93479-97-1 Usage
Description
Different sources of media describe the Description of 93479-97-1 differently. You can refer to the following data:
1. 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.
2. 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.
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
Originator
Hoechst Marion Roussel (Germany)
Uses
Different sources of media describe the Uses of 93479-97-1 differently. You can refer to the following data:
1. For concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus.
2. 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.
3. A sulfonylurea hypoglycemic agent. Used as an antidiabetic
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).
General Description
Different sources of media describe the General Description of 93479-97-1 differently. You can refer to the following data:
1. 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).
2. 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 93479-97-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,3,4,7 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 93479-97:
(7*9)+(6*3)+(5*4)+(4*7)+(3*9)+(2*9)+(1*7)=181
181 % 10 = 1
So 93479-97-1 is a valid CAS Registry Number.
InChI:InChI=1/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)/t16-,19?
93479-97-1Relevant articles and documents
Preparation method of high-purity glimepiride
-
, (2020/03/29)
The invention discloses a preparation method of high-purity glimepiride. The preparation method comprises the following specific steps: 1, adding 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonamide and potassium carbonate into a mixed solvent, and raising the temperature to dissolve the added substances; and 2, carrying out cooling crystallization on a solution obtained in step 1, and filtering the cooled solution to obtain 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-3-(trans-4-methylcyclohexyl)-urea. The glimepiride obtained by the preparation method has a purity of above 99.9% and a high yield, impurity research is sufficient and controllable, the crystal form is correct, and the preparation product quality is good,so the use requirements of people are met.
Process for synthesizing glimepiride raw material medicine
-
, (2018/09/08)
The invention discloses a process for synthesizing a glimepiride raw material medicine. A compound A, namely 3-ethyl-4-methyl-3-pyrroline-2-ketone and a compound B, namely 2-phenethyl isocyanate are taken as start raw materials. The process is characterized in that when an intermediate 1 is synthesized, filtrate is applied mechanically, so that the loss of the intermediate 1 can be reduced, the yield can be increased, and the production efficiency can be improved; when an intermediate 2 is synthesized, hydrochloric ether is adopted as a solvent, so that isomer impurities can be greatly reduced, the content of the isomer impurities can be reduced to 0.5% or less from 8%, and later purification procedures can be simple to operate; when a glimepiride metallic salt is synthesized, acetonitrileis adopted as a solvent, sufficient reactions can be achieved, the reaction time can be greatly shortened, the residue of an intermediate 3 is reduced to 0.2% or less from 5-10%, in addition, a highsolvent recycling rate can be achieved. The process disclosed by the invention is simple and safe, low in production cost, high in yield, stable in intermediate and finished product quality and applicable to industrial large-scale production and hypoglycemic drug, namely glimepiride, synthesis processes with relatively great social, economic and environmental-friendly benefits.
Method for manufacture of compounds related to the class of substituted sulfonyl urea anti-diabetics
-
Page/Page column 6, (2008/06/13)
The present invention relates to a process for preparation of sulfonyl urea compounds in high conversion rates and purity. More specifically, this invention relates to a process for manufacture of sulfonyl urea class of anti-diabetic pharmaceutical drugs in higher purity and yield. The process may effectively and economically be used to produce anti-diabetic drugs, such as glimepiride, glipizide, gliclazide, glibenclamide, glibornuride, and glisoxepide.
