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

General Information of Drug (ID: DR1649)
Drug Name
Trimipramine
Synonyms
Trimeprimina; Trimeprimina [Italian]; Trimeprimine; Trimeproprimin; Trimeproprimine; Trimipramina; Trimipramina [INN-Spanish]; Trimipramine [USAN:INN:BAN]; Trimipraminum; Trimipraminum [INN-Latin]; beta-Methylimipramine; trimipramine; (+)-Trimipramine; FI 6120; IL 6001; RP-7162; Sapilent; Surmontil; Surmontyl; (-)-Trimipramine; 2'-Metil-3'-dimetilamino-propil-5-iminodibenzile; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N,2-trimethylpropan-1-amine; 7162 RP; 739-71-9; CHEMBL644; EINECS 212-008-3; UNII-9K5931C1H5; UNII-QJ9MUH57H8
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 294.4 Topological Polar Surface Area 6.5
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5584
PubChem SID
4752050 ; 7847460 ; 7980837 ; 8153438 ; 10534352 ; 11335268 ; 11360507 ; 11364316 ; 11366878 ; 11369440 ; 11372300 ; 11374257 ; 11377602 ; 11461479 ; 11466834 ; 11467954 ; 11485056 ; 11486328 ; 11489346 ; 11490966 ; 11492574 ; 11495236 ; 14751475 ; 29214834 ; 29224622 ; 46507121 ; 47216629 ; 47365025 ; 47515163 ; 47588839 ; 47810599 ; 47959573 ; 48034950 ; 48259062 ; 48334324 ; 48416674 ; 49698932 ; 49761600 ; 49961515 ; 49961516 ; 49961517 ; 50111256 ; 57322857 ; 78776395 ; 85209670 ; 85789363 ; 90341093 ; 92714629 ; 92729770 ; 103189045
ChEBI ID
ChEBI:9738
CAS Number
739-71-9
TTD Drug ID
D00HZV
Formula
C20H26N2
Canonical SMILES
CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C
InChI
1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
InChIKey
ZSCDBOWYZJWBIY-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-hydroxytrimipramine DM002402
160610
Oxidation - Hydroxylation 1 [5] , [6] , [7]
Desmethyltrimipramine DM002401
160632
Oxidation - Demethylation 1 [8] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002462 Trimipramine Desmethyltrimipramine Oxidation - Demethylation Unclear [8], [7]
MR002463 Trimipramine 2-hydroxytrimipramine Oxidation - Hydroxylation Unclear [5], [6], [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Homo sapiens
UDB10_HUMAN
2.4.1.17
[4]
References
1 Trimipramine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effects of polymorphisms in CYP2D6, CYP2C9, and CYP2C19 on trimipramine pharmacokinetics. J Clin Psychopharmacol. 2003 Oct;23(5):459-66.
3 Galactorrhea during treatment with trimipramine. A case report. Pharmacopsychiatry. 2005 Nov;38(6):326-7.
4 Role of human UGT2B10 in N-glucuronidation of tricyclic antidepressants, amitriptyline, imipramine, clomipramine, and trimipramine. Drug Metab Dispos. 2010 May;38(5):863-70.
5 Metabolism of trimipramine in vitro by human CYP2D6 isozyme Res Commun Chem Pathol Pharmacol. 1993 Oct;82(1):111-20.
6 Simultaneous determination of trimipramine and its major metabolites by high-performance liquid chromatography J Chromatogr. 1991 May 3;566(1):228-33. doi: 10.1016/0378-4347(91)80128-y.
7 Determination of trimipramine and metabolites in plasma by liquid chromatography with electrochemical detection J Pharm Sci. 1984 Dec;73(12):1745-8. doi: 10.1002/jps.2600731221.
8 Nonlinear kinetics of trimipramine in depressed patients J Clin Pharmacol. 1989 Aug;29(8):746-7. doi: 10.1002/j.1552-4604.1989.tb03410.x.

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