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HomeProduct name listDinoprost tromethamine

Dinoprost tromethamine

Synonym(s):(5Z,9α,11α,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoic acid tris salt;PGF−Tris;Prostaglandin F tris salt

  • CAS NO.:38562-01-5
  • Empirical Formula: C24H45NO8
  • Molecular Weight: 475.62
  • MDL number: MFCD00077863
  • EINECS: 254-002-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
Dinoprost tromethamine Structural

What is Dinoprost tromethamine?

Absorption

Slowly absorbed from the amniotic fluid into systemic circulation.

Toxicity

Although overdose by intra-amniotic administration of dinoprost has not been reported, exaggeration of the nausea, vomiting, and diarrhea that occur with normal doses would be expected.

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

The Uses of Dinoprost tromethamine

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.

The Uses of Dinoprost tromethamine

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.

Background

The tromethamine (THAM) salt of the naturally occurring prostaglandin F2 alpha, dinoprost tromethamine occurs as a white to off-white, very hygroscopic, crystalline powder. Dinoprost tromethamine may also be known as dinoprost trometamol, PGF2 alpha THAM, or prostaglandin F2 alpha tromethamine.

Indications

Used for aborting second-trimester pregnancy (between the twelfth to eighteenth week of gestation) and in incomplete abortion or for therapeutic abortion in cases of intrauterine fetal death and congenital abnormalities incompatible with life. Also used at low-doses for medically indicated induction of labor at term. Also injected intra-arterially for use as a vasodilator to assist in angiography.

What are the applications of Application

PGF2α (Prostaglandin F2α) is binds to PGF2Rα, shown to stimulate COX2 expression, and regulate adrenal endocrine function

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.

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.

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.

Pharmacokinetics

Dinoprost tromethamine is the tromethamine (THAM) salt of the naturally occurring prostaglandin F2alpha. Prostaglandin F2alpha?has several pharmacologic effects on the female reproductive system, including stimulation of myometrial activity, relaxation of the cervix, inhibition of steroidogenesis by corpora lutea, and can potentially lyse corpora lutea.

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.

Metabolism

Enzymatic dehydrogenation primarily in the maternal lungs and also in the liver.

storage

Store at -20°C

Properties of Dinoprost tromethamine

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

Safety information for Dinoprost tromethamine

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Dinoprost tromethamine

InChIKey IYGXEHDCSOYNKY-RZHHZEQLSA-N

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