ChemicalBook >> CAS DataBase List >>Gliquidone

Gliquidone

CAS No.
33342-05-1
Chemical Name:
Gliquidone
Synonyms
ardf26;ardf26se;Glurenorm;GLIQUIDONE;Gliquidone>Gliquidone D6;GLIQUIDONE 99%;Gliquidone powder;Gliquidone Tablets;Gliquidone USP/EP/BP
CBNumber:
CB1183076
Molecular Formula:
C27H33N3O6S
Molecular Weight:
527.63
MDL Number:
MFCD00631870
MOL File:
33342-05-1.mol
Last updated:2023-05-18 11:31:21

Gliquidone Properties

Melting point 179 °C
Density 1.34±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
solubility ≥22.4 mg/mL in DMSO; insoluble in H2O; ≥2.455 mg/mL in EtOH with gentle warming and ultrasonic
pka 5.12±0.10(Predicted)
form powder to crystal
color White to Almost white
Merck 14,4443
CAS DataBase Reference 33342-05-1(CAS DataBase Reference)
FDA UNII C7C2QDD75P
NCI Drug Dictionary gliquidone
ATC code A10BB08

SAFETY

Risk and Safety Statements

Safety Statements  24/25
RTECS  DB1584250
HS Code  29147000

Gliquidone price More Price(26)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich CDS021537 Gliquidone 33342-05-1 100MG $41 2023-06-20 Buy
TCI Chemical G0332 Gliquidone >98.0%(HPLC)(T) 33342-05-1 1g $55 2024-03-01 Buy
TCI Chemical G0332 Gliquidone >98.0%(HPLC)(T) 33342-05-1 5g $166 2024-03-01 Buy
Cayman Chemical 29596 Gliquidone 33342-05-1 1g $61 2024-03-01 Buy
Cayman Chemical 29596 Gliquidone 33342-05-1 10g $335 2024-03-01 Buy
Product number Packaging Price Buy
CDS021537 100MG $41 Buy
G0332 1g $55 Buy
G0332 5g $166 Buy
29596 1g $61 Buy
29596 10g $335 Buy

Gliquidone Chemical Properties,Uses,Production

Oral hypoglycemic agents

Gliquidone is an oral hypoglycemic agent, and was called as the second generation sulfonylurea oral hypoglycemic drug together with glyburide, gliclazide and glipizide, primarily for the treatment of non-insulin-dependent (namely, II type) diabetes. Its mechanism of action is the same as other sulfonylurea drugs and can stimulate insulin secretion from pancreatic β cells, and can enhance the action of insulin, enhance the sensitivity of tissues to insulin action, increase the number of insulin receptor and strengthen post-receptor action of insulin. During the early phase of treatment, it is mainly used for promoting the secretion of endogenous insulin; after a period of time of treatment, its main role is to improve the sensitivity of peripheral tissues to insulin. Diabetic nephropathy is one of the late complications of diabetes while gliquidone is the only sulfonylurea drugs that not affected by renal function and therefore can be applied to diabetic patients with impaired renal function. It is the primary-choice of drug for the treatment of patients of non-insulin dependent diabetes accompanied with insufficiency of renal function. Gliquidone is characterized by short duration of action and seldom undergoing of renal excretion with a small dose being able to control postprandial blood glucose. Oral absorption is quick and complete. After the first oral administration of 30mg, the plasma concentration reaches its peak value, 500~700μg/L after 2 to 3 hours. The efficacy onset occurs at 1 hour after administration, the maximal effect can be extended up to 2 to 3 hours with the duration of 8 hours and the plasma protein binding rate being 99% and the half-life of about 1.5 hours. It is mainly metabolized in the liver through hydroxylation or demethylation with its metabolites having no significant hypoglycemic activity and most of them being discharged through feces via biliary while only 5% being subject to renal excretion. This product has mild effect and can be subject to dose adjustment timely based on blood sugar or urine glucose and rarely cause hypoglycemia reaction. It is suitable for the treatment of adult-type mild, moderate diabetes which can’t be simply treated through diet, especially for patients with renal insufficiency.

