Gliquidone | CAS#33342-05-1 | K+ channel Blocker

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

MedKoo CAT#: 317973

CAS#: 33342-05-1

Description: Gliquidone is an ATP-dependent K+ (KATP) channel blocker. Gliquidone is an anti-diabetic drug in the sulfonylurea class. Gliquidone is used in the treatment of diabetes mellitus type 2. This block causes a depolarization which leads to activation of voltage-dependent Ca channels and Ca2+ influx and eventually increases insulin release.

Chemical Structure

Gliquidone

CAS# 33342-05-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317973
Name: Gliquidone
CAS#: 33342-05-1
Chemical Formula: C27H33N3O6S
Exact Mass: 527.21
Molecular Weight: 527.636
Elemental Analysis: C, 61.46; H, 6.30; N, 7.96; O, 18.19; S, 6.08

Price and Availability

Size	Price	Availability
100mg	USD 150
200mg	USD 250
1g	USD 450
5g	USD 750
10g	USD 1150	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Gliquidone; Glurenorm; Beglynor; Glikvidon; Glycvidon; Sanofi Synthelabo brand of gliquidone; Yamanouchi brand of gliquidone;

IUPAC/Chemical Name: 1-cyclohexyl-3-[4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxoisoquinolin-2-yl)ethyl]phenyl]sulfonylurea

InChi Key: LLJFMFZYVVLQKT-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H33N3O6S/c1-27(2)23-14-11-20(36-3)17-22(23)24(31)30(25(27)32)16-15-18-9-12-21(13-10-18)37(34,35)29-26(33)28-19-7-5-4-6-8-19/h9-14,17,19H,4-8,15-16H2,1-3H3,(H2,28,29,33)

SMILES Code: CC1(C2=C(C=C(C=C2)OC)C(=O)N(C1=O)CCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C

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: 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:	Gliquidone (Glurenorm) is an ATP-sensitive K+ channel antagonist with IC50 of 27.2 nM.
In vitro activity:	In HRECs, HG (high glucose) treatment remarkably decreased the cell viability, but promoted caspase-3 activity and apoptosis (Fig. 2A-C, P < 0.01). After addition of GLI, HG-induced HRECs showed the increased cell viability and the reduced caspase-3 activity and apoptosis rate (P < 0.01). Reference: BMC Ophthalmol. 2021 Dec 27;21(1):451. https://pubmed.ncbi.nlm.nih.gov/34961513/
In vivo activity:	Treatment with 20 mg/kg gliquidone significantly decreased the LPS-induced increases in Iba-1 immunoreactivity, Iba-1-positive cells, and Iba-1-labeled area in the cortex and hippocampal CA1 and CA3 regions (Figures 1A–E). By contrast, administration of 10 mg/kg gliquidone significantly reduced the LPS-induced increases in Iba-1 intensity, Iba-1-positive cells, and Iba-1-labeled area only in the hippocampal CA3 region (Figures 1C–E). These results indicated that a gliquidone dose of 20 mg/kg more effectively downregulates LPS-mediated microgliosis and changes in microglial kinetics and morphology in the wild-type mouse brain. Reference: Front Aging Neurosci. 2021 Oct 29;13:754123. https://pubmed.ncbi.nlm.nih.gov/34776934/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	56.86
	DMSO	60.0	113.71
	DMSO:PBS (pH 7.2) (1:5)	0.2	0.30
	Ethanol	1.0	1.90

