Glimepiride

Bezeichnung:Glimepiride

CAS-Nr93479-97-1

Englisch Name:Glimepiride

CBNumberCB8318552

SummenformelC24H34N4O5S

Molgewicht490.62

MOL-Datei93479-97-1.mol

Glimepiride physikalisch-chemischer Eigenschaften

Schmelzpunkt	212.2-214.5 °C
Dichte	1.29±0.1 g/cm3(Predicted)
storage temp.	room temp
Löslichkeit	DMSO: >10 mg/mL
pka	5.10±0.10(Predicted)
Aggregatzustand	solid
Farbe	white
Merck	14,4440
BCS Class	2
CAS Datenbank	93479-97-1(CAS DataBase Reference)
EPA chemische Informationen	1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans- 4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo- (93479-97-1)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	21-36/38-46-62-63
S-Sätze:	25-26-36/37-53
WGK Germany	3
RTECS-Nr.	UX9363950
HS Code	2935904000

Gefahreninformationscode (GHS)

Glimepiride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R21:Gesundheitsschädlich bei Berührung mit der Haut.
R36/38:Reizt die Augen und die Haut.
R46:Kann vererbbare Schäden verursachen.
R62:Kann möglicherweise die Fortpflanzungsfähigkeit beeinträchtigen.
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
S-Sätze Betriebsanweisung:
S25:Berührung mit den Augen vermeiden.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
Beschreibung
Glimepiride, the first of a new generation of sulfonylurea drugs, was introduced in Sweden in 1995 as a first-line therapy to lower blood glucose in patients with type II diabetes. Sulfonylureas exert their hypoglycemic function primarily by direct stimulation of insulin secretion in glucose-insensitive pancreatic β-cells and GLUT translocation in insulin-resistant fat and muscle cells. Once-daily, orally administered glimepiride in diabetes patients showed a more rapid and longer lasting glucose-lowering effect than the commonly used agent glibenclamide. Glimepiride can be used either as a monotherapy or in combination with insulin.
Chemische Eigenschaften
White Cyrstalline Solid
Originator
Hoechst Marion Roussel (Germany)
Verwenden
For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
Verwenden
anticonvulsant
Verwenden
A sulfonylurea hypoglycemic agent. Used as an antidiabetic
Verwenden
Glimepiride induces the PI3 kinase (PI3K) and Akt pathway, along with insulin receptor substrate-1/2 and endothelial nitric oxide synthase. Glimepiride also increases osteoblast proliferation and differentiation, which is thought to be related to its ability to activate the PI3K and Akt pathway. Furthermore, Glimepiride enhances intrinsic peroxisome proliferator-activated receptor γ activity. Glimepiride also increases protein expression of glucose transports 1 and 4, and is a potent KIR channel blocker. Potent Kir6 (KATP) channel blocker and anti-diabetic agent. Inhibits pinacidil-activated cardiac Kir6 channels with an IC50 of 6.8 nM.
Definition
ChEBI: Glimepiride is a sulfonamide, a N-acylurea and a N-sulfonylurea. It has a role as a hypoglycemic agent and an insulin secretagogue.
Manufacturing Process
By heating of a mixture of 3-ethyl-4-methyl-2-pyrrolone and 2- phenylethylisocyanate at 150°C is obtained 3-ethyl-4-methyl-2-oxo-3- pyrroline-1-(N-2-phenylethyl)-carboxamide, melting point 106°-108°C. Then the carboxamide are introduced in portions at 30°C into chlorosulfonic acid, and agitated for 1 hour at 40°C. The sulfochloride (melting point 172-175°C), introduced into concentrated ammonia, and heated for 30 min on a steam bath. The mixture of sulfonamide obtained (melting point 180°-182°C), of acetone and K2CO3 are refluxed with agitation for 6 hours. Subsequently the cyclohexyl isocyanate are added dropwise, and agitation is continued for 6 hours at boiling temperature. After standing overnight, the product is filtered, the crystals obtained are treated with dilute hydrochloric acid, and again filtered. It is prepared N-(4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1- carboxamido)ethyl]benzenesulfonyl)-N'-cyclohexyl urea; melting point 185°- 187°C (from acetone) (Glimepiride).
Trademarks
Amaryl (Sanofi Aventis).
Therapeutic Function
Oral hypoglycemic
Allgemeine Beschreibung
Glimepiride is 3-ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans-4-methylcyclohexyl)amino]-carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide; thiscompound can also be named as the urea—see precedingdiscussion (Amaryl, generic). Combinations are availablewith rosiglitazone in the United States (Avandaryl tablets;mg glimepiride/mg rosiglitazone as maleate salt: 1/4,2/4, 4/4, 2/8, 4/8); and with pioglitazone (Duetact tablets;mg glimepiride/ mg pioglitazone as hydrochloride salt:2/30, 4/30).
Allgemeine Beschreibung
Glimepiride, 1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea (Amaryl), is very similarto glipizide with the exception of their heterocyclic rings.Instead of the pyrazine ring found in glipizide, glimepiridecontains a pyrrolidine system. It is metabolized primarilythrough oxidation of the alkyl side chain of the pyrrolidine,with a minor metabolic route involving acetylation of theamine.
Biologische Aktivität
Potent K ATP channel blocker and anti-diabetic agent. Inhibits pinacidil-activated cardiac K ATP channels with an IC 50 of 6.8 nM.
Biochem/physiol Actions
Glimepiride is a potent blocker of cardiac KATP channels activated by pinacidil with an IC50 of 6.8 nM.
Clinical Use
Non-insulin dependent diabetes mellitus
Veterinary Drugs and Treatments
Glimepiride may potentially be a useful adjunct in the treatment of non-insulin dependent diabetes mellitus (NIDDM) in cats. Its duration of action in humans allows it to be dosed once daily, which could be of benefit in cats. It may also have fewer side effects than glipizide in cats.
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Analgesics: effects enhanced by NSAIDs.
Antibacterials: effects enhanced by chloramphenicol, sulphonamides, tetracyclines and trimethoprim; effect reduced by rifamycins.
Anticoagulants: effect possibly enhanced by coumarins; also possibly changes to INR.
Antifungals: concentration increased by fluconazole and miconazole and possibly voriconazole.
Lipid-regulating drugs: possibly additive hypoglycaemic effect with fibrates.
Sulfinpyrazone: enhanced effect of sulphonylureas.
Stoffwechsel
The drug is extensively metabolised in the liver to two main metabolites. The cytochrome P450 isoenzyme CYP2C9 is involved in the formation of a hydroxy derivative, which is further metabolised to a carboxy derivative by cytosolic enzymes.
About 60% of a dose is eliminated in the urine and 40% in the faeces.

Glimepiride Upstream-Materialien And Downstream Produkte

Glimepiride Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

93479-97-1, Glimepiride Verwandte Suche:

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