Diabetes

Diabetes is a group of syndrome of carbohydrate, fat, water and electrolyte metabolic disorder caused by the interaction of genetic and environmental factors, absolute or relative lack of insulin, and reduced cellular insulin sensitivity. According to the suggestion of ADA (in 1997) and WHO (in 1999), the diabetes are divided into four types, namely type 1 diabetes, type 2 diabetes, other specific types, and gestational diabetes. The vast majority belongs to type 2 diabetes (non-insulin-dependent diabetes mellitus, NIDDM), type 1 diabetes (insulin-dependent, IDDM) accounted for only 10% to 15%. The main clinical manifestations: polydipsia, polyphagia, polyuria, weight loss, fatigue, etc., advanced case is often accompanied with cataracts, abnormal reflexes in depth of feeling, urinary retention and skin infections. Type 1 " three polys and one little " is more obvious and is susceptible; the majority of patients with type 2 have no typical performances and is mainly in the form of complications or complications. Common complication mainly includes diabetic ketoacidosis and diabetic nonketotic hyperosmotic syndrome.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Medicine interactions

The hypoglycemic effect of gliquidone can be enhanced by salicylates, sulfonamides, phenylbutazone, anti-tuberculosis drugs, tetracyclines, monoamine oxidase inhibitors, β receptor blockers and cyclophosphamide.
Combination with chlorpromazine, sympathomimetic drugs, corticosteroids, thyroid hormones, oral contraceptives and niacin preparations can reduce the hypoglycemic effect of this product.

Side effects

This product can be well tolerated. There is rare case of hypoglycemia during the treatment. There are only individual cases of patients who get gastrointestinal symptoms and skin allergy. Rare symptoms also include rash, jaundice, liver damage, bone marrow suppression, neutropenia, thrombocytopenia psychosis.

Precautions

1. Only 5% of this product is excreted through the kidneys. Therefore, for patients of diabetes with mild to moderate renal insufficiency, it is significantly better to adopt gliquidone rather than other sulfonylurea drug. However, for patients of severe renal dysfunction, insulin is still appropriate. Patients of pregnancy and those who are allergic to sulfonylureas, patients of insulin-dependent diabetes mellitus, patients of pre-coma and coma of diabetes, diabetic patients with acidosis or ketosis should be banned.
2. Children and lactating women should apply with caution. During medication, elderly should start from small dose and gradually adjust the dose.
3. In case of hypoglycemia reaction, the patients should immediately have carbohydrates diet. If hypoglycemia continues, the patients should consider discontinuing.

Uses

It is a kind of hypoglycemic agents and can be used for the treatment of non-insulin-dependent diabetes.

Description

Gliquidone is a second generation sulfonylurea that selectively inhibits ATP-sensitive potassium channel currents (IKATP) in pancreatic β-cells (IC50s = 0.45, 119.1, and 149.7 μM for HIT-T15 cells, cardiomyocytes, and vascular smooth muscle cells, respectively). It is also a peroxisome proliferator-activated receptor γ (PPARγ) agonist (EC50 = 10 μM in a transactivation assay). Gliquidone (0.2 nmol/g) decreases plasma levels of D-glucose and stimulates insulin release in anesthetized rats. It decreases blood glucose levels, serum alkaline phosphatase (ALP), aspartate aminotransferase (AST), and alanine aminotransferase (ALT) activities, and hepatic lipid peroxidation and increases hepatic glutathione (GSH) levels in a rat model of diabetes induced by streptozotocin (STZ; ) when administered at a dose of 10 mg/kg.

Originator

Glurenorm,Thornae,W. Germany,1975

Uses

Gliquidone is an anti diabetic agent used in the treatment of hypoglycemia which leads to an increased risk in diabetic cardiovascular disease. Also used in the treatment diabetic nephropathy.

Definition

ChEBI: 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea is a member of isoquinolines.

Manufacturing Process

A mixture consisting of 4 grams of 1,2,3,4-tetrahydro-4,4-dimethyl-7- methoxy-isochromanedione-(1,3) (MP 95° to 97°C), 2.53 grams of 4- aminosulfonyl-phenyl-(2)-ethylamine and 150 ml of xylene was heated for 2 hours at its boiling point in an apparatus provided with a water separator. Thereafter, the reaction mixture was allowed to cool and was then vacuumfiltered, and the filter cake was recrystallized from n-propanol in the presence of activated charcoal. 2.9 grams (58% of theory) of 1,2,3,4-tetrahydro-4,4- dimethyl-2-[p-aminosulfonylphenyl-(2)-ethyl]-7-methoxy-isoquinolinedione- (1,3), MP 203° to 205°C, of the formula below were obtained.
32.2 grams of 1,2,3,4-tetrahydro-4,4-dimethyl-2-[p-aminosulfonylphenyl-(2)-ethyl]-7-methoxy-isoquinolinedione-(1,3) were dissolved in 700 ml of dimethylformamide, 9.1 grams of potassium tert-butylate were added to the solution, and, while cooling the mixture with ice, 14.9 grams of cyclohexyl isocyanate were added dropwise thereto.
Subsequently, the reaction mixture was stirred for 5 hours on an ice bath and was then allowed to stand overnight at -2°C. Thereafter, the reaction solution was admixed with water, the precipitate formed thereby was separated by vacuum-filtration, the filtrate was admixed with more water, and the aqueous solution was acidified with 2N hydrochloric acid. A greasy substance precipitated out which crystallized after a brief period of contact with boiling methanol. 2.6 grams (85% of theory) of 1,2,3,4-tetrahydro-2-[p-(N'- cyclohexyl-ureido-N-sulfonyl)-phenethyl]-4,4-dimethyl-7-methoxyisoquinolinedione-(1,3), MP 180° to 182°C, were obtained.

