GLIQUIDONE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H33N3O6S
Molecular Weight	527.632
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2C(=C1)C(=O)N(CCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C(=O)C2(C)C

InChI

InChIKey=LLJFMFZYVVLQKT-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C27H33N3O6S
Molecular Weight	527.632
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1439462/
Curator's Comment: description was created based on several sources, including: http://edudrugs.com/G/Glurenorm/more.html | http://www.e-compendium.be/topdf/1969/spc/H | http://www.rlsnet.ru/mnn_index_id_183.htm

Glurenorm is an anti-diabetic drug in the sulfonylurea class. It is used in the treatment of diabetes mellitus type 2. It is an ATP-dependent K+ (KATP) channel blocker. This block causes a depolarization which leads to activation of voltage-dependent Ca channels and Ca2+ influx, and eventually increases insulin release. Minor skin allergies, gastric upsets and other non-specific side effects have been reported. Hypoglycaemic reactions have been reported but they are infrequent. Glurenorm effect increase butadion, chloramphenicol, tetracycline, coumarin derivatives, cyclophosphamide, sulfonamides, MAO inhibitors, thiazide diuretics, beta-blockers, salicylates, alcohol.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sulfonylurea receptors; K-ATP channels 11 Target ID: CHEMBL2095152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8223904 \| http://edudrugs.com/G/Glurenorm.html	Blocker 534
Cytochrome P450 3A4 126 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23987740	Substrate 656
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23987740	Substrate 656

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 256 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1439462/pdf/jrsocmed00254-0106.pdf	Primary		Approved 8360	Glurenorm Approved Use Used in the treatment of diabetes mellitus type 2.

PubMed

Title	Date	PubMed
Role of K+ -channels in homotaurine-induced analgesia.	2001 Jun	11468027
The effect of Glurenorm (gliquidone) on lenses and skin in experimental diabetes.	2001 Nov 1	11677036
Methylamine and benzylamine induced hypophagia in mice: modulation by semicarbazide-sensitive benzylamine oxidase inhibitors and aODN towards Kv1.1 channels.	2001 Oct	11606329
Antiaggregatory activity of hypoglycaemic sulphonylureas.	2002 Jul	12136403
Screening, library-assisted identification and validated quantification of oral antidiabetics of the sulfonylurea-type in plasma by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry.	2002 Jun 15	12015271
Effect of pH and complexation on transdermal permeation of gliquidone.	2002 Sep	12369452
[Severe hypoglycemia in diabetics with impaired renal function].	2003 Feb 7	12571792
Hydroxyl-substituted sulfonylureas as potent inhibitors of specific [3H]glyburide binding to rat brain synaptosomes.	2003 May 1	12670661
Enhancement of dissolution and oral bioavailability of gliquidone with hydroxy propyl-beta-cyclodextrin.	2003 Nov	14664337
[Effect of liuwei dihuang pill on erythrocyte aldose reductase activity in early diabetic nephropathy patients].	2004 Dec	15658651
[Gliquidon induced-desensitization of pancreatic beta cells and the partial reversion of responsiveness after the desensitization of exposure to drug in normal and STZ type 2 diabetic rats].	2004 May	15181848
Improvement of gliquidone hypoglycaemic effect in rats by cyclodextrin formulations.	2004 Sep	15324923
Protective effects of glurenorm (gliquidone) treatment on the liver injury of experimental diabetes.	2005	16298877
Effect of glurenorm on immunohistochemical changes in pancreatic beta cells of rats in experimental diabetes.	2005 Mar	15816415
Gliquidone contributes to improvement of type 2 diabetes mellitus management: a review of pharmacokinetic and clinical trial data.	2006	17073516
Spectrophotometric method for quantitative determination of gliquidone in bulk drug, pharmaceutical formulations and human serum.	2006 Jul	16935824
Sulfonylureas and glinides exhibit peroxisome proliferator-activated receptor gamma activity: a combined virtual screening and biological assay approach.	2007 Feb	17082235
Determination of glibenclamide in human plasma by liquid chromatography and atmospheric pressure chemical ionization/MS-MS detection.	2007 Feb 1	17011248
Simultaneous assay of metformin and glibenclamide in human plasma based on extraction-less sample preparation procedure and LC/(APCI)MS.	2007 Jul 1	17500048
Development of a RP-HPLC method for screening potentially counterfeit anti-diabetic drugs.	2007 Jun 15	17409031
Bioavailability of the amino acid-attached prodrug as a new anti-HIV agent in rats.	2007 Sep	17679773
Gliquidone therapy of new-onset diabetes mellitus after kidney transplantation.	2008 Jul	18793545
Rapid simultaneous quantification of five active constituents in rat plasma by high-performance liquid chromatography/tandem mass spectrometry after oral administration of Da-Cheng-Qi decoction.	2008 Jul 15	18358661
Metformin, sulfonylureas, or other antidiabetes drugs and the risk of lactic acidosis or hypoglycemia: a nested case-control analysis.	2008 Nov	18782901
Glucose and pharmacological modulators of ATP-sensitive K+ channels control [Ca2+]c by different mechanisms in isolated mouse alpha-cells.	2009 Feb	19008345
Sulfonylurea-induced hypoglycaemia: use of octreotide.	2009 Jan-Feb	19317242
Twice daily fractionated dose administration of prednisolone compared to standard once daily administration to patients with glomerulonephritis or with kidney transplants.	2009 Jun 15	19533049
Determination of glycyrrhizin in dog plasma by liquid chromatography-mass spectrometry and its application in pharmacokinetic studies.	2010	21173464
Simultaneous determination of gliquidone, fexofenadine, buclizine, and levocetirizine in dosage formulation and human serum by RP-HPLC.	2010 May-Jun	20515533
Efficacy of anti-wrinkle products in skin surface appearance: a comparative study using non-invasive methods.	2010 Nov	20923458
Drug therapy in patients with chronic renal failure.	2010 Sep	20959896
Severe sulfonylurea-induced hypoglycemia: a problem of uncritical prescription and deficiencies of diabetes care in geriatric patients.	2010 Sep	20553106
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013 Nov	23956101
In vitro inhibition of AKR1Cs by sulphonylureas and the structural basis.	2015 Oct 5	26362498

Patents

Sample Use Guides

In Vivo Use Guide

45-60 mg daily in divided doses taken before meals. Maximum single dose 60 mg, maximum daily dose 180 mg.

Route of Administration: Oral

In Vitro Use Guide

Gliquidone inhibits the [3H]glibenclamide (0.5 nM) binding to the rat cortex membranes (0.5-0.8 mg/ml) – IC50=27.2 nM.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:59:20 UTC 2023` Edited by `admin` on `Wed Jul 05 22:59:20 UTC 2023`
Record UNII	C7C2QDD75P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLIQUIDONE

Official Name

English

ARDF 26

Code

English

gliquidone [INN]

Common Name

English

GLURENORM

Brand Name

English

GLIQUIDONE [MART.]

Common Name

English

Gliquidone [WHO-DD]

Common Name

English

GLIQUIDONE [MI]

Common Name

English

ARDF-26

Code

English

1-CYCLOHEXYL-3-(((P-(2-(3,4-DIHYDRO-7-METHOXY-4,4-DIMETHYL-1,3-DIOXO-2(1H)-ISOQUINOLYL)ETHYL)PHENYL)SULFONYL)UREA

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

A10BB08