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

General Information of Drug (ID: DR1679)
Drug Name
Venlafaxine hydrochloride
Synonyms
Venlafaxine (hydrochloride); Venlafaxine Hydorchloride; Venlafaxine hydrochloride; Venlafaxinehydrochloride; Venlafaxin; Venlafaxina; Venlafaxina [INN-Spanish]; Venlafaxine [INN:BAN]; VenlafaxineXR; Venlafaxinum; Venlafaxinum [INN-Latin]; Venlafexine; Venlafaxine; 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol; 1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol; 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol; 93413-69-5; CHEBI:9943; D,L-Venlafaxine; DSSTox_CID_3737; DSSTox_GSID_23737; DSSTox_RID_77175; Elafax; NCGC00095109-01; PNVNVHUZROJLTJ-UHFFFAOYSA-N; S-Venlafaxine; Wy 45030; Wy-45,030; Wy-45030; 1-(2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol hydrochloride; 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride; 99300-78-4; Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochloride; Dobupal; Efexor; Effexor; Effexor XR; Trevilor; VENLAFAXINE HCl; Vandral
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 313.9 Topological Polar Surface Area 32.7
Heavy Atom Count 21 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
62923
ChEBI ID
CHEBI:9944
CAS Number
99300-78-4
TTD Drug ID
D0P1UX
Formula
C17H28ClNO2
Canonical SMILES
CN(C)CC(C1=CC=C(C=C1)OC)C2(CCCCC2)O.Cl
InChI
1S/C17H27NO2.ClH/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14;/h7-10,16,19H,4-6,11-13H2,1-3H3;1H
InChIKey
QYRYFNHXARDNFZ-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
Desvenlafaxine DM005247
125017
Oxidation - O-demethylation 1 [2] , [6] , [7]
N-Desmethylvenlafaxine DM005251
3501942
Oxidation - N-demethylation 1 [2] , [6] , [7]
N,O-Didesmethylvenlafaxine DM000786
3451347
Oxidation - O-demethylation 2 [2] , [6] , [7]
N,O-Didesmethylvenlafaxine DM000786
3451347
Oxidation - N-demethylation 2 [2] , [6] , [7]
O-Desmethylvenlafaxine glucuronide DM005250
71315801
Conjugation - Glucuronidation 2 [2] , [6] , [7]
N,N,O-tridesmethylvenlafaxine DM005249
9859500
Oxidation - N-demethylation 3 [2] , [6] , [7]
N,O-didesmethylvenlafaxine glucuronide DM005248
71316036
Conjugation - Glucuronidation 3 [2] , [6] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005637 Venlafaxine hydrochloride Desvenlafaxine Oxidation - O-demethylation CYP2D6 ... [2], [6], [7]
MR005642 Venlafaxine hydrochloride N-Desmethylvenlafaxine Oxidation - N-demethylation CYP3A4 ... [2], [6], [7]
MR005638 Desvenlafaxine N,O-Didesmethylvenlafaxine Oxidation - N-demethylation CYP3A4 ... [2], [6], [7]
MR005641 Desvenlafaxine O-Desmethylvenlafaxine glucuronide Conjugation - Glucuronidation Unclear [2], [6], [7]
MR005643 N-Desmethylvenlafaxine N,O-Didesmethylvenlafaxine Oxidation - O-demethylation CYP3A4 ... [2], [6], [7]
MR005639 N,O-Didesmethylvenlafaxine N,O-didesmethylvenlafaxine glucuronide Conjugation - Glucuronidation Unclear [2], [6], [7]
MR005640 N,O-Didesmethylvenlafaxine N,N,O-tridesmethylvenlafaxine Oxidation - N-demethylation Unclear [2], [6], [7]
⏷ 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 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]
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
[2]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
⏷ Show the Full List of 8  DME(s)
References
1 Venlafaxine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 O- and N-demethylation of venlafaxine in vitro by human liver microsomes and by microsomes from cDNA-transfected cells: effect of metabolic inhibitors and SSRI antidepressants. Neuropsychopharmacology. 1999 May;20(5):480-90.
3 The associations between CYP2D6 metabolizer status and pharmacokinetics and clinical outcomes of venlafaxine: a systematic review and meta-analysis. Pharmacopsychiatry. 2019 Sep;52(5):222-231.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Venlafaxine oxidation in vitro is catalysed by CYP2D6. Br J Clin Pharmacol. 1996 Feb;41(2):149-56.
7 Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers

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