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=C(OC)C=C(N)C(Cl)=C1
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)
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 |
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 |
---|---|---|---|---|
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 Date3.46896007E11 |
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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 Date3.46896007E11 |
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
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 |
---|---|---|
Metoclopramide and pimozide in Parkinson's disease and levodopa-induced dyskinesias. | 1975 Apr |
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Cloning, expression, and characterization of ferret 5-HT(3) receptor subunit. | 2000 Jul 7 |
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Tetanus-like syndrome secondary to metoclopramide administration. | 2000 Oct-Dec |
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Mongolian spots with involvement of the temporal area. | 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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Variation in practice patterns of anesthesiologists in California for prophylaxis of postoperative nausea and vomiting. | 2001 Aug |
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Prevention of vomiting after general anesthesia for pediatric ophthalmic surgery. | 2001 Feb |
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Metoclopramide versus ondansetron in prophylaxis of nausea and vomiting for laparoscopic cholecystectomy. | 2001 Feb |
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Galactorrhoea, hyperprolactinaemia, and protease inhibitors. | 2001 Feb 10 |
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Prevention of postoperative nausea and vomiting with antiemetics in patients undergoing middle ear surgery: comparison of a small dose of propofol with droperidol or metoclopramide. | 2001 Jan |
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Gastroparesis following bone marrow transplantation. | 2001 Jul |
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Preparation and in vivo evaluation of parenteral metoclopramide-loaded poly(alkylcyanoacrylate) nanospheres in rats. | 2001 Jul-Aug |
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Pre-emptive metoclopramide and ondansetron for nausea and vomiting associated with iloprost infusions. | 2001 Jun |
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Decreased dopaminergic tone and increased basal bioactive prolactin in men with human immunodeficiency virus infection. | 2001 Jun |
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Gastric emptying in the critically ill. | 2001 Jun |
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Gastroesophageal reflux medications in the treatment of apnea in premature infants. | 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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Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats. | 2001 May |
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Nasty shock after an anti-emetic. | 2001 May |
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AS-924, a novel, orally active, bifunctional prodrug of ceftizoxime: physicochemical properties, oral absorption in animals, and antibacterial activity. | 2001 Nov |
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Aberrant membrane hormone receptors in incidentally discovered bilateral macronodular adrenal hyperplasia with subclinical Cushing's syndrome. | 2001 Nov |
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Low-dose dexamethasone effectively prevents postoperative nausea and vomiting after ambulatory laparoscopic surgery. | 2001 Nov |
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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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Preoperative diagnosis and localization of aldosterone-producing adenoma by adrenal venous sampling after administration of metoclopramide. | 2001 Sep |
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Serotonin syndrome caused by selective serotonin reuptake-inhibitors-metoclopramide interaction. | 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
Substance Class |
Chemical
Created
by
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on
Edited
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on
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Record UNII |
L4YEB44I46
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C267
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WHO-ESSENTIAL MEDICINES LIST |
17.2
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NDF-RT |
N0000175799
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WHO-VATC |
QA03FA01
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WHO-ATC |
A03FA01
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LIVERTOX |
NBK548630
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N0000175800
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SUB08902MIG
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D008787
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L4YEB44I46
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M7489
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7841
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4168
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241
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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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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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METABOLIC ENZYME -> INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO AND IN VIVO
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METABOLITE -> PARENT |
IN VITRO AND IN VIVO
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METABOLITE -> PARENT |
IN VITRO AND IN VIVO
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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SINGLE ORAL ADMINISTRATION |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Population PHARMACOKINETIC PHARMACOKINETIC |
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