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prostaglandin F2α

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Origin: China

Cas No: 551-11-1

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CAS No.: 551-11-1 Formula: C20H34O5 Molecular Weight: 354.48100

Description

Prostaglandin F2α (PGF2α 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 PGF2α is dependent on the number of receptors on the corpus luteum membrane.
The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.

Basic Info

Chemical Name	prostaglandin F2α
Synonyms	glandin; cyclosin; [3H]-PGF2alpha; (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-cyclopentyl]hept-5-enoic acid; Dinprost; Prostaglandin F2α; Glandin N; enzaprost; panacelan; prostaglandin F2alpha; PGF2ALPHA; Prostaglandin F2a; DINOPROST; dinolytic;
CAS No.	551-11-1
Molecular Formula	C20H34O5
Molecular Weight	354.48100
PSA	97.99000
LogP	3.04290

Properties

Appearance & Physical State	White to off-white crystalline solid.
Density	1.153 g/cm3
Boiling Point	531ºC at 760 mmHg
Melting Point	25-35ºC
Flash Point	289ºC
Refractive Index	1.569
Stability	Stable for 2 yr in light resistant containers at 5-15ºC degrades in 1 wk when exposed to sunlight or in 3 mo at 40ºC stable in light, air, and heat.
Storage Condition	Store in a tightly closed container.

Synthesis Route

arachidonic acid→prostaglandin D2+prostaglandin E2
(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol+4-carboxybutyl(triphenyl)phosphanium,bromide→prostaglandin F2α
Prostaglandin F2α methyl ester→prostaglandin F2α

Toxicity

Exposure Route	Type of Test	Species Observed	Dose/Duration	Toxic Effects
Intravenous	TDLo - Lowest published toxic dose	Human - woman	20 ug/kg	1.Gastrointestinal-hypermotility, diarrhea 2.Gastrointestinal-nausea or vomiting
Oral	LD50 - Lethal dose, 50 percent kill	Rodent - rat	1170 mg/kg	1.Lungs, Thorax, or Respiration-respiratory depression 2.Gastrointestinal-hypermotility, diarrhea 3.Nutritional and Gross Metabolic-body temperature decrease
Subcutaneous	LD50 - Lethal dose, 50 percent kill	Rodent - rat	95 mg/kg	1.Details of toxic effects not reported other than lethal dose value

Precursor

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol
(Z)-7-((1R,2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoic acid
4-carboxybutyl(triphenyl)phosphanium,bromide
Prostaglandin F2α methyl ester

Downstream Product

7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoctyl]cyclopentyl]heptanoic acid
Prostaglandin F2α methyl ester
9ALPHA, 11ALPHA, 15S-TRIHYDROXY-PROSTA-5Z, 13E-DIEN-1-OIC ACID, 1,9-LACTONE

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