Prostaglandin F2alpha

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List of terms related to Prostaglandin F2alpha

Dinoprost Tromethamine
Gene therapy
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intravenous (to induce labor), intra-amniotic (to induce abortion)
ATC code	G02AD01 (WHO) ;
Physiological data
Legal status
Pharmacokinetic data
Elimination half-life	3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
	IUPAC name (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid;
CAS Number	551-11-1 38562-01-5;
PubChem Template:Abbreviation	5280363;
IUPHAR/BPS	1884;
DrugBank	DB01160 ;
ChemSpider	4444062 ;
KEGG	D01352 ;
ChEMBL	ChEMBL815 ;
Chemical and physical data
Formula	C20H34O5
Molar mass	354.48 g/mol
3D model (JSmol)	Interactive image;
	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 ; Key:PXGPLTODNUVGFL-YNNPMVKQSA-N ;
	Template:Xmark (what is this?) (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

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,^[1] and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst.

Analogs

The following medications are analogs of prostaglandin F_2α:

References

↑ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.

Template:Prostaglandins

[coreybook-1] Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.

[1]