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Glimepiride

Description References
Product Name
Glimepiride
CAS No.
93479-97-1
Chemical Name
Glimepiride
Synonyms
AMARYL;Glimpiride;GliMipride;N-(4-ethyl-3-methyl-5-oxo-2H-pyrrol-1-yl)-3-[4-[[[(4-methylcyclohexyl)amino]-oxomethyl]sulfamoyl]phenyl]propanamide;amary;hoe490;Grimepride;glimepirid;GliMperide;Glenn urea
CBNumber
CB8318552
Molecular Formula
C24H34N4O5S
Formula Weight
490.62
MOL File
93479-97-1.mol
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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)
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)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
G2295
Product name
Glimepiride
Purity
≥98% (HPLC), solid
Packaging
50mg
Price
$196
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1144
Product name
Glimepiride
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$255
Updated
2024/03/01
Sigma-Aldrich
Product number
BP1141
Product name
Glimepiride for system suitability
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
25MG
Price
$251
Updated
2024/03/01
Sigma-Aldrich
Product number
1292303
Product name
Glimepiride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$678
Updated
2024/03/01
TCI Chemical
Product number
G0395
Product name
Glimepiride
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$99
Updated
2024/03/01
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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

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. 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.

Glimepiride Preparation Products And Raw materials

Raw materials

Methyl carbamate Pyrrole Phenylethyl isocyanate Methylcyclohexylamine

Preparation Products

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Glimepiride Suppliers

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View Lastest Price from Glimepiride manufacturers

PUSHAN INDUSTRIAL (SHAANXI) CO.,LTD
Product
Glimepiride 93479-97-1
Price
US $0.00/kg
Min. Order
1kg
Purity
98% HPLC
Supply Ability
500 kgs
Release date
2024-05-17
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Glimepiride 93479-97-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%-102%;USP
Supply Ability
100KGS
Release date
2021-07-14
Nanjing Fred Technology Co., Ltd
Product
Glimepiride 93479-97-1
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%, Single impurity＜0.1
Supply Ability
1 ton
Release date
2024-01-04

93479-97-1, GlimepirideRelated Search:

Methyl acrylate Methanol Basic Violet 1 N,N-Dimethylformamide Acetonitrile Methylparaben Paraquat dichloride Formamide Pyrrole Foramsulfuron Kresoxim-methyl PHENYL VALERATE Chlorantraniliprole Repaglinide Nateglinide Methyl rac trans-Hydroxy Glimepiride-D5,trans-Hydroxy Glimepiride Glimepiride sulfonamide,Des[(trans-4-methylcyclohexyl)amino]carbonyl Glimepiride

  • 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
  • 1H-Pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-N-2-4-(trans-4-methylcyclohexyl)aminocarbonylaminosulfonylphenylethyl-2-oxo-
  • 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
  • Grimepride
  • GliMepiride(AMaryl)
  • 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
  • GLIMEPIRIDE
  • amary
  • Glimepiride (200 mg)
  • 3-ethyl-4-Methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-Methylcyclohexyl]carbaMoyl}aMino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxaMide
  • GliMperide
  • trans-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
  • GliMepiride COS
  • 1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea
  • GliMipride
  • 1-(4-(2-(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamido)ethyl)phenylsulfonyl)-3-((1r,4r)-4-methylcyclohexyl)urea
  • Glimepiride Solution, 100ppm
  • Glimepiride 93479-97-1
  • Customization Available
  • High Quality With Factory Price
  • Professional Manufacturer
  • N-(4-ethyl-3-methyl-5-oxo-2H-pyrrol-1-yl)-3-[4-[[[(4-methylcyclohexyl)amino]-oxomethyl]sulfamoyl]phenyl]propanamide
  • Glimepiride RS
  • Glimepiride CRS
  • Glimepiride&gt
  • Glimepiride for system suitability CRS
  • Glimepiride solution in Acetonitrile/Methanol, 1000ug/ml
  • Glenn urea
  • Glimepiride USP/EP/BP
  • Glimepiride (Glimperide
  • Glimepiride (Y0000515)
  • Glimepiride for system suitability (Y0000516)
  • GlimepirideQ: What is Glimepiride Q: What is the CAS Number of Glimepiride Q: What is the storage condition of Glimepiride Q: What are the applications of Glimepiride
  • Glimepiride (1292303)
  • 3-Ethyl-4-methyl-N-(4-(N-((rel-(1r,4r)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide
  • 7,8-Dihydroxyflavone 38183-03-8
  • Glimepiride IP/EP/USP
  • Glimepiride 1-[[p-[2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea
  • Glimepiride Reference Standard
  • GLIMEPIRIDE IP
  • Glimepiride in methanol
  • 3-Ethyl-4-methyl-N-(4-(N-(((1r,4r)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide (Glimepiride Impurity)
  • 93479-97-1
  • 93479-91-1
  • C24H30D4N4O5S
  • C24H34N4O5S