Lansoprazole

Bezeichnung:Lansoprazole

CAS-Nr103577-45-3

Englisch Name:Lansoprazole

CBNumberCB6396972

SummenformelC16H14F3N3O2S

Molgewicht369.36

MOL-Datei103577-45-3.mol

Lansoprazole physikalisch-chemischer Eigenschaften

Schmelzpunkt	178-182°C dec.
Siedepunkt	555.8±60.0 °C(Predicted)
Dichte	1.50±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	Practically insoluble in water, soluble in anhydrous ethanol, very slightly soluble in acetonitrile.
pka	pKa 2.34±0.37 (Occasionally);3.53±0.37 (Occasionally);8.48±0.30 (Occasionally)
Aggregatzustand	powder
Farbe	off-white
Merck	14,5362
BCS Class	2
InChIKey	MJIHNNLFOKEZEW-UHFFFAOYSA-N
CAS Datenbank	103577-45-3(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	2
RTECS-Nr.	DD9487500
HS Code	29339900
Giftige Stoffe Daten	103577-45-3(Hazardous Substances Data)
Toxizität	dog,LD,oral,> 2gm/kg (2000mg/kg),Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 387, 1993.

Gefahreninformationscode (GHS)

Lansoprazole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Lansoprazole is a proton pump inhibitor that inhibits the H⁺/K⁺-ATPase. It inhibits K⁺ and H⁺ accumulation in gastric microsomes in a concentration-dependent manner (IC₅₀s = 6.3 and 7.0 μM, respectively) and inhibits H⁺/K⁺-ATPase activity by approximately 60% when used at a concentration of 10 μM. Lansoprazole inhibits the H⁺/K⁺-ATPase in parietal cells, thus inhibiting gastric acid secretion and increasing intragastric pH. It is a substituted benzimidazole that binds covalently to proton pumps, providing complete and prolonged inhibition of acid secretion. Formulations containing lansoprazole have been used as a proton pump inhibitor and in combination with antibiotics in the treatment of H. pylori infections and duodenal ulcer disease.
Beschreibung
Lansoprazole is the second proton pump inhibitor approved as an antiulcer agent for the short term treatment of duodenal ulcer and gastroesophageal reflux disease. Like omeprazole, lansoprazole is reported to be more efficacious than the H₂-antagonists in treating peptic ulcer disease.Other potential uses could be in the treatment of Zollinger-Ellison syndrome.
Chemische Eigenschaften
White Crystalline Powder
Originator
Takeda (Japan)
Verwenden
For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Verwenden
A H+,K+-ATPase inhibitor that displays antisecretory activity
Verwenden
Used as a gastric proton pump inhibitor. An antiulcerative
Verwenden
Treatment of gastroesophageal reflux disease (GERD), erosive esophagitis, duodenal ulcers, Helicobacter pylori (H. pylori) infections,stomach ulcers, prevention of stomach ulcers in those people taking non-steroidal anti-inflammatory drugs (NSAIDs), such
Definition
ChEBI: Lansoprazole is a member of benzimidazoles, a member of pyridines and a sulfoxide. It has a role as an EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor and an anti-ulcer drug.
Manufacturing Process
Preparation of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio-1Hbenzimidazole:
A mixture of 6.63 g of 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy) pyridine (30 mmol), 4.5 g of 2-mercaptobenzimidazol (30 mmol) and 8.67 g of triphenylphosphine (33 mmol) was dissolved in 100 ml of tetrahydrofuran, 5.75 g of diethyl azodicarboxylate (33 mmol) dissolved in 30 ml of tetrahydrofuran was added dropwise thereto at room temperature, and stirred for 1 hour. The reaction mixture was concentrated under a reduced pressure, the resulting residue was combined with 100 ml of ethylacetate, and extracted twice with 50 ml portions of 1 N HCl. The aqueous layer was then washed with 50 ml of diethylether; neutralized with 1 N NaOH to adjust the pH to 7. The resulting precipitates were filtrated, washed with water, and dried, to obtain 10.06 g of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio- 1H-benzimidazole as a white solid (yield: 95%), m.p.142-144°C.
4.46 g of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methylthio-1Hbenzimidazole (12 mmol) and 18.74 mg of tetramethyl-1-piperidinyloxy free radical (1 mol %, used as a catalyst) were dissolved in 40 ml of tetrahydrofuran, and combined with 166.76 mg of tetrabutylammonium chloride (5 mol %) dissolved in 20 ml of distilled water. The resulting mixture was cooled to 0°C and 13.6 ml of NaOCl (12%, 2.2 equivalent) dissolved in 20 ml of distilled water was added thereto over 2 hours at 0°C, stirred for 10 min, and then for additional 10 min at 20°C. Then, the reaction mixture was extracted with 40 ml of ethylacetate and the organic layer was washed with sat. NaHCO3 (30 ml) and then with sat. brine (30 ml), dried over anhydrous MgSO4, and the solvent was removed therefrom. The resulting crude product as recrystallized from acetone/hexane, to obtain 3.99 g of 2-[3-methyl-4- (2,2,2-trifluoroethoxy)-2-pyridyl]methylsulphinyl-1H-benzimidazol (lansoprazole) as a white-light brown solid (yield: 90%), melting point 164- 165°C (decomposition).
Trademarks
Prevacid (TAP);Ogast;Lanzor.
Therapeutic Function
Antiulcer
Allgemeine Beschreibung
Lansoprazole, 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole(Prevacid), is a white to brownish white, odorless crystallinepowder that is practically insoluble in water.Lansoprazole is a weak base (pyridine N, pKa 3.83.) and aweak acid (benzimidazole N-H, pK 0.62). Like other PPIs,lansoprazole is essentially a prodrug that, in the acidic biophaseof the parietal cell, forms an active metabolite thatirreversibly interacts with the target ATPase of the pump.Lansoprazole must be formulated as encapsulated entericcoatedgranules for oral administration to protect the drugfrom the acidic environment of the stomach.
In the fasting state, about 80% of a dose of lansoprazole(vs. 50% of omeprazole) reaches the systemic circulation,where it is 97% bound to plasma proteins. Thedrug is metabolized in the liver (sulfone and hydroxymetabolites) and excreted in bile and urine, with a plasmahalf-life of about 1.5 hours.
Biologische Aktivität
H + ,K + -ATPase inhibitor (IC 50 = 6.3 μ M) that displays antisecretory and antiulcer activity. Inhibits gastric acid secretion (IC 50 = 0.09 μ M for histamine-induced acid formation) and reduces gastric lesion formation induced by a variety of ulcerative stimuli. Antibacterial against Helicobacter pylori in vitro . Also blocks swelling-dependent chloride channel (ICIswell) in NIH3T3 fibroblasts. More potent than omeprazole (5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole ).
Biochem/physiol Actions
Gastric proton pump inhibitor.

Lansoprazole Upstream-Materialien And Downstream Produkte

Lansoprazole Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

103577-45-3, Lansoprazole Verwandte Suche:

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