U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C14H22ClN3O2
Molecular Weight 299.796
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOCLOPRAMIDE

SMILES

CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC

InChI

InChIKey=TTWJBBZEZQICBI-UHFFFAOYSA-N
InChI=1S/C14H22ClN3O2/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)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/017854s058lbl.pdf

Metoclopramide is a dopamine D2 antagonist that is used as an antiemetic. Metoclopramide inhibits gastric smooth muscle relaxation produced by dopamine, therefore increasing cholinergic response of the gastrointestinal smooth muscle. It accelerates intestinal transit and gastric emptying by preventing relaxation of gastric body and increasing the phasic activity of antrum. Simultaneously, this action is accompanied by relaxation of the upper small intestine, resulting in an improved coordination between the body and antrum of the stomach and the upper small intestine. Metoclopramide also decreases reflux into the esophagus by increasing the resting pressure of the lower esophageal sphincter and improves acid clearance from the esophagus by increasing amplitude of esophageal peristaltic contractions. Metoclopramide's dopamine antagonist action raises the threshold of activity in the chemoreceptor trigger zone and decreases the input from afferent visceral nerves. Studies have also shown that high doses of metoclopramide can antagonize 5-hydroxytryptamine (5-HT) receptors in the peripheral nervous system in animals. Metoclopramide is used for the treatment of gastroesophageal reflux disease (GERD). It is also used in treating nausea and vomiting, and to increase gastric emptying.

CNS Activity

Curator's Comment: metoclopramide readily crosses the blood-brain barrier

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
REGLAN

Approved Use

Symptomatic Gastroesophageal Reflux Reglan® tablets are indicated as short-term (4 to 12 weeks) therapy for adults with symptomatic, documented gastroesophageal reflux who fail to respond to conventional therapy Diabetic Gastroparesis (Diabetic Gastric Stasis) Reglan® tablets (metoclopramide tablets, USP) is indicated for the relief of symptoms associated with acute and recurrent diabetic gastric stasis.

Launch Date

1980
Palliative
REGLAN

Approved Use

Symptomatic Gastroesophageal Reflux Reglan® tablets are indicated as short-term (4 to 12 weeks) therapy for adults with symptomatic, documented gastroesophageal reflux who fail to respond to conventional therapy Diabetic Gastroparesis (Diabetic Gastric Stasis) Reglan® tablets (metoclopramide tablets, USP) is indicated for the relief of symptoms associated with acute and recurrent diabetic gastric stasis.

