Gliclazide | CAS#21187-98-4 | Antihyperglycemic Agent

MedKoo Cat#: 317969 | Name: Gliclazide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gliclazide is an oral anti-hyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus. It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. Gliclazide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels.

Chemical Structure

Gliclazide

CAS#21187-98-4

Theoretical Analysis

MedKoo Cat#: 317969

Name: Gliclazide

CAS#: 21187-98-4

Chemical Formula: C15H21N3O3S

Exact Mass: 323.1304

Molecular Weight: 323.41

Elemental Analysis: C, 55.71; H, 6.54; N, 12.99; O, 14.84; S, 9.91

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350.00	2 Weeks
25g	USD 650.00	2 Weeks

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Synonym

Gliclazide; Gliclazida; Diamicron; Glimicron; Gliclazidum; Nordialex; Diaikron; S-1702; S1702; S 1702; S-852; S852; S 852; NSC-758673; NSC758673; NSC 758673;

IUPAC/Chemical Name

1-(3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-3-(4-methylphenyl)sulfonylurea

InChi Key

BOVGTQGAOIONJV-UHFFFAOYSA-N

InChi Code

InChI=1S/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)

SMILES Code

CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CC3CCCC3C2

Appearance

White to off-white crystalline powder.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Gliclazide (S1702) is a whole-cell beta-cell ATP-sensitive potassium currents blocker with an IC50 of 184 nM.

In vitro activity:

Similarly, this study found that Glz (gliclazide) at 100 μM exhibited the strongest inhibitory effect, an approximately 2-fold decrease in AGEs-induced RAGE expression, while 0.7-fold stronger effect than PDTC (Fig. 7C). These results suggest that Glz suppresses the macrophages inflammatory state apparently through inhibiting the RAGE/NF-kβ/i-NOS nexus. Reference: Eur J Pharmacol. 2021 Mar 5;894:173874. https://pubmed.ncbi.nlm.nih.gov/33460615/

In vivo activity:

The findings revealed that IR induces atypical features in heart and lung histostructure, and oxidative stress (an increase of MDA, PC levels, and decrease of GSH content) in these tissues. GLZ (gliclazide) administration preserved heart and lung damages and improves oxidative stress markers in mice. Reference: Med Oncol. 2022 Sep 7;39(12):199. https://pubmed.ncbi.nlm.nih.gov/36071308/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	61.84
	DMSO	61.7	190.68
	DMSO:PBS (pH 7.2) (1:3)	0.3	0.77

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 323.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Jahan H, Choudhary MI. Gliclazide alters macrophages polarization state in diabetic atherosclerosis in vitro via blocking AGE-RAGE/TLR4-reactive oxygen species-activated NF-kβ nexus. Eur J Pharmacol. 2021 Mar 5;894:173874. doi: 10.1016/j.ejphar.2021.173874. Epub 2021 Jan 15. PMID: 33460615. 2. Yang PY, Li PC, Feng B. Protective effects of gliclazide on high glucose and AGEs-induced damage of glomerular mesangial cells and renal tubular epithelial cells via inhibiting RAGE-p22phox-NF-kB pathway. Eur Rev Med Pharmacol Sci. 2019 Oct;23(20):9099-9107. doi: 10.26355/eurrev_201910_19313. PMID: 31696501. 3. Talebpour Amiri F, Arzani S, Farzipour S, Hosseinimehr SJ. Radioprotective effects of gliclazide against irradiation-induced cardiotoxicity and lung injury through inhibiting oxidative stress. Med Oncol. 2022 Sep 7;39(12):199. doi: 10.1007/s12032-022-01803-y. PMID: 36071308. 4. Taghizadeh F, Hosseinimehr SJ, Zargari M, Karimpour Malekshah A, Talebpour Amiri FB. Gliclazide attenuates cisplatin-induced nephrotoxicity through inhibiting NF-κB and caspase-3 activity. IUBMB Life. 2020 Sep;72(9):2024-2033. doi: 10.1002/iub.2342. Epub 2020 Jul 20. PMID: 32687680.

