Gliclazide-d4
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MedKoo CAT#: 464193

CAS#: 1185039-30-8

Description: Gliclazide-d4 is intended for use as an internal standard for the quantification of gliclazide by GC- or LC-MS. Gliclazide is a sulfonylurea and an inhibitor of pancreatic β-cell ATP-sensitive potassium (KATP) channels. It is selective for pancreatic β-cell over cardiac and arterial smooth muscle cell KATP channels. Gliclazide (5 μM) increases insulin-induced glucose uptake and glucose transporter 4 (GLUT4) translocation to the plasma membrane in a differentiated 3T3L1 adipocyte model of insulin resistance induced by hydrogen peroxide. Gliclazide (5 and 10 μg/ml) reduces LDL oxidation by human aortic smooth muscle cells (HASMCs), decreasing TBARS content and 8-isoprostane levels. It also decreases oxidized LDL-induced HASMC proliferation and monocyte adhesion when used at concentrations ranging from 1 to 10 μg/ml. Gliclazide (5 mg/kg) reduces serum glucose levels and increases glucose uptake by isolated rat hindquarters in a model of diabetes induced by streptozotocin (STZ).

Chemical Structure

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Gliclazide-d4
CAS# 1185039-30-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464193
Name: Gliclazide-d4
CAS#: 1185039-30-8
Chemical Formula: C15H17D4N3O3S
Exact Mass: 327.16
Molecular Weight: 327.435
Elemental Analysis: C, 55.02; H, 7.69; N, 12.83; O, 14.66; S, 9.79

Price and Availability

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1mg USD 350 2 Weeks
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Synonym: Gliclazide-d4; Gliclazide d4;

IUPAC/Chemical Name: N-((hexahydrocyclopenta[c]pyrrol-2(1H)-yl)carbamoyl)-4-methylbenzene-2,3,5,6-d4-sulfonamide

InChi Key: BOVGTQGAOIONJV-KDWZCNHSSA-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)/i5D,6D,7D,8D

SMILES Code: CC1=C(C([2H])=C(C([2H])=C1[2H])S(NC(NN2CC3C(C2)CCC3)=O)(=O)=O)[2H]

Appearance: Solid 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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: to be determined

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:
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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
To be determined 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 327.44 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: Lee D, Qi Y, Kim R, Song J, Kim H, Kim HY, Jang DS, Kang KS. Methyl Caffeate Isolated from the Flowers of Prunus persica (L.) Batsch Enhances Glucose- Stimulated Insulin Secretion. Biomolecules. 2021 Feb 14;11(2):279. doi: 10.3390/biom11020279. PMID: 33672801; PMCID: PMC7917615.

2: Szymczak-Pajor I, Fleszar K, Kasznicki J, Gralewska P, Śliwińska A. A potential role of calpains in sulfonylureas (SUs) -mediated death of human pancreatic cancer cells (1.2B4). Toxicol In Vitro. 2021 Feb 27;73:105128. doi: 10.1016/j.tiv.2021.105128. Epub ahead of print. PMID: 33652124.

3: Pan WQ, Wang SF, Ding BP, Huang ZG. [Protective effects of gliclazide on myocardium of diabetic rats and its mechanism]. Zhongguo Ying Yong Sheng Li Xue Za Zhi. 2020 Sep;36(5):402-407. Chinese. doi: 10.12047/j.cjap.5999.2020.086. PMID: 33629551.

4: Karalis DT, Karalis T, Karalis S, Kleisiari AS, Malakoudi F, Maimari KEV. The Effect of Alpha-Lipoic Acid on Diabetic Peripheral Neuropathy and the Upcoming Depressive Disorders of Type II Diabetics. Cureus. 2021 Jan 18;13(1):e12773. doi: 10.7759/cureus.12773. PMID: 33614362; PMCID: PMC7888960.

5: Kalra S, Unnikrishnan AG, Bantwal G, Das S, Polavarapu NK, Gaurav K. The Position of Gliclazide in the Evolving Landscapes and Disease Continuum of T2DM: A Collaborative Delphi Survey-Based Consensus from India. Diabetes Ther. 2021 Jan 28. doi: 10.1007/s13300-021-01002-4. Epub ahead of print. PMID: 33511553.

6: Aljohani M, McArdle P, Erxleben A. Dual-drug amorphous formulation of gliclazide. Drug Dev Ind Pharm. 2021 Feb;47(2):302-307. doi: 10.1080/03639045.2021.1879838. Epub 2021 Feb 1. PMID: 33492999.

7: Tatlisoz MM, Demirturk E, Canpolat C. Release characteristics of gliclazide in a matrix system. In Silico Pharmacol. 2021 Jan 11;9(1):12. doi: 10.1007/s40203-020-00068-5. PMID: 33489711; PMCID: PMC7801577.

8: Iancu VI, Scutariu RE, Chiriac FL, Radu GL. Sensitive detection of antidiabetic compounds and one degradation product in wastewater samples by a new SPE-LC-MS/MS method. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2021 Jan 20:1-14. doi: 10.1080/10934529.2021.1873671. Epub ahead of print. PMID: 33471573.

