ChemicalBook > CAS DataBase List > Glimepiride

Glimepiride

Description References

Glimepiride

CAS No.93479-97-1
Chemical Name:Glimepiride
CBNumber:CB8318552
Molecular Formula:C24H34N4O5S
Formula Weight:490.62
MOL File:93479-97-1.mol

Glimepiride Property

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
CAS DataBase Reference 93479-97-1(CAS DataBase Reference)
FDA UNII 6KY687524K
NCI Drug Dictionary Amaryl
ATC code A10BB12
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)
UNSPSC Code 41116107
NACRES NA.77

Safety

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

NFPA 704:

	0
4		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H361
Precautionary statements P201-P202-P280-P308+P313-P405-P501

Glimepiride Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: PHR1617
Product name : Glimepiride
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 1G
Price: ₹15966.88
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: G2295
Product name : Glimepiride
Purity: ≥98% (HPLC), solid
Packaging: 50MG
Price: ₹17060.2
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: G2295
Product name : Glimepiride
Purity: ≥98% (HPLC), solid
Packaging: 250MG
Price: ₹76283.78
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: G0395
Product name : Glimepiride
Purity:
Packaging: 1G
Price: ₹8400
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: G0395
Product name : Glimepiride
Purity:
Packaging: 5G
Price: ₹11800
Updated: 2022/05/26
Buy: Buy

Glimepiride Chemical Properties,Usage,Production

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 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 Properties White Cyrstalline Solid
Originator Hoechst Marion Roussel (Germany)
Uses A sulfonylurea hypoglycemic agent. Used as an antidiabetic
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 For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
Uses anticonvulsant
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, 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.
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).
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.