metabolite M10 Oxidation - Dihydroxylation Unclear [5]
MR003052 Atazanavir metabolite M2 Atazanavir metabolite M6 Other reaction - Monodehydrogenation Unclear [5]
MR003053 Atazanavir metabolite M2 Atazanavir metabolite M7 Other reaction - Monodehydrogenation Unclear [5]
MR003054 Atazanavir metabolite M2 Atazanavir metabolite M12 Unclear Unclear [5]
MR003051 Atazanavir metabolite M10 Atazanavir metabolite M11 Unclear Unclear [5]
MR003049 Atazanavir metabolite M8 Atazanavir metabolite M9 Unclear Unclear [5]
⏷ Show the Full List of 17 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
References
1 Indinavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Atazanavir for the treatment of human immunodeficiency virus infection. Pharmacotherapy. 2004 Dec;24(12):1732-47.
3 Atazanavir: effects on P-glycoprotein transport and CYP3A metabolism in vitro. Drug Metab Dispos. 2005 Jun;33(6):764-70.
4 In vitro inhibition of UDP glucuronosyltransferases by atazanavir and other HIV protease inhibitors and the relationship of this property to in vivo bilirubin glucuronidation. Drug Metab Dispos. 2005 Nov;33(11):1729-39.
5 CYP3A-mediated generation of aldehyde and hydrazine in atazanavir metabolism Drug Metab Dispos. 2011 Mar;39(3):394-401. doi: 10.1124/dmd.110.036327.

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