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

General Information of Drug (ID: DR0861)
Drug Name
Imipramine hydrochloride
Synonyms
Imidobenzyle; Imipramin; Imipramina; Imipramina [Italian]; Imipramine [INN:BAN]; Imipraminum; Imipraminum [INN-Latin]; Imiprin; Imizine; Impramine; Intalpram; Iramil; Janimine; Melipramin; Melipramine; Nelipramin; Prazepine; Promiben; Psychoforin; SK-Pramine; Surplix; Timolet; Tofranil, base; Tofranil-PM; imipramine; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine; 50-49-7; Dpid; Irmin; Antideprin; Berkomine; Censtim; Censtin; Declomipramine; Dimipressin; Dyna-zina; Dynaprin; Eupramin; Imavate; Antideprin hydrochloride; Chimoreptin; Chrytemin; Co cap imipramine 25; Deprinol; Dynazina; Efuranol; Feinalmin; Fujisawa; IMP hydrochloride; Imidol; Imilanyle; Imipramine Hcl; Imipramine hydrochloride; Imipramine monohydrochloride; Imipramine, Hydrochloride; Imipramini; Imipramini hydrochloridum; Imizinum; Iprogen; Odeoxil; Persamine; Pertofram; Pramine; Presamine; Pryleugan; Psicopramine; SK-Pramine hydrochloride; Teperine; Thymopramin; Tipramine; Tofranile; Venefon; Vionyl; 113-52-0; IA-Pram; UNII-BKE5Q1J60U
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 316.9 Topological Polar Surface Area 6.5
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
8228
ChEBI ID
CHEBI:5882
CAS Number
113-52-0
TTD Drug ID
D06ZUK
Formula
C19H25ClN2
Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
InChI
1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H
InChIKey
XZZXIYZZBJDEEP-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
2-hydroxyimipramine DM004319
108051
Oxidation - 2-hydroxylation 1 [9]
Desipramine DM004232
2995
Oxidation - N-demethylation 1 [10]
Didemethylimipramine DM004321 N. A. Oxidation - Demethylation 1 [11]
Imidodibenzyl Metabolite DM004324 N. A. Oxidation - N-dealkylation 1 [11]
Imipramine N-oxide DM004323
65589
Oxidation - N-oxidation 1 [11]
10-hydroxydidemethylimipramine DM004322 N. A. Oxidation - Hydrolyzationn 2 [11]
2-hydroxy-imipramine glucuronide DM004320
10874382
Conjugation - Glucuronidation 2 [9]
2-hydroxydesipramine DM000777
121249
Oxidation - Hydrolyzationn 2 [12]
2-hydroxydesipramine glucuronide DM000778
71748973
Conjugation - O-glucuronidation 3 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012986 Imipramine hydrochloride Desipramine Oxidation - N-demethylation CYP1A2 ... [10]
MR012989 Imipramine hydrochloride 2-hydroxyimipramine Oxidation - 2-hydroxylation CYP1A2 ... [9]
MR012991 Imipramine hydrochloride Didemethylimipramine Oxidation - Demethylation Unclear [11]
MR012993 Imipramine hydrochloride Imipramine N-oxide Oxidation - N-oxidation Unclear [11]
MR012994 Imipramine hydrochloride Imidodibenzyl Metabolite Oxidation - N-dealkylation Unclear [11]
MR012990 2-hydroxyimipramine 2-hydroxy-imipramine glucuronide Conjugation - Glucuronidation Unclear [9]
MR012987 Desipramine 2-hydroxydesipramine Oxidation - Hydrolyzationn CYP2D6 [12]
MR012992 Didemethylimipramine 10-hydroxydidemethylimipramine Oxidation - Hydrolyzationn Unclear [11]
MR012988 2-hydroxydesipramine 2-hydroxydesipramine glucuronide Conjugation - O-glucuronidation Unclear [11]
⏷ Show the Full List of 9 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]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DME0616 Homo sapiens
CP4FB_HUMAN
1.14.14.1
[6]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[7]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[8]
⏷ Show the Full List of 9  DME(s)
References
1 Desipramine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210.
3 QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine. Ann Pharmacother. 2005 Mar;39(3):543-6.
4 Variability in metabolism of imipramine and desipramine using urinary excretion data. J Anal Toxicol. 2014 Jul-Aug;38(6):368-74.
5 Catalysis of drug oxidation during embryogenesis in human hepatic tissues using imipramine as a model substrate. Drug Metab Dispos. 1999 Nov;27(11):1306-8.
6 Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.
7 Inhibitory effects of tricyclic antidepressants (TCAs) on human cytochrome P450 enzymes in vitro: mechanism of drug interaction between TCAs and phenytoin. Drug Metab Dispos. 2002 Oct;30(10):1102-7.
8 Liquid chromatography-tandem mass spectrometry method for measurement of nicotine N-glucuronide: a marker for human UGT2B10 inhibition. J Pharm Biomed Anal. 2011 Jul 15;55(5):964-71.
9 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
10 Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin, and imipramine metabolism. Drug Metab Dispos. 1999 Jan;27(1):102-9.
11 Clinical pharmacokinetics of imipramine and desipramine
12 The Use of In Vitro Data and Physiologically-Based Pharmacokinetic Modeling to Predict Drug Metabolite Exposure: Desipramine Exposure in Cytochrome P4502D6 Extensive and Poor Metabolizers Following Administration of Imipramine

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