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Details

Stereochemistry ACHIRAL
Molecular Formula C14H22ClN3O2.ClH.H2O
Molecular Weight 354.273
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOCLOPRAMIDE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=KJBLQGHJOCAOJP-UHFFFAOYSA-N
InChI=1S/C14H22ClN3O2.ClH.H2O/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;1H2

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Metoclopramide and pimozide in Parkinson's disease and levodopa-induced dyskinesias.
1975 Apr
Letter: Involuntary facial movements.
1975 Mar 29
Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs.
1999 Mar
Cloning, expression, and characterization of ferret 5-HT(3) receptor subunit.
2000 Jul 7
[Extrapyramidal reactions after epidural droperidol].
2000 Oct
Pharmacological options for the treatment of Tourette's disorder.
2001
Erythromycin as a gastrointestinal prokinetic agent.
2001 Apr
Mongolian spots with involvement of the temporal area.
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
Nonulcer Dyspepsia.
2001 Aug
[Acute treatment of infantile headache].
2001 Aug 1-15
[Pheochromocytoma with severe paralytic ileus occurred from acute pulmonary edema caused by metoclopramide].
2001 Aug 10
[Acute dystonia caused by metoclopramide (Afipran) therapy].
2001 Aug 10
Effects of dopamine antagonists in human eye accommodation.
2001 Feb
What is the optimal strategy for managing acute migraine headaches?
2001 Feb
Galactorrhoea, hyperprolactinaemia, and protease inhibitors.
2001 Feb 10
Generalised seizures following ondansetron.
2001 Jan
Clearance of barium from the oesophagus with diet cola and metoclopramide: a one stop approach to patients with dysphagia.
2001 Jan
Impact of an antiemetic protocol on postoperative nausea and vomiting in children.
2001 Jan
Pharmacoeconomic issues of the treatment of gastroesophageal reflux disease.
2001 Jul
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.
2001 Jul 7
Gastric residual volume in children: a study comparing efficiency of erythromycin and metoclopramide as prokinetic agents.
2001 Jun
Laryngeal dystonia in psychiatry.
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
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
Metoclopramide-induced akathisia during the second trimester of a 37-year-old woman's first pregnancy.
2001 Mar-Apr
Study of drug release from pellets coated with Surelease containing hydroxypropylmethylcellulose.
2001 May
Impact of antiemetic selection on postoperative nausea and vomiting and patient satisfaction.
2001 May
AS-924, a novel, orally active, bifunctional prodrug of ceftizoxime: physicochemical properties, oral absorption in animals, and antibacterial activity.
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
Efficacy of metoclopramide in postoperative ileus after exploratory laparotomy.
2001 Oct
[ 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
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
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 21:01:13 UTC 2021
Edited
by admin
on Fri Jun 25 21:01:13 UTC 2021
Record UNII
W1792A2RVD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METOCLOPRAMIDE HYDROCHLORIDE
EP   JAN   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN  
Official Name English
METOCLOPRAMIDE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
METOCLOPRAMIDE MONOHYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
METOZOLV ODT
Brand Name English
NSC-757117
Code English
REGLAN
Brand Name English
METOCLOPRAMIDE HYDROCHLORIDE [USP]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE MONOHYDRATE [EP MONOGRAPH]
Common Name English
METOCLOPRAMIDI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
CLOPRA
Brand Name English
METIPAMID
WHO-DD  
Brand Name English
METIPAMID [WHO-DD]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE MONOHYDRATE
WHO-DD  
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [EP]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [USP-RS]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [VANDF]
Common Name English
GIMOTI
Brand Name English
METOCLOPRAMIDE HCL MONOHYDRATE
Common Name English
AHR-3070-C
Code English
4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-O-ANISAMIDE MONOHYDROCHLORIDE MONOHYDRATE
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE MONOHYDRATE [WHO-DD]
Common Name English
MAXOLON
Brand Name English
METOCLOPRAMIDE HYDROCHLORIDE [WHO-IP]
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-, MONOHYDROCHLORIDE, MONOHYDRATE
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [WHO-DD]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [USAN]
Common Name English
METOCLOPRAMIDE MONOHYDROCHLORIDE MONOHYDRATE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C649
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
CAS
54143-57-6
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
EVMPD
SUB16443MIG
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
DRUG BANK
DBSALT000393
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
USP_CATALOG
1440808
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY USP-RS
RXCUI
267036
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY RxNorm
EVMPD
SUB03271MIG
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
PUBCHEM
441347
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METOCLOPRAMIDE HYDROCHLORIDE
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Very soluble in water; freely soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antiemetic drug. Storage: Metoclopramide hydrochloride should be kept in a well-closed container, protected from light. Definition: Metoclopramide hydrochloride contains not less than 98.0% and not more than 101.0% of C14H22ClN3O2,HCl, calculated with reference to the anhydrous substance.
EVMPD
SUB14566MIG
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
FDA UNII
W1792A2RVD
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
WIKIPEDIA
Metoclopramide hydrochloride
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY
MERCK INDEX
M7489
Created by admin on Fri Jun 25 21:01:13 UTC 2021 , Edited by admin on Fri Jun 25 21:01:13 UTC 2021
PRIMARY Merck Index
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