Gliclazide
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MedKoo CAT#: 317969

CAS#: 21187-98-4

Description: 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

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Gliclazide
CAS# 21187-98-4

Theoretical Analysis

MedKoo Cat#: 317969
Name: Gliclazide
CAS#: 21187-98-4
Chemical Formula: C15H21N3O3S
Exact Mass: 323.13
Molecular Weight: 323.411
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 250 2 Weeks
25g USD 450 2 Weeks
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Synonym: Gliclazide; Diamicron; Glimicron; Nordialex; Diaikron; S-1702; S-852; S1702; S852; S 1702; S 852

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:
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/

Solubility Data

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

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.

Recalculate based on batch purity %
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: 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.
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.

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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
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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
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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
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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:
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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.