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

General Information of Drug (ID: DR1344)
Drug Name
Procarbazine
Synonyms
Procarbazin; Procarbazin [German]; Procarbazina; Procarbazina [INN-Spanish]; Procarbazine [INN:BAN]; Procarbazinum; Procarbazinum [INN-Latin]; Ibenzmethyzine; Natulan; Ro 4-6467; procarbazine; 1-Methyl-2-(p-(isopropylcarbamoyl)benzyl)hydrazine; 2-(p-Isopropylcarbamoylbenzyl)-1-methylhydrazine; 4-((2-Methylhydrazino)methyl)-N-isopropylbenzamide; 671-16-9; Ibenzmethyzin; N-4-Isopropylcarbamoylbenzyl-N'-methylhydrazine; N-Isopropyl-4-((2-methylhydrazinyl)methyl)benzamide; p-(2-Methylhydrazinomethyl)-N-isopropylbenzamide
Indication Anaplastic large cell lymphoma [ICD11: 2A90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 221.3 Topological Polar Surface Area 53.2
Heavy Atom Count 16 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4915
PubChem SID
9606 ; 5227622 ; 7980389 ; 8153026 ; 10532324 ; 11112335 ; 11446055 ; 11451557 ; 11467140 ; 11468260 ; 11486848 ; 15195970 ; 29223993 ; 46507706 ; 47440427 ; 47736658 ; 47810931 ; 48259429 ; 48414372 ; 48416472 ; 49699412 ; 49857646 ; 50100422 ; 53790978 ; 57288818 ; 57322522 ; 60975981 ; 75023517 ; 92309185 ; 92720556 ; 93166341 ; 96025109 ; 103411217 ; 104224963 ; 104307787 ; 119525894 ; 125564988 ; 126619890 ; 126653077 ; 126667406 ; 127660052 ; 134338256 ; 134977726 ; 136342514 ; 137001449 ; 140349398 ; 144076104 ; 144212055 ; 152030630 ; 160655721
ChEBI ID
CHEBI:71417
CAS Number
671-16-9
TTD Drug ID
D08GYO
Formula
C12H19N3O
Canonical SMILES
CC(C)NC(=O)C1=CC=C(C=C1)CNNC
InChI
1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16)
InChIKey
CPTBDICYNRMXFX-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
Azoprocarbazine DM002975
75230
Unclear 1 [3] , [5]
Hydrazine DM001007
9321
Unclear 1 [6]
Azoxy-1-procarbazine DM002979
48599
Unclear 2 [5] , [7]
Methylazoxyprocarbazine DM002976
125651
Unclear 2 [5] , [7]
Aldehyde derivative DM002977
83270
Unclear 3 [5] , [7]
N-isopropylterephthalamic acid DM002978
69903
Oxidation - Oxidation 4 [5] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002164 Procarbazine Hydrazine Unclear Unclear [6]
MR002165 Procarbazine Azoprocarbazine Unclear CYP1B1 ... [3], [5]
MR002159 Azoprocarbazine Methylazoxyprocarbazine Unclear Unclear [5], [7]
MR002160 Azoprocarbazine Azoxy-1-procarbazine Unclear Unclear [5], [7]
MR002163 Azoxy-1-procarbazine Aldehyde derivative Unclear Unclear [5], [7]
MR002161 Methylazoxyprocarbazine Aldehyde derivative Unclear Unclear [5], [7]
MR002162 Aldehyde derivative N-isopropylterephthalamic acid Oxidation - Oxidation Unclear [5], [7]
⏷ Show the Full List of 7 MR(s)
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
[2]
Cytochrome P450 1B1 (CYP1B1) DME0023 Homo sapiens
CP1B1_HUMAN
1.14.14.1
[3]
Monoamine oxidase (MAO) DMEN059 . Not Available Not Available [2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
⏷ Show the Full List of 15  DME(s)
References
1 Procarbazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro and in vivo evidence for the formation of methyl radical from procarbazine: a spin-trapping study. Carcinogenesis. 1992 May;13(5):799-805.
3 Tumour cytochrome P450 and drug activation. Curr Pharm Des. 2002;8(15):1335-47.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Plasma kinetics of procarbazine and azo-procarbazine in humans Anticancer Drugs. 2006 Jan;17(1):75-80. doi: 10.1097/01.cad.0000181591.85476.aa.
6 DrugBank(Pharmacology-Metabolism)Procarbazine
7 Quantitative analysis of procarbazine, procarbazine metabolites and chemical degradation products with application to pharmacokinetic studies J Chromatogr. 1982 May 14;229(2):397-407. doi: 10.1016/s0378-4347(00)84282-6.

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