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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=C(OC)C=C(N)C(Cl)=C1

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 299.796
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
Metoclopramide and pimozide in Parkinson's disease and levodopa-induced dyskinesias.
1975 Apr
Cloning, expression, and characterization of ferret 5-HT(3) receptor subunit.
2000 Jul 7
Tetanus-like syndrome secondary to metoclopramide administration.
2000 Oct-Dec
Mongolian spots with involvement of the temporal area.
2001 Apr
Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients.
2001 Apr-Jun
Variation in practice patterns of anesthesiologists in California for prophylaxis of postoperative nausea and vomiting.
2001 Aug
Prevention of vomiting after general anesthesia for pediatric ophthalmic surgery.
2001 Feb
Metoclopramide versus ondansetron in prophylaxis of nausea and vomiting for laparoscopic cholecystectomy.
2001 Feb
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.
2001 Feb 10
Prevention of postoperative nausea and vomiting with antiemetics in patients undergoing middle ear surgery: comparison of a small dose of propofol with droperidol or metoclopramide.
2001 Jan
Gastroparesis following bone marrow transplantation.
2001 Jul
Preparation and in vivo evaluation of parenteral metoclopramide-loaded poly(alkylcyanoacrylate) nanospheres in rats.
2001 Jul-Aug
Pre-emptive metoclopramide and ondansetron for nausea and vomiting associated with iloprost infusions.
2001 Jun
Decreased dopaminergic tone and increased basal bioactive prolactin in men with human immunodeficiency virus infection.
2001 Jun
Gastric emptying in the critically ill.
2001 Jun
Gastroesophageal reflux medications in the treatment of apnea in premature infants.
2001 Mar
Effects of i.v. metoclopramide, atropine and their combination on gastric insufflation in children anaesthetized with sevoflurane and nitrous oxide.
2001 Mar
Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats.
2001 May
Nasty shock after an anti-emetic.
2001 May
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
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
Serotonin syndrome caused by selective serotonin reuptake-inhibitors-metoclopramide interaction.
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 Dec 16 16:31:01 UTC 2022
Edited
by admin
on Fri Dec 16 16:31:01 UTC 2022
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 Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 17.2
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
NDF-RT N0000175799
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
WHO-VATC QA03FA01
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
WHO-ATC A03FA01
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
LIVERTOX NBK548630
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
NDF-RT N0000175800
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
Code System Code Type Description
EVMPD
SUB08902MIG
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
MESH
D008787
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
DAILYMED
L4YEB44I46
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
MERCK INDEX
M7489
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY Merck Index
HSDB
7841
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
PUBCHEM
4168
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
DRUG CENTRAL
1782
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
CAS
364-62-5
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
IUPHAR
241
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
WIKIPEDIA
METOCLOPRAMIDE
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
ChEMBL
CHEMBL86
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
NCI_THESAURUS
C62046
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
INN
1740
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
DRUG BANK
DB01233
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
EPA CompTox
DTXSID6045169
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
FDA UNII
L4YEB44I46
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
RXCUI
6915
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY RxNorm
CHEBI
107736
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
ECHA (EC/EINECS)
206-662-9
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
LACTMED
Metoclopramide
Created by admin on Fri Dec 16 16:31:01 UTC 2022 , Edited by admin on Fri Dec 16 16:31:01 UTC 2022
PRIMARY
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Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
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Volume of Distribution PHARMACOKINETIC
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