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

General Information of Drug (ID: DR1004)
Drug Name
Maprotiline hydrochloride
Synonyms
Maprotilina; Maprotilina [INN-Spanish]; Maprotilinum; Maprotilinum [INN-Latin]; Maprotylina; Maprotylina [Polish]; maprotiline; 10262-69-8; 276-Ba; 2U1W68TROF; 3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)-N-methylpropan-1-amine; 3-(9,10-Dihydro-9,10-ethanoanthracen-9-yl)propylmethylamine; 9,10-Ethanoanthracene-9(10H)-propanamine, N-methyl-; 9,10-Ethanoanthracene-9(10H)-propylamine, N-methyl-; BA-34276; BRN 2385493; CHEBI:6690; EINECS 233-599-4; N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine; UNII-2U1W68TROF; Ciba 34276 Ba; Deprilept; Ludiomil; Maprotiline (hydrochloride); Maprotiline Hcl; Maprotiline hydrochloride; Maprotilline HCl; Psymion; 10347-81-6; 7C8J54PVFI; 9,10-Ethanoanthracene-9(10H)-propanamine, N-methyl-, hydrochloride; 9-(gamma-Methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride; BA 34276; CPD000148117; EINECS 233-758-8; MFCD00079464; MLS000069552; MLS000557000; N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine hydrochloride; SMR000058834; SMR000148117; UNII-7C8J54PVFI
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 313.9 Topological Polar Surface Area 12
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
71478
ChEBI ID
CHEBI:6691
CAS Number
10347-81-6
TTD Drug ID
D03KQF
Formula
C20H24ClN
Canonical SMILES
CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24.Cl
InChI
1S/C20H23N.ClH/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20;/h2-5,7-10,15,21H,6,11-14H2,1H3;1H
InChIKey
NZDMFGKECODQRY-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-OH-maprotiline DM006469
58600339
Oxidation - Aromatic hydroxylation 1 [3]
3-OH-maprotiline DM006468
86125615
Oxidation - Aromatic hydroxylation 1 [3]
Desmethylmaprotiline DM006467
119409
Oxidation - N-demethylation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013438 Maprotiline hydrochloride Desmethylmaprotiline Oxidation - N-demethylation CYP2D6 [3]
MR013439 Maprotiline hydrochloride 3-OH-maprotiline Oxidation - Aromatic hydroxylation CYP2D6 ... [3]
MR013440 Maprotiline hydrochloride 2-OH-maprotiline Oxidation - Aromatic hydroxylation CYP2D6 ... [3]
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
[2]
References
1 Maprotiline Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Cytochrome P450 enzymes contributing to demethylation of maprotiline in man. Pharmacol Toxicol. 2002 Mar;90(3):144-9.
3 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.

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