Prostaglandin F2alpha

This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see Prostaglandin E2.

Dinoprost

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
Routes of administration	Intravenous (to induce labor), intra-amniotic (to induce abortion)
Pharmacokinetic data
Biological half-life	3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
CAS Number	551-11-1 Y Template:CAS
ATC code	G02AD01 (WHO)
PubChem	CID: 5280363
IUPHAR/BPS	1884
DrugBank	DB01160 Y
ChemSpider	4444062 N
KEGG	D01352 N
ChEMBL	CHEMBL815 N
Chemical data
Formula	C20H34O5
Molecular mass	354.48 g/mol
SMILES 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 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
NY (what is this?)  (verify)

Prostaglandin F_2α (PGF_2α 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_2α is dependent on the number of receptors on the corpus luteum membrane.

The PGF_2α isoform 8-iso-PGF_2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.

Mechanism of action

Further information: Prostaglandin F2α receptor

PGF_2α acts by binding to the prostaglandin F2α receptor.

Synthesis

In 2012 a concise and highly stereoselective total synthesis of PGF_2α 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.

Analogues

The following medications are analogues of prostaglandin F_2α:

• Latanoprost
• Bimatoprost
• Travoprost
• Carboprost