U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H22ClN3O2
Molecular Weight 299.7969
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOCLOPRAMIDE

SMILES

CCN(CC)CCN=C(c1cc(c(cc1OC)N)Cl)O

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

Molecular Formula C14H22ClN3O2
Molecular Weight 299.7969
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

3.46896007E11
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

3.46896007E11
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: Metoclopramide and facial dyskinesia.
1975 Feb 8
Erythromycin as a gastrointestinal prokinetic agent.
2001 Apr
Iatrogenic metoclopramide toxicity in an infant presenting to a pediatric emergency department.
2001 Apr
Nonulcer Dyspepsia.
2001 Aug
[Acute dystonia caused by metoclopramide (Afipran) therapy].
2001 Aug 10
RP-HPLC method with electrochemical detection for the determination of metoclopramide in serum and its use in pharmacokinetic studies.
2001 Dec
[Evaluation and treatment of hyperemesis gravidarum].
2001 Dec
Randomized clinical trial of intravenous magnesium sulfate as an adjunctive medication for emergency department treatment of migraine headache.
2001 Dec
Gastroesophageal reflux in infants and children.
2001 Dec 1
Metoclopramide versus ondansetron in prophylaxis of nausea and vomiting for laparoscopic cholecystectomy.
2001 Feb
Evaluation of the effective drugs for the prevention of nausea and vomiting induced by morphine used for postoperative pain: a quantitative systematic review.
2001 Feb
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.
2001 Feb 10
Maternal prolactin secretion during labor. The role of dopamine.
2001 Jan
Impact of an antiemetic protocol on postoperative nausea and vomiting in children.
2001 Jan
Comparison of ondansetron-dexamethasone-lorazepam versus metoclopramide-dexamethasone-lorazepam in the control of cisplatin induced emesis.
2001 Jul
Pharmacoeconomic issues of the treatment of gastroesophageal reflux disease.
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
Laryngeal dystonia in psychiatry.
2001 Jun
Metoclopramide-induced methemoglobinemia in a patient with co-existing deficiency of glucose-6-phosphate dehydrogenase and NADH-cytochrome b5 reductase: failure of methylene blue treatment.
2001 Jun
Serum prolactin is associated with apoptosis in men with human immunodeficiency virus infection.
2001 Jun
Supraglottic dystonic reaction to metoclopramide in a child.
2001 Jun 4
Reproductive experience modulates dopamine-related behavioral responses.
2001 Mar
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
Nasty shock after an anti-emetic.
2001 May
A simple method to investigate the inhibitory effects of drugs on gastric emptying in the mouse in vivo.
2001 May-Jun
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
AS-924, a novel, orally active, bifunctional prodrug of ceftizoxime: physicochemical properties, oral absorption in animals, and antibacterial activity.
2001 Nov
Aberrant membrane hormone receptors in incidentally discovered bilateral macronodular adrenal hyperplasia with subclinical Cushing's syndrome.
2001 Nov
Low-dose dexamethasone effectively prevents postoperative nausea and vomiting after ambulatory laparoscopic surgery.
2001 Nov
Endoscopic balloon dilation of benign esophageal strictures in dogs and cats.
2001 Nov-Dec
Initial experience with the stretta procedure for the treatment of gastroesophageal reflux disease.
2001 Oct
In vitro release of metoclopramide from hydrophobic matrix tablets. influence of hydrodynamic conditions on kinetic release parameters.
2001 Oct
Preoperative diagnosis and localization of aldosterone-producing adenoma by adrenal venous sampling after administration of metoclopramide.
2001 Sep
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility].
2001 Sep
Comparing the efficacy of prophylactic metoclopramide, ondansetron, and placebo in cesarean section patients given epidural anesthesia.
2001 Sep
Growth hormone and prolactin secretion after metoclopramide administration (DA2 receptor blockade) in fertile women.
2001 Sep
Prevention of postoperative nausea and vomiting after laparoscopic gynaecological surgery. Combined antiemetic treatment with tropisetron and metoclopramide vs. metoclopramide alone.
2001 Sep
Metoclopramide-related pisa syndrome in clozapine treatment.
2001 Summer
Comparison of ondansetron with metoclopramide in the symptomatic relief of uremia-induced nausea and vomiting.
2002
[Syncope - a systematic overview of classification, pathogenesis, diagnosis and management].
2002 Feb
Acute dystonia due to metoclopramide: increased risk in AIDS.
2002 Feb 11
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:13:10 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:10 UTC 2021
Record UNII
L4YEB44I46
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
ELIETEN
Brand 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 Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 17.2
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
NDF-RT N0000175799
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
WHO-VATC QA03FA01
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
WHO-ATC A03FA01
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
LIVERTOX 629
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
NDF-RT N0000175800
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
Code System Code Type Description
EVMPD
SUB08902MIG
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
MESH
D008787
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
MERCK INDEX
M7489
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY Merck Index
HSDB
7841
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
PUBCHEM
4168
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
DRUG CENTRAL
1782
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
CAS
364-62-5
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
IUPHAR
241
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
WIKIPEDIA
METOCLOPRAMIDE
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL86
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
NCI_THESAURUS
C62046
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
INN
1740
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
DRUG BANK
DB01233
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
EPA CompTox
364-62-5
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
FDA UNII
L4YEB44I46
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
RXCUI
6915
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
206-662-9
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
LACTMED
Metoclopramide
Created by admin on Fri Jun 25 21:13:10 UTC 2021 , Edited by admin on Fri Jun 25 21:13:10 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
METABOLIC ENZYME -> INHIBITOR
IC50
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO AND IN VIVO
METABOLITE -> PARENT
IN VITRO AND IN VIVO
METABOLITE -> PARENT
IN VITRO AND IN VIVO
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC SINGLE ORAL ADMINISTRATION

Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Population
PHARMACOKINETIC
Population
PHARMACOKINETIC