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Misoprostol

Misoprostol Struktur
59122-46-2
CAS-Nr.
59122-46-2
Englisch Name:
Misoprostol
Synonyma:
Misoprosto;(11α,13E)-(-)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oicacidmethylester;SC 2933;CYTOTEC;Misogon;SC-29333;Misoprostil;MISOPROSTOL;Mesoprostal;DL-MISOPROSTOL
CBNumber:
CB7713293
Summenformel:
C22H38O5
Molgewicht:
382.54
MOL-Datei:
59122-46-2.mol

Misoprostol Eigenschaften

Schmelzpunkt:
261-263°C
Siedepunkt:
429.67°C (rough estimate)
Dichte
1.0323 (rough estimate)
Brechungsindex
1.6120 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
L?slichkeit
Practically insoluble in water, soluble in ethanol (96 per cent), sparingly soluble in acetonitrile.
pka
13.92±0.60(Predicted)
CAS Datenbank
59122-46-2(CAS DataBase Reference)
EPA chemische Informationen
Misoprostol (59122-46-2)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher T
R-S?tze: 45-60-61-25-36/37/38
S-S?tze: 53-22-36/37/39-45
RIDADR  UN 2810 6.1/PG 3
WGK Germany  2
RTECS-Nr. UK8390000
HS Code  2937500000
Giftige Stoffe Daten 59122-46-2(Hazardous Substances Data)
Toxizit?t LD50 in rats, mice (mg/kg): 40-62, 70-160 i.p.; 81-100, 27-138 orally (Kotsonis)
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizit?t oral Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
H360 Kann die Fruchtbarkeit beeintr?chtigen oder das Kind im Mutterleib sch?digen. Fertility (Fruchtbarkeit) Kategorie 1 Achtung GHS hazard pictogramssrc="/GHS08.jpg" width="20" height="20" />
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P308+P313 BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.

Misoprostol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R45:Kann Krebs erzeugen.
R60:Kann die Fortpflanzungsf?higkeit beeintr?chtigen.
R61:Kann das Kind im Mutterleib sch?digen.
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S22:Staub nicht einatmen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).

Beschreibung

Misoprostol is an orally-active PGEl analog useful in the treatment of gastric and duodenal ulcers. As with other agents of this type, misoprostol may prove useful as a gastric cytoprotective when administered concurrently with irritating drugs such as nonsteroidal antiinflammatories.

Chemische Eigenschaften

Misoprostol is a yellow, viscous liquid with a musty odour. Miscible with ethanol, ether or chloroform, extremely insoluble in water or n-hexane. Very unstable at room temperature and undergoes thermal epimerization to the 8-isomer. It is also extremely sensitive to the Ph value. It removes the hydroxyl group at the 11α position in acidity and alkalinity, converts it into A-type prostaglandins, and isomerizes into B-type prostaglandins. However, it is relatively stable in the dispersion system of hydroxypropyl methylcellulose and can be stored at room temperature.

Verwenden

Misoprostol is a cytoprotective prostaglandin PGE1 analogue that inhibits gastric acid secretion. It has many medical uses, including nine obstetric indications. The drug was originally produced by Pfizer for the treatment of gastric ulcers. Misoprostol is commonly used to prevent NSAID-induced gastric ulcers in patients at high risk of complications from a gastric ulcer, such as elderly patients and patients with a history of ulcer. It has also been used in treating duodenal ulcers unresponsive to histamine H2-antagonists; the drug does not prevent duodenal ulcers,however, in patients taking NSAIDS. Misoprostol can cause miscarriage, often associated with potentially dangerous bleeding.

Indications

Misoprostol (Cytotec), which is an analogue of prostaglandin E1, has been approved for use in the prevention of nonsteroidal antiinflammatory drug–induced ulceration. It also is approved in other countries for the treatment of peptic ulcer disease.

synthetische

synthesis of Misoprostol
To a 1000 ml dried flask under a nitrogen atmosphere was added 74.6 g of(E)-trimethyl-[[1-methyl-1-[3-(tributylstannyl)-2-propenyl]pentyl]oxy]silane,125 ml anhydrous THF and 24.2 g of copper (I) iodide. The mixture wasstirred at room temperature for 30 minutes and then it was cooled to -25 to -30°C. 98.8 ml of methyllithium (2.86 M) in DEM was added dropwise and theresultant solution was stirred at -15°C for 2 hours. Then the reaction mixturewas cooled to -78°C and 25 g of methyl-5-oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoate in 100 ml of THF was added rapidly. After stirringthe mixture for 5 min at -78°C, it was quenched into a mixture of 750 ml ofaqueous ammonium chloride solution and 200 ml of ammonium hydroxide.The resulting mixture was warmed to room temperature and stirred until adeep blue aqueous layer was obtained. Ethyl acetate (250 ml) was used forextraction. Then the combined organic layers were washed with brine andsubsequently dried over magnesium sulfate. After a filtration andconcentration under reduced pressure, an oil (105 g) was obtained. This oilcontaining the protected prostaglandin was subjected to acidic deprotection(cat. PPTS, acetone and water) and purification (chromatography on silica gel)to provide 15.8 g (60%) of misoprostol was identical.

