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Gliclazide

Description Hypoglycemic agents Pharmacological effects Pharmacokinetics Synthetic method Uses Side effects Contraindications Precautions Drug interactions References
Gliclazide
Gliclazide structure
CAS No.
21187-98-4
Chemical Name:
Gliclazide
Synonyms
s852;se1702;S-1702;Diaprel;Glyzide;GLIMICRON;DIAMICRON;Glinormax;NORDIALEX;GLICLAZIDE
CBNumber:
CB5113462
Molecular Formula:
C15H21N3O3S
Formula Weight:
323.41
MOL File:
21187-98-4.mol

Gliclazide Properties

Melting point:
163-169 °C(lit.)
Density 
1.2205 (rough estimate)
refractive index 
1.6740 (estimate)
storage temp. 
-20°C Freezer
solubility 
methylene chloride: soluble
form 
powder
color 
white
Merck 
14,4439
InChIKey
BOVGTQGAOIONJV-UHFFFAOYSA-N
CAS DataBase Reference
21187-98-4(CAS DataBase Reference)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xn,Xi
Risk Statements  21-36/38-46-62-63
Safety Statements  25-26-36/37-53-24/25
RIDADR  3077
WGK Germany  2
RTECS  YT4500000
HS Code  29350090
Toxicity LD50 orally in mice: >3 g/kg (Duhault)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
Precautionary statements:

Gliclazide price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1288 Gliclazide Pharmaceutical Secondary Standard; Certified Reference Material 21187-98-4 1g $62.3 2018-11-13 Buy
Sigma-Aldrich G2167 Gliclazide powder, ≥98% 21187-98-4 5g $122 2018-11-13 Buy
TCI Chemical G0381 Gliclazide >98.5%(HPLC)(T) 21187-98-4 5g $60 2018-11-22 Buy
Cayman Chemical 25503 Gliclazide ≥98% 21187-98-4 1g $25 2018-11-19 Buy
Cayman Chemical 25503 Gliclazide ≥98% 21187-98-4 5g $94 2018-11-19 Buy

Gliclazide Chemical Properties,Uses,Production

Description

Gliclazide is an oral antihyperglycemic agent used for the treatment of diabetes mellitus type II. It belongs to the sulfonylurea class of insulin secretagogues, which stimulates β cells of the pancreas to release insulin. Gliclazide binds to the β cell sulfonyl urea receptor (SUR1), further blocking the ATP sensitive potassium channels. Therefore, the potassium efflux substantially decreases, causing depolarization of the β cells. Then the voltage-dependent calcium channels in the β cell are open, resulting in calmodulin activation, which in turn leads to exocytosis of insulin containing secretorty granules. Recent studies have also shown that gliclazide can effectiveimprove anti-oxidant status and nitric oxide-mediated vasodilation in Type 2 diabetes and protect pancreatic beta-cells from damage by hydrogen peroxide.

Hypoglycemic agents

Gliclazide, chemical name is 1-(hexahydrocyclopenta [c] pyrrole-2 (1H)-yl)-3-(4-methylphenyl) sulfonyl urea, is the second generation of sulfur ureide oral hypoglycemic agents, and it also has dual function of hypoglycemic and improving blood clotting. It not only can improve the metabolism of diabetic patients, but also can improve or delay the occurrence of diabetic vascular complications. Gliclazide was developed by the French SERVIER company, and listed in France as early as 1972. Its trade names are diamicron gliclazide, methanesulfonic bicyclic urea to g pancreas, methanesulfonic grid urea, glick that sa. It is mainly used for the treatment of the onset of diet and exercise alone control ineffective of adulthood, and no ketosis tendency of light, moderate the type II diabetes. It also can improve diabetic retinopathy and metabolic disorders, vascular function. It can be used with biguanide oral hypoglycemic drugs, and used with insulin to treat insulin-dependent diabetes mellitus, in which condition that insulin dosage can be reduced. 1980s, it began to be supplied into the Chinese market. Now there has been more than 130 countries worldwide that registered and sold.

Pharmacological effects

1. Hypoglycemic effect: gliclazide is the second-generation oral sulfonylurea hypoglycemic agents. Its role is more than ten times stronger than tolbutamide. Mechanism of action is to stimulate pancreatic β cells to release insulin, and then the high blood sugar drops. This may be because that sulfonylurea combines with β cell surface receptor, and increases the activation and simultaneously improves the sensitivity of outer periphery of the target tissue to insulin.
2. It can reduce platelet aggregation and adhesion, and prevent fibrin depositing in the microvasculature.
3. It can lower cholesterol savings, and reduce plasma concentrations of arterial triphosphate glycerides and fatty acids. The role of the three not only can treat diabetes metabolic disorders, but also prevent and treat complications like the development and progression of diabetes-blood vessels, retinal, renal disease.

