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Details

Stereochemistry ACHIRAL
Molecular Formula C27H33N3O6S
Molecular Weight 527.6345
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLIQUIDONE

SMILES

CC1(C)c2ccc(cc2C(=O)N(CCc3ccc(cc3)S(=O)(=O)NC(=NC4CCCCC4)O)C1=O)OC

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 527.6345
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Unknown
109281
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
511
Substrate
609
Substrate
609
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
Glurenorm

Approved Use

Used in the treatment of diabetes mellitus type 2.
PubMed

PubMed

TitleDatePubMed
Role of K+ -channels in homotaurine-induced analgesia.
2001 Jun
The effect of Glurenorm (gliquidone) on lenses and skin in experimental diabetes.
2001 Nov 1
Methylamine and benzylamine induced hypophagia in mice: modulation by semicarbazide-sensitive benzylamine oxidase inhibitors and aODN towards Kv1.1 channels.
2001 Oct
Antiaggregatory activity of hypoglycaemic sulphonylureas.
2002 Jul
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
Effect of pH and complexation on transdermal permeation of gliquidone.
2002 Sep
[Severe hypoglycemia in diabetics with impaired renal function].
2003 Feb 7
Hydroxyl-substituted sulfonylureas as potent inhibitors of specific [3H]glyburide binding to rat brain synaptosomes.
2003 May 1
Enhancement of dissolution and oral bioavailability of gliquidone with hydroxy propyl-beta-cyclodextrin.
2003 Nov
[Effect of liuwei dihuang pill on erythrocyte aldose reductase activity in early diabetic nephropathy patients].
2004 Dec
[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
Improvement of gliquidone hypoglycaemic effect in rats by cyclodextrin formulations.
2004 Sep
Effect of glurenorm on immunohistochemical changes in pancreatic beta cells of rats in experimental diabetes.
2005 Mar
Gliquidone contributes to improvement of type 2 diabetes mellitus management: a review of pharmacokinetic and clinical trial data.
2006
Sulfonylureas and glinides exhibit peroxisome proliferator-activated receptor gamma activity: a combined virtual screening and biological assay approach.
2007 Feb
Simultaneous assay of metformin and glibenclamide in human plasma based on extraction-less sample preparation procedure and LC/(APCI)MS.
2007 Jul 1
Development of a RP-HPLC method for screening potentially counterfeit anti-diabetic drugs.
2007 Jun 15
Bioavailability of the amino acid-attached prodrug as a new anti-HIV agent in rats.
2007 Sep
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
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 Dec 3
Twice daily fractionated dose administration of prednisolone compared to standard once daily administration to patients with glomerulonephritis or with kidney transplants.
2009 Jun 15
Determination of glycyrrhizin in dog plasma by liquid chromatography-mass spectrometry and its application in pharmacokinetic studies.
2010
Drug therapy in patients with chronic renal failure.
2010 Sep
Patents

Patents

20010036478
4
JP2003501350A
1

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 Sat Jun 26 08:53:18 UTC 2021
Edited
by admin
on Sat Jun 26 08:53:18 UTC 2021
Record UNII
C7C2QDD75P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLIQUIDONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ARDF 26
Code English
GLIQUIDONE [WHO-DD]
Common Name English
GLIQUIDONE [INN]
Common Name English
GLURENORM
Brand Name English
GLIQUIDONE [MART.]
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
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
WHO-VATC QA10BB08
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
NCI_THESAURUS C97936
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
Code System Code Type Description
PUBCHEM
91610
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
MERCK INDEX
M5748
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
251-463-2
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
EPA CompTox
33342-05-1
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
DRUG BANK
DB01251
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
CAS
33342-05-1
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
DRUG CENTRAL
1302
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
ChEMBL
CHEMBL383634
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
WIKIPEDIA
GLIQUIDONE
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
RXCUI
25793
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY RxNorm
FDA UNII
C7C2QDD75P
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
MESH
C010969
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
INN
3308
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
EVMPD
SUB07928MIG
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
NCI_THESAURUS
C72798
Created by admin on Sat Jun 26 08:53:18 UTC 2021 , Edited by admin on Sat Jun 26 08:53:18 UTC 2021
PRIMARY
Related Record Type Details
ATP-BINDING CASSETTE SUB-FAMILY C MEMBER 8
TARGET -> INHIBITOR
Related Record Type Details
Structure of GLIQUIDONE
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