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Details

Stereochemistry ACHIRAL
Molecular Formula C14H22ClN3O2.2ClH
Molecular Weight 372.7186
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOCLOPRAMIDE DIHYDROCHLORIDE

SMILES

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

InChI

InChIKey=HPPDSFRJRMUHSC-UHFFFAOYSA-N
InChI=1S/C14H22ClN3O2.2ClH/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);2*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
Ondansetron: a review of its use as an antiemetic in children.
2001
Erythromycin as a gastrointestinal prokinetic agent.
2001 Apr
Mongolian spots with involvement of the temporal area.
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
[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
Gastroparesis: prevalence, clinical significance and treatment.
2001 Dec
Randomized clinical trial of intravenous magnesium sulfate as an adjunctive medication for emergency department treatment of migraine headache.
2001 Dec
Gastroesophageal reflux in infants and children.
2001 Dec 1
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
Comparison of ondansetron-dexamethasone-lorazepam versus metoclopramide-dexamethasone-lorazepam in the control of cisplatin induced emesis.
2001 Jul
Pharmacoeconomic issues of the treatment of gastroesophageal reflux disease.
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
[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
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
Laryngeal dystonia in psychiatry.
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
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
Effect of transitory hyperprolactinemia on in vitro fertilization of human oocytes.
2001 May
Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats.
2001 May
Laryngospasm: an atypical manifestation of severe gastroesophageal reflux disease (GERD).
2001 Nov
Comparison of cisapride and metoclopramide for facilitating gastric emptying and improving tolerance to intragastric enteral nutrition in critically III, mechanically ventilated adults.
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
Efficacy of metoclopramide in postoperative ileus after exploratory laparotomy.
2001 Oct
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
Acute dystonia due to metoclopramide: increased risk in AIDS.
2002 Feb 11
Serotonin syndrome caused by selective serotonin reuptake-inhibitors-metoclopramide interaction.
2002 Jan
Why not to use erythromycin in GI motility.
2002 Jan
Effect of prolactin and dopaminergic drugs on uterine response to chronic estrogen exposure.
2002 Jan
Physical compatibility and in vivo evaluation of drug mixtures for subcutaneous infusion to cancer patients in palliative care.
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 Sat Jun 26 11:43:46 UTC 2021
Edited
by admin
on Sat Jun 26 11:43:46 UTC 2021
Record UNII
5YNA80E9TO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METOCLOPRAMIDE DIHYDROCHLORIDE
WHO-DD  
Common Name English
ANHYDROUS METOCLOPRAMIDE DIHYDROCHLORIDE
Common Name English
O-ANISAMIDE, 4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-, DIHYDROCHLORIDE
Common Name English
4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXYBENZAMIDE DIHYDROCHLORIDE
Systematic Name English
METOCLOPRAMIDE DIHYDROCHLORIDE [WHO-DD]
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-, HYDROCHLORIDE (1:2)
Systematic Name English
Code System Code Type Description
EVMPD
SUB179286
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY
RXCUI
267035
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY RxNorm
FDA UNII
5YNA80E9TO
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
219-926-3
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY
CAS
2576-84-3
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY
EPA CompTox
2576-84-3
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY
PUBCHEM
21761
Created by admin on Sat Jun 26 11:43:46 UTC 2021 , Edited by admin on Sat Jun 26 11:43:46 UTC 2021
PRIMARY
Related Record Type Details
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