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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
Structure of METOCLOPRAMIDE

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)

HIDE SMILES / InChI

Molecular Formula C14H22ClN3O2
Molecular Weight 299.796
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
24.0 µM [IC50]
100.0 nM [IC50]
0.064 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
REGLAN
Palliative
REGLAN

Cmax

ValueDoseCo-administeredAnalytePopulation
41 ng/mL
15 mg single, nasal
METOCLOPRAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
367 ng × h/mL
15 mg single, nasal
METOCLOPRAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.1 h
15 mg single, nasal
METOCLOPRAMIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
15 mg single, nasal
METOCLOPRAMIDE plasma
Homo sapiens

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
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
200 nM metoclopramide led to 79% peak current suppression in HEK-293 cells
Substance Class Chemical
Record UNII
L4YEB44I46
Record Status Validated (UNII)
Record Version