Prostaglandin F2alpha

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Dinoprost Tromethamine
Dinoprost.png
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Intravenous (to induce labor), intra-amniotic (to induce abortion)
ATC code
Pharmacokinetic data
Elimination half-life3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
KEGG
ChEMBL
E number{{#property:P628}}
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Chemical and physical data
FormulaC20H34O5
Molar mass354.48 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.

Mechanism of action

PGF acts by binding to the prostaglandin F2α receptor.

Synthesis

In 2012 a concise and highly stereoselective total synthesis of PGF 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:

References

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

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