9: 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.

10: Morieri ML, Vitturi N, Avogaro A, Targher G, Fadini GP; DARWIN-T2D Network of the Italian Diabetes Society. Prevalence of hepatic steatosis in patients with type 2 diabetes and response to glucose-lowering treatments. A multicenter retrospective study in Italian specialist care. J Endocrinol Invest. 2021 Jan 11. doi: 10.1007/s40618-021-01501-y. Epub ahead of print. PMID: 33432553.

11: Fang D, Yang Y, Cui M, Pan H, Wang L, Li P, Wu W, Qiao S, Pan W. Three- Dimensional (3D)-Printed Zero-Order Released Platform: a Novel Method of Personalized Dosage Form Design and Manufacturing. AAPS PharmSciTech. 2021 Jan 6;22(1):37. doi: 10.1208/s12249-020-01886-8. PMID: 33409925.

12: Sasongko L, Pratiwi GK, Leo M, Adiwidjaja J. Simultaneous HPLC Assay of Gliclazide and Ciprofloxacin in Plasma and its Implementation for Pharmacokinetic Study in Rats. J Chromatogr Sci. 2021 Jan 6:bmaa111. doi: 10.1093/chromsci/bmaa111. Epub ahead of print. PMID: 33401303.

13: Đanić M, Pavlović N, Stanimirov B, Lazarević S, Vukmirović S, Al-Salami H, Mikov M. PAMPA model of gliclazide permeability: The impact of probiotic bacteria and bile acids. Eur J Pharm Sci. 2021 Mar 1;158:105668. doi: 10.1016/j.ejps.2020.105668. Epub 2020 Dec 7. PMID: 33301903.

14: Sanyal D, Biswas M, Chaudhari N. Long-term efficacy and safety of anti- hyperglycaemic agents in new-onset diabetes after transplant: Results from outpatient-based 1-year follow-up and a brief review of treatment options. Diabetes Metab Syndr. 2021 Jan-Feb;15(1):13-19. doi: 10.1016/j.dsx.2020.11.019. Epub 2020 Nov 23. PMID: 33278690.

15: Marchetti G, Ardengh AO, Colombo-Souza P, Kassab P, Freitas-Jr WR, Ilias EJ. The effect of Roux-en-Y gastric bypass in the treatment of hypertension and diabetes. Rev Col Bras Cir. 2020 Nov 23;47:e20202655. English, Portuguese. doi: 10.1590/0100-6991e-20202655. PMID: 33237184.

16: Rodriguez EL, Tao P, Woolfork AG, Li Z, Matsuda R, Sun Z, Hage DS. Studies of binding by sulfonylureas with glyoxal- and methylglyoxal-modified albumin by immunoextraction using affinity microcolumns. J Chromatogr A. 2021 Feb 8;1638:461683. doi: 10.1016/j.chroma.2020.461683. Epub 2020 Nov 10. PMID: 33223150; PMCID: PMC7870548.

17: van Bommel EJM, Geurts F, Muskiet MHA, Post A, Bakker SJL, Danser AHJ, Touw DJ, van Berkel M, Kramer MHH, Nieuwdorp M, Ferrannini E, Joles JA, Hoorn EJ, van Raalte DH. SGLT2 inhibition versus sulfonylurea treatment effects on electrolyte and acid-base balance: secondary analysis of a clinical trial reaching glycemic equipoise: Tubular effects of SGLT2 inhibition in Type 2 diabetes. Clin Sci (Lond). 2020 Dec 11;134(23):3107-3118. doi: 10.1042/CS20201274. PMID: 33205810.

18: Nguyen-Thi HY, Nguyen NT, Le NDT, Beillat M, Ethgen O. Cost-Effectiveness of Gliclazide-Based Intensive Glucose Control vs. Standard Glucose Control in Type 2 Diabetes Mellitus. An Economic Analysis of the ADVANCE Trial in Vietnam. Front Public Health. 2020 Oct 30;8:562023. doi: 10.3389/fpubh.2020.562023. PMID: 33194963; PMCID: PMC7661634.

19: Wang X, Feng A, Yuan P, Fu Y, Bai Z, Zhou N, Zheng X. The total flavonoids from Selaginella tamariscina (beauv.) Spring improve glucose and lipid metabolism in db/db mice. Iran J Basic Med Sci. 2020 Oct;23(10):1286-1292. doi: 10.22038/ijbms.2020.40532.9594. PMID: 33149860; PMCID: PMC7585538.

20: Mizar SMM, Kozman MR, Abo-Saif AA, Messiha BAS. Combination of Captopril with Gliclazide Decreases Vascular and Renal Complications and Improves Glycemic Control in Rats with Streptozotocin-induced Diabetes Mellitus. Endocr Metab Immune Disord Drug Targets. 2020 Aug 21. doi: 10.2174/1871530320666200821160436. Epub ahead of print. PMID: 32955003.