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
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
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 |
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 |
|||
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 |
|||
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 |
---|---|---|---|---|
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 |
||
minor | ||||
minor |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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
admin
on
Edited
Sat Jun 26 03:48:16 UTC 2021
by
admin
on
Sat Jun 26 03:48:16 UTC 2021
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Record UNII |
7B1QZY5SWZ
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Record Status |
Validated (UNII)
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Record Version |
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-
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C66883
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C87710
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DBSALT002458
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23659
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7B1QZY5SWZ
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SUB03271MIG
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230-634-5
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CHEMBL86
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7232-21-5
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SUB179494
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SUBSTANCE->BASIS OF STRENGTH |
ASSAY (TITRATION)
USP
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |