Metoclopramide

Metoclopramide
Clinical data
Pronunciation	/ˌmɛtəˈklɒprəmaɪd/
Trade names	Primperan, Maxolon, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684035
License data	US DailyMed: Metoclopramide;
Pregnancy; category	AU: A;
Routes of; administration	By mouth, intravenous, intramuscular, nasal spray
Drug class	D2 receptor antagonist; 5-HT3 receptor antagonist; 5-HT4 receptor agonist; Prolactin releaser
ATC code	A03FA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	80 ± 15% (by mouth)
Metabolism	Liver
Elimination half-life	5–6 hours
Excretion	Urine: 70–85%; Feces: 2%
Identifiers
	IUPAC name 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide;
CAS Number	364-62-5 ;
PubChem CID	4168;
IUPHAR/BPS	241;
DrugBank	DB01233 ;
ChemSpider	4024 ;
UNII	L4YEB44I46;
KEGG	D00726 ; as HCl: D05008 ;
ChEBI	CHEBI:107736 ;
ChEMBL	ChEMBL86 ;
CompTox Dashboard (EPA)	DTXSID6045169 ;
ECHA InfoCard	100.006.058
Chemical and physical data
Formula	C14H22ClN3O2
Molar mass	299.80 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	147.3 °C (297.1 °F)
	SMILES Clc1cc(c(OC)cc1N)C(=O)NCCN(CC)CC;
	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) ; Key:TTWJBBZEZQICBI-UHFFFAOYSA-N ;
	(verify)

Metoclopramide is a medication used to treat nausea, vomiting, gastroparesis, and gastroesophageal reflux disease. It is also used to treat migraine headaches.

Common side effects include feeling tired, diarrhea, akathisia, and tardive dyskinesia. More serious side effects include neuroleptic malignant syndrome and depression. It is thus rarely recommended that people take the medication for longer than twelve weeks. No evidence of harm has been found after being taken by many pregnant women. It belongs to the group of medications known as dopamine-receptor antagonists and works as a prokinetic.

In 2012, metoclopramide was one of the top 100 most prescribed medications in the United States. It is available as a generic medication. It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 245th most commonly prescribed medication in the United States, with more than 1 million prescriptions.