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Metoclopramide

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  Post Date: Dec 07,2018
  Expiry Date: Dec 07,2019
  Detailed Description: Cas No. :364-62-5 Clinical data


Pronunciation
/ˌmɛtəˈklɒprəmaɪd/


Trade names
Primperan, Reglan, others[1]


AHFS/Drugs.com
Monograph


MedlinePlus
a684035


License data



US FDA: Metoclopramide





Pregnancy
category



AU: A
US: B (No risk in non-human studies)








Routes of
administration
By mouth, intravenous, intramuscular


ATC code



A03FA01 (WHO)





Legal status


Legal status



AU: S3 (Pharmacist only)
CA: ℞-only
UK: POM (Prescription only)
US: ℞-only





Pharmacokinetic data


Bioavailability
80±15% (by mouth)


Metabolism
Liver


Biological half-life
5 h to 6 h


Excretion
70–85% kidney, 2% faecal


Identifiers




IUPAC name[show]

4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide





CAS Number



364-62-5 Y





PubChem CID



4168





IUPHAR/BPS



241





DrugBank



DB01233 Y





ChemSpider



4024 Y





UNII



L4YEB44I46





KEGG



D00726 Y





ChEBI



CHEBI:107736 Y





ChEMBL



CHEMBL86 Y





ECHA InfoCard
100.006.058


Chemical and physical data


Formula
C14H22ClN3O2


Molar mass
299.80 g/mol


3D model (Jmol)



Interactive image





Melting point
147.3 °C (297.1 °F)




SMILES[show]


Clc1cc(c(OC)cc1N)C(=O)NCCN(CC)CC








InChI[show]


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) Y


Key:TTWJBBZEZQICBI-UHFFFAOYSA-N Y






(verify)


Metoclopramide is a medication used mostly for stomach and esophageal problems.[2] 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.[3] It is also used to treat migraine headaches.[4]
Common side effects include: feeling tired, diarrhea, and feeling restless. More serious side effects include: movement disorder like tardive dyskinesia, a condition called neuroleptic malignant syndrome, and depression.[3] It is thus rarely recommended that people take the medication for longer than twelve weeks.[3] It is pregnancy category B in the United States and category A in Australia, meaning no evidence of harm has been found after being taken by many pregnant women.[3][5] It belongs to the group of medications known as dopamine-receptor antagonists.[3]
In 2012, metoclopramide was one of the top 100 most prescribed medications in the United States.[6] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] It is available as a generic medication.[3] The wholesale cost in the developing world as of 2014 is 0.003 to 0.08 USD per pill.[8] In the United States a month worth of medication is generally less than 25 USD.[9]

  CAS Registry Number:

364-62-5
  Synonyms: ;4-amino-5-chloro-N-(2-diethylaminoethyl)-2-methoxybenzamide;4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide;Metoclopramide anhydrous;
  Molecular Formula: C14H22ClN3O2
  Molecular Weight: 299.7964
  Molecular Structure: 364-62-5 metoclopramide

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