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Details

Stereochemistry RACEMIC
Molecular Formula C20H19N3O4S
Molecular Weight 397.4494
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIVOGLITAZONE

SMILES

Cn1c2cc(ccc2nc1COc3ccc(cc3)CC4C(=NC(=O)S4)O)OC

InChI

InChIKey=XMSXOLDPMGMWTH-UHFFFAOYSA-N
InChI=1S/C20H19N3O4S/c1-23-16-10-14(26-2)7-8-15(16)21-18(23)11-27-13-5-3-12(4-6-13)9-17-19(24)22-20(25)28-17/h3-8,10,17H,9,11H2,1-2H3,(H,22,24,25)

HIDE SMILES / InChI
Molecular Formula C20H19N3O4S
Molecular Weight 397.4494
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Rivoglitazone hydrochloride (CS-011) is a thiazolidinedione-derivative peroxisome proliferator–activated receptor (PPAR)-γ agonist. It has been developed as potential treatment in type 2 diabetes mellitus and was shown to decrease plasma glucose and triglyceride levels in a dose-dependent manner in animals. Phase II and III clinical studies have assessed the efficacy and safety of rivoglitazone hydrochloride in patients with type 2 diabetes mellitus.

Approval Year

Unknown
116683
PubMed

PubMed

TitleDatePubMed
Drug evaluation: rivoglitazone, a new oral therapy for the treatment of type 2 diabetes.
2007 Apr
A randomized-controlled trial to investigate the effects of rivoglitazone, a novel PPAR gamma agonist on glucose-lipid control in type 2 diabetes.
2011 Sep
Patents

Patents

05798375
2
05886014
4
06159997
3
06525220
2
06569877
2
06706746
2
06753347
2
07199139
2
07816552
2
08106079
2
JP2000001487A
2
JP2001039976A
2
JP2002220336A
2
JP2005145961A
2
JP2006182758A
2
JP2006193516A
2
JP2008162949A
2
JP2009221147A
2
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:04:50 UTC 2021
Edited
by admin
on Sat Jun 26 00:04:50 UTC 2021
Record UNII
3A3N0634Q6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIVOGLITAZONE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
R-106056
Code English
DE-101
Code English
5-(4-(6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YLMETHOXY)BENZYL)THIAZOLIDIN-2,4-DIONE
Systematic Name English
RIVOGLITAZONE [WHO-DD]
Common Name English
RIVOGLITAZONE [INN]
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)PHENYL)METHYL)-
Systematic Name English
RIVOGLITAZONE [USAN]
Common Name English
CS-011
Common Name English
(+/-)-5-(P-((6-METHOXY-1-METHYL-2-BENZIMIDAZOLYL)METHOXY)BENZYL)-2,4-THIAZOLIDINEDIONE
Common Name English
R 106056
Code English
Classification Tree Code System Code
NCI_THESAURUS C98241
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
Code System Code Type Description
EVMPD
SUB129557
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
WIKIPEDIA
RIVOGLITAZONE
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
MESH
C521549
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
CAS
185428-18-6
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
NCI_THESAURUS
C72841
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
DRUG BANK
DB09200
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
INN
8081
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
FDA UNII
3A3N0634Q6
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
PUBCHEM
3055168
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
ChEMBL
CHEMBL2104753
Created by admin on Sat Jun 26 00:04:51 UTC 2021 , Edited by admin on Sat Jun 26 00:04:51 UTC 2021
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A3
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR ALPHA
TARGET -> AGONIST
SELECTIVE
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B7
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A5
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Structure of RIVOGLITAZONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of O-DEMETHYL RIVOGLITAZONE
METABOLITE -> PARENT
IN VITRO
Structure of BENZENEPROPANAMIDE, .ALPHA.-HYDROXY-4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)-
METABOLITE -> PARENT
IN VITRO
Structure of 2,4-THIAZOLIDINEDIONE, 5-((4-((1-METHYL-6-(SULFOOXY)-1H-BENZIMIDAZOL-2-YL)METHOXY)PHENYL)METHYL)-
METABOLITE -> PARENT
IN VITRO
Structure of N-DEMETHYL RIVOGLITAZONE
METABOLITE -> PARENT
IN VITRO
Structure of 4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)-.ALPHA.-(METHYLTHIO)BENZENEPROPANAMIDE
METABOLITE -> PARENT
IN VITRO
Structure of .BETA.-D-GLUCOPYRANURONIC ACID, 1-DEOXY-1-(5-((4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)PHENYL)METHYL)-2,4-DIOXO-3-THIAZOLIDINYL)-
METABOLITE -> PARENT
IN VITRO
Structure of 2,4-THIAZOLIDINEDIONE, 5-HYDROXY-5-((4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)PHENYL)METHYL)-
METABOLITE -> PARENT
IN VITRO
Structure of .ALPHA.-(((2R)-2-AMINO-2-CARBOXYETHYL)DITHIO)-4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)BENZENEPROPANOIC ACID
METABOLITE -> PARENT
IN VITRO
Structure of 4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)-.ALPHA.-(METHYLSULFINYL)BENZENEPROPANAMIDE
METABOLITE -> PARENT
IN VITRO
Structure of .BETA.-D-GLUCOPYRANURONIC ACID, 1-((((1-CARBOXY-2-(4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)PHENYL)ETHYL)THIO)CARBONYL)AMINO)-1-DEOXY-
METABOLITE -> PARENT
IN VITRO
Structure of 4-((6-METHOXY-1-METHYL-1H-BENZIMIDAZOL-2-YL)METHOXY)-.ALPHA.-(METHYLSULFONYL)BENZENEPROPANAMIDE
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
Structure of RIVOGLITAZONE
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