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
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
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

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