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

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
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
[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
Gliquidone contributes to improvement of type 2 diabetes mellitus management: a review of pharmacokinetic and clinical trial data.	2006	17073516
Determination of glibenclamide in human plasma by liquid chromatography and atmospheric pressure chemical ionization/MS-MS detection.	2007 Feb 1	17011248
Development of a RP-HPLC method for screening potentially counterfeit anti-diabetic drugs.	2007 Jun 15	17409031
Determination of glycyrrhizin in dog plasma by liquid chromatography-mass spectrometry and its application in pharmacokinetic studies.	2010	21173464
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
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.

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