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Glimepiride

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.
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CAS:93479-97-1
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CAS:93479-97-1
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Glimepiride manufacturers

  • Glimepiride
  • $15.00 / KG
  • 2022-01-07
  • CAS:93479-97-1
  • Min. Order: 1KG
  • Purity: 99%
  • Supply Ability: 500MT/month
  • Glimepiride
  • $1.00 / KG
  • 2021-12-10
  • CAS:93479-97-1
  • Min. Order: 1KG
  • Purity: 99%
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  • Glimepiride
  • $6.00 / Kg/Bag
  • 2021-12-01
  • CAS:93479-97-1
  • Min. Order: 1g
  • Purity: 99%
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Glimepiride Basic information
Description 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;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds;NEURONTIN;Active Pharmaceutical Ingredients;APIs;Intermediates & Fine Chemicals;Pharmaceuticals;Monovalent Ion Channels;Potassium Channel Modulators;Voltage-gated Ion Channels;API's
Mol File:93479-97-1.mol
Glimepiride Structure
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
form solid
pka5.10±0.10(Predicted)
color white
Merck 14,4440
CAS DataBase Reference93479-97-1(CAS DataBase Reference)
EPA Substance Registry System1H-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
MSDS Information
ProviderLanguage
Amary English
SigmaAldrich English
Glimepiride Usage And Synthesis
DescriptionGlimepiride (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.
References1. 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
DescriptionGlimepiride, 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.
Chemical PropertiesWhite Cyrstalline Solid
OriginatorHoechst Marion Roussel (Germany)
Usesanticonvulsant
UsesFor concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
UsesA sulfonylurea hypoglycemic agent. Used as an antidiabetic
UsesGlimepiride 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.
Manufacturing ProcessBy 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 nameAmaryl (Sanofi Aventis).
Therapeutic FunctionOral hypoglycemic
General DescriptionGlimepiride 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 DescriptionGlimepiride, 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 ActivityPotent 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 ActionsGlimepiride is a potent blocker of cardiac KATP channels activated by pinacidil with an IC50 of 6.8 nM.
Veterinary Drugs and TreatmentsGlimepiride 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.
Tag:Glimepiride(93479-97-1) Related Product Information
Repaglinide Nateglinide rac trans-Hydroxy Glimepiride-D5,trans-Hydroxy Glimepiride GLIMEPIRIDE RELATED COMPOUND C (20 MG) (GLIMEPIRIDE URETHANE) Glimepiride sulfonamide,Des[(trans-4-methylcyclohexyl)amino]carbonyl Glimepiride Phenethyl isocyanate 3-Ethyl-2,5-Dihydro-4-Methyl-2-Oxo-N-(2-Phenylethyl)-1h-Pyrrole-1-Carboxamide 4-12-00-02470 (Beilstein Handbook Reference) Glimepiride Impurity 19 trans-4-Methylcyclohexyl amine methyl hydrogen sulphate Meta-GliMepiride IMpurity GliMepiride EP IMpurity J 4-(2-Aminoethyl)benzenesulfonamide Benzenesulfonamide, 3-(2-aminoethyl)- (9CI) trans-4-Methycyclohexyl isocyanate ortho-GliMepiride IMpurity [[4-[2-[[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulfonyl]-carbamic acid ethyl ester