Dinoprost tromethamine Chemical Properties

Melting point:

100-101°

storage temp. 

-20°C

solubility 

H₂O: 1 mg/mL Aqueous solutions are stable for 30 days at 2-8°C and for several months frozen at −0°C in single use aliquots. Avoid repeated freeze/thaw cycles.

form 

powder

color 

white

Merck 

13,7970

BRN 

4087514

Stability:

Hygroscopic

InChIKey

IYGXEHDCSOYNKY-RZHHZEQLSA-N

Safety Information

Hazard Codes 

T

Risk Statements 

60-22

Safety Statements 

53-45

WGK Germany 

3

RTECS 

UK8025000

F 

8-10

HS Code 

2937500000

MSDS

• Language:English Provider:SigmaAldrich

Dinoprost tromethamine Usage And Synthesis

Description

Dinoprost tromethamine is a synthetic analogue of prostaglandin. F2α is an autocrine hormone present in many mammalian tissues. It is used to cause luteolysis in the cow, sow and mare. It is given as a single injection by im or sc routes, the recommended dosage rate is 25 mg cow; 10 mg sow and 5 mg mare. It is rapidly absorbed from the injection site. It has an extremely short half life of only a few minutes, it is almost completely cleared following one or two passages through the liver and/or lungs.

Chemical Properties

White Solid

Originator

Prostin F2A,Upjohn,UK,1972

Uses

One of the most biologically studied of the primary prostaglandins. Closely related to Prostaglandin E2 (PGE2) in that both prostaglandins are biosynthesized from the same precursors and that PGF2 is the synthetic reduction product of PGE2. Phospholipase A2 (PLA2) is a key enzyme for biosynthesis of PGF2α. Oxytocic; abortifacient.

Indications

Dinoprost tromethamine salt (Prostaglandin F2α tromethamine salt) is an orally active, potent prostaglandin F (PGF) receptor (FP receptor) agonist. Dinoprost tromethamine salt is a luteolytic hormone produced locally in the endometrial luminal epithelium and corpus luteum (CL). Dinoprost tromethamine salt plays a key role in the onset and progression of labour.

Definition

dinoprost tromethamine is a synthetic analogue of the naturally occurring prostaglandin F2 alpha. Prostaglandin F2 alpha stimulates myometrial activity, relaxes the cervix, inhibits corpus luteal steroidogenesis, and induces luteolysis by direct action on the corpus luteum.

Manufacturing Process

A solution of tris(hydroxymethyl)aminomethane (1.645 grams) in 3.0 ml of water at 60°C is added with vigorous stirring to a solution of PGF2α, (5.00 grams) in 700 ml of acetonitrile which has just been
ought to its boiling point. The vessel which contained the aqueous amine solution is rinsed with three 0.66 ml portions of water, each rinsing being added with vigorous stirring to the acetonitrile solution. The mixture is then cooled to 25°C by immersion of the vessel in cool water. At the cloud point, the vessel wall (glass) below the liquid surface is scratched vigorously with a glass rod. The mixture is then maintained at 25°C for 24 hours.
The resulting crystals are collected by filtration under nitrogen, washed on the filter with 50 ml of acetonitrile, and then dried by passing nitrogen at 50°C through the filter cake for one hour. Drying is completed in an oven at 70°C for 8 hours to give 5.965 grams of the tris(hydroxymethyl)aminomethane salt of PGF2α in free flowing crystalline form; MP 100°-101°C.

brand name

Prostin F2 Alpha (Pharmacia & Upjohn).

Therapeutic Function

Smooth muscle stimulant

Biochem/physiol Actions

Prostaglandin F2α is induced by uterine-produced oxytocin and acts on the corpus luteum to cause luteolysis and inhibit progesterone production.

Safety Profile

Poison by intraperitoneal, subcutaneous, intravenous, and intramuscular routes. Moderately toxic by ingestion. Human reproductive effects by intervagmal route: terminates pregnancy, effects on fertility. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also other prostaglandin entries.

storage

Store at -20°C

Dinoprost tromethamine(38562-01-5)Related Product Information

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