Prostaglandin E2

Prostaglandin E2
Clinical data
Trade names PGE2, Cervidil, Propess, others
AHFS/Drugs.com Monograph
MedlinePlus a682512
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration		 intravaginal, IV
ATC code
Identifiers
Synonyms (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
ChEBI
ChEMBL
ECHA InfoCard 100.006.052
Chemical and physical data
Formula C20H32O5
Molar mass 352.465 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Prostaglandin E2 (PGE2), also known as dinoprostone, is a naturally occurring prostaglandin which is used as a medication.[1] As a medication it is used in labor induction, bleeding after delivery, termination of pregnancy, and in newborn babies to keep the ductus arteriosus open.[1][2] In babies it is used in those with congenital heart defects until surgery can be carried out.[2] It may be used within the vagina or by injection into a vein.[1][3]

Common side effects include vomiting, fever, diarrhea, and excessive uterine contraction.[1] In babies there may be decreased breathing and low blood pressure.[2] Care should be taken in people with asthma or glaucoma and it is not recommended in those who have had a prior C-section.[4] Prostaglandin E2 is in the oxytocics family of medications. It works by binding and activating the prostaglandin E2 receptor which results in the opening and softening of the cervix and dilation of blood vessels.[1][2]

Prostaglandin E2 was first made in 1970 and approved for medical use in the United States in 1977.[2][1] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[5] In the United Kingdom a dose costs the NHS about 8.50 to 30.00 pounds.[3][6] In the United States a course of treatment costs more than 200 USD.[4] Prostaglandin E2 works as well as prostaglandin E1 in babies; however, it is much less expensive.[2]

Physiological effects

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. 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.

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.

PGE2 also suppresses T cell receptor signaling and may play a role in resolution of inflammation.[7] Up-regulation of PGE2 has been implicated as a possible cause of nail clubbing. Furthermore, its postpartal synthesis in newborns is considered as one cause of patent ductus arteriosus.[8]

Side effects

Common side effects include vomiting, fever, diarrhea, and excessive uterine contraction.[1] In babies there may be decreased breathing and low blood pressure.[2] Care should be taken in people with asthma or glaucoma and it is not recommended in those who have had a prior C-section.[4]

Mechanism of action

PGE2 is a potent activator of the Wnt signaling pathway. It has been implicated in regulating the developmental specification and regeneration of hematopoietic stem cells through cAMP/PKA activity.[9]

History

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

Society and culture

It is sold under the trade name of Cervidil(US) 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.

References

  1. 1 2 3 4 5 6 7 "Dinoprostone". The American Society of Health-System Pharmacists. Retrieved 8 January 2017.
  2. 1 2 3 4 5 6 7 Northern Neonatal Network (208). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (5 ed.). John Wiley & Sons. p. 2010. ISBN 9780470750353.
  3. 1 2 British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 538–540. ISBN 9780857111562.
  4. 1 2 3 Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 361. ISBN 9781284057560.
  5. ↑ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016.
  6. ↑ Ainsworth, Sean B. (2014). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life. John Wiley & Sons. p. 436. ISBN 9781118819593.
  7. ↑ 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. PMC 3178752 Freely accessible. PMID 21900181. doi:10.4049/jimmunol.1100103.
  8. ↑ Textbook of Pathology 7th Edition © 2015, Harsh Mohan; ISBN 978-93-5152-369-7; p. 404
  9. ↑ Goessling, Wolfram; North, Trista E.; Loewer, Sabine; Lord, Allegra M.; Lee, Sang; Stoick-Cooper, Cristi L.; Weidinger, Gilbert; Puder, Mark; Daley, George Q. (2009-03-20). "Genetic interaction of PGE2 and Wnt signaling regulates developmental specification of stem cells and regeneration". Cell. 136 (6): 1136–1147. ISSN 1097-4172. PMC 2692708 Freely accessible. PMID 19303855. doi:10.1016/j.cell.2009.01.015.
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