|AHFS/Drugs.com||International Drug Names|
|Intravenous (to induce labor), intra-amniotic (to induce abortion)|
|ATC code||G02AD01 (WHO)|
|Biological half-life||3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma|
|CAS Number||551-11-1 38562-01-5|
|Chemical and physical data|
|Molar mass||354.48 g/mol|
|3D model (Jmol)||Interactive image|
|(what is this?)|
In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the follicular 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.
Mechanism of action
PGF2α acts by binding to the prostaglandin F2α receptor.
In 2012 a concise and highly stereoselective total synthesis of PGF2α was described. The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng, and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst.
The following medications are analogues of prostaglandin F2α:
- Sharma, I.; Dhaliwal, L.; Saha, S.; Sangwan, S.; Dhawan, V. (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.
- Coulthard, G.; Erb, W.; Aggarwal, V. K. (2012). "Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps". Nature. 489 (7415): 278–281. doi:10.1038/nature11411. PMID 22895192.
- Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.