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Molecular Formula: C15H21N3O3S
Molecular Weight: 323.4
CAS No.: 21187-98-4
| Name | Gliclazide |
| Synonyms | Gliclazide )-4-methyl- Gliclazide, BP Tetrabenzyl Voglibose HCl 1-(3-azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea 1-(3-Azabicyclo[3.3.0]oct-3-yl)-3-(p-tolylsulfonyl)urea n-(4-methylbenzenesulfonyl)-n’-(3-azabicyclo(3.3.0)oct-3-yl)urea N-(4-Methylbenzenesulfonyl)-N’-(3-azabicyclo[3.3.0]oct-3-yl)urea 1-(hexahydrocyclopenta(c)pyrrol-2(1h)-yl)-3-(p-tolylsulfonyl)urea 1-(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea 1-(hexahydrocyclopenta(c)pyrrol-2(1h)-yl)-3-(p-tolylsulfonyl)-ure benzenesulfonamide,n-(((hexahydrocyclopenta(c)pyrrol-2(1h)-yl)amino)carbonyl N-(hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamoyl)-4-methylbenzenesulfonamide N-[(hexahydrocyclopenta[c]pyrrol-2(1H)-ylamino)carbonyl]-4-methylbenzenesulfonamide N-[[(Hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-methylbenzenesulfonamide Benzenesulfonamide, N-(((hexahydrocyclopenta(c)pyrrol-2(1H)-yl)amino)carbonyl)-4-methyl- benzenesulfonamide, N-[[(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)amino]carbonyl]-4-methyl- |
| CAS | 21187-98-4 |
| EINECS | 244-260-5 |
| 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) |
| InChIKey | BOVGTQGAOIONJV-UHFFFAOYSA-N |
| Molecular Formula | C15H21N3O3S |
| Molar Mass | 323.41 |
| Density | 1.2205 (rough estimate) |
| Melting Point | 163-169 °C (lit.) |
| Solubility | methylene chloride: soluble |
| Appearance | White powder |
| Color | white |
| Merck | 14,4439 |
| pKa | 6.07±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.6740 (estimate) |
| MDL | MFCD00409893 |
| Physical and Chemical Properties | Melting point 163-169°C |
| Use | Hypoglycemic agents for the treatment of non-insulin-dependent diabetes mellitus |
| Risk Codes | R21 – Harmful in contact with skin R36/38 – Irritating to eyes and skin. R46 – May cause heritable genetic damage R62 – Possible risk of impaired fertility R63 – Possible risk of harm to the unborn child |
| Safety Description | S25 – Avoid contact with eyes. S26 – In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 – Wear suitable protective clothing and gloves. S53 – Avoid exposure – obtain special instructions before use. S24/25 – Avoid contact with skin and eyes. |
| UN IDs | 3077 |
| WGK Germany | 2 |
| RTECS | YT4500000 |
| HS Code | 29350090 |
| Toxicity | LD50 orally in mice: >3 g/kg (Duhault) |
| Hypoglycemic drug | Gliclazide (G1iclazide), the chemical name is 1-(hexahydrocyclopentane [c] pyrrole -2(1H)-yl)-3-(4-methylphenyl) sulfonylurea is the second-generation sulfonylurea oral hypoglycemic drug, which also has the dual effects of lowering blood sugar and improving coagulation function, it can not only improve the metabolism of diabetic patients, but also improve or delay the occurrence of diabetic vascular complications. Developed by a French SERVIER company, it was first listed in France in 1972. The trade names are Damikang, Methylpyridoxene, Methylsulfonyl Bicyclic Urea, Leicepam, Methylsulfonyl Urea, Glicnassa, mainly used for In adulthood, the onset of mild and middle type II diabetes, which is ineffective in diet and exercise control, and has no tendency to ketosis, can also improve fundus diseases and metabolic and vascular dysfunction in diabetic patients. It can be combined with biguanide oral hypoglycemic drugs, combined with insulin to treat insulin-dependent diabetes, which can reduce the amount of insulin. It began to supply the Chinese market in the 1980 s and has now been registered and sold in more than 130 countries around the world. |
