Prostaglandin E2

This article is about the pharmaceutical agent 'dinoprostone'. For the drug 'dinoprost', see Prostaglandin F2alpha.
Prostaglandin E2
Systematic (IUPAC) name
(5Z,11α,13E,15S)-7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)- 5-oxo-cyclopentyl] hept-5-enoic acid
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a682512
Identifiers
363-24-6 Yes
G02AD02
PubChem CID 9691
IUPHAR ligand 1883
DrugBank DB00917 
ChEBI CHEBI:15551 
ChEMBL CHEMBL548 
Synonyms (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid
Chemical data
Formula C20H32O5
352.465 g/mol
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The naturally occurring prostaglandin E2 (PGE2 or PGE2) is known in medicine as dinoprostone. It has important effects in labour (softening the cervix and causing uterine contraction) and also stimulates osteoblasts to release factors that stimulate bone resorption by osteoclasts. PGE2 is also the prostaglandin that ultimately induces fever.

PGE2 also suppresses T cell receptor signaling and may play a role in resolution of inflammation.[1]

It is sold under the trade name of Cervidil (by Forest Laboratories, Inc. and Propess (by Ferring Pharmaceuticals). This is a controlled release vaginal insert. Prostin E2 (by Pfizer Inc.), and Glandin (by Nabiqasim Pharmaceuticals Pakistan) as a vaginal suppository, to prepare the cervix for labour; it is used to induce labour.

Like other prostaglandins, dinoprostone can be used as an abortifacient. It is a direct vasodilator, relaxing smooth muscles, and it inhibits the release of noradrenaline from sympathetic nerve terminals. It does not inhibit platelet aggregation, where PGI2 does.

It works by binding and activating the prostaglandin E2 receptor.

It was discovered by Bunting, Gryglewski, Moncada and Vane in 1976.

Up-regulation of PGE2 has been implicated as a possible etiology of nail clubbing.

It is also implicated in duct-dependent congenital heart diseases and is used in infusion in order to open the duct although PGE1 is more commonly used.

Precautions: uterine scar tissues; asthma; low blood pressure; heart disease; adrenal problems; anemia; diabetes; glaucoma; icterus (jaundice); multiparity (twins, triplets, etc.); heart, lung or liver disease.

References

  1. ↑ Wiemer, AJ; Hegde, S; Gumperz, JE; Huttenlocher, A (1 October 2011). "A live imaging cell motility screen identifies prostaglandin E2 as a T cell stop signal antagonist.". Journal of immunology (Baltimore, Md. : 1950) 187 (7): 3663–70. doi:10.4049/jimmunol.1100103. PMID 21900181.

Pharmacology 2007. Rang, Ritter, Dale, Flower. Churchill Livingstone Elsevier.
Judiths Hopfer Deglin and April Hazard Vallerand (2006), Davis Drug Guide for Nurses,F.A Davis, Philadelphia, Pennsylvania, U.S.A Copyright, 1427 pages.

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