In vitro protocol:

In vivo protocol:

1. Talebpour Amiri F, Arzani S, Farzipour S, Hosseinimehr SJ. Radioprotective effects of gliclazide against irradiation-induced cardiotoxicity and lung injury through inhibiting oxidative stress. Med Oncol. 2022 Sep 7;39(12):199. doi: 10.1007/s12032-022-01803-y. PMID: 36071308. 2. Taghizadeh F, Hosseinimehr SJ, Zargari M, Karimpour Malekshah A, Talebpour Amiri FB. Gliclazide attenuates cisplatin-induced nephrotoxicity through inhibiting NF-κB and caspase-3 activity. IUBMB Life. 2020 Sep;72(9):2024-2033. doi: 10.1002/iub.2342. Epub 2020 Jul 20. PMID: 32687680.

1: Leiter LA, Shestakova MV, Trubitsyna NP, Piletič M, Satman I. Implementing an optimized glucose-lowering strategy with a novel once daily modified release gliclazide formulation. Diabetes Res Clin Pract. 2016 Feb;112:50-6. doi: 10.1016/j.diabres.2015.11.001. Epub 2015 Nov 23. PubMed PMID: 26653612. 2: Singh AK, Singh R. Is gliclazide a sulfonylurea with difference? A review in 2016. Expert Rev Clin Pharmacol. 2016 Feb 27. [Epub ahead of print] PubMed PMID: 26924475. 3: Duan F, Guo Y, Zhang L, Chen P, Wang X, Liu Z, Hu Y, Chen S, Chen D. Association of KCNQ1 polymorphisms with gliclazide efficacy in Chinese type 2 diabetic patients. Pharmacogenet Genomics. 2016 Feb 10. [Epub ahead of print] PubMed PMID: 26866747. 4: Zhang QJ, Liu BS, Li GX, Han R. Using resonance light scattering and UV/vis absorption spectroscopy to study the interaction between gliclazide and bovine serum albumin. Luminescence. 2015 Dec 14. doi: 10.1002/bio.3079. [Epub ahead of print] PubMed PMID: 26663583. 5: Mathavan S, Chen-Tan N, Arfuso F, Al-Salami H. A comprehensive study of novel microcapsules incorporating gliclazide and a permeation enhancing bile acid: hypoglycemic effect in an animal model of Type-1 diabetes. Drug Deliv. 2015 Nov 26:1-12. [Epub ahead of print] PubMed PMID: 26610261. 6: Alvares J, Araujo VE, Izidoro JB, Diniz LM, Nascimento RC, Silva MR, Dias CZ, Moreira DP, Guerra-Júnior AA, Fd A. Efficacy And Safety of Antidiabetic Drugs Available on Brazilian Public Health System (Sus) - Regular Insulin, Nph Insulin, Metformin, Glibenclamide And Gliclazide - In Treatment of Type 2 Diabetes (T2dm) - Systematic Review And Meta-Analysis. Value Health. 2015 Nov;18(7):A862. doi: 10.1016/j.jval.2015.09.499. Epub 2015 Oct 20. PubMed PMID: 26534614. 7: Clemens KK, McArthur E, Dixon SN, Fleet JL, Hramiak I, Garg AX. The hypoglycemic risk of glyburide (glibenclamide) compared with modified-release gliclazide. Can J Diabetes. 2015 Nov;39 Suppl 4:32-40. doi: 10.1016/j.jcjd.2015.09.087. PubMed PMID: 26541489. 8: Zhou J, Zheng F, Guo X, Yang H, Zhang M, Tian H, Guo L, Li Q, Mo Y, Jia W. Glargine insulin/gliclazide MR combination therapy is more effective than premixed insulin monotherapy in Chinese patients with type 2 diabetes inadequately controlled on oral antidiabetic drugs. Diabetes Metab Res Rev. 2015 Oct;31(7):725-33. doi: 10.1002/dmrr.2661. Epub 2015 Jun 16. PubMed PMID: 25952634. 9: Chan SP, Colagiuri S. Systematic review and meta-analysis of the efficacy and hypoglycemic safety of gliclazide versus other insulinotropic agents. Diabetes Res Clin Pract. 2015 Oct;110(1):75-81. doi: 10.1016/j.diabres.2015.07.002. Epub 2015 Jul 9. PubMed PMID: 26361859. 