Preparing Stock Solutions

The following data is based on the product molecular weight 527.64 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. Yu M, Zhang L, Sun S, Zhang Z. Gliquidone improves retinal injury to relieve diabetic retinopathy via regulation of SIRT1/Notch1 pathway. BMC Ophthalmol. 2021 Dec 27;21(1):451. doi: 10.1186/s12886-021-02215-8. PMID: 34961513; PMCID: PMC8711144. 2. Kim J, Park JH, Shah K, Mitchell SJ, Cho K, Hoe HS. The Anti-diabetic Drug Gliquidone Modulates Lipopolysaccharide-Mediated Microglial Neuroinflammatory Responses by Inhibiting the NLRP3 Inflammasome. Front Aging Neurosci. 2021 Oct 29;13:754123. doi: 10.3389/fnagi.2021.754123. PMID: 34776934; PMCID: PMC8587901. 3. Tian H, Yang J, Xie Z, Liu J. Gliquidone Alleviates Diabetic Nephropathy by Inhibiting Notch/Snail Signaling Pathway. Cell Physiol Biochem. 2018;51(5):2085-2097. doi: 10.1159/000495827. Epub 2018 Dec 6. PMID: 30522115.
In vitro protocol:	1. Yu M, Zhang L, Sun S, Zhang Z. Gliquidone improves retinal injury to relieve diabetic retinopathy via regulation of SIRT1/Notch1 pathway. BMC Ophthalmol. 2021 Dec 27;21(1):451. doi: 10.1186/s12886-021-02215-8. PMID: 34961513; PMCID: PMC8711144.
In vivo protocol:	1. Kim J, Park JH, Shah K, Mitchell SJ, Cho K, Hoe HS. The Anti-diabetic Drug Gliquidone Modulates Lipopolysaccharide-Mediated Microglial Neuroinflammatory Responses by Inhibiting the NLRP3 Inflammasome. Front Aging Neurosci. 2021 Oct 29;13:754123. doi: 10.3389/fnagi.2021.754123. PMID: 34776934; PMCID: PMC8587901. 2. Tian H, Yang J, Xie Z, Liu J. Gliquidone Alleviates Diabetic Nephropathy by Inhibiting Notch/Snail Signaling Pathway. Cell Physiol Biochem. 2018;51(5):2085-2097. doi: 10.1159/000495827. Epub 2018 Dec 6. PMID: 30522115.

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Reconstitution Calculator

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1: Liu SY, Tian HM, Liao DQ, Chen YF, Gou ZP, Xie XY, Li XJ. The effect of
gliquidone on KATP channels in pancreatic β-cells, cardiomyocytes, and vascular
smooth muscle cells. Diabetes Res Clin Pract. 2015 Aug;109(2):334-9. doi:
10.1016/j.diabres.2015.05.036. Epub 2015 May 18. PubMed PMID: 26044612.

2: Zhang F, Wei Y, Zhou Y, Wang D, Zhou L, Zhang J, Wu X. Pharmacokinetics and
hepatic uptake of gliquidone affected by Huangqi injection. Eur J Drug Metab
Pharmacokinet. 2014 Dec;39(4):255-61. doi: 10.1007/s13318-013-0154-9. Epub 2013
Oct 2. PubMed PMID: 24085486.

3: He F, Li Y, Zeng C, Xia C, Xiong Y, Zhang H, Huang S, Liu M. Contribution of
cytochrome P450 isoforms to gliquidone metabolism in rats and human. Xenobiotica.
2014 Mar;44(3):229-34. doi: 10.3109/00498254.2013.831957. Epub 2013 Aug 29.
PubMed PMID: 23987740.

4: Ke JT, Li M, Xu SQ, Zhang WJ, Jiang YW, Cheng LY, Chen L, Lou JN, Wu W.
Gliquidone decreases urinary protein by promoting tubular reabsorption in
diabetic Goto-Kakizaki rats. J Endocrinol. 2014 Jan 8;220(2):129-41. doi:
10.1530/JOE-13-0199. Print 2014 Feb. PubMed PMID: 24254365.

5: Tan Z, Xu Z, Gui Q, Wu W, Yang Y. Gliquidone versus metformin: differential
effects on aorta in streptozotocin induced diabetic rats. Chin Med J (Engl).
2014;127(7):1298-303. PubMed PMID: 24709184.

6: Mirza AZ, Arayne MS, Sultana N. RP-LC method for the simultaneous
determination of gliquidone, pioglitazone hydrochloride, and atorvastatin in
formulations and human serum. J AOAC Int. 2013 Jan-Feb;96(1):56-9. PubMed PMID:
23513958.

7: Gelbrich T, Haddow MF, Griesser UJ. Gliquidone. Acta Crystallogr Sect E Struct
Rep Online. 2011 Jun 1;67(Pt 6):o1343. doi: 10.1107/S1600536811016680. Epub 2011
May 7. PubMed PMID: 21754738; PubMed Central PMCID: PMC3120417.

