ContaminantDB: Metoclopramide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:02:43 UTC

Update Date

2016-10-28 10:03:45 UTC

Accession Number

CHEM018176

Identification

Common Name

Metoclopramide

Class

Small Molecule

Description

Diabetic gastroparesis is a condition that causes frequent nausea and vomiting, which has a negative impact on quality of life and poses a significant burden on the healthcare system. Metoclopramide is a dopamine antagonist used to treat nausea and vomiting that may be associated with diabetic gastroparesis in addition to gastroesophageal reflux disease (GERD). It can also be used to prevent nausea or vomiting associated with chemotherapy or certain surgical or diagnostic procedures. One unique property of this drug is that it does not increase gastric acid secretion. It is available in the oral tablet form or in solution, and can also be administered through the intravenous route. Metoclopramide was initially approved by the FDA in 1980.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds - Waste Water
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

299.796 g/mol

Monoisotopic Mass

299.140 g/mol

CAS Registry Number

364-62-5

IUPAC Name

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

Traditional Name

metoclopramide

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-9610000000-b6fe5f492b0d4ca6c150	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0090000000-10fdf9db1550886fc034	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-fcc278321866ecdee26f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0193000000-c044c04d9d51d66ba5a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0290000000-45d3c52d766c4cd8ae93	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-003r-0970000000-2f2d709cad2c27f798e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0920000000-ccce0f42f04edf0ecfb3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00lr-0900000000-93aec7dddb8a098f7483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0009000000-e7b25ddf867c24be5347	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0093000000-dc0ce524de60c6a189a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0290000000-2bca02d9f4cee5acca4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-003r-0970000000-50fe530dffb9aa59d433	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0920000000-0bb9973fdbe0820dc3d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00lr-0900000000-4cc6fae9bec9d4c40dbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0090000000-1c4a27b221c7a053d2c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0fb9-0595000000-db3b50f051cfcc835a69	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0ufr-0069000000-93c3839d751c69450f14	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0ufr-0069000000-81fd95d3b4b8a739b1b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-0290000000-6741a21b4bd686e97955	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-004l-9400000000-e6a69fee2535079fef49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1759000000-14b767e1985b55c13727	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ugr-4940000000-2016fe8b0b0d4e5aa870	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fk9-9500000000-94bfb5af9b1e4e11a705	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0190000000-6b24c4fdc3e3fbf344c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-2590000000-1429e8508288721a0e7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9810000000-f5f978ef1ee636729e5f	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01233

HMDB ID

HMDB0015363

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Tonini M, Candura SM, Messori E, Rizzi CA: Therapeutic potential of drugs with mixed 5-HT4 agonist/5-HT3 antagonist action in the control of emesis. Pharmacol Res. 1995 May;31(5):257-60.

2. JUSTIN-BESANCON L, LAVILLE C: [ANTIEMETIC ACTION OF METOCLOPRAMIDE WITH RESPECT TO APOMORPHINE AND HYDERGINE]. C R Seances Soc Biol Fil. 1964;158:723-7.

Metoclopramide (CHEM018176)

Structure for CHEM018176: Metoclopramide