Glipizide

Bezeichnung:Glipizide

CAS-Nr29094-61-9

Englisch Name:Glipizide

CBNumberCB9185001

SummenformelC21H27N5O4S

Molgewicht445.54

MOL-Datei29094-61-9.mol

Glipizide physikalisch-chemischer Eigenschaften

Schmelzpunkt	208-209°C
Dichte	1.34±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	methanol: 1.9 mg/mL
Aggregatzustand	solid
pka	pKa 5.9 (Uncertain)
Farbe	white
Merck	14,4442
BCS Class	2 (CLogP), 4 (LogP)
CAS Datenbank	29094-61-9(CAS DataBase Reference)
EPA chemische Informationen	2-Pyrazinecarboxamide, N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl- (29094-61-9)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	21-36/38-46-62-63
S-Sätze:	24/25-53-36/37-26-25
WGK Germany	3
RTECS-Nr.	YS7640000
F	10
HS Code	29350090
Toxizität	LD50 in mice, rats (g/kg): >3, 1.2 i.p. (Ambrogi)

Gefahreninformationscode (GHS)

Glipizide 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:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S25:Berührung mit den Augen vermeiden.
Chemische Eigenschaften
Crystalline Solid
Originator
Minidiab,Carlo Erba,Italy,1973
Verwenden
Labelled Glipizide . A sulfonylurea hypoglycemic agent. Used as an antidiabetic.;Labeled Glipizide, intended for use as an internal standard for the quantification of Glipizide by GC- or LC-mass spectrometry.
Verwenden
A hypoglycemic agent that enhances insulin secretion.
Verwenden
sweetener, treatment of portoencephalopathy
Definition
ChEBI: An N-sulfonylurea that is glyburide in which the (5-chloro-2-methoxybenzoyl group is replaced by a (5-methylpyrazin-2-yl)carbonyl group. An oral hypoglycemic agent, it is used in the treatment of type 2 diabetes mellitus.
Manufacturing Process
5-Methyl pyrazine-2-carboxylic acid is refluxed with thionyl chloride in anhydrous benzene for approximately 12 hours. Benzene and thionyl chloride excess is removed by distillation. Then some anhydrous dioxane is added and this acid chloride solution is allowed to drop into p-(β-aminoethyl)- benzenesulfonamide suspension in dioxane and anhydrous pyridine. The resulting mixture is then refluxed for 3 hours. Dioxane is removed by distillation and then the residue is washed with water and acetic acid. The raw acylated sulfonamide is then filtered and crystallized from 95% ethanol, thus obtaining a product of MP 200° to 203°C.
This product is then reacted with cyclohexyl isocyanate to give glipizide.
Trademarks
Glucotrol (Pfizer).
Therapeutic Function
Oral hypoglycemic
Allgemeine Beschreibung
Glipizide is N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-2-pyrazinecarboxamide;this compound can also be named as the urea—seepreceding discussion (Glucotrol, generic). In the UnitedStates, combinations are available with metformin (Metaglip,generic; tablets, mg glipizide/mg metformin as hydrochloride:2.5/250, 2.5/500, 5/500). Extended-release tablets are available(Glucotrol XL, generic). The pyrazine moiety within thisstructure renders the molecule significantly more hydrophilicthan the similar molecule glyburide, albeit also moderatelyless potent on a dosage as well as target-level basis.
Allgemeine Beschreibung
Structurally, glipizide, 1-cyclohexyl-3-[[p-[2(methylpyrazinecarboxamido)ethyl]phenyl]sulfonyl]urea(Glucotrol), is a cyclohexylsulfonylurea analog similar toacetohexamide and glyburide. The drug is absorbed rapidlyon oral administration. Its serum half-life is 2 to 4 hours, andit has a hypoglycemic effect that ranges from 12 to 24 hours.
Allgemeine Beschreibung
Glipizide, 1-cyclohexyl-3-[[p-(2-(5-methylpyrazinecarboxamido)ethyl]phenyl]sulfonyl]urea(Glucotrol), is an off-white, odorless powder with a pKa of5.9. It is insoluble in water and alcohols, but soluble in 0.1 NNaOH. Even though on a weight basis, it is approximately100 times more potent than tolbutamide, the maximal hypoglycemiceffects of these two agents are similar. It is rapidlyabsorbed on oral administration, with a serum half-life of 2 to4 hours, whereas the hypoglycemic effects range from 12 to24 hours. Metabolism of glipizide is generally through oxidationof the cyclohexane ring to the p-hydroxy and m-hydroxymetabolites. A minor metabolite that occurs involves theN-acetyl derivative, which results from the acetylation of theprimary amine following hydrolysis of the amide system byamidase enzymes.
Biochem/physiol Actions
Potassium inwardly-rectifying channel, subfamily J, member 1 (KCNJ1) plays a vital role in potassium balance. It is an ATP-dependent K+?channel blocker. The encoded protein is liable for the elimination of potassium in exchange for the absorption of sodium by the epithelial sodium channel (ENaC). Mutation in KCNJ1 is linked with several diseases, such as, antenatal Bartter syndrome and diabetes. Glipizide helps to repress the development of tumors and metastasis by preventing angiogenesis.
Clinical Use
Non-insulin dependent diabetes mellitus
Synthese
Glipizide, 1-cyclohexyl-3-[[p-[2-(5-methylpyrazincarboxamido)ethyl]phenyl] sulfonyl]urea (26.2.13), differs from glyburide in the structure of the amide region of the molecule, in which the 2-methoxy-5-chlorobenzoic acid part is replaced with 6- methylpyrazincarboxylic acid. It is also synthesized by a synthesis alternative to those described above. In the given scheme, 6-methylpyrazincarboxylic acid is initially reacted with thionyl chloride, resulting in the corresponding chloride, which undergoes further action with 4-(2-aminoethyl)benzenesulfonamide, forming the corresponding amide 26.2.12. The resulting sulfonamide is reacted in a traditional scheme with cyclohexylisocyanate, forming the desired glipizide (26.2.13).
Veterinary Drugs and Treatments
Glipizide may be of benefit in treating cats with type II diabetes if they have a population of functioning beta cells. It has been suggested that there are two situations when glipizide can be recommended, 1) If an owner refuses to consider using insulin usually due to a fear of needles, and 2) the cat appears to be relatively well controlled on quite small doses of insulin and the owner would strongly prefer to no longer give insulin (Feldman 2005b).
While glipizide potentially could be useful in treating canine patients with type II or III diabetes, however, by the time dogs present with hyperglycemia, they are absolutely or relatively insulinopenic and glipizide would unlikely be effective.
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, posaconazole and miconazole and possibly voriconazole - avoid with miconazole.
Ciclosporin: may increase ciclosporin levels.
Lipid-regulating drugs: possibly additive hypoglycaemic effect with fibrates.
Sulfinpyrazone: enhanced effect of sulphonylureas.
Stoffwechsel
The metabolism of glipizide is extensive and occurs mainly in the liver. The primary metabolites are inactive hydroxylation products and polar conjugates and are excreted mainly in the urine.

Glipizide Upstream-Materialien And Downstream Produkte

Glipizide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

29094-61-9, Glipizide Verwandte Suche:

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