Prostaglandin F2alpha

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Dinoprost
Dinoprost.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Intravenous (to induce labor), intra-amniotic (to induce abortion)
ATC code
Pharmacokinetic data
Biological half-life 3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
KEGG
ChEMBL
ECHA InfoCard 100.209.720
Chemical and physical data
Formula C20H34O5
Molar mass 354.48 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Prostaglandin F (PGF in prostanoid nomenclature), pharmaceutically termed dinoprost (INN), is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.

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 PGF is dependent on the number of receptors on the corpus luteum membrane.

The PGF isoform 8-iso-PGF was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.[1]

Mechanism of action[edit]

PGF acts by binding to the prostaglandin F2α receptor.

Synthesis[edit]

In 2012 a concise and highly stereoselective total synthesis of PGF was described.[2] The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng,[3] and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst.

Analogues[edit]

The following medications are analogues of prostaglandin F:

References[edit]

  1. ^ 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. PMID 19324352. doi:10.1016/j.fertnstert.2009.01.141. 
  2. ^ Coulthard, G.; Erb, W.; Aggarwal, V. K. (2012). "Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps". Nature. 489 (7415): 278–281. PMID 22895192. doi:10.1038/nature11411. 
  3. ^ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.