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Details

Stereochemistry ACHIRAL
Molecular Formula C14H22ClN3O2.ClH
Molecular Weight 336.2577
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOCLOPRAMIDE HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=RVFUNJWWXKCWNS-UHFFFAOYSA-N
InChI=1S/C14H22ClN3O2.ClH/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

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 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: Involuntary facial movements.
1975 Mar 29
Pharmacological options for the treatment of Tourette's disorder.
2001
Ondansetron: a review of its use as an antiemetic in children.
2001
Mongolian spots with involvement of the temporal area.
2001 Apr
Placebo-controlled comparison of dolasetron and metoclopramide in preventing postoperative nausea and vomiting in patients undergoing hysterectomy.
2001 Apr
An endogenous 5-HT(7) receptor mediates pigment granule dispersion in Xenopus laevis melanophores.
2001 Apr
Variation in practice patterns of anesthesiologists in California for prophylaxis of postoperative nausea and vomiting.
2001 Aug
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
Nonulcer Dyspepsia.
2001 Aug
Gastroparesis: prevalence, clinical significance and treatment.
2001 Dec
RP-HPLC method with electrochemical detection for the determination of metoclopramide in serum and its use in pharmacokinetic studies.
2001 Dec
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
Effects of dopamine antagonists in human eye accommodation.
2001 Feb
[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
Gastroparesis following bone marrow transplantation.
2001 Jul
[Sinus arrest after the administration of intravenous metoclopramide].
2001 Jul 14
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.
2001 Jul 7
Preparation and in vivo evaluation of parenteral metoclopramide-loaded poly(alkylcyanoacrylate) nanospheres in rats.
2001 Jul-Aug
The cardiovascular effects of metoclopramide in multiple system atrophy and pure autonomic failure.
2001 Jun
Gastric residual volume in children: a study comparing efficiency of erythromycin and metoclopramide as prokinetic agents.
2001 Jun
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
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
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
Gastroesophageal reflux medications in the treatment of apnea in premature infants.
2001 Mar
Dopaminergic modulation of human bronchial tone.
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
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
Impact of antiemetic selection on postoperative nausea and vomiting and patient satisfaction.
2001 May
Nasty shock after an anti-emetic.
2001 May
Initial experience with the stretta procedure for the treatment of gastroesophageal reflux disease.
2001 Oct
Efficacy of metoclopramide in postoperative ileus after exploratory laparotomy.
2001 Oct
Preoperative diagnosis and localization of aldosterone-producing adenoma by adrenal venous sampling after administration of metoclopramide.
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
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 Sat Jun 26 03:48:16 UTC 2021
Edited
by admin
on Sat Jun 26 03:48:16 UTC 2021
Record UNII
7B1QZY5SWZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METOCLOPRAMIDE HYDROCHLORIDE ANHYDROUS
Common Name English
NSC-354467
Code English
METOCLOPRAMIDE HCL
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-, MONOHYDROCHLORIDE
Common Name English
4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-O-ANISAMIDE MONOHYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C87710
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
DRUG BANK
DBSALT002458
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
PUBCHEM
23659
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
FDA UNII
7B1QZY5SWZ
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
EVMPD
SUB03271MIG
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
ECHA (EC/EINECS)
230-634-5
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL86
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
CAS
7232-21-5
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
EVMPD
SUB179494
Created by admin on Sat Jun 26 03:48:16 UTC 2021 , Edited by admin on Sat Jun 26 03:48:16 UTC 2021
PRIMARY
Related Record Type Details
SUBSTANCE->BASIS OF STRENGTH
ASSAY (TITRATION)
USP
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY