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

General Information of Drug (ID: DR0350)
Drug Name
Clomipramine hydrochloride
Synonyms
Chlorimipramine hydrochloride; Chloroimipramine monohydrochloride; Clomipramine (hydrochloride); Clomipramine HCL; Clomipramine Monohydrochloride; Clomipramine hydrochloride; Chlorimipramine; Clomipramine; Clomipramina; Clomipramina [INN-Spanish]; Clomipramine [INN:BAN]; Clomipraminum; Clomipraminum [INN-Latin]; Hydiphen; Monochlorimipramine; NSC 169865; UNII-NUV44L116D; 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine; 3-Chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine; 3-Chloroimipramine; 303-49-1; 5H-Dibenz[b,f]azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-; Anafranil (free base); Anafranil base; EINECS 241-344-3; I615; MFCD00069234; MLS000028511; SMR000058295; UNII-2LXW0L6GWJ; 17321-77-6; 2LXW0L6GWJ; 3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine hydrochloride; 3-Chloroimipramine hydrochloride; Anafranil; Anaphranil; C19H23ClN2.HCl; CHEBI:3755; CPD000058295
Indication Obsessive-compulsive disorder [ICD11: 6B20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 351.3 Topological Polar Surface Area 6.5
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
68539
PubChem SID
855785 ; 3146444 ; 7847876 ; 8150146 ; 8192195 ; 10321173 ; 11528647 ; 14925416 ; 17404870 ; 24278087 ; 24714730 ; 25624751 ; 26514064 ; 26543492 ; 26613159 ; 26680358 ; 26747483 ; 43125096 ; 50064402 ; 50106071 ; 50122894 ; 50122895 ; 53777413 ; 56311677 ; 56422907 ; 57316916 ; 79827483 ; 85084917 ; 85149187 ; 85174244 ; 88565714 ; 92125084 ; 92303620 ; 103770693 ; 103819575 ; 103913653 ; 104170176 ; 104342415 ; 117447143 ; 124637328 ; 124891638 ; 124891639 ; 125312387 ; 125342946 ; 126617326 ; 126645822 ; 126664318 ; 135027196 ; 135610155 ; 135697887
ChEBI ID
CHEBI:3755
CAS Number
17321-77-6
TTD Drug ID
D05AAW
Formula
C19H24Cl2N2
Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2CCC3=C1C=C(C=C3)Cl.Cl
InChI
1S/C19H23ClN2.ClH/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22;/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3;1H
InChIKey
WIMWMKZEIBHDTH-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
10-OH-clomipramine DM006112
154699866
Oxidation - Aliphatic hydroxylation 1 [7]
2-hydroxyclomipramine DM006104
10246110
Oxidation - 2-hydroxylation 1 [8]
8-hydroxyclomipramine DM006106
11724232
Oxidation - 8-hydroxylation 1 [7]
8-OH-clomipramine DM006111
134222
Oxidation - Aromatic hydroxylation 1 [8]
Clomipramine N-oxide DM006110
29976360
Oxidation - Oxidationn 1 [7]
Desmethylclomipramine DM006100
622606
Oxidation - N-demethylation 1 [7] , [9]
2-hydroxyclomipramine glucuronide DM006105
165361827
Conjugation - Glucuronidation 2 [8]
2-hydroxydesmethyl clomipramine DM006101
91617717
Oxidation - Demethylation 2 [8]
8-hydroxyclomipramine glucuronide DM006109 N. A. Conjugation - Glucuronidation 2 [7]
8-hydroxydesmethyl clomipramine DM006107
10018695
Unclear 2 [7]
Didesmethylclomipramine DM006103
3085253
Oxidation - N-demethylation 2 [7] , [9]
2-hydroxydesmethyl clomipramine glucuronide DM006102
165361770
Conjugation - Glucuronidation 3 [8]
8-hyroxydesmethyl clomipramine glucuronide DM006108 N. A. Conjugation - Glucuronidation 3 [7]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006567 Clomipramine hydrochloride Desmethylclomipramine Oxidation - N-demethylation CYP1A2 ... [7], [9]
MR006571 Clomipramine hydrochloride 2-hydroxyclomipramine Oxidation - 2-hydroxylation Unclear [8]
MR006574 Clomipramine hydrochloride 8-hydroxyclomipramine Oxidation - 8-hydroxylation CYP2D6 [7]
MR006578 Clomipramine hydrochloride Clomipramine N-oxide Oxidation - Oxidationn CYP2D6 [7]
MR006579 Clomipramine hydrochloride 8-OH-clomipramine Oxidation - Aromatic hydroxylation CYP2D6 [8]
MR006580 Clomipramine hydrochloride 10-OH-clomipramine Oxidation - Aliphatic hydroxylation CYP2D6 [7]
MR006572 2-hydroxyclomipramine 2-hydroxydesmethyl clomipramine Oxidation - Demethylation CYP2D6 [8]
MR006573 2-hydroxyclomipramine 2-hydroxyclomipramine glucuronide Conjugation - Glucuronidation Unclear [8]
MR006575 8-hydroxyclomipramine 8-hydroxydesmethyl clomipramine Unclear Unclear [7]
MR006577 8-hydroxyclomipramine 8-hydroxyclomipramine glucuronide Conjugation - Glucuronidation Unclear [7]
MR006568 Desmethylclomipramine 2-hydroxydesmethyl clomipramine Oxidation - Demethylation CYP2D6 [8]
MR006570 Desmethylclomipramine Didesmethylclomipramine Oxidation - N-demethylation CYP1A2 [7], [9]
MR006569 2-hydroxydesmethyl clomipramine 2-hydroxydesmethyl clomipramine glucuronide Conjugation - Glucuronidation Unclear [8]
MR006576 8-hydroxydesmethyl clomipramine 8-hyroxydesmethyl clomipramine glucuronide Conjugation - Glucuronidation Unclear [7]
⏷ Show the Full List of 14 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 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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
References
1 Clomipramine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Erythromycin interaction with risperidone or clomipramine in an adolescent. J Child Adolesc Psychopharmacol. 1996 Summer;6(2):133-8.
3 The biotransformation of clomipramine in vitro, identification of the cytochrome P450s responsible for the separate metabolic pathways. J Pharmacol Exp Ther. 1996 Jun;277(3):1659-64.
4 Tricyclic antidepressant pharmacology and therapeutic drug interactions updated. Br J Pharmacol. 2007 Jul;151(6):737-48.
5 Serum clomipramine and desmethylclomipramine levels in a CYP2C19 and CYP2D6 intermediate metabolizer. Pharmacogenomics. 2017 May;18(7):601-605.
6 Role of human UGT2B10 in N-glucuronidation of tricyclic antidepressants, amitriptyline, imipramine, clomipramine, and trimipramine. Drug Metab Dispos. 2010 May;38(5):863-70.
7 Metabolism of clomipramine in a Japanese psychiatric population: hydroxylation, desmethylation, and glucuronidation
8 Determination of clomipramine or imipramine and their mono-demethylated metabolites in human blood or plasma by high-performance liquid chromatography
9 Population pharmacokinetics of clomipramine, desmethylclomipramine, and hydroxylated metabolites in patients with depression receiving chronic treatment: model evaluation

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