ChemFOnt: Showing chemical card for Metoclopramide (CFc000009642)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:50 UTC

Chemfont ID

CFc000009642

Molecule Identification

Common Name

Metoclopramide

Definition

Metoclopramide is only found in individuals that have used or taken this drug. It is a dopamine D2 antagonist that is used as an antiemetic. [PubChem]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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide	ChEBI
2-Methoxy-5-chloroprocainamide	ChEBI
4-Amino-5-chloro-2-methoxy-N-(beta-diethylaminoethyl)benzamide	ChEBI
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide	ChEBI
4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-O-anisamide	ChEBI
Elieten	ChEBI
Metoclopramida	ChEBI
Metoclopramidum	ChEBI
Reliveran	ChEBI
Terperan	Kegg
4-Amino-5-chloro-2-methoxy-N-(b-diethylaminoethyl)benzamide	Generator
4-Amino-5-chloro-2-methoxy-N-(β-diethylaminoethyl)benzamide	Generator
Metaclopramide	HMDB
Metaclopromide	HMDB
Methochlopramide	HMDB
Methoclopramide	HMDB
Metochlopramide	HMDB
Berk brand OF metoclopramide hydrochloride	HMDB
Dihydrochloride, metoclopramide	HMDB
Maxolon	HMDB
Primperan	HMDB
Cerucal	HMDB
Temmler brand OF metoclopramide hydrochloride	HMDB
Hydrochloride, metoclopramide	HMDB
Monohydrochloride, metoclopramide	HMDB
Rimetin	HMDB
Metoclopramide dihydrochloride	HMDB
Metoclopramide hydrochloride	HMDB
Metoclopramide monohydrochloride	HMDB
Metoclopramide monohydrochloride, monohydrate	HMDB
Reglan	HMDB

Chemical Formula

C₁₄H₂₂ClN₃O₂

Average Molecular Weight

299.796

Monoisotopic Molecular Weight

299.14005467

IUPAC Name

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide

Traditional Name

metoclopramide

CAS Registry Number

364-62-5

SMILES

CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC

InChI Identifier

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)

InChI Key

TTWJBBZEZQICBI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Aminophenyl ether
Methoxyaniline
Phenoxy compound
Anisole
Methoxybenzene
Aniline or substituted anilines
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Organic 1,3-dipolar compound
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Ether
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:107736 )
substituted aniline (CHEBI:107736 )
benzamides (CHEBI:107736 )
monochlorobenzenes (CHEBI:107736 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015363)
Membrane (HMDB: HMDB0015363)

Source

Exogenous

Exogenous (HMDB: HMDB0015363)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	83.52 m³·mol⁻¹	ChemAxon
Polarizability	32.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon