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
SMILES
CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB01233Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/017854s058lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01233
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
Sources: http://www.medscape.com/viewarticle/429668_3
Curator's Comment: metoclopramide readily crosses the blood-brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB01233 |
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Target ID: CHEMBL320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15105209 |
24.0 µM [IC50] | ||
Target ID: CHEMBL217 Sources: http://www.drugbank.ca/drugs/DB01233 |
100.0 nM [IC50] | ||
Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16041395 |
0.064 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | REGLAN Approved UseSymptomatic 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 Date1980 |
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Palliative | REGLAN Approved UseSymptomatic 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 Date1980 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 15.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 13.0 |
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 |
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minor | ||||
minor |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Letter: Involuntary facial movements. | 1975 Mar 29 |
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Pharmacological options for the treatment of Tourette's disorder. | 2001 |
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Ondansetron: a review of its use as an antiemetic in children. | 2001 |
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Erythromycin as a gastrointestinal prokinetic agent. | 2001 Apr |
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Mongolian spots with involvement of the temporal area. | 2001 Apr |
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Placebo-controlled comparison of dolasetron and metoclopramide in preventing postoperative nausea and vomiting in patients undergoing hysterectomy. | 2001 Apr |
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Iatrogenic metoclopramide toxicity in an infant presenting to a pediatric emergency department. | 2001 Apr |
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An endogenous 5-HT(7) receptor mediates pigment granule dispersion in Xenopus laevis melanophores. | 2001 Apr |
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Ondansetron versus dehydrobenzoperidol and metoclopramide for management of postoperative nausea in laparoscopic surgery patients. | 2001 Apr-Jun |
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Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors. | 2001 Aug |
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[Acute treatment of infantile headache]. | 2001 Aug 1-15 |
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Gastroparesis: prevalence, clinical significance and treatment. | 2001 Dec |
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Metoclopramide versus ondansetron in prophylaxis of nausea and vomiting for laparoscopic cholecystectomy. | 2001 Feb |
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Effects of dopamine antagonists in human eye accommodation. | 2001 Feb |
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[Prevention of postoperative nausea and vomiting in gynecologic surgery with 3 fixed doses of metoclopramide, droperidol or placebo]. | 2001 Feb |
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Galactorrhoea, hyperprolactinaemia, and protease inhibitors. | 2001 Feb 10 |
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Galactorrhoea, hyperprolactinaemia, and protease inhibitors. | 2001 Feb 10 |
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Generalised seizures following ondansetron. | 2001 Jan |
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Gastroparesis following bone marrow transplantation. | 2001 Jul |
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[Prophylaxis of nausea and vomiting after thyroid surgery: comparison of oral and intravenous dolasetron with intravenous droperidol and placebo]. | 2001 Jul |
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[Sinus arrest after the administration of intravenous metoclopramide]. | 2001 Jul 14 |
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The cardiovascular effects of metoclopramide in multiple system atrophy and pure autonomic failure. | 2001 Jun |
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Gastric emptying in the critically ill. | 2001 Jun |
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Serum prolactin is associated with apoptosis in men with human immunodeficiency virus infection. | 2001 Jun |
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A spectrophotometric method for the determination of metoclopramide HCl and dapsone. | 2001 Jun |
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Supraglottic dystonic reaction to metoclopramide in a child. | 2001 Jun 4 |
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Reproductive experience modulates dopamine-related behavioral responses. | 2001 Mar |
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Gastroesophageal reflux medications in the treatment of apnea in premature infants. | 2001 Mar |
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Small doses of propofol, droperidol, and metoclopramide for the prevention of postoperative nausea and vomiting after thyroidectomy. | 2001 Mar |
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Effects of i.v. metoclopramide, atropine and their combination on gastric insufflation in children anaesthetized with sevoflurane and nitrous oxide. | 2001 Mar |
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Induction of lactation in the intended mother of a surrogate pregnancy: case report. | 2001 Mar |
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Comparison of granisetron, droperidol, and metoclopramide for prevention of postoperative vomiting in children with a history of motion sickness undergoing tonsillectomy. | 2001 Mar |
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Dopaminergic modulation of human bronchial tone. | 2001 Mar-Apr |
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Metoclopramide-induced akathisia during the second trimester of a 37-year-old woman's first pregnancy. | 2001 Mar-Apr |
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Effect of ATP sensitive potassium channel modifiers on antinociceptive effect of metoclopramide. | 2001 May |
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Study of drug release from pellets coated with Surelease containing hydroxypropylmethylcellulose. | 2001 May |
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Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats. | 2001 May |
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Ondansetron rather than metoclopramide for bupropion-induced nausea. | 2001 May |
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Impact of antiemetic selection on postoperative nausea and vomiting and patient satisfaction. | 2001 May |
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Nasty shock after an anti-emetic. | 2001 May |
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Laryngospasm: an atypical manifestation of severe gastroesophageal reflux disease (GERD). | 2001 Nov |
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Comparison of cisapride and metoclopramide for facilitating gastric emptying and improving tolerance to intragastric enteral nutrition in critically III, mechanically ventilated adults. | 2001 Nov |
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Endoscopic balloon dilation of benign esophageal strictures in dogs and cats. | 2001 Nov-Dec |
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In vitro release of metoclopramide from hydrophobic matrix tablets. influence of hydrodynamic conditions on kinetic release parameters. | 2001 Oct |
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[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility]. | 2001 Sep |
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Metoclopramide-related pisa syndrome in clozapine treatment. | 2001 Summer |
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Serotonin syndrome caused by selective serotonin reuptake-inhibitors-metoclopramide interaction. | 2002 Jan |
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Why not to use erythromycin in GI motility. | 2002 Jan |
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Effect of prolactin and dopaminergic drugs on uterine response to chronic estrogen exposure. | 2002 Jan |
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Physical compatibility and in vivo evaluation of drug mixtures for subcutaneous infusion to cancer patients in palliative care. | 2002 Jan |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16041395
200 nM metoclopramide led to 79% peak current suppression in HEK-293 cells
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NCI_THESAURUS |
C267
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WHO-ESSENTIAL MEDICINES LIST |
17.2
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A03FA01
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m7489
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METOCLOPRAMIDE
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CHEMBL86
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C62046
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1740
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DB01233
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DTXSID6045169
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107736
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206-662-9
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Metoclopramide
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)