Biologische Aktivit?t

Cytoprotective prostaglandin E 1 analog that displays agonist activity at EP receptors. K i values are 120, 250, 67 and 67 nM at cloned mouse EP 1 , EP 2 , EP 3 and EP 4 receptors respectively. Prevents NSAID-induced gastric ulceration.

Pharmakologie

Misoprostol is absorbed rapidly after oral administration and is hydrolyzed to the active compound. It is metabolized by the liver and excreted mainly in the urine. Adverse effects include crampy abdominal pain, dose-related diarrhea, and uterine contractions. The last-named effect has led to its use in the control of postpartum bleeding.

Mode of action

Misoprostol is a synthetic prostaglandin E1 analogue which has ulcer healing, gastric acid antisecretory and mucosal protective properties. The antisecretory activity is mediated by direct action on specific prostaglandin receptors on the surface of gastric parietal cells. In dogs with innervated Pavlov pouches, inhibition of secretion is achieved at a lower dosage by intrapouch injection than by intravenous or intragastric administration, suggesting that the local effect may predominate. The mucosal protective effect against various damaging agents has been demonstrated in humans with doses that inhibit and doses which minimally affect acid secretion.

Misoprostol Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Misoprostol Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 324)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Wuhan Nutra Biotechnology Co.,Ltd
+8617786394783
nutrabiotech@outlook.com China 300 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12834 58
Shanghai UCHEM Inc.
+862156762820 +86-13564624040
sales@myuchem.com China 7629 58
Wuhan Fortuna Chemical Co., Ltd
+86-027-59207850
info@fortunachem.com China 5975 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3619 58
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28172 58
Hubei xin bonus chemical co. LTD
86-13657291602
linda@hubeijusheng.com CHINA 22963 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58

59122-46-2()Verwandte Suche:


  • DL-MISOPROSTOL
  • Misoprostol API
  • Misogon
  • Misoprostil
  • Misoprostol, 1% in cellulose
  • SC 2933
  • Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11a,13E)- (9CI)
  • (11α,13E)-1l,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester
  • Misoprostol acid (Rac)
  • CYTOTEC
  • Methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
  • Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11a,13E)-
  • (11-alpha,13E)-(±)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester
  • rac-(11α*,13E)-11,16-Dihydroxy-16-methyl-9-oxoprosta-13-ene-1-oic acid methyl ester
  • Misoprostol (100 mg)
  • Misoprostol Powder
  • (11A,13E)-(-)-11,16-DIHYDROXY-16-METHYL-9-OXO-PROST-13-EN-1-OIC ACID METHYL ESTER
  • (11alpha,13e)-(+)-11alpha,16-dihydroxy-16-methyl-9-oxoprost-13e-en-1-oic acid methyl ester
  • (+/-)-15-DEOXY-[16RS]-16-HYDROXY-16-METHYLPROSTAGLANDIN E1
  • (+/-)-15-DEOXY-(16R,S)-16-HYDROXY-16-METHYL-PROSTAGLANDIN E1, METHYL ESTER
  • 9-OXO-11ALPHA,16-DIHYDROXY-16-METHYL-PROST-13E-EN-1-OIC ACID
  • 9-OXO-11ALPHA,16-DIHYDROXY-16-METHYL-PROST-13E-EN-1-OIC ACID, METHYL ESTER
  • SC-29333
  • MISOPROSTOL
  • MISOPROSTOL FREE ACID
  • Misoprostol 1:100
  • MISOPROSTOL (SC-29333)
  • Misoprostol(W.S)
  • Misoprostol (Mixture of Diastereomers)
  • Misoprostol-d5
  • Misoprostol, HPMC premix
  • Misoprostol, 99.0%
  • misoprostaglandin
  • Misoprostol for system suitability CRS
  • Misoprostol CRS
  • Misoprostol,racemic mixture
  • Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11α,13E)-(±)-
  • Misoprostol USP/EP/BP
  • Misoprostol, isomeric mixture
  • MISOPROSTOL (1%) DISPERSION
  • Misoprostol (Y0000490)
  • Misoprostol for system suitability (Y0001162)
  • MisoprostolQ: What is Misoprostol Q: What is the CAS Number of Misoprostol Q: What is the storage condition of Misoprostol Q: What are the applications of Misoprostol
  • Misoprostol (1444300)
  • Misoprosto
  • (11α,13E)-(-)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oicacidmethylester
  • Mesoprostal
  • 59122-46-2
  • BioChemical
  • Biochemicals and Reagents
  • Prostaglandins
  • Lipids
  • Fatty Acids
  • Active Pharmaceutical Ingredients
  • Prostaglandin
  • Fatty Acid Derivatives & Lipids
  • Glycerols
  • Intermediates & Fine Chemicals
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