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

General Information of Drug (ID: DR0436)
Drug Name
Desipramine
Synonyms
Demethylimipramine; Desimipramine; Desimpramine; Desipramin; Desipramina; Desipramine (D4); Desipramine [INN:BAN]; Desmethylimipramine; Dezipramine; Dimethylimipramine; Imipramine, demethyl-; Methylaminopropyliminodibenzyl; DMI (pharmaceutical); DMI 50475; Monodemethylimipramine; Norimipramine; Norpramine; Pertrofane; Sertofran; desipramine; desipraminum; 3-(10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N-METHYLPROPAN-1-AMINE; 5-(gamma-Methylaminopropyl)iminodibenzyl; 50-47-5; N-(3-Methylaminopropyl)iminobibenzyl
Indication Attention deficit hyperactivity disorder [ICD11: 6A05] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 266.4 Topological Polar Surface Area 15.3
Heavy Atom Count 20 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2995
PubChem SID
9158 ; 647048 ; 3249345 ; 3727070 ; 5321893 ; 7737258 ; 7979043 ; 8151907 ; 10524411 ; 11111066 ; 11111067 ; 11335365 ; 11360604 ; 11363335 ; 11365897 ; 11368459 ; 11371457 ; 11374067 ; 11376621 ; 11461576 ; 11466371 ; 11467491 ; 11483778 ; 11486062 ; 11487907 ; 11490195 ; 11492129 ; 11494255 ; 14774838 ; 29214812 ; 29222144 ; 46504624 ; 47291013 ; 47291014 ; 47736341 ; 47736342 ; 47736343 ; 47959596 ; 48259094 ; 48259095 ; 48415856 ; 49698852 ; 49961473 ; 50100220 ; 50104283 ; 53787179 ; 57321547 ; 76076257 ; 85209781 ; 85753308
ChEBI ID
ChEBI:47781
CAS Number
50-47-5
TTD Drug ID
D01UTL
Formula
C18H22N2
Canonical SMILES
CNCCCN1C2=CC=CC=C2CCC3=CC=CC=C31
InChI
1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3
InChIKey
HCYAFALTSJYZDH-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-hydroxydesipramine DM000777
121249
Oxidation - 2-Hydroxylation 1 [7]
2-hydroxydesipramine glucuronide DM000778
71748973
Conjugation - Glucuronidation 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002595 Desipramine 2-hydroxydesipramine Oxidation - 2-Hydroxylation CYP2D6 [7]
MR002594 2-hydroxydesipramine 2-hydroxy-desipramine glucuronide Conjugation - Glucuronidation Unclear [7]
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
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[6]
References
1 Desipramine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Drugs that may have potential CYP2B6 interactions.
4 Dose-dependent inhibition of CYP1A2, CYP2C19 and CYP2D6 by citalopram, fluoxetine, fluvoxamine and paroxetine. Eur J Clin Pharmacol. 1996;51(1):73-8.
5 Variability in metabolism of imipramine and desipramine using urinary excretion data. J Anal Toxicol. 2014 Jul-Aug;38(6):368-74.
6 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.
7 Clinical pharmacokinetics of imipramine and desipramine

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