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

General Information of Drug (ID: DR0404)
Drug Name
Dacarbazine
Prodrug Info Dacarbazine is the prodrug of 5-[3-hydroxymethyl-3-methyl-triazen-1-yl]-imidazole-4-carboxamide (HMMTIC)
Synonyms
Dacarbazino [INN-Spanish]; Dacarbazinum; Dacarbazinum [INN-Latin]; Decarbazine; Deticene; Di-me-triazenoimidazolecarboxamide; Dtic-Dome (TN); dacarbazine; (Dimethyltriazeno)imidazolecarboxamide; 4-(Dimethyltriazeno)imidazole-5-carboxamide; Biocarbazine; Biocarbazine R; DTIC-Dome; 5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide; 5-(3,3-Dimethyltriazeno)imidazole-4-carboxamide; 5-(Dimethyltriazeno)imidazole-4-carboxamide; DTIC; DTIE; ICDMT; ICDT; NSC 45388; NSC-45388; NSC45388
Indication Melanoma [ICD11: 2C30] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 182.18 Topological Polar Surface Area 99.7
Heavy Atom Count 13 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
135398738
ChEBI ID
CHEBI:94587
CAS Number
4342-03-4
TTD Drug ID
D0Y7ZU
Formula
C6H10N6O
Canonical SMILES
CN(C)N=NC1=C(NC=N1)C(=O)N
InChI
1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)/b11-10+
InChIKey
FDKXTQMXEQVLRF-ZHACJKMWSA-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
5-[3-hydroxymethyl-3-methyl-triazen-1-yl]-imidazole-4-carboxamide (HMMTIC) DM006159
135518056
Unclear 1 [5]
(5-[3-methyl-triazen-1-yl]-imidazole-4-carboxamide (MTIC) DM006160
135804075
Unclear 2 [5]
5-aminoimidazole-4-carboxamide (AIC) DM006161
9679
Unclear 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006605 Dacarbazine 5-[3-hydroxymethyl-3-methyl-triazen-1-yl]-imidazole-4-carboxamide (HMMTIC) Unclear CYP1A2 ... [5]
MR006606 5-[3-hydroxymethyl-3-methyl-triazen-1-yl]-imidazole-4-carboxamide (HMMTIC) (5-[3-methyl-triazen-1-yl]-imidazole-4-carboxamide (MTIC) Unclear Unclear [5]
MR006607 (5-[3-methyl-triazen-1-yl]-imidazole-4-carboxamide (MTIC) 5-aminoimidazole-4-carboxamide (AIC) Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
References
1 Dacarbazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolic activation of dacarbazine by human cytochromes P450: the role of CYP1A1, CYP1A2, and CYP2E1. Clin Cancer Res. 1999 Aug;5(8):2192-7.
3 Study on mesenchymal stem cells mediated enzyme-prodrug gene CYP1A2 targeting anti-tumor effect. Zhonghua Xue Ye Xue Za Zhi. 2009 Oct;30(10):667-71.
4 Role of cytochrome P450 isoenzymes in metabolism of O(6)-benzylguanine: implications for dacarbazine activation. Clin Cancer Res. 2001 Dec;7(12):4239-44.
5 Pharmacokinetics of dacarbazine (DTIC) in pregnancy

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