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

General Information of Drug (ID: DR1729)
Drug Name
Zidovudine
Synonyms
Zidovudina [Spanish]; Zidovudinum; Zidovudinum [Latin]; Azidothymidine; Compound S; Retrovir; Thymidine, 3'-azido-3'-deoxy-; ZIDOVUDINE [AZT]; zidovudin; zidovudine; 3'-Azido-3'-deoxythymidine; 3'-Azido-3'-deoxythymidine (AIDS); 3'-Deoxy-3'-azidothymidine; 30516-87-1; 4B9XT59T7S; AZT; Aztec; BW A509U; BW-A 509U; BW-A-509U; BW-A509U; BWA509U; CCRIS 105; CHEMBL129; DRG-0004; HSDB 6515; MFCD00006536; MLS000028548; NSC 602670; UNII-4B9XT59T7S; ZDV
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 267.24 Topological Polar Surface Area 93.2
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
35370
PubChem SID
9419 ; 595886 ; 596433 ; 596437 ; 596594 ; 596595 ; 597291 ; 597292 ; 597293 ; 597457 ; 597458 ; 597459 ; 597460 ; 597461 ; 597462 ; 597463 ; 597555 ; 597641 ; 597664 ; 597665 ; 600904 ; 601536 ; 602048 ; 622272 ; 624122 ; 643735 ; 644084 ; 855980 ; 7846195 ; 7847479 ; 7980906 ; 8149829 ; 8173993 ; 11335699 ; 11360938 ; 11364242 ; 11366804 ; 11369366 ; 11372752 ; 11373842 ; 11377528 ; 11461910 ; 11484570 ; 11488743 ; 11491322 ; 11492147 ; 11495162 ; 12013681 ; 12146009 ; 14799161
ChEBI ID
CHEBI:10110
CAS Number
30516-87-1
TTD Drug ID
D01XYJ
Formula
C10H13N5O4
Canonical SMILES
CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)N=[N+]=[N-]
InChI
1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1
InChIKey
HBOMLICNUCNMMY-XLPZGREQSA-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
3'-Aminothymidine DM005340
108074
Reduction - Reduction 1 [2] , [3]
3'-azido-3'-deoxy-5'- O-beta-D-glucopyranuronosylthymidine DM005342
105108
Conjugation - Glucuronidation 1 [2] , [3]
5'glucuronyl zidovudine DM005343 N. A. Unclear 1 [8]
3'-amino-3'-deoxythimidine glucuronide metabolite DM005341
131769941
Conjugation - Glucuronidation 2 [2] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005676 Zidovudine 3'-Aminothymidine Reduction - Reduction CYP3A4 ... [2], [3]
MR005678 Zidovudine 3'-azido-3'-deoxy-5'- O-beta-D-glucopyranuronosylthymidine Conjugation - Glucuronidation UGT2B7 [2], [3]
MR005679 Zidovudine 5'glucuronyl zidovudine Unclear Unclear [8]
MR005677 3'-Aminothymidine 3'-amino-3'-deoxythimidine glucuronide metabolite Conjugation - Glucuronidation Unclear [2], [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[6]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1406 Collinsella aerofaciens Not Available Not Available [7]
⏷ Show the Full List of 10  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Km = 0.551 microM
UD2B7_HUMAN
[6]
References
1 Zidovudine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Metabolism and pharmacokinetics of the combination Zidovudine plus Lamivudine in the adult Erythrocebus patas monkey determined by liquid chromatography-tandem mass spectrometric analysis
4 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
5 Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90.
6 Determination of UDP-glucuronosyltransferase UGT2B7 activity in human liver microsomes by ultra-performance liquid chromatography with MS detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Jul 1;870(1):84-90.
7 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
8 DrugBank(Pharmacology-Metabolism):Zidovudine

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