10: Hassan MH, Abd-Allah GM. Effects of metformin plus gliclazide versus metformin plus glimepiride on cardiovascular risk factors in patients with type 2 diabetes mellitus. Pak J Pharm Sci. 2015 Sep;28(5):1723-30. PubMed PMID: 26408873. 11: Mbanya JC, Al-Sifri S, Abdel-Rahim A, Satman I. Incidence of hypoglycemia in patients with type 2 diabetes treated with gliclazide versus DPP-4 inhibitors during Ramadan: A meta-analytical approach. Diabetes Res Clin Pract. 2015 Aug;109(2):226-32. doi: 10.1016/j.diabres.2015.04.030. Epub 2015 May 8. Review. PubMed PMID: 26003888. 12: Clemens KK, McArthur E, Dixon SN, Fleet JL, Hramiak I, Garg AX. The Hypoglycemic Risk of Glyburide (Glibenclamide) Compared with Modified-Release Gliclazide. Can J Diabetes. 2015 Aug;39(4):308-16. doi: 10.1016/j.jcjd.2015.01.001. Epub 2015 Mar 31. PubMed PMID: 25840942. 13: Ding CY, Tan QY, Shi NC. [Alisma versus Gliclazide in the Treatment of Primary Diabetes in Goto-Kakizaki Rats]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 2015 Aug;37(4):451-5. doi: 10.3881/j.issn.1000-503X.2015.04.015. Chinese. PubMed PMID: 26564464. 14: Mathavan S, Chen-Tan N, Arfuso F, Al-Salami H. The role of the bile acid chenodeoxycholic acid in the targeted oral delivery of the anti-diabetic drug gliclazide, and its applications in type 1 diabetes. Artif Cells Nanomed Biotechnol. 2015 Aug 27:1-12. [Epub ahead of print] PubMed PMID: 26212118. 15: Glyburide, Gliclazide or Glimepiride for Elderly Patients with Type 2 Diabetes: A Review of the Clinical Effectiveness and Safety – An Update [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Aug 18. Available from http://www.ncbi.nlm.nih.gov/books/NBK315876/ PubMed PMID: 26355189. 16: Ezel T, Kocyigit Y, Deveci E, Atamer Y, Sermet A, Uysal E, Aktaş A, Yavuz D. Biochemical and Histopathological Investigation of Resveratrol, Gliclazide, and Losartan Protective Effects on Renal Damage in a Diabetic Rat Model. Anal Quant Cytopathol Histpathol. 2015 Jun;37(3):187-98. PubMed PMID: 26173356. 17: Banerjee A, Verma PR, Gore S. Controlled porosity solubility modulated osmotic pump tablets of gliclazide. AAPS PharmSciTech. 2015 Jun;16(3):554-68. doi: 10.1208/s12249-014-0246-0. Epub 2014 Nov 7. PubMed PMID: 25378281; PubMed Central PMCID: PMC4444634. 18: Mansour HF, Aly UF. In vitro evaluation and in vivo performance of lyophilized gliclazide. Drug Dev Ind Pharm. 2015 Apr;41(4):650-7. doi: 10.3109/03639045.2014.891131. Epub 2014 Feb 26. PubMed PMID: 24568609. 19: Yazgan ÜC, Taşdemir E, Bilgin HM, Deniz Obay B, Şermet A, Elbey B. Comparison of the anti-diabetic effects of resveratrol, gliclazide and losartan in streptozotocin-induced experimental diabetes. Arch Physiol Biochem. 2015;121(4):157-61. doi: 10.3109/13813455.2015.1062898. Epub 2015 Jul 10. PubMed PMID: 26161595. 20: Hissa MR, Cavalcante LL, Guimarães SB, Hissa MN. A 16-week study to compare the effect of vildagliptin versus gliclazide on postprandial lipoprotein concentrations and oxidative stress in patients with type 2 diabetes inadequately controlled with metformin monotherapy. Diabetol Metab Syndr. 2015 Jul 11;7:62. doi: 10.1186/s13098-015-0058-8. eCollection 2015. PubMed PMID: 26170902; PubMed Central PMCID: PMC4499917.