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

General Information of Drug (ID: DR1068)
Drug Name
Metoclopramide hydrochloride
Synonyms
Metoclopramide Intensol; Metoclopramide hydrochloride; Metoclopramide monohydrochloride; Metaclopramide; Metaclopromide; Methochlopramide; Methoclopramide; Metochlopramide; Metoclol; Metoclopramida; Metoclopramida [INN-Spanish]; Metoclopramidum; Metoclopramidum [INN-Latin]; Metocobil; Metramid; Moriperan; Parmid; Plasil; Plasil (pharmaceutical); Primperan; Reglan; Reliveran; Terperan; metoclopramide; 2-Methoxy-5-chloroprocainamide; 364-62-5; 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide; 5-Chloro-2-methoxyprocainamide; Metozolv; Paspertin; Primperan (tablet); Rimetin; 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide hydrochloride; 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-o-anisamide hydrochloride; 7232-21-5; 7B1QZY5SWZ; AHR-3070-C; C14H22ClN3O2.HCl; CCRIS 7142; EINECS 230-634-5; MFCD00058011; MLS000069667; Metoclopramide hydrochloride anhydrous; NSC 354467; SMR000058471; UNII-7B1QZY5SWZ; Clopra; DEL 1267; Elieten; Gastromax; Maxeran; METOCLOPRAMIDE HCL
Indication Functional nausea/vomiting [ICD11: DD90] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 336.3 Topological Polar Surface Area 67.6
Heavy Atom Count 21 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
23659
CAS Number
7232-21-5
TTD Drug ID
D08VYV
Formula
C14H23Cl2N3O2
Canonical SMILES
CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl.Cl
InChI
1S/C14H22ClN3O2.ClH/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3;/h8-9H,4-7,16H2,1-3H3,(H,17,19);1H
InChIKey
RVFUNJWWXKCWNS-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
Metoclopramide Conjugated metabolite DM004382 N. A. Conjugation - Sulfation 1 [3] , [2]
Metoclopramide hydrochloride Metabolite M1 DM004383 N. A. Multi-steps Reaction - Oxidationn; followed by glucuronidation 1 [4]
Metoclopramide hydrochloride Metabolite M10 DM004389 N. A. Oxidation - Nitration 1 [4]
Metoclopramide hydrochloride Metabolite M2 DM004384 N. A. Conjugation - Sulfonylation 1 [4]
Metoclopramide hydrochloride Metabolite M3 DM004385 N. A. Oxidation - N-dealkylation 1 [4]
Metoclopramide hydrochloride Metabolite M4 DM004379 N. A. Oxidation - Oxidationn 1 [4]
Metoclopramide hydrochloride Metabolite M5 DM004386 N. A. Unclear 1 [4]
Metoclopramide hydrochloride Metabolite M6 DM004380 N. A. Unclear 1 [4]
Metoclopramide hydrochloride Metabolite M7 DM004387 N. A. Conjugation - Glucuronidation 1 [4]
Metoclopramide hydrochloride Metabolite M9 DM004388 N. A. Other reaction - N-carbamoylation 1 [4]
Monodeethylmetoclopramide DM004381
101676518
Unclear 1 [5] , [6] , [2]
Metoclopramide hydrochloride Metabolite M6 DM004380 N. A. Other reaction - Oxidationn followed by glucuronidation 2 [4]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013395 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M4 Oxidation - Oxidationn CYP2D6 ... [4]
MR013397 Metoclopramide hydrochloride Monodeethylmetoclopramide Unclear CYP2D6 [5], [6], [2]
MR013398 Metoclopramide hydrochloride Metoclopramide Conjugated metabolite Conjugation - Sulfation Unclear [3], [2]
MR013399 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M1 Multi-steps Reaction - Oxidationn; followed by glucuronidation Unclear [4]
MR013400 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M2 Conjugation - Sulfonylation Unclear [4]
MR013401 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M3 Oxidation - N-dealkylation CYP2D6 ... [4]
MR013402 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M5 Unclear Unclear [4]
MR013403 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M6 Unclear Unclear [4]
MR013404 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M7 Conjugation - Glucuronidation Unclear [4]
MR013405 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M9 Other reaction - N-carbamoylation Unclear [4]
MR013406 Metoclopramide hydrochloride Metoclopramide hydrochloride Metabolite M10 Oxidation - Nitration CYP2D6 ... [4]
MR013396 Metoclopramide hydrochloride Metabolite M4 Metoclopramide hydrochloride Metabolite M6 Other reaction - Oxidationn followed by glucuronidation Unclear [4]
⏷ Show the Full List of 12 MR(s)
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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Metoclopramide Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metoclopramide is metabolized by CYP2D6 and is a reversible inhibitor, but not inactivator, of CYP2D6. Xenobiotica. 2014 Apr;44(4):309-319.
3 Clinical pharmacokinetics of metoclopramide
4 Identification of novel metoclopramide metabolites in humans: in vitro and in vivo studies
5 The gastroprokinetic and antiemetic drug metoclopramide is a substrate and inhibitor of cytochrome P450 2D6. Drug Metab Dispos. 2002 Mar;30(3):336-43.
6 Lessons from pharmacogenetics and metoclopramide: toward the right dose of the right drug for the right patient. J Clin Gastroenterol. 2012 Jul;46(6):437-9.

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