Metoclopramide

Metoclopramide
Clinical data
Pronunciation	/ˌmɛtəˈklɒprəmaɪd/
Trade names	Primperan, Maxolon, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684035
License data	US DailyMed: Metoclopramide; US FDA: 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: WARNINGRx-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 for stomach and esophageal problems.^[5] It is commonly used to treat and prevent nausea and vomiting, to help with emptying of the stomach in people with delayed stomach emptying, and to help with gastroesophageal reflux disease.^[6] It is also used to treat migraine headaches.^[7]

Common side effects include: feeling tired, diarrhea, akathisia, and tardive dyskinesia. More serious side effects include neuroleptic malignant syndrome and depression.^[6] It is thus rarely recommended that people take the medication for longer than twelve weeks.^[6] No evidence of harm has been found after being taken by many pregnant women.^[6]^[8] It belongs to the group of medications known as dopamine-receptor antagonists and works as a prokinetic.^[6]

In 2012, metoclopramide was one of the top 100 most prescribed medications in the United States.^[9] It is available as a generic medication.^[6] It is on the World Health Organization's List of Essential Medicines.^[10] In 2020, it was the 352nd most commonly prescribed medication in the United States, with more than 600,000 prescriptions.^[11]

^ Cite error: The named reference generics was invoked but never defined (see the help page).
^ "Metoclopramide Use During Pregnancy". Drugs.com. 27 February 2020. Archived from the original on 21 March 2023. Retrieved 22 November 2020.
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ Cite error: The named reference Reglan FDA label was invoked but never defined (see the help page).
^ "Metoclopramide". MedlinePlus. Archived from the original on 5 October 2016. Retrieved 22 November 2020.
^ ^a ^b ^c ^d ^e ^f "Metoclopramide hydrochloride". Monograph. The American Society of Health-System Pharmacists. Archived from the original on 19 August 2011. Retrieved 27 September 2014.
^ Becker WJ (June 2015). "Acute Migraine Treatment in Adults". Headache. 55 (6): 778–793. doi:10.1111/head.12550. PMID 25877672. S2CID 23327034.
^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
^ Bartholow M. "Top 200 Drugs of 2012". Pharmacy Times. Archived from the original on 17 May 2014. Retrieved 22 April 2014.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ "Metoclopramide - Drug Usage Statistics". ClinCalc. Archived from the original on 13 November 2022. Retrieved 7 October 2022.

[generics-1] Cite error: The named reference generics was invoked but never defined (see the help page).

[Drugs.com_pregnancy-2] "Metoclopramide Use During Pregnancy". Drugs.com. 27 February 2020. Archived from the original on 21 March 2023. Retrieved 22 November 2020.

[FDA-AllBoxedWarnings-3] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[Reglan_FDA_label-4] Cite error: The named reference Reglan FDA label was invoked but never defined (see the help page).

[5] "Metoclopramide". MedlinePlus. Archived from the original on 5 October 2016. Retrieved 22 November 2020.

[AHFS-6] ^ ^a ^b ^c ^d ^e ^f "Metoclopramide hydrochloride". Monograph. The American Society of Health-System Pharmacists. Archived from the original on 19 August 2011. Retrieved 27 September 2014.

[7] Becker WJ (June 2015). "Acute Migraine Treatment in Adults". Headache. 55 (6): 778–793. doi:10.1111/head.12550. PMID 25877672. S2CID 23327034.

[8] "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.

[9] Bartholow M. "Top 200 Drugs of 2012". Pharmacy Times. Archived from the original on 17 May 2014. Retrieved 22 April 2014.

[WHO22nd-10] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[11] "Metoclopramide - Drug Usage Statistics". ClinCalc. Archived from the original on 13 November 2022. Retrieved 7 October 2022.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]