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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 of GLIQUIDONE

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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Glurenorm

Approved Use

Used in the treatment of diabetes mellitus type 2.
PubMed

PubMed

TitleDatePubMed
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
Effect of pH and complexation on transdermal permeation of gliquidone.
2002 Sep
[Severe hypoglycemia in diabetics with impaired renal function].
2003 Feb 7
Protective effects of glurenorm (gliquidone) treatment on the liver injury of experimental diabetes.
2005
Gliquidone contributes to improvement of type 2 diabetes mellitus management: a review of pharmacokinetic and clinical trial data.
2006
Determination of glibenclamide in human plasma by liquid chromatography and atmospheric pressure chemical ionization/MS-MS detection.
2007 Feb 1
Gliquidone therapy of new-onset diabetes mellitus after kidney transplantation.
2008 Jul
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
Metformin, sulfonylureas, or other antidiabetes drugs and the risk of lactic acidosis or hypoglycemia: a nested case-control analysis.
2008 Nov
Glucose and pharmacological modulators of ATP-sensitive K+ channels control [Ca2+]c by different mechanisms in isolated mouse alpha-cells.
2009 Feb
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
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
In vitro inhibition of AKR1Cs by sulphonylureas and the structural basis.
2015 Oct 5
Patents

Sample Use Guides

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 Wed Jul 05 22:59:20 UTC 2023
Edited
by admin
on Wed Jul 05 22:59:20 UTC 2023
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 [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
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
WHO-VATC QA10BB08
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
NCI_THESAURUS C97936
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
Code System Code Type Description
PUBCHEM
91610
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
MERCK INDEX
M5748
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY Merck Index
SMS_ID
100000092780
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
251-463-2
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID4023096
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
DRUG BANK
DB01251
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
CAS
33342-05-1
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
DRUG CENTRAL
1302
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL383634
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
WIKIPEDIA
GLIQUIDONE
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
RXCUI
25793
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY RxNorm
FDA UNII
C7C2QDD75P
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
MESH
C010969
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
INN
3308
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
EVMPD
SUB07928MIG
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
NCI_THESAURUS
C72798
Created by admin on Wed Jul 05 22:59:20 UTC 2023 , Edited by admin on Wed Jul 05 22:59:20 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY