Prostaglandin F2alpha

	WikiDoc Resources for Prostaglandin F2alpha
Articles
Most recent articles on Prostaglandin F2alpha Most cited articles on Prostaglandin F2alpha Review articles on Prostaglandin F2alpha Articles on Prostaglandin F2alpha in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Prostaglandin F2alpha Images of Prostaglandin F2alpha Photos of Prostaglandin F2alpha Podcasts & MP3s on Prostaglandin F2alpha Videos on Prostaglandin F2alpha
Evidence Based Medicine
Cochrane Collaboration on Prostaglandin F2alpha Bandolier on Prostaglandin F2alpha TRIP on Prostaglandin F2alpha
Clinical Trials
Ongoing Trials on Prostaglandin F2alpha at Clinical Trials.gov Trial results on Prostaglandin F2alpha Clinical Trials on Prostaglandin F2alpha at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Prostaglandin F2alpha NICE Guidance on Prostaglandin F2alpha NHS PRODIGY Guidance FDA on Prostaglandin F2alpha CDC on Prostaglandin F2alpha
Books
Books on Prostaglandin F2alpha
News
Prostaglandin F2alpha in the news Be alerted to news on Prostaglandin F2alpha News trends on Prostaglandin F2alpha
Commentary
Blogs on Prostaglandin F2alpha
Definitions
Definitions of Prostaglandin F2alpha
Patient Resources / Community
Patient resources on Prostaglandin F2alpha Discussion groups on Prostaglandin F2alpha Patient Handouts on Prostaglandin F2alpha Directions to Hospitals Treating Prostaglandin F2alpha Risk calculators and risk factors for Prostaglandin F2alpha
Healthcare Provider Resources
Symptoms of Prostaglandin F2alpha Causes & Risk Factors for Prostaglandin F2alpha Diagnostic studies for Prostaglandin F2alpha Treatment of Prostaglandin F2alpha
Continuing Medical Education (CME)
CME Programs on Prostaglandin F2alpha
International
Prostaglandin F2alpha en Espanol Prostaglandin F2alpha en Francais
Business
Prostaglandin F2alpha in the Marketplace Patents on Prostaglandin F2alpha
Experimental / Informatics
List of terms related to Prostaglandin F2alpha

Dinoprost Tromethamine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intravenous (to induce labor), intra-amniotic (to induce abortion)
ATC code	G02AD01 (WHO) ;
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 CID	5280363;
IUPHAR/BPS	1884;
DrugBank	DB01160 ;
ChemSpider	4444062 ;
KEGG	D01352 ;
ChEMBL	ChEMBL815 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
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 ;
(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]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous (to induce labor), intra-amniotic (to induce abortion)
ATC code	G02AD01 (WHO)
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^Y 38562-01-5
PubChem CID	5280363
IUPHAR/BPS	1884
DrugBank	DB01160^Y
ChemSpider	4444062^N
KEGG	D01352^N
ChEMBL	ChEMBL815^N
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
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^N Key:PXGPLTODNUVGFL-YNNPMVKQSA-N^N
^NY (what is this?) (verify)