| Identification | More | [Name]
Glimepiride | [CAS]
93479-97-1 | [Synonyms]
1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea
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
3-ETHYL-2,5-DIHYDRO-4-METHYL-N-[2-[4-[[[[(TRANS-4-METHYLCYCLOHEXYL)AMINO]CARBONYL]AMINO]SULFONYL]PHENYL]ETHYL]-2-OXO-1H-PYRROLE-1-CARBOXYAMIDE
amary
AMARYL
GLIMEPIRIDE
1h-pyrrole-1-carboxamide,2,5-dihydro-3-ethyl-4-methyl-n-(2-(4-(((((4-methylcyc
glimepirid
hoe490
trans-lohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo
Gliclazide(diamicron)
CLIMEPIRIDE
Glimpiride
3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxyamide
1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-2-4-(trans-4-methylcyclohexyl)aminocarbonylaminosulfonylphenylethyl-2-oxo-
1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea
trans-3-Ethyl-2，5-dihydro-4-methyl-N-[2-[4-[[[[(4-methyleyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide
1H-Pyrrole-1-carboxamide, 2,5-dihydro-3-ethyl-4-methyl-N-(2-(4-(((((4-methylcyclohexyl)amino) carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-, trans
1-[[4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-ylcarbonyl)amino]ethyl]phenyl]sulfonyl]-3-(4α-methylcyclohexan-1β-yl)urea
1-[[p-[2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-ylcarbonylamino)ethyl]phenyl]sulfonyl]-3-[(1β)-4α-methylcyclohexyl]urea | [EINECS(EC#)]
642-919-5 | [Molecular Formula]
C24H34N4O5S | [MDL Number]
MFCD00878417 | [Molecular Weight]
490.62 | [MOL File]
93479-97-1.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R21:Harmful in contact with skin.
R36/38:Irritating to eyes and skin .
R62:Possible risk of impaired fertility.
R63:Possible risk of harm to the unborn child. | [Safety Statements ]
S25:Avoid contact with eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S53:Avoid exposure-obtain special instruction before use . | [WGK Germany ]
3
| [RTECS ]
UX9363950
| [HS Code ]
2935904000 |
| Questions And Answer | Back Directory | [Description]
Glimepiride (original trade name Amaryl) is an orally available medium-to-long-acting sulfonylurea antidiabetic drug. It is sometimes classified as either the first third-generation sulfonylurea, or as second-generation. Like all sulfonylureas, glimepiride acts as an insulin secretagogue. It lowers blood sugar by stimulating the release of insulin from functioning pancreatic beta cells and by increasing sensitivity of peripheral tissues to insulin. Glimepiride likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin. Glimepiride is mainly used to treat patients with type 2 diabetes and can also decrease the chances that someone will develop complications of type 2 diabetes, such as kidney damage, blindness, nerve problems, loss of limbs, sexual function problems and heart attack or stroke. The drug was approved by the FDA in 1995 and is manufactured by Sanofi-Aventis. It can be used along with proper diet and exercise program and may also be used alone or with other antidiabetic medicines if need. The drug is available only with your doctor's prescription. | [References]
1. https://en.wikipedia.org/wiki/Glimepiride
2. http://www.webmd.com/drugs/2/drug-12271/glimepiride-oral/details
3. https://www.drugs.com/cdi/glimepiride.html
4. http://www.medicinenet.com/glimepiride/article.htm
5. http://www.everydayhealth.com/drugs/glimepiride
6. http://www.emedicinehealth.com/drug-glimepiride/article_em.htm
7. https://www.ghc.org/kbase/topic.jhtml?docId=d03864a1
8. http://www.emedicinehealth.com/drug-glimepiride/article_em.htm
9. http://drugs.healthgrove.com/l/3454/Glimepiride
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| Hazard Information | Back Directory | [Chemical Properties]
White Cyrstalline Solid | [Originator]
Hoechst Marion Roussel (Germany) | [Uses]
A sulfonylurea hypoglycemic agent. Used as an antidiabetic | [Uses]
anticonvulsant | [Uses]
For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus. | [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). | [Brand name]
Amaryl (Sanofi Aventis). | [Therapeutic Function]
Oral hypoglycemic | [General Description]
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). | [General Description]
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. | [Biological Activity]
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. | [Drug interactions]
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. | [Metabolism]
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. |
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