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

General Information of Drug (ID: DR0618)
Drug Name
Escitalopram
Synonyms
Escitalopram; Escitalopram (INN); Escitalopram [INN]; Esertia; Lexapro; S(+)-Citalopram; S-(+)-Citalopram; Seroplex; escitalopram oxalate inn; escitalopramum; (+)-(S)-1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile; (+)-Citalopram; (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; (S)-(+)-Citalopram Oxalate; (S)-Citalopram; 128196-01-0; 4O4S742ANY; CHEBI:36791; CHEMBL1508; UNII-4O4S742ANY
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 324.4 Topological Polar Surface Area 36.3
Heavy Atom Count 24 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
146570
PubChem SID
10249284 ; 11110983 ; 11114081 ; 11364295 ; 11366857 ; 11369419 ; 11371963 ; 11374782 ; 11377581 ; 11484357 ; 11488367 ; 11490877 ; 11493026 ; 11495215 ; 14777200 ; 14826334 ; 17425394 ; 46223778 ; 46507040 ; 47736762 ; 48185248 ; 50067335 ; 50100207 ; 50123207 ; 57346404 ; 80123692 ; 85789669 ; 92308964 ; 93167153 ; 96024609 ; 103558387 ; 104156586 ; 104414365 ; 124879737 ; 124879740 ; 126525322 ; 126626833 ; 126667435 ; 126669969 ; 127339776 ; 127339777 ; 127339778 ; 135103622 ; 137002472 ; 141023772 ; 141191354 ; 160964509 ; 163124265 ; 164834640 ; 172914696
ChEBI ID
ChEBI:36791
CAS Number
128196-01-0
TTD Drug ID
D08RBC
Formula
C20H21FN2O
Canonical SMILES
CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
InChI
1S/C20H21FN2O/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/t20-/m0/s1
InChIKey
WSEQXVZVJXJVFP-FQEVSTJZSA-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
Escitalopram propionic acid DM002011 N. A. Unclear 1 [5]
S-desmethylcitalopram DM002009
11255350
Oxidation - N-Demethylation 1 [3] , [6]
S-didesmethylcitalopram DM002010
40582667
Oxidation - N-Demethylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000942 Escitalopram S-desmethylcitalopram Oxidation - N-Demethylation CYP3A4 ... [3], [6]
MR000943 Escitalopram Escitalopram propionic acid Unclear CYP2C19 ... [5]
MR000941 S-desmethylcitalopram S-didesmethylcitalopram Oxidation - N-Demethylation CYP2D6 [3]
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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Escitalopram was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP2D6 P34S Polymorphism and Outcomes of Escitalopram Treatment in Koreans with Major Depression. Psychiatry Investig. 2013 Sep;10(3):286-93.
3 PharmGKB summary: citalopram pharmacokinetics pathway. Pharmacogenet Genomics. 2011 Nov;21(11):769-72.
4 Escitalopram pharmacogenetics: CYP2C19 relationships with dosing and clinical outcomes in autism spectrum disorder. Pharmacogenet Genomics. 2015 Nov;25(11):548-54.
5 Identification of a novel CYP2C19-mediated metabolic pathway of S-citalopram in vitro Drug Metab Dispos. 2009 Dec;37(12):2340-8. doi: 10.1124/dmd.109.029355.
6 Escitalopram (S-citalopram) and its metabolites in vitro: cytochromes mediating biotransformation, inhibitory effects, and comparison to R-citalopram Drug Metab Dispos. 2001 Aug;29(8):1102-9.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.