Metoclopramide hydrochlorideProduct ingredient for Metoclopramide

Name
Metoclopramide hydrochloride
Drug Entry
Metoclopramide

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.6 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.19

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.17 Metoclopramide was initially approved by the FDA in 1980.5

Accession Number
DBSALT000393
Structure
Thumb
Synonyms
Metoclopramide HCl / Metoclopramide HCl monohydrate / Metoclopramide hydrochloride / Metoclopramide hydrochloride monohydrate / Metoclopramide monohydrochloride monohydrate
UNII
W1792A2RVD
CAS Number
54143-57-6
Weight
Average: 354.273
Monoisotopic: 353.127297095
Chemical Formula
C14H25Cl2N3O3
InChI Key
KJBLQGHJOCAOJP-UHFFFAOYSA-N
InChI
InChI=1S/C14H22ClN3O2.ClH.H2O/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;1H2
IUPAC Name
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide hydrate hydrochloride
SMILES
O.Cl.CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC
KEGG Drug
D05008
PubChem Compound
441347
ChemSpider
10481968
ChEBI
6899
ChEMBL
CHEMBL1200940
Wikipedia
Metoclopramide
Predicted Properties
PropertyValueSource
Water Solubility0.31 mg/mLALOGPS
logP2.18ALOGPS
logP1.4ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.59 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity83.52 m3·mol-1ChemAxon
Polarizability32.73 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon