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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

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: Involuntary facial movements.
1975 Mar 29
[Extrapyramidal syndromes as side-effects of metoclopramide (Cerucal) medication].
1976 Dec
Drug-induced motor complications in dopa-responsive dystonia: implications for the pathogenesis of dyskinesias and motor fluctuations.
1999 Jul-Aug
Acute dystonia associated with fluvoxamine-metoclopramide.
1999 Mar
[Extrapyramidal reactions after epidural droperidol].
2000 Oct
Pharmacological options for the treatment of Tourette's disorder.
2001
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
Gastroesophageal reflux in infants and children.
2001 Dec 1
[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
Comparison of ondansetron-dexamethasone-lorazepam versus metoclopramide-dexamethasone-lorazepam in the control of cisplatin induced emesis.
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
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
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
Nasty shock after an anti-emetic.
2001 May
Comparison of cisapride and metoclopramide for facilitating gastric emptying and improving tolerance to intragastric enteral nutrition in critically III, mechanically ventilated adults.
2001 Nov
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
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
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
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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
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PRIMARY
MESH
D008787
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PRIMARY
MERCK INDEX
M7489
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PRIMARY Merck Index
HSDB
7841
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PRIMARY
PUBCHEM
4168
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PRIMARY
DRUG CENTRAL
1782
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PRIMARY
CAS
364-62-5
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PRIMARY
IUPHAR
241
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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
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PRIMARY
INN
1740
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PRIMARY
DRUG BANK
DB01233
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PRIMARY
EPA CompTox
364-62-5
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PRIMARY
FDA UNII
L4YEB44I46
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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