Dinoprost, Trometamolsalz
[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]azanium;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
Grundinformationen
- CAS
38562-01-5- Standard-SMILES
CCCCC[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)[O-])[C@@H](O)C[C@H]1O.[NH3+]C(CO)(CO)CO- InChIKey
IYGXEHDCSOYNKY-RZHHZEQLSA-N- Summenformel
- C24H45NO8
- Durchschnittliche Molmasse
- 475,6 g/mol
- Monoisotopische Masse
- 475,31451739
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- [1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]azanium;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
- IUPAC
- [1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]azanium;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
- Lokaler Name
- Dinoprost, Trometamolsalz
- Englischer Name
- Dinoprost tromethamine
- Summenformel
- C24H45NO8
- Molmasse
- 475.62
Namen und Synonyme
HMS3648P03prostaglandin f2a tris salt583eu14585lutalysePGF2αTrisEnsaprostu-14,583ePGF2ALPHAZinoprostPGF2a-THAM
Datenbank-Bezeichner
- CAS
38562-01-5- PubChem CID
- 71684398
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 189 Ų
- H-Brücken-Donoren
- 7
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 14
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 480
Experimentelle und physikochemische Eigenschaften
Melting Point100-101
Physikochemische Eigenschaften
- Schmelzpunkt
- 100 · 100-101°
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- 2 O: · 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.
- Aggregatzustand
- powder
- Farbe
- white
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- 2 O: · H2O: 1mg/mLethanol: 50mg/mL
- Merck
- 13 · 13,7970
- BRN
- 4087514 · 4087514
- Stabilität
- Hygroscopic
- InChIKey
- IYGXEHDCSOYNKY-RZHHZEQLSA-N
- SMILES
- [C@@]1(C/C=C\CCCC(=O)O)([C@H](C[C@@H](O)[C@@]1(/C=C/[C@@H](O)CCCCC)[H])O)[H].C(N)(CO)(CO)CO |&1:0,10,12,14,17,r|
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 8-10
- wgk
- 3
- hs_code
- 2937500000
- RTECS-Nr.
- UK8025000
- risk_code
- 60-22
- hazard_code
- T
- safety_code
- 53-45
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 4 OralRepr. 1B
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
Dinoprost tromethamine is the tromethamine (THAM) salt of the naturally occurring prostaglandin F2<sub>alpha</sub>. Prostaglandin F2<sub>alpha</sub> 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.
Mechanism of Action
Dinoprost tromethamine appears to act directly on the myometrium, but this has not been completely established. Dinoprost stimulates myometrial contractions (via its interaction with the prostaglandin receptors) in the gravid uterus that are similar to the contractions that occur in the term uterus during labor. These contractions are usually sufficient to cause abortion. Uterine response to prostaglandins increases gradually throughout pregnancy. Dinoprost also facilitates cervical dilatation and softening.
Biological Half-LifeThe half-life of dinoprost in amniotic fluid is 3 to 6 hours. The plasma half-life of dinoprost after intravenous administration is reported to be less than 1 minute.
Metabolism/MetabolitesEnzymatic dehydrogenation primarily in the maternal lungs and also in the liver.
Absorption, Distribution and ExcretionSlowly absorbed from the amniotic fluid into systemic circulation.
Anwendungen
BeschreibungDinoprost 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.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Ergänzende Hinweise
Definitiondinoprost 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.
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