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

General Information of Drug (ID: DR0164)
Drug Name
Azathioprine
Prodrug Info Azathioprine is the prodrug of 6-mercaptopurine
Synonyms
Azamun; Azamun [Czech]; Azanin; Azasan; Azathioprin; Azathioprinum [INN-Latin]; Azathiopurine; Azatioprin; Azatioprina [INN-Spanish]; Azothioprine; Ccucol; Imuran; Imuran (TN); Imurek; Imurel; azathioprine; 446-86-6; 6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine; 6-(1-Methyl-p-nitro-5-imidazolyl)-thiopurine; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)sulfanyl]-7H-purine; BW 57-322; BW-57-322; C9H7N7O2S; CCRIS 62; Methylnitroimidazolylmercaptopurine; Muran; NCI-C03474; NSC 39084; NSC-39084; UNII-MRK240IY2L
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 277.27 Topological Polar Surface Area 143
Heavy Atom Count 19 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
2265
PubChem SID
9055 ; 545491 ; 4476272 ; 4486208 ; 4503338 ; 7592075 ; 7695226 ; 7847305 ; 7978746 ; 8149210 ; 8151523 ; 10321142 ; 10560483 ; 10584680 ; 11110740 ; 11110741 ; 11142069 ; 11335761 ; 11361000 ; 11362878 ; 11364839 ; 11365440 ; 11367401 ; 11368002 ; 11369963 ; 11371476 ; 11373003 ; 11373785 ; 11375563 ; 11376164 ; 11378131 ; 11461972 ; 11466122 ; 11467242 ; 11483991 ; 11485723 ; 11487884 ; 11490124 ; 11492058 ; 11493878 ; 11524329 ; 11533962 ; 11536345 ; 12294767 ; 14775167 ; 14824335 ; 15222101 ; 17390031 ; 17404591 ; 24278074
ChEBI ID
ChEBI:2948
CAS Number
446-86-6
TTD Drug ID
D07QCE
Formula
C9H7N7O2S
Canonical SMILES
CN1C=NC(=C1SC2=NC=NC3=C2NC=N3)[N+](=O)[O-]
InChI
1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)
InChIKey
LMEKQMALGUDUQG-UHFFFAOYSA-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
6-mercaptopurine DM016198
58102027
Unclear - Non-enzymaticreduction 1 [3]
6-methylmercaptopurine DM014884
5778
Unclear - Unclear 2 [3]
6-thioinosine-monophosphate DM015390
3034391
Unclear - Unclear 2 [3]
6-thioxanthine DM015353
1268107
Unclear - Unclear 2 [3]
6-thioxanthosine-monophosphate DM015403
3081384
Unclear - Unclear 3 [3]
Methyl-6-thioinosine-monophosphate DM015613
10091038
Unclear - Unclear 3 [3]
Thiouric acid DM015386
3032417
Unclear - Unclear 3 [3]
6-thioguanine nucleotides DM018064 N. A. Unclear - Unclear 4 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009897 Azathioprine 6-mercaptopurine Unclear - Non-enzymaticreduction GST [3]
MR009898 6-mercaptopurine 6-thioinosine-monophosphate Unclear - Unclear HPRT [3]
MR009902 6-mercaptopurine 6-methylmercaptopurine Unclear - Unclear TPMT [3]
MR009903 6-mercaptopurine 6-thioxanthine Unclear - Unclear XD [3]
MR009899 6-thioinosine-monophosphate 6-thioxanthosine-monophosphate Unclear - Unclear IMPDH [3]
MR009901 6-thioinosine-monophosphate Methyl-6-thioinosine-monophosphate Unclear - Unclear TPMT [3]
MR009904 6-thioxanthine Thiouric acid Unclear - Unclear XD [3]
MR009900 6-thioxanthosine-monophosphate 6-thioguanine nucleotides Unclear - Unclear GMPS [3]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Glutamine amidotransferase (GMPS) DME0159 Homo sapiens
GUAA_HUMAN
6.3.5.2
[3]
Glutathione S-transferase alpha-2 (GSTA2) DME0081 Homo sapiens
GSTA2_HUMAN
2.5.1.18
[4]
Glutathione S-transferase mu-1 (GSTM1) DME0308 Homo sapiens
GSTM1_HUMAN
2.5.1.18
[4]
Inosine-5'-monophosphate dehydrogenase (IMPDH) DMEN801 Homo sapiens
A0A384N6C2_HUMAN
1.1.1.205
[3]
Thiopurine methyltransferase (TPMT) DME0014 Homo sapiens
TPMT_HUMAN
2.1.1.67
[5]
⏷ Show the Full List of 6  DME(s)
References
1 Mercaptopurine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Brassica vegetables increase and apiaceous vegetables decrease cytochrome P450 1A2 activity in humans: changes in caffeine metabolite ratios in response to controlled vegetable diets. Carcinogenesis. 2000 Jun;21(6):1157-62.
3 Gut Microbiota Metabolism of Azathioprine: A New Hallmark for Personalized Drug-Targeted Therapy of Chronic Inflammatory Bowel Disease
4 PharmGKB: A worldwide resource for pharmacogenomic information. Wiley Interdiscip Rev Syst Biol Med. 2018 Jul;10(4):e1417. (ID: PA2040)
5 Nodular regenerative liver hyperplasia as a complication of azathioprine-containing immunosuppressive treatment for Crohn's disease. Immunopharmacol Immunotoxicol. 2011 Jun;33(2):398-402.

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