| pharmacological action | 1. hypoglycemic effect: this product is the second generation of oral sulfonylurea hypoglycemic drugs, and its effect is more than 10 times stronger than tolbutamide. The mechanism of action is to stimulate islet β cells to release insulin and reduce hyperglycemia. This may be due to the fact that sulfonylurea drugs bind to receptors on the surface of β cells and increase their activation and increase the sensitivity of peripheral target tissues to insulin. 2. Reduce platelet aggregation and adhesion, prevent fibrin deposition on microvessels. 3. Reduce cholesterol accumulation and plasma concentrations of arterial triglycerides and fatty acids. The three functions, in addition to the treatment of diabetic metabolic disorders, can also prevent and treat diabetic complications-the occurrence and development of vascular, retinal, and renal dysfunction. |
| mechanism of action | gliclazide has a strong effect. its mechanism is to selectively act on islet β cells to promote insulin secretion and improve insulin release after eating glucose, thus inhibiting glycogen production and output. It has a hypoglycemic effect on adult diabetic patients, and can reduce cholesterol accumulation, reduce the plasma concentration of aortic glycerin triphosphate and fatty acids, so gliclazide can not only treat diabetic metabolic disorders, but also prevent diabetic microangiopathy, Improve retinopathy and renal function. |
| pharmacokinetics | oral absorption is faster; plasma concentration peaks in 2~6 hours. The plasma protein binding rate is 94.2%, T1/2 is about 12 hours. This product is mainly metabolized in the liver, and the metabolites have no hypoglycemic effect. The 98% is excreted by the kidney within 48 hours, and the content of primary drugs in the urine is less than 5%. |
| synthesis method | using cyclopentane o-diformic anhydride as raw material, ammoniated to obtain cyclopentane o-diformimide, catalyzed by LiAlH4, KBH4/ZnCl2 or platinum black to obtain azabicyclo, and then reduced by nitrosation and zinc powder to obtain N-amino -3-azabicyclo [3,3,O] octane hydrochloride, finally, it is condensed with p-toluene sulfonylurea to obtain gliclazide. Fig. 2 shows the synthesis route of gliclazide |
| use | for adults with type 2 diabetes, diabetes with obesity or with vascular disease. hypoglycemic drugs, used for the treatment of non-insulin-dependent diabetes hypoglycemic drugs, non-insulin-dependent diabetes. |
| adverse reactions | occasionally mild nausea, vomiting, epigastric pain, constipation, diarrhea, erythema, urticaria, thrombocytopenia, neutropenia, anemia, etc., most of which disappeared after drug withdrawal. |
| taboo | 1. those who are allergic to this product, sulfonylureas and sulfonamides are prohibited. It is forbidden for patients with type 2.1 diabetes. 3. Patients with pre-diabetic coma and diabetic ketoacidosis are prohibited. 4. Patients with severe liver and kidney insufficiency are prohibited. 5. Patients with leukopenia are disabled. 6. Patients with stress such as coma, severe burns, infection, trauma and major surgery are prohibited. 7. Pregnant and lactating women are prohibited. |
| precautions | patients with type 1.2 diabetes should switch to insulin therapy when they have stress such as infection, trauma, surgery, ketoacidosis and non-ketotic hyperosmolar diabetic coma. 2. When the dosage of this product is too large, eating too little or strenuous exercise, attention should be paid to prevent hypoglycemia. 3. The patient’s blood sugar and urine sugar must be checked regularly, and ophthalmic examination must be carried out. 4. When combined with anticoagulant drugs, regular coagulation examination should be done. (2015-12-02) |
| drug interaction | when combined with non-steroidal anti-inflammatory drugs (especially salicylate), sulfonamides, dicoumarin anticoagulants, monoamine oxidase inhibitors, β-receptor blockers, tetracycline, chloramphenicol, bicyclohexyperidine, chlorobebutyl ester, ethanol and other drugs, the dosage should be reduced to avoid hypoglycemia. |
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