Therapeutic Function

Oral hypoglycemic

Hazard

Low toxicity by ingestion. A reproductive hazard.

References

[1]. ocaña m, del pozo e, baeyens jm. gliquidone, an atp-dependent k+ channel antagonist, antagonizes morphine-induced hypermotility. eur j pharmacol, 1993, 239(1-3): 253-255.
[2]. ocaña m, baeyens jm. role of atp-sensitive k+ channels in antinociception induced by r-pia, an adenosine a1 receptor agonist. naunyn schmiedebergs arch pharmacol, 1994, 350(1): 57-62.
[3]. von nicolai h, brickl r, eschey h, et al. duration of action and pharmacokinetics of the oral antidiabetic drug gliquidone in patients with non-insulin-dependent (type 2) diabetes mellitus. arzneimittelforschung, 1997, 47(3): 247-252.
[4]. tuerk tr, bandur s, nuernberger j, et al. gliquidone therapy of new-onset diabetes mellitus after kidney transplantation. clin nephrol, 2008, 70(1): 26-32.

33456-68-7
3173-53-3
33342-05-1
Synthesis of Gliquidone from p-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolyl)ethyl]benzenesulphonamide and Isocyanatocyclohexane
Global( 254)Suppliers
Supplier Tel Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9354 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682 bruce@xrdchem.cn CHINA 566 55
Zjartschem
+86-571-8723 8903 jocelynpan@zjarts.com jocelynpan@zjarts.com CHINA 993 58
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Xiamen AmoyChem Co., Ltd
+86-592-6051114 +8618959220845 sales@amoychem.com China 6387 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460 faith@widelychemical.com CHINA 742 58

View Lastest Price from Gliquidone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Gliquidone pictures 2023-06-15 Gliquidone
33342-05-1
US $1143.00 / KG 1KG 99% 10kg Baoji Guokang Bio-Technology Co., Ltd.
Gliquidone pictures 2023-03-27 Gliquidone
33342-05-1
US $85.00 / KG 1KG 99.9% 500MT/month XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD
Gliquidone powder pictures 2023-03-06 Gliquidone powder
33342-05-1
US $1.90 / KG 1KG 99% 10 ton Hebei Guanlang Biotechnology Co,.LTD
  • Gliquidone pictures
  • Gliquidone
    33342-05-1
  • US $1143.00 / KG
  • 99%
  • Baoji Guokang Bio-Technology Co., Ltd.
  • Gliquidone pictures
  • Gliquidone
    33342-05-1
  • US $85.00 / KG
  • 99.9%
  • XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD

Gliquidone Spectrum

,4-dimethyl-1,3-dioxo-2(1h)-isoquinolinyl)ethyl)- ardf26 ardf26se benzenesulfonamide,n-((cyclohexylamino)carbonyl)-4-(2-(3,4-dihydro-7-methoxy-4 GLIQUIDONE 99% GLIQUIDONE Gliquidone Tablets Glurenorm N-[(Cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2(1H)-yl)ethyl]benzenesulfonamide 3-Cyclohexyl-1-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-isoquinolin-2-yl)ethyl]phenyl]sulfonyl-urea Benzenesulfonamide, N-[(cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]- Gliquidone, 98%, an anti-diabetic compound Gliquidone 33342-05-1 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea Gliquidone, 98%, anti-diabetic compound 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-2-isoquinolinyl)ethyl]phenyl]sulfonylurea Gliquidone> Gliquidone Gliquidone Gliquidone Suphonamide Gliquidone USP/EP/BP Gliquidone powder Gliquidone (AR-DF26) Gliquidone D6 GliquidoneQ: What is Gliquidone Q: What is the CAS Number of Gliquidone Q: What is the storage condition of Gliquidone Gliquidone reference 33342-05-1 3342-05-1 C27H33N3O6S Glurenorm API Active Pharmaceutical Ingredients