GLIQUIDONE

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 537
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 259 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1439462/pdf/jrsocmed00254-0106.pdf	Primary		Approved 8429	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
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
Improvement of gliquidone hypoglycaemic effect in rats by cyclodextrin formulations.	2004 Sep	15324923
Spectrophotometric method for quantitative determination of gliquidone in bulk drug, pharmaceutical formulations and human serum.	2006 Jul	16935824
Simultaneous assay of metformin and glibenclamide in human plasma based on extraction-less sample preparation procedure and LC/(APCI)MS.	2007 Jul 1	17500048
Bioavailability of the amino acid-attached prodrug as a new anti-HIV agent in rats.	2007 Sep	17679773
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
Smoking and risk for diabetes incidence and mortality in Korean men and women.	2010 Dec	20823342
Simultaneous determination of gliquidone, fexofenadine, buclizine, and levocetirizine in dosage formulation and human serum by RP-HPLC.	2010 May-Jun	20515533
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 `Fri Dec 15 15:29:37 GMT 2023` Edited by `admin` on `Fri Dec 15 15:29:37 GMT 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