Prostaglandin F2alpha

This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.
Dinoprost
Clinical data
Other namesAmoglandin, Croniben, Cyclosin, Dinifertin, Enzaprost, Glandin, PGF2α, Panacelan, Prostamodin
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intravenous (cannot used to induce labor)because it cannot be used in cervix, intra-amniotic (to induce abortion)
ATC code
Pharmacokinetic data
Elimination half-life3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
  • (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.209.720 Edit this at Wikidata
Chemical and physical data
FormulaC20H34O5
Molar mass354.487 g·mol−1
3D model (JSmol)
Solubility in water200 mg/mL (20 °C)
  • O=C(O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC
  • InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 ☒N
  • Key:PXGPLTODNUVGFL-YNNPMVKQSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Prostaglandin F2α (PGF2α in prostanoid nomenclature), pharmaceutically termed dinoprost, is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.[1] Prostaglandins are lipids throughout the entire body that have a hormone-like function.[2] In pregnancy, PGF2α is medically used to sustain contracture and provoke myometrial ischemia to accelerate labor and prevent significant blood loss in labor.[3] Additionally, PGF2α has been linked to being naturally involved in the process of labor. It has been seen that there are higher levels of PGF2α in maternal fluid during labor when compared to at term.[4] This signifies that there is likely a biological use and significance to the production and secretion of PGF2α in labor. Prostaglandin is also used to treat uterine infections in domestic animals.

In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the luteal phase. It acts on the corpus luteum to cause luteolysis, forming a corpus albicans and stopping the production of progesterone. Action of PGF2α is dependent on the number of receptors on the corpus luteum membrane.

The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.[5]

  1. ^ O'Neil MJ, ed. (2013). The Merck index: an encyclopedia of chemicals, drugs, and biologicals (15th ed.). Cambridge, UK: Royal Society of Chemistry. ISBN 978-1849736701. OCLC 824530529.
  2. ^ "Prostaglandin". Britannica. September 28, 2022. Retrieved November 6, 2022.
  3. ^ Kerekes L, Domokos N (July 1979). "The effect of prostaglandin F2 alpha on third stage labor". Prostaglandins. 18 (1): 161–166. doi:10.1016/S0090-6980(79)80034-9. PMID 392622.
  4. ^ Sahmay S, Coke A, Hekim N, Atasu T (1988). "Maternal, umbilical, uterine and amniotic prostaglandin E and F2 alpha levels in labour". The Journal of International Medical Research. 16 (4): 280–285. doi:10.1177/030006058801600405. PMID 3169373. S2CID 73028858.
  5. ^ Sharma I, Dhaliwal LK, Saha SC, Sangwan S, Dhawan V (June 2010). "Role of 8-iso-prostaglandin F2alpha and 25-hydroxycholesterol in the pathophysiology of endometriosis". Fertility and Sterility. 94 (1): 63–70. doi:10.1016/j.fertnstert.2009.01.141. PMID 19324352.