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High Quality Gliclazide Powder
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USD $ 695.0-700.0 / Kilogram 10 Kilogram 100 Kilogram/Day Arshine Pharmaceutical Co., Limited Contact Supplier
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CAS:1267610-26-3 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone
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1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea
Cas No: 21187-98-4
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier

21187-98-4 Usage

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.

Uses

A sulfonylurea hypoglycemic agent. Used as an antidiabetic

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.

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.

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.

Uses

antidiabetic, adhesion inhibitor

Chemical Properties

White Cyrstalline Solid

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

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%.

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.

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.

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.

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
InChI:InChI=1/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)

21187-98-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (G2167)  Gliclazide  powder, ≥98% 21187-98-4 G2167-5G 1,301.04CNY Detail
Sigma-Aldrich (G0326000)  Gliclazide  European Pharmacopoeia (EP) Reference Standard 21187-98-4 G0326000 1,880.19CNY Detail
TCI America (G0381)  Gliclazide  >98.5%(HPLC)(T) 21187-98-4 5g 640.00CNY Detail

21187-98-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name gliclazide

1.2 Other means of identification

Product number -
Other names 1-[3-Azabicyclo[3.3.0]oct-3-yl]-3-p-toluenesulfonylurea

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:21187-98-4 SDS

21187-98-4Synthetic route

N-(hexahydrocyclopenta[c]pyrrole-2-(1H)-yl)aminocarbonyl chloride

N-(hexahydrocyclopenta[c]pyrrole-2-(1H)-yl)aminocarbonyl chloride

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
With N,N-dimethyl-formamide In toluene for 2h; Reagent/catalyst; Reflux;91.9%
3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride
58108-05-7

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride

4-toluenesulfonylurea
1694-06-0

4-toluenesulfonylurea

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
In toluene for 3h; Reflux;86%
phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: phenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h; Reagent/catalyst; Solvent;
70%
p-methoxyphenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

p-methoxyphenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: p-methoxyphenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h;
60%
p-fluorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

p-fluorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: p-fluorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h;
52%
p-chlorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

p-chlorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonamide With potassium tert-butylate In dimethyl sulfoxide at 100℃; for 3h;
Stage #2: p-chlorophenyl hexahydrocyclopenta[c]pyrrol-2(1H)-yl carbamate In dimethyl sulfoxide at 25℃; for 2h;
40%
N-amino-1,2-cyclopentanedicarboximide

N-amino-1,2-cyclopentanedicarboximide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; pyrographite; ruthenium(III) chloride trihydrate; hydrogen / water / 16 h / 140 °C / 60006 Torr / Autoclave
2: hydrogenchloride
3: toluene / 3 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; hydrogen / 4 h / 80 °C / 15001.5 Torr / Autoclave
2: N,N-dimethyl-formamide / dichloromethane / 3 h / 50 °C / 4500.45 Torr / Autoclave; Inert atmosphere
3: N,N-dimethyl-formamide / toluene / 2 h / Reflux
View Scheme
N-[N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-N'-hydroxycarbamimidoyl]-4-methylbenzenesulfonamide

N-[N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-N'-hydroxycarbamimidoyl]-4-methylbenzenesulfonamide

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
With Simulated Gastric Fluid at 37℃; for 2h; pH=1.2; Time;
N-amino-aza-3-bicyclo<3.3.0>octane
54528-00-6

N-amino-aza-3-bicyclo<3.3.0>octane

gliclazide
21187-98-4

gliclazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-heptane / 1 h / 0 - 25 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 3 h / 100 °C
2.2: 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-heptane / 1 h / 0 - 25 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 3 h / 100 °C
2.2: 2 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: n-heptane / 1 h / 0 - 25 °C
2.1: potassium tert-butylate / dimethyl sulfoxide / 3 h / 100 °C
2.2: 2 h / 25 °C
View Scheme
gliclazide
21187-98-4

gliclazide

copper dichloride

copper dichloride

C30H44CuN6O6S2

C30H44CuN6O6S2

Conditions
ConditionsYield
Reflux;74%
gliclazide
21187-98-4

gliclazide

water
7732-18-5

water

Co metal salt solution

Co metal salt solution

C30H48CoN6O8S2

C30H48CoN6O8S2

Conditions
ConditionsYield
Reflux;70%
gliclazide
21187-98-4

gliclazide

zinc(II) chloride
7646-85-7

zinc(II) chloride

C30H40N6O6S2Zn

C30H40N6O6S2Zn

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 3h; pH=6 - 6.5; Reflux;53.16%
gliclazide
21187-98-4