Pharmacokinetics

The absorption of gliclazide is rapidly when it is taken orally. The plasma concentration peaks after two to six hours. Plasma protein binding rate is 94.2%. Τ1/2 is about 12 hours. Gliclazide is mainly used in the liver metabolism, and its metabolites has no hypoglycemic effect. 98% is excreted by kidney in less than 48 hours, and the content of unchanged drug in the urine is less than 5%.

Synthetic method

Cyclopentane ortho anhydride as raw materials, ammoniates to obtain cyclopentane phthalimide. It reacts to obtain azabicyclo through catalytic reduction by catalysts like LiAlH4, KBH4/ZnCl2 or black platinum. And then azabicyclo reacts to give N-3-azabicyclo [3, 3, O] octane hydrochloride by nitrosation, zinc reduction. Finally it reacts with toluene sulfonylurea to obtain gliclazide through condensation.

Figure 1 The synthetic route of gliclazide

Uses

1. For adults with type 2 diabetes, diabetes associated with obesity or vascular lesions.
2. Hypoglycemic agents. It can be used for the treatment of non-insulin dependent diabetes mellitus.
3. Hypoglycemic agents, non-insulin dependent diabetes mellitus.
The above information is edited by the Chemicalbook of Ge Qian.

Side effects

Occasional mild nausea, vomiting, abdominal pain, constipation, diarrhea, erythema, urticaria, thrombocytopenia, neutropenia, anemia. Most adverse reactions disappeared after withdrawal.

Contraindications

1. Forbidden for patients allergic to gliclazide or sulfonylureas, sulfa drugs.
2. Forbidden for patients with type 1 diabetes.
3. Forbidden for patients with diabetic pre-coma, diabetic ketoacidosis.
4. Forbidden for patients with severe liver and kidney dysfunction.
5. Forbidden for leukopenia patients.
6. Forbidden for patients with stress situations like coma, severe burns, infection, trauma and major surgery.
7. Forbidden for patients with pregnant and lactating women

Precautions

1. When patients with type 2 diabetes have infection, trauma, surgery, stress situations and ketoacidosis and hyperosmolar nonketotic diabetic coma, insulin therapy should be used instead.
2. When the overdose of gliclazide, eating too little or strenuous exercise, you should take attention to prevent hypoglycemia.
3. You must regularly check blood sugar, urine, and take eye examinations.
4. When gliclazide is combined with anticoagulants, you should have regular blood clotting check.

Drug interactions

When gliclazide is used with nonsteroidal anti-inflammatory drug (especially salicylates), sulfa antibiotic, double coumarin anticoagulants, monoamine oxidase inhibitors, β-blockers, tetracycline, chloramphenicol, dicyclohexyl B piperidine, clofibrate, ethanol and other drugs, its dosage should be reduced to avoid hypoglycemia reaction.

References

https://www.drugbank.ca/drugs/DB01120
https://en.wikipedia.org/wiki/Gliclazide
Fava, D, et al. "Gliclazide improves anti-oxidant status and nitric oxide-mediated vasodilation in Type 2 diabetes." Diabetic Medicine A Journal of the British Diabetic Association 19.9(2002):752.
Kimoto, K, et al. "Gliclazide protects pancreatic beta-cells from damage by hydrogen peroxide. " Biochemical & Biophysical Research Communications 303.1(2003):112-119.

Chemical Properties

White Cyrstalline Solid

Uses

antidiabetic, adhesion inhibitor

Uses

A sulfonylurea hypoglycemic agent. Used as an antidiabetic

General Description

Chemically, gliclazide, 1-(3-azabicyclo[3.3.0]oct-3-yl)-3-p-tolylsulphonylurea (Diamicron), isvery similar to tolbutamide, with the exception of the bicyclicheterocyclic ring found in gliclazide. The pyrrolidineincreases its lipophilicity over that of tolbutamide,which increases its half-life. Even so, the p-methyl is susceptibleto the same oxidative metabolic fate as observedfor tolbutamide, namely, it will be metabolized to a carboxylicacid.

Gliclazide Preparation Products And Raw materials

Raw materials

Preparation Products


Gliclazide Suppliers

Global( 266)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1530 55
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3217 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22043 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32651 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile; WhatsApp; Telegram)
+86-571-56059825 fandachem@gmail.com CHINA 2464 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2548 55
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 24118 58
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20229 58
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 4558 58

View Lastest Price from Gliclazide manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-06 Gliclazide
21187-98-4
US $93.00 / KG 100KG 98% 10T career henan chemical co
2018-11-06 Gliclazide
21187-98-4
US $100.00 / G 10G 99.8% 500kg/month Hebei Huanhao Biotechnology Co., Ltd.

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