Launch Date

1980
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
41 ng/mL
15 mg single, nasal
dose: 15 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
METOCLOPRAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
367 ng × h/mL
15 mg single, nasal
dose: 15 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
METOCLOPRAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.1 h
15 mg single, nasal
dose: 15 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
METOCLOPRAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
15 mg single, nasal
dose: 15 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
METOCLOPRAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
unlikely (co-administration study)
Comment: metoclopramide is unlikely to interact with CYP2D6 substrates in vivo at therapeutically relevant concentrations
Page: 15.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: patients who received concomitant metoclopramide and fluoxetine had a 40% and 90% increase in metoclopramide Cmax and AUC0-∞, respectively
Page: 13.0
minor
minor
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Letter: Involuntary facial movements.
1975 Mar 29
Pharmacological options for the treatment of Tourette's disorder.
2001
Ondansetron: a review of its use as an antiemetic in children.
2001
Erythromycin as a gastrointestinal prokinetic agent.
2001 Apr
Mongolian spots with involvement of the temporal area.
2001 Apr
Placebo-controlled comparison of dolasetron and metoclopramide in preventing postoperative nausea and vomiting in patients undergoing hysterectomy.
2001 Apr
Iatrogenic metoclopramide toxicity in an infant presenting to a pediatric emergency department.
2001 Apr
An endogenous 5-HT(7) receptor mediates pigment granule dispersion in Xenopus laevis melanophores.
2001 Apr
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.
2001 Apr-Jun
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.
2001 Aug
[Acute treatment of infantile headache].
2001 Aug 1-15
Gastroparesis: prevalence, clinical significance and treatment.
2001 Dec
Metoclopramide versus ondansetron in prophylaxis of nausea and vomiting for laparoscopic cholecystectomy.
2001 Feb
Effects of dopamine antagonists in human eye accommodation.
2001 Feb
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].
2001 Feb
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.
2001 Feb 10
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.
2001 Feb 10
Generalised seizures following ondansetron.
2001 Jan
Gastroparesis following bone marrow transplantation.
2001 Jul
[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo].
2001 Jul
[Sinus arrest after the administration of intravenous metoclopramide].
2001 Jul 14
The cardiovascular effects of metoclopramide in multiple system atrophy and pure autonomic failure.
2001 Jun
Gastric emptying in the critically ill.
2001 Jun
Serum prolactin is associated with apoptosis in men with human immunodeficiency virus infection.
2001 Jun
A spectrophotometric method for the determination of metoclopramide HCl and dapsone.
2001 Jun
Supraglottic dystonic reaction to metoclopramide in a child.
2001 Jun 4
Reproductive experience modulates dopamine-related behavioral responses.
2001 Mar
Gastroesophageal reflux medications in the treatment of apnea in premature infants.
2001 Mar
Small doses of propofol, droperidol, and metoclopramide for the prevention of postoperative nausea and vomiting after thyroidectomy.
2001 Mar
Effects of i.v. metoclopramide, atropine and their combination on gastric insufflation in children anaesthetized with sevoflurane and nitrous oxide.
2001 Mar
Induction of lactation in the intended mother of a surrogate pregnancy: case report.
2001 Mar
Comparison of granisetron, droperidol, and metoclopramide for prevention of postoperative vomiting in children with a history of motion sickness undergoing tonsillectomy.
2001 Mar
Dopaminergic modulation of human bronchial tone.
2001 Mar-Apr
Metoclopramide-induced akathisia during the second trimester of a 37-year-old woman's first pregnancy.
2001 Mar-Apr
Effect of ATP sensitive potassium channel modifiers on antinociceptive effect of metoclopramide.
2001 May
Study of drug release from pellets coated with Surelease containing hydroxypropylmethylcellulose.
2001 May
Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats.
2001 May
Ondansetron rather than metoclopramide for bupropion-induced nausea.
2001 May
Impact of antiemetic selection on postoperative nausea and vomiting and patient satisfaction.
2001 May
Nasty shock after an anti-emetic.
2001 May
Laryngospasm: an atypical manifestation of severe gastroesophageal reflux disease (GERD).
2001 Nov
Comparison of cisapride and metoclopramide for facilitating gastric emptying and improving tolerance to intragastric enteral nutrition in critically III, mechanically ventilated adults.
2001 Nov
Endoscopic balloon dilation of benign esophageal strictures in dogs and cats.
2001 Nov-Dec
In vitro release of metoclopramide from hydrophobic matrix tablets. influence of hydrodynamic conditions on kinetic release parameters.
2001 Oct
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility].
2001 Sep
Metoclopramide-related pisa syndrome in clozapine treatment.
2001 Summer
Serotonin syndrome caused by selective serotonin reuptake-inhibitors-metoclopramide interaction.
2002 Jan
Why not to use erythromycin in GI motility.
2002 Jan
Effect of prolactin and dopaminergic drugs on uterine response to chronic estrogen exposure.
2002 Jan
Physical compatibility and in vivo evaluation of drug mixtures for subcutaneous infusion to cancer patients in palliative care.
2002 Jan
Patents

Sample Use Guides

For the relief of Symptomatic Gastroesophageal Reflux Administer from 10 mg to 15 mg reglan® (metoclopramide hydrochloride, USP) orally up to q.i.d. 30 minutes before each meal and at bedtime, depending upon symptoms being treated and clinical response
Route of Administration: Oral
200 nM metoclopramide led to 79% peak current suppression in HEK-293 cells
Name Type Language
ELIETEN
Preferred Name English
METOCLOPRAMIDE
EP   HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
METOCLOPRAMIDE [HSDB]
Common Name English
4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-O-ANISAMIDE
Common Name English
METOCLOPRAMIDE [JAN]
Common Name English
METOCLOPRAMIDE [MART.]
Common Name English
METOCLOPRAMIDE [MI]
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-
Systematic Name English
METHOXYCLOPRAMIDE
Common Name English
METOCLOPRAMIDE [EP MONOGRAPH]
Common Name English
METOCLOPRAMIDE [VANDF]
Common Name English
Metoclopramide [WHO-DD]
Common Name English
metoclopramide [INN]
Common Name English
TERPERAN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 17.2
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
NDF-RT N0000175799
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
WHO-VATC QA03FA01
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
WHO-ATC A03FA01
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
LIVERTOX NBK548630
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
NDF-RT N0000175800
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
Code System Code Type Description
EVMPD
SUB08902MIG
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
MESH
D008787
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
DAILYMED
L4YEB44I46
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
MERCK INDEX
m7489
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY Merck Index
SMS_ID
100000091624
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
HSDB
7841
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
PUBCHEM
4168
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
DRUG CENTRAL
1782
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
CAS
364-62-5
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
IUPHAR
241
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
WIKIPEDIA
METOCLOPRAMIDE
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
ChEMBL
CHEMBL86
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
NCI_THESAURUS
C62046
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
INN
1740
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
DRUG BANK
DB01233
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID6045169
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
FDA UNII
L4YEB44I46
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
RXCUI
6915
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY RxNorm
CHEBI
107736
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-662-9
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY
LACTMED
Metoclopramide
Created by admin on Mon Mar 31 17:50:22 GMT 2025 , Edited by admin on Mon Mar 31 17:50:22 GMT 2025
PRIMARY