Glimepiride CAS 93479-97-1
Introduction：Basic information about Glimepiride CAS 93479-97-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Glimepiride Basic informationDescription References
| Product Name: | Glimepiride |
| Synonyms: | AMARYL;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;Gliclazide(diamicron);CLIMEPIRIDE;Glimpiride;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;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 |
| CAS: | 93479-97-1 |
| MF: | C24H34N4O5S |
| MW: | 490.62 |
| EINECS: | 642-919-5 |
| Product Categories: | Diabetes Research;API;NEURONTIN;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds;Active Pharmaceutical Ingredients;APIs;Intermediates & Fine Chemicals;Pharmaceuticals;Monovalent Ion Channels;Potassium Channel Modulators;Voltage-gated Ion Channels;API's;93479-97-1 |
| Mol File: | 93479-97-1.mol |
Glimepiride Chemical Properties
| Melting point | 212.2-214.5 °C |
| density | 1.29±0.1 g/cm3(Predicted) |
| storage temp. | room temp |
| solubility | DMSO: >10 mg/mL |
| pka | 5.10±0.10(Predicted) |
| form | solid |
| color | white |
| Merck | 14,4440 |
| BCS Class | 2 |
| InChIKey | WIGIZIANZCJQQY-RUCARUNLSA-N |
| SMILES | N1(C(NCCC2=CC=C(S(NC(N[C@@H]3CC[C@@H](C)CC3)=O)(=O)=O)C=C2)=O)CC(C)=C(CC)C1=O |
| CAS DataBase Reference | 93479-97-1(CAS DataBase Reference) |
| EPA Substance Registry System | 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) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 21-36/38-46-62-63 |
| Safety Statements | 25-26-36/37-53 |
| WGK Germany | 3 |
| RTECS | UX9363950 |
| HS Code | 2935904000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Repr. 2 |
| 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 |
| Description | Glimepiride, the first of a new generation of sulfonylurea drugs, was introduced inSweden in 1995 as a first-line therapy to lower blood glucose in patients with type IIdiabetes. Sulfonylureas exert their hypoglycemic function primarily by directstimulation of insulin secretion in glucose-insensitive pancreatic β-cells and GLUTtranslocation in insulin-resistant fat and muscle cells. Once-daily, orally administeredglimepiride in diabetes patients showed a more rapid and longer lasting glucose-loweringeffect than the commonly used agent glibenclamide. Glimepiride can be used either asa monotherapy or in combination with insulin. |
| Chemical Properties | White Cyrstalline Solid |
| Originator | Hoechst Marion Roussel (Germany) |
| Uses | anticonvulsant |
| Uses | For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus. |
| Uses | 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. |
| Uses | A sulfonylurea hypoglycemic agent. Used as an antidiabetic |
| 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. Thenthe 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 steambath. The mixture of sulfonamide obtained (melting point 180°-182°C), ofacetone and K2CO3 are refluxed with agitation for 6 hours. Subsequently thecyclohexyl isocyanate are added dropwise, and agitation is continued for 6hours at boiling temperature. After standing overnight, the product is filtered,the crystals obtained are treated with dilute hydrochloric acid, and againfiltered. 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 ofnon-insulin dependent diabetes mellitus (NIDDM) in cats. Its durationof action in humans allows it to be dosed once daily, whichcould be of benefit in cats. It may also have fewer side effects thanglipizide 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 bycoumarins; also possibly changes to INR. Antifungals: concentration increased by fluconazoleand miconazole and possibly voriconazole. Lipid-regulating drugs: possibly additivehypoglycaemic effect with fibrates. Sulfinpyrazone: enhanced effect of sulphonylureas. |
| Metabolism | The drug is extensively metabolised in the liver to twomain metabolites. The cytochrome P450 isoenzymeCYP2C9 is involved in the formation of a hydroxyderivative, which is further metabolised to a carboxyderivative by cytosolic enzymes. About 60% of a dose is eliminated in the urine and 40%in the faeces. |
Glimepiride Preparation Products And Raw materials
| Raw materials | Pyrrole-->Methyl carbamate-->Phenylethyl isocyanate-->Isocyanatocyclohexane-->Chlorosulfonic acid-->Ammonium hydroxide-->Phenethyl isocyanate-->3-Ethyl-4-methyl-3-pyrrolin-2-one-->trans-4-Methycyclohexyl isocyanate-->3-Ethyl-2,5-Dihydro-4-Methyl-2-Oxo-N-(2-Phenylethyl)-1h-Pyrrole-1-Carboxamide-->4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide |
