{"ATC Code":"A03FA01","Abbreviation":"","Aliases":["Methochlopramide","Metochlopramide","Metaclopramide","Reliveran","Metaclopromide","Elieten","Metoclopramida","Terperan","4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide","Metoclopramidum","2-Methoxy-5-chloroprocainamide","Plasil","5-Chloro-2-methoxyprocainamide","Megaldrate","Methoxyclopramide","DEL 1267","Gimoli","4-Amino-5-chloro-2-methoxy-N-(β-diethylaminoethyl)benzamide","Benzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-","N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide","Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-","2-Methoxy-4-amino-5-chloro-N,N-dimethylaminoethyl)benzamide","2-methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide","Gimoti","A03FA01"],"Biological Half-Life":"The mean elimination half-life of metoclopramide in people with healthy renal function ranges from 5 to 6 hours but is prolonged in patients with renal impairment. Downward dose adjustment should be considered.","CAS":"364-62-5","ChEBI":"CHEBI:107736","ChEMBL":"CHEMBL86","ChemicalClasses":["benzamide"],"Classes":["Antiemetics","CYP2D6 inhibitors"],"Decomposition":"When heated to decomposition it emits very toxic fumes of /nitrogen oxides and hydrogen chloride/.","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Antiemetics; Dopamine Antagonists; Galactogogues; Gastrointestinal Agents","Drug Indication":"Metoclopramide in the oral tablet form is used for symptomatic treatment of both acute and recurrent diabetic gastroparesis, in addition to the treatment of gastroesophageal reflux disease (GERD) in patients who have failed to respond to traditional therapy. A nasal spray formulation is also indicated to treat adults with acute, recurrent diabetic gastroparesis.  In the intravenous injection form, it is indicated for the above conditions as well as for the prevention of vomiting that may follow emetogenic chemotherapy or nausea and vomiting after surgery. Intravenous metoclopramide facilitates intubation of the small bowel and stimulates gastric emptying and barium flow in patients who require radiological examination of the stomach or small intestine.  In some cases, the delay of gastrointestinal emptying interferes with the radiographic visualization of the gastrointestinal tract, and metoclopramide is used to facilitate emptying in these cases, allowing for adequate diagnostic visualization.  Some off-label uses of metoclopramide include the management of radiation-induced nausea and vomiting, gastric bezoars, intractable hiccups, and migraine pain.","Drug Warnings":"WARNING: TARDIVE DYSKINESIA-Treatment with metoclopramide can cause tardive dyskinesia, a serious movement disorder that is often irreversible. The risk of developing tardive dyskinesia increases with duration of treatment and total cumulative dose. Metoclopramide therapy should be discontinued in patients who develop signs or symptoms of tardive dyskinesia.  There is no known treatment for tardive dyskinesia.  In some patients, symptoms may lessen or resolve after metoclopramide treatment is stopped. Treatment with metoclopramide for longer than 12 weeks should be avoided in all but rare cases where therapeutic benefit is thought to outweigh the risk of developing tardive dyskinesia.","EINECS":"206-662-9","Esters":[],"European Community (EC) Number":"206-662-9","FDA Pharmacological Classification":"L4YEB44I46","Formating":[],"HMDB ID":"HMDB0015363","HeavyAtomCount":20,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Antiemetics; Dopamine Antagonists; Galactogogues; Gastrointestinal Agents","IUPACName":"4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide","InChI":"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)","InChIKey":"TTWJBBZEZQICBI-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)","Melting Point":"171-173","MolecularFormula":"C\u003csub\u003e14\u003c/sub\u003eH\u003csub\u003e22\u003c/sub\u003eClN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"299.79 g/mol","Pharmacodynamics":"Metoclopramide increases gastric emptying by decreasing lower esophageal sphincter (LES) pressure. It also exerts effects on the area postrema of the brain, preventing and relieving the symptoms of nausea and vomiting. In addition, this drug increases gastrointestinal motility without increasing biliary, gastric, or pancreatic secretions.  Because of its antidopaminergic activity, metoclopramide can cause symptoms of tardive dyskinesia (TD), dystonia, and akathisia, and should therefore not be administered for longer than 12 weeks.","Physical Description":"Solid","PubChemId":4168,"RefCount":2,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Metoclopramide","Name":"Metoclopramide","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q421095","Name":"Metoclopramide","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01233","Name":"Metoclopramide","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/4168","Name":"Metoclopramide","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL86","Name":"Metoclopramide","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:107736","Name":"Metoclopramide","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=364-62-5","Name":"Metoclopramide","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015363","Name":"Metoclopramide","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07868","Name":"Metoclopramide","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/L4YEB44I46","Name":"Metoclopramide","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID6045169","Name":"Metoclopramide","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 4168, Metoclopramide. Accessed July 7, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/4168\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/4168\u003c/a\u003e"],"SMILES":"CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl","SaltData":[],"Salts":[],"Solubility":"Crystal; decomposes at 145 °C. Solubility at 25 °C (g/100 mL): water 48; ethanol (95%) 9; absolute ethanol 6; benzene 0.10; chloroform 0.10. Stable in acidic solutions. Unstable in strongly alkaline solutions. /Metoclopramide Dihydrochloride monohydrate/","Stability/Shelf Life":"Metoclopramide hydrochloride is photosensitive and will degrade when exposed to light. Commercially available preparations of metoclopramide hydrochloride should be protected from light. The commercially available tablets are stable for 3 years and the oral solution and injection are stable for 5 years after manufacture.","StereoisomerData":[{"Aliases":["Methochlopramide","Metochlopramide","Metaclopramide","Reliveran","Metaclopromide","Elieten","Metoclopramida","Terperan","4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide","Metoclopramidum","2-Methoxy-5-chloroprocainamide","Plasil","5-Chloro-2-methoxyprocainamide","Megaldrate","Methoxyclopramide","DEL 1267","Gimoli","4-Amino-5-chloro-2-methoxy-N-(β-diethylaminoethyl)benzamide","Benzamide, 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxy-","N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorobenzamide","Benzamide, 4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxy-","2-Methoxy-4-amino-5-chloro-N,N-dimethylaminoethyl)benzamide","2-methoxy-4-amino-5-chloro-N,N-(dimethylaminoethyl)benzamide","Gimoti","A03FA01"],"PubChemId":4168,"SMILES":"CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl","Structure":null,"Title":null,"UNII":"L4YEB44I46"}],"Stereoisomers":["Metoclopramide"],"Structure":"\u003csvg  preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 142.332 70.535\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h143v71H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m141.294 23.898-13.198 7.62M128.096 31.518l-10.045-5.799M114.898 20.048V8.658M114.898 8.658l13.198-7.62M111.744 25.719l-10.045 5.799M101.699 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