Prostaglandin F _2α

Structural formula
General
Non-proprietary name	Dinoprost
other names	(5 Z , 9α, 11α, 13 E , 15 S ) -9,11,15-trihydroxyprosta-5,13-dien-1-acid
Molecular formula	C 20 H 34 O 5
External identifiers / databases
EC number	684-259-0
ECHA InfoCard	100.209.720
PubChem	5280363
DrugBank	DB01160
Wikidata	Q421375
Drug information
ATC code	G02 AD01
properties
Molar mass	354.48 g · mol -1
Physical state	firmly
Melting point	25-35 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-360
	P: 201-280-301 + 312 + 330-308 + 313
Toxicological data	1170 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Prostaglandin F _2α (or PGF _{2α for} short ) is a tissue hormone from the group of prostaglandins . It is involved in processes related to reproduction in mammals .

Biosynthesis and Effect

Prostaglandin F _2α is formed from PGH ₂ with the help of the enzyme prostaglandin F synthase and acts via the FP receptors (prostaglandin F binding receptors). In humans, cyclooxygenase-2 is induced in the placenta and amnion around birth , which leads to the synthesis of PGF _2α and PGE ₂ , which stimulate uterine smooth muscles to contract or sensitize them to oxytocin . Mice that cannot develop an FP receptor due to a genetic defect cannot give birth. The effect of PGF _2α to the FP receptor luteum there ended the progesterone production and causes luteolysis .

Medical use

Prostaglandin F _2α ( drug name : Dinoprost) is used in veterinary medicine to break down the corpus luteum (luteolysis) and to induce childbirth or abortion . In cattle, it is also used after birth to empty the uterus (uterus), in dogs for a pyometra in the anestrus.
Dinoprost can also be used in human medicine in gynecological indications. In the Czech Republic it is approved for therapeutic abortion and induction of labor in the event of fetal death. In Germany, after the fictitious approval expired, marketability ended in June 2003.

It is assumed that prostaglandin D _{2 could be} involved in the development of androgenetic hair loss (alopecia) and that PGF _2α could counteract this. In animal experiments on mice, PGD ₂ shortens hair growth phases. In the opinion of the researchers, however, hair follicles are still present even with a bald head , but at best they still develop downy hair due to their significant reduction in size.

Synthetic derivatives of prostaglandin F _2α are used, among other things, in ophthalmology to lower intraocular pressure. As a side effect, the eyelashes grow longer. This side effect is also used cosmetically (" eyelash growth serum ").

The 1: 1 mixture with trometamol, C ₂₀ H ₃₄ O ₅ ⋅ C ₄ H ₁₁ NO ₃ is used pharmaceutically .

Others

PGF _2α and PGF _2β differ stereochemically in the position of the hydroxyl groups on C-9 and C-10.

Finished medicinal products

Veterinary medicine: Dinolytic (D), Enzaprost T (D)
Human medicine: Enzaprost F (CZ), Minoprostin F2 alpha (D; except sales)

Web links

Entry on Prostaglandin F2α from Vetpharm, accessed on August 5, 2012.

Individual evidence

↑ ^a ^b Entry on Dinoprost. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
↑ ^a ^b Datasheet Dinoprost trometamol, European Pharmacopoeia (EP) Reference Standard from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).
↑ Data sheet Prostaglandin F _2α (PDF) from Calbiochem, accessed on December 8, 2015.
↑ Wolfgang Heuwieser, Marc Drillich: Managing dairy cows correctly after calving. In: tier-vital.com. Kamlage Verlag, archived from the original on August 3, 2012 ; Retrieved April 25, 2017 .
↑ Axel Wehrend: Key symptoms of gynecology and obstetrics in dogs. Enke Stuttgart 2010, ISBN 978-3-8304-1076-8 , p. 105.
↑ database of the Czech State Intsitut of Drug Control [1] , accessed on February 21 of 2019.
↑ Deletion list of pharmaceuticals , accessed on February 21, 2019.
↑ ^a ^b Androgenetic alopecia: prostaglandin explains hair loss. In: aerzteblatt.de . March 22, 2012, accessed December 8, 2015 .
↑ Tina Hesman Saey: The yin and yang of male pattern baldness. In: Science News. September 23, 2013, archived from the original on July 9, 2012 ; accessed on April 25, 2017 (English).

[roempp-1] Entry on Dinoprost. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.

[Sigma-2] Datasheet Dinoprost trometamol, European Pharmacopoeia (EP) Reference Standard from Sigma-Aldrich , accessed on October 31, 2016 ( PDF ).

[Calbiochem-3] Data sheet Prostaglandin F _2α (PDF) from Calbiochem, accessed on December 8, 2015.

[4] Wolfgang Heuwieser, Marc Drillich: Managing dairy cows correctly after calving. In: tier-vital.com. Kamlage Verlag, archived from the original on August 3, 2012 ; Retrieved April 25, 2017 .

[5] Axel Wehrend: Key symptoms of gynecology and obstetrics in dogs. Enke Stuttgart 2010, ISBN 978-3-8304-1076-8 , p. 105.

[6] tabase of the Czech State Intsitut of Drug Control [1] , accessed on February 21 of 2019.

[7] Deletion list of pharmaceuticals , accessed on February 21, 2019.

[dÄB-8] Androgenetic alopecia: prostaglandin explains hair loss. In: aerzteblatt.de . March 22, 2012, accessed December 8, 2015 .

[9] Tina Hesman Saey: The yin and yang of male pattern baldness. In: Science News. September 23, 2013, archived from the original on July 9, 2012 ; accessed on April 25, 2017 (English).

Prostaglandin F 2α