gliclazide

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride
58108-05-7

3-azabicyclo<3.3.0>oct-3-yl-amine monohydrochloride

Conditions
ConditionsYield
With chloride ions In various solvent(s) at 37℃; for 24h; Product distribution; various concentrations of anions and cations, with and without human serum proteins;
gliclazide
21187-98-4

gliclazide

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

C15H21N3O3S*C6N4

C15H21N3O3S*C6N4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.5h;
1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

gliclazide
21187-98-4

gliclazide

C15H21N3O3S*C10H18O4

C15H21N3O3S*C10H18O4

Conditions
ConditionsYield
In acetone at 20℃; for 1h;
glycolic Acid
79-14-1

glycolic Acid

gliclazide
21187-98-4

gliclazide

C15H21N3O3S*C2H4O3

C15H21N3O3S*C2H4O3

Conditions
ConditionsYield
In acetone at 20℃; for 1h;
4-aminopyridine
504-24-5

4-aminopyridine

gliclazide
21187-98-4

gliclazide

gliclazide-4-aminopyridine salt

gliclazide-4-aminopyridine salt

Conditions
ConditionsYield
In diethyl ether; ethanol for 168h;
3,4-diaminopyridine
54-96-6

3,4-diaminopyridine

gliclazide
21187-98-4

gliclazide

gliclazide-3,4-aminopyridine salt

gliclazide-3,4-aminopyridine salt

Conditions
ConditionsYield
In diethyl ether; ethanol for 336h;
gliclazide
21187-98-4

gliclazide

benzene-1,2-diol
120-80-9

benzene-1,2-diol

gliclazide*catechol

gliclazide*catechol

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 3h;
gliclazide
21187-98-4

gliclazide

recorcinol
108-46-3

recorcinol

gliclazide*resorcinol

gliclazide*resorcinol

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 3h;
piperazine
110-85-0

piperazine

gliclazide
21187-98-4

gliclazide

gliclazide*piperazine

gliclazide*piperazine

Conditions
ConditionsYield
In methanol for 0.333333h;
gliclazide
21187-98-4

gliclazide

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

gliclazide*p-toluenesulfonic acid

gliclazide*p-toluenesulfonic acid

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 0.333333h;
gliclazide
21187-98-4

gliclazide

N-[N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-N'-hydroxycarbamimidoyl]-4-methylbenzenesulfonamide

N-[N-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-N'-hydroxycarbamimidoyl]-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 100℃;
gliclazide
21187-98-4

gliclazide

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

GZD-AMP salt

GZD-AMP salt

Conditions
ConditionsYield
In methanol; water
gliclazide
21187-98-4

gliclazide

2C15H21N3O3S*I(1+)*I3(1-)

2C15H21N3O3S*I(1+)*I3(1-)

Conditions
ConditionsYield
With iodine In methanol; chloroform at 20℃; for 24h;
gliclazide
21187-98-4

gliclazide

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

C15H21N3O3S*C6H3N3O7

C15H21N3O3S*C6H3N3O7

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 24h;
gliclazide
21187-98-4

gliclazide

2,3-dicyano-5,6-dichloro-p-benzoquinone
84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

C15H21N3O3S*C8Cl2N2O2

C15H21N3O3S*C8Cl2N2O2

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 24h;
In acetonitrile at 20℃; for 2h;
gliclazide
21187-98-4

gliclazide

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

hydrogen cyanide
74-90-8

hydrogen cyanide

B

4-methyl-N-(1-(1,2,2-tricyanovinyl)hexahydropenta[c]pyrrol-2-(1H)-ylcarbamoyl)benzenesulfonamide

4-methyl-N-(1-(1,2,2-tricyanovinyl)hexahydropenta[c]pyrrol-2-(1H)-ylcarbamoyl)benzenesulfonamide

Conditions
ConditionsYield
In methanol; chloroform at 20℃; for 24h;
gliclazide
21187-98-4

gliclazide

3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone
87-88-7

3,6-dichloro-2,5-dihydroxy-1,4-benzoquinone

C15H21N3O3S*C6H2Cl2O4

C15H21N3O3S*C6H2Cl2O4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2h;

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