Prostaglandin F2alpha

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This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.
Dinoprost Tromethamine
Dinoprost.svg
Systematic (IUPAC) name
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
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Routes Intravenous (to induce labor), intra-amniotic (to induce abortion)
Pharmacokinetic data
Half-life 3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
CAS number 551-11-1 YesY 38562-01-5
ATC code G02AD01
PubChem CID 5280363
IUPHAR ligand 1884
DrugBank DB01160
ChemSpider 4444062 N
KEGG D01352 N
ChEMBL CHEMBL815 N
Chemical data
Formula C20H34O5 
Mol. mass 354.48 g/mol
 N (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 follicular 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]

Further information: Prostaglandin F2α receptor

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.

Analogs[edit]

The following medications are analogs 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. doi:10.1016/j.fertnstert.2009.01.141. PMID 19324352.  edit
  2. ^ 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.  edit
  3. ^ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.