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 555
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23987740	Substrate 661
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23987740	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1439462/pdf/jrsocmed00254-0106.pdf	Primary		Approved 8583	Glurenorm Approved Use Used in the treatment of diabetes mellitus type 2.

C_max

Value	Dose	Co-administered	Analyte	Population
0.65 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9105542/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		GLIQUIDONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.87 μg/mL EXPERIMENT https://www.jstage.jst.go.jp/article/amjsphcs/20/0/20_504/_article/-char/en	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		GLIQUIDONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
5.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9105542/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		GLIQUIDONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4.98 μg × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/amjsphcs/20/0/20_504/_article/-char/en	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		GLIQUIDONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9105542/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:		GLIQUIDONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.06 h EXPERIMENT https://www.jstage.jst.go.jp/article/amjsphcs/20/0/20_504/_article/-char/en	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:		GLIQUIDONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
60 mg 2 times / day multiple, oral Recommended Dose: 60 mg, 2 times / day Route: oral Route: multiple Dose: 60 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1560186/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1560186/	Sources: https://pubmed.ncbi.nlm.nih.gov/1560186/

PubMed

Title	Date	PubMed
In vitro inhibition of AKR1Cs by sulphonylureas and the structural basis.	2015-10-05	26362498
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013-11	23956101
Smoking and risk for diabetes incidence and mortality in Korean men and women.	2010-12	20823342
Efficacy of anti-wrinkle products in skin surface appearance: a comparative study using non-invasive methods.	2010-11	20923458
Drug therapy in patients with chronic renal failure.	2010-09	20959896
Severe sulfonylurea-induced hypoglycemia: a problem of uncritical prescription and deficiencies of diabetes care in geriatric patients.	2010-09	20553106
Simultaneous determination of gliquidone, fexofenadine, buclizine, and levocetirizine in dosage formulation and human serum by RP-HPLC.	2010-06-03	20515533
Determination of glycyrrhizin in dog plasma by liquid chromatography-mass spectrometry and its application in pharmacokinetic studies.	2010	21173464
Risk of cardiovascular disease and all cause mortality among patients with type 2 diabetes prescribed oral antidiabetes drugs: retrospective cohort study using UK general practice research database.	2009-12-03	19959591
Twice daily fractionated dose administration of prednisolone compared to standard once daily administration to patients with glomerulonephritis or with kidney transplants.	2009-06-15	19533049
Sulfonylurea-induced hypoglycaemia: use of octreotide.	2009-03-26	19317242
Glucose and pharmacological modulators of ATP-sensitive K+ channels control [Ca2+]c by different mechanisms in isolated mouse alpha-cells.	2009-02	19008345
Metformin, sulfonylureas, or other antidiabetes drugs and the risk of lactic acidosis or hypoglycemia: a nested case-control analysis.	2008-11	18782901
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.	2008-07-15	18358661
Gliquidone therapy of new-onset diabetes mellitus after kidney transplantation.	2008-07	18793545
Bioavailability of the amino acid-attached prodrug as a new anti-HIV agent in rats.	2007-09	17679773
Simultaneous assay of metformin and glibenclamide in human plasma based on extraction-less sample preparation procedure and LC/(APCI)MS.	2007-07-01	17500048
Development of a RP-HPLC method for screening potentially counterfeit anti-diabetic drugs.	2007-06-15	17409031
Determination of glibenclamide in human plasma by liquid chromatography and atmospheric pressure chemical ionization/MS-MS detection.	2007-02-01	17011248
Sulfonylureas and glinides exhibit peroxisome proliferator-activated receptor gamma activity: a combined virtual screening and biological assay approach.	2007-02	17082235
Spectrophotometric method for quantitative determination of gliquidone in bulk drug, pharmaceutical formulations and human serum.	2006-07	16935824
Gliquidone contributes to improvement of type 2 diabetes mellitus management: a review of pharmacokinetic and clinical trial data.	2006	17073516
Effect of glurenorm on immunohistochemical changes in pancreatic beta cells of rats in experimental diabetes.	2005-03	15816415
Protective effects of glurenorm (gliquidone) treatment on the liver injury of experimental diabetes.	2005	16298877
[Effect of liuwei dihuang pill on erythrocyte aldose reductase activity in early diabetic nephropathy patients].	2004-12	15658651
Improvement of gliquidone hypoglycaemic effect in rats by cyclodextrin formulations.	2004-09	15324923
[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].	2004-05	15181848
Enhancement of dissolution and oral bioavailability of gliquidone with hydroxy propyl-beta-cyclodextrin.	2003-11	14664337
Hydroxyl-substituted sulfonylureas as potent inhibitors of specific [3H]glyburide binding to rat brain synaptosomes.	2003-05-01	12670661
[Severe hypoglycemia in diabetics with impaired renal function].	2003-02-07	12571792
Effect of pH and complexation on transdermal permeation of gliquidone.	2002-09	12369452
Antiaggregatory activity of hypoglycaemic sulphonylureas.	2002-07	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.	2002-06-15	12015271
The effect of Glurenorm (gliquidone) on lenses and skin in experimental diabetes.	2001-11-01	11677036
Methylamine and benzylamine induced hypophagia in mice: modulation by semicarbazide-sensitive benzylamine oxidase inhibitors and aODN towards Kv1.1 channels.	2001-10	11606329
Role of K+ -channels in homotaurine-induced analgesia.	2001-06	11468027

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 `Mon Mar 31 17:58:58 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:58 GMT 2025`
Record UNII	C7C2QDD75P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLURENORM

Preferred Name

English

GLIQUIDONE

Official Name

English

ARDF 26

Code

English

gliquidone [INN]

Common 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