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

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

O.Cl.CCN(CC)CCNC(=O)C1=C(OC)C=C(N)C(Cl)=C1

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 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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H22ClN3O2
Molecular Weight 299.796
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
Letter: Metoclopramide and facial dyskinesia.
1975 Feb 8
Letter: Involuntary facial movements.
1975 Mar 29
Acute dystonia associated with fluvoxamine-metoclopramide.
1999 Mar
Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs.
1999 Mar
Tetanus-like syndrome secondary to metoclopramide administration.
2000 Oct-Dec
Placebo-controlled comparison of dolasetron and metoclopramide in preventing postoperative nausea and vomiting in patients undergoing hysterectomy.
2001 Apr
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.
2001 Aug
Persistent hiccup associated with thoracic epidural injection.
2001 Aug
[Acute treatment of infantile headache].
2001 Aug 1-15
[Acute dystonia caused by metoclopramide (Afipran) therapy].
2001 Aug 10
Gastroparesis: prevalence, clinical significance and treatment.
2001 Dec
Metoclopramide versus ondansetron in prophylaxis of nausea and vomiting for laparoscopic cholecystectomy.
2001 Feb
[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo].
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
Clearance of barium from the oesophagus with diet cola and metoclopramide: a one stop approach to patients with dysphagia.
2001 Jan
Comparison of ondansetron-dexamethasone-lorazepam versus metoclopramide-dexamethasone-lorazepam in the control of cisplatin induced emesis.
2001 Jul
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
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
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
Comparison of granisetron, droperidol, and metoclopramide for prevention of postoperative vomiting in children with a history of motion sickness undergoing tonsillectomy.
2001 Mar
Effect of ATP sensitive potassium channel modifiers on antinociceptive effect of metoclopramide.
2001 May
Impact of antiemetic selection on postoperative nausea and vomiting and patient satisfaction.
2001 May
A simple method to investigate the inhibitory effects of drugs on gastric emptying in the mouse in vivo.
2001 May-Jun
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
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility].
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
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 Wed Jul 05 22:35:00 UTC 2023
Edited
by admin
on Wed Jul 05 22:35:00 UTC 2023
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
METOCLOPRAMIDE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
NSC-757117
Code English
REGLAN
Brand 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
Metoclopramide hydrochloride [WHO-DD]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE MONOHYDRATE
WHO-DD  
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [USP-RS]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [VANDF]
Common Name English
GIMOTI
Brand Name English
Metipamid [WHO-DD]
Common 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
MAXOLON
Brand Name English
METOCLOPRAMIDE HYDROCHLORIDE [WHO-IP]
Common Name English
Metoclopramide hydrochloride monohydrate [WHO-DD]
Common Name English
METOCLOPRAMIDE HYDROCHLORIDE [EP IMPURITY]
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-, MONOHYDROCHLORIDE, MONOHYDRATE
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 Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C649
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
CAS
54143-57-6
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
EVMPD
SUB16443MIG
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
DRUG BANK
DBSALT000393
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
SMS_ID
100000091552
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
RXCUI
267036
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY RxNorm
NSC
757117
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
DAILYMED
W1792A2RVD
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
EVMPD
SUB03271MIG
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
PUBCHEM
441347
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METOCLOPRAMIDE HYDROCHLORIDE
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
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 Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
FDA UNII
W1792A2RVD
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
RS_ITEM_NUM
1440808
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
WIKIPEDIA
Metoclopramide hydrochloride
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
MERCK INDEX
M7489
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY Merck Index
CHEBI
6899
Created by admin on Wed Jul 05 22:35:00 UTC 2023 , Edited by admin on Wed Jul 05 22:35:00 UTC 2023
PRIMARY
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