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

General Information of Drug (ID: DR0334)
Drug Name
Citalopram hydrobromide
Synonyms
Cipramil; Citalopram (hydrobromide); Citalopram HBr; Citalopram hydrobromide [USAN]; EINECS 261-890-6; Elopram; HSDB 7042; Lu 10-171 HBr; Lu 10-171-B; MFCD02101306; Nitalapram HBr; Prepram HBr; Q-200865; Seropram; W-105304; citalopram hydrobromide; Cipram; Citalopram; Citalopramum [INN-Latin]; EINECS 261-891-1; Lu-10-171; Nitalapram; WSEQXVZVJXJVFP-UHFFFAOYSA-N; [3H]Citalopram; citalopram; 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile; 1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile; 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; 59729-33-8; Bonitrile; C20H21FN2O; CHEBI:77397; CHEMBL549; 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile hydrobromide; 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile hydrobromide; 59729-32-7; AK-72795; Bonitrile HBr; CPD000326936
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 405.3 Topological Polar Surface Area 36.3
Heavy Atom Count 25 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
77995
CAS Number
59729-32-7
TTD Drug ID
D0Y5DO
Formula
C20H22BrFN2O
Canonical SMILES
CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.Br
InChI
1S/C20H21FN2O.BrH/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;/h4-9,12H,3,10-11,14H2,1-2H3;1H
InChIKey
WIHMBLDNRMIGDW-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
Citalopram propionaldehyde DM006055
9944000
Oxidation - Oxidationn 1 [6]
Citalopram-N-oxide DM006057
10068142
Oxidation - Oxidationn 1 [6]
Demethylcitalopram DM006053
162180
Oxidation - N-demethylation 1 [4] , [6]
Citalopram propionaldehyde DM006055
9944000
Oxidation - Oxidationn 2 [6]
Citalopram propionic acid DM006056
10403174
Oxidation - Oxidationn 2 [6]
Didemethylcitalopram DM006054
162976
Oxidation - N-demethylation 2 [6]
Citalopram propionaldehyde DM006055
9944000
Oxidation - Oxidationn 3 [6]
Citalopram propionic acid DM006056
10403174
Oxidation - Oxidationn 3 [6]
Citalopram propionic acid DM006056
10403174
Oxidation - Oxidationn 4 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006517 Citalopram hydrobromide Demethylcitalopram Oxidation - N-demethylation CYP2D6 ... [4], [6]
MR006522 Citalopram hydrobromide Citalopram propionaldehyde Oxidation - Oxidationn MAOA ... [6]
MR006523 Citalopram hydrobromide Citalopram-N-oxide Oxidation - Oxidationn CYP2D6 [6]
MR006518 Demethylcitalopram Didemethylcitalopram Oxidation - N-demethylation CYP2D6 [6]
MR006521 Demethylcitalopram Citalopram propionaldehyde Oxidation - Oxidationn MAOA ... [6]
MR006519 Didemethylcitalopram Citalopram propionaldehyde Oxidation - Oxidationn MAOA ... [6]
MR006520 Citalopram propionaldehyde Citalopram propionic acid Oxidation - Oxidationn CYP2C19 [6]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_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]
Monoamine oxidase type A (MAO-A) DME0044 Homo sapiens
AOFA_HUMAN
1.4.3.4
[6]
Monoamine oxidase type B (MAO-B) DME0045 Homo sapiens
AOFB_HUMAN
1.4.3.4
[6]
⏷ Show the Full List of 6  DME(s)
References
1 Fluvoxamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69.
3 Antidepressant drugs in the elderly--role of the cytochrome P450 2D6. World J Biol Psychiatry. 2003 Apr;4(2):74-80.
4 PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72.
5 Citalopram and desmethylcitalopram in vitro: human cytochromes mediating transformation, and cytochrome inhibitory effects. Biol Psychiatry. 1999 Sep 15;46(6):839-49.
6 Analytical methodologies for the enantiodetermination of citalopram and its metabolites

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