8: Arayne MS, Sultana N, Mirza AZ. Simultaneous determination of gliquidone,
pioglitazone hydrochloride, and verapamil in formulation and human serum by
RP-HPLC. J Chromatogr Sci. 2011 Feb;49(2):114-7. PubMed PMID: 21223635.

9: Arayne MS, Sultana N, Mirza AZ, Siddiqui FA. Simultaneous determination of
gliquidone, fexofenadine, buclizine, and levocetirizine in dosage formulation and
human serum by RP-HPLC. J Chromatogr Sci. 2010 May-Jun;48(5):382-5. PubMed PMID:
20515533.

10: Tuerk TR, Bandur S, Nuernberger J, Kribben A, Mann K, Philipp T, Heemann U,
Viklicky O, Witzke O. Gliquidone therapy of new-onset diabetes mellitus after
kidney transplantation. Clin Nephrol. 2008 Jul;70(1):26-32. PubMed PMID:
18793545.

11: Yanardag R, Ozsoy-Sacan O, Orak H, Ozgey Y. Protective effects of glurenorm
(gliquidone) treatment on the liver injury of experimental diabetes. Drug Chem
Toxicol. 2005;28(4):483-97. PubMed PMID: 16298877.

12: Courtois P, Sener A, Herbaut C, Turc A, Malaisse WJ. Pharmacokinetics of
gliquidone, glibenclamide, gliclazide and glipizide in middle-aged and aged
subjects. Res Commun Mol Pathol Pharmacol. 1999 Feb;103(2):211-22. PubMed PMID:
10461687.

13: Martnez P, Goñi MM, Cantera RG, Martin C, Dios-Viéitez C, Martínez-Ohárriz C.
Preparation and dissolution rate of gliquidone-PVP K30 solid dispersions. Eur J
Drug Metab Pharmacokinet. 1998 Apr-Jun;23(2):113-7. PubMed PMID: 9725467.

14: Nitiyanant W, Sriussadaporn S, Deerochanawong C, Ngawngamrat S,
Benjasuratwong Y, Patanaungkul S. The efficacy and safety of gliquidone in Thai
diabetics. J Med Assoc Thai. 1997 Dec;80(12):771-7. PubMed PMID: 9470330.

15: García-Martínez JA, Villanueva-Peñacarrillo ML, Valverde I, Björkling F,
Malaisse WJ. Potentiation of the insulinotropic and hypoglycemic action of
gliquidone by succinic acid esters. Eur J Pharmacol. 1997 Apr 23;325(1):65-8.
PubMed PMID: 9151940.

16: von Nicolai H, Brickl R, Eschey H, Greischel A, Heinzel G, König E, Limmer J,
Rupprecht E. Duration of action and pharmacokinetics of the oral antidiabetic
drug gliquidone in patients with non-insulin-dependent (type 2) diabetes
mellitus. Arzneimittelforschung. 1997 Mar;47(3):247-52. PubMed PMID: 9105542.

17: Degtiareva II, Lodianaia EV, Opanasiuk ND, Palladina OL. [The use of the
hypoglycemic preparation gliquidone in patients with digestive organ diseases
combined with diabetes mellitus]. Lik Sprava. 1995 Jul-Aug;(7-8):84-7. Russian.
PubMed PMID: 8846383.

18: Grzeszczak W, Strojek K. [Effect of short term hypoglycemic treatment with
gliclazide and gliquidone on platelet function in patients with diabetes mellitus
type II]. Pol Tyg Lek. 1993 Apr;48 Suppl 1:38-9. Polish. PubMed PMID: 8516206.

19: Strojek K, Bresler M, Gumprecht J, Grzeszczak W, Trautsolt W. [Does
hypoglycemic treatment with gliclazide and gliquidone affect platelet function in
type II diabetic patients?]. Pol Arch Med Wewn. 1993 Apr;89(4):315-9. Polish.
PubMed PMID: 8351232.

20: Podrouzková B, Krusová D. [Combined therapy with insulin/gliquidone
(Glurenorm) in type 2 diabetes after treatment failure using oral antidiabetic
agents]. Vnitr Lek. 1992 Oct;38(10):963-7. Czech. PubMed PMID: 1481374.

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