Prostaglandin E2

This article is about the medication "dinoprostone". For the medication "dinoprost", see Prostaglandin F2alpha.
Prostaglandin E2
Clinical data
Trade namesProstin E2, Cervidil, Propess, others
Other namesPGE2, (5Z,11α,13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-oic acid
AHFS/Drugs.comMonograph
MedlinePlusa682512
License data
Pregnancy
category
Routes of
administration		Intravaginal, IV
ATC code
Legal status
Legal status
Identifiers
  • (5Z,11α,13E,15S)-7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)- 5-oxo-cyclopentyl] hept-5-enoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.052 Edit this at Wikidata
Chemical and physical data
FormulaC20H32O5
Molar mass352.471 g·mol−1
3D model (JSmol)
  • CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
  • InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1 ☒N
  • Key:XEYBRNLFEZDVAW-ARSRFYASSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Prostaglandin E2 (PGE2), also known as dinoprostone, is a naturally occurring prostaglandin with oxytocic properties that is used as a medication.[2][3][4] Dinoprostone is used in labor induction, bleeding after delivery, termination of pregnancy, and in newborn babies to keep the ductus arteriosus open.[2][5] In babies it is used in those with congenital heart defects until surgery can be carried out.[5] It is also used to manage gestational trophoblastic disease.[4] It may be used within the vagina or by injection into a vein.[2][6]

PGE2 synthesis within the body begins with the activation of arachidonic acid (AA) by the enzyme phospholipase A2. Once activated, AA is oxygenated by cyclooxygenase (COX) enzymes to form prostaglandin endoperoxides. Specifically, prostaglandin G2 (PGG2) is modified by the peroxidase moiety of the COX enzyme to produce prostaglandin H2 (PGH2) which is then converted to PGE2.[7][8]

Common side effects of PGE2 include nausea, vomiting, diarrhea, fever, and excessive uterine contraction.[2] In babies there may be decreased breathing and low blood pressure.[5] Caution should be taken in people with asthma or glaucoma and it is not recommended in those who have had a prior C-section.[9] 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.[2][5]

Prostaglandin E2 was first synthesized in 1970 and approved for medical use by the FDA in the United States in 1977.[5][2] It is on the World Health Organization's List of Essential Medicines.[10] Prostaglandin E2 works as well as prostaglandin E1 in babies.[5]

  1. ^ a b "Dinoprostone topical Use During Pregnancy". Drugs.com. 17 December 2019. Retrieved 27 July 2020.
  2. ^ a b c d e f "Dinoprostone". The American Society of Health-System Pharmacists. Archived from the original on 16 January 2017. Retrieved 8 January 2017.
  3. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  4. ^ a b Cite error: The named reference Xi_2020 was invoked but never defined (see the help page).
  5. ^ a b c d e f 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. Archived from the original on 2017-01-13.
  6. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 538–540. ISBN 9780857111562.
  7. ^ Hwa J, Martin K (2017). "Chapter 18: The Eicosanoids: Prostaglandins, Thromboxanes, Leukotrienes, & Related Compounds". In Katzung BG (ed.). Basic & Clinical Pharmacology (14th ed.). New York, NY: McGraw-Hill Education.
  8. ^ Smith WL, Urade Y, Jakobsson PJ (October 2011). "Enzymes of the cyclooxygenase pathways of prostanoid biosynthesis". Chemical Reviews. 111 (10): 5821–65. doi:10.1021/cr2002992. PMC 3285496. PMID 21942677.
  9. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 361. ISBN 9781284057560.
  10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.