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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H25O6.Na
Molecular Weight 444.4522
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAVEGLITAZAR SODIUM

SMILES

[Na+].CO[C@@H](CC1=CC=C(OCCCOC2=CC=C(OC3=CC=CC=C3)C=C2)C=C1)C([O-])=O

InChI

InChIKey=QRZVPGNFLXIZON-JIDHJSLPSA-M
InChI=1S/C25H26O6.Na/c1-28-24(25(26)27)18-19-8-10-20(11-9-19)29-16-5-17-30-21-12-14-23(15-13-21)31-22-6-3-2-4-7-22;/h2-4,6-15,24H,5,16-18H2,1H3,(H,26,27);/q;+1/p-1/t24-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C25H25O6
Molecular Weight 421.4624
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Naveglitazar is an oral dual peroxisome proliferator-activated receptor (PPAR) agonist, which was under development with Ligand Pharmaceuticals for the treatment of type 2 diabetes mellitus. Naveglitazar is a nonthiozolidinedione peroxisome proliferator-activated receptor (PPAR) α-γ dual, γ-dominant agonist that has shown glucose-lowering potential in animal models and in the clinic. Naveglitazar had been in phase II clinical trials for the once-daily oral treatment of type 2 diabetes, however, the development was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.71 µM [IC50]
0.024 µM [IC50]
PubMed

PubMed

TitleDatePubMed
The disposition and metabolism of naveglitazar, a peroxisome proliferator-activated receptor alpha-gamma dual, gamma-dominant agonist in mice, rats, and monkeys.
2007 Jan
Rat Urinary Bladder Carcinogenesis by Dual-Acting PPARalpha + gamma Agonists.
2008
Cross-Species Differential Plasma Protein Binding of MBX-102/JNJ39659100: A Novel PPAR-gamma Agonist.
2008
Urothelial carcinogenesis in the urinary bladder of rats treated with naveglitazar, a gamma-dominant PPAR alpha/gamma agonist: lack of evidence for urolithiasis as an inciting event.
2008 Feb
Allometric prediction of the human pharmacokinetic parameters for naveglitazar.
2008 Jul-Sep
Neoplastic and non-neoplastic changes in F-344 rats treated with Naveglitazar, a gamma-dominant PPAR alpha/gamma agonist.
2009 Oct
Patents

Sample Use Guides

The carcinogenic potential of naveglitazar, a gamma-dominant peroxisome proliferator-activated receptor (PPAR) alpha/gamma dual agonist, was evaluated in a two-year study in F344 rats (0, 0.3, 1.0, or 3.0 mg/kg, males; 0, 0.1, 0.3, or 1.0 mg/kg, females). Rats were randomly assigned to treatment groups based on weight. Rats (60/sex/group) were assigned to groups receiving 0, 0.3, 1.0, or 3.0 mg naveglitazar/kg body weight/day (males) or 0, 0.1, 0.3, or 1.0 mg naveglitazar/kg body weight/day (females) by oral gavage.
Route of Administration: Oral
In vitro, naveglitazar binds selectively to PPAR g with high affinity (IC50 =0.024 uM, Ki = 0.022uM) and to PPAR a with lower affinity (IC50 =1.71 uM, Ki = 1.66 uM)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:25:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:25:41 GMT 2023
Record UNII
9EPC7SXH23
Record Status Validated (UNII)
Record Version
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Name Type Language
NAVEGLITAZAR SODIUM
Common Name English
LY-519818 SODIUM
Code English
BENZENEPROPANOIC ACID, .ALPHA.-METHOXY-4-(3-(4-PHENOXYPHENOXY)PROPOXY)-, SODIUM SALT (1:1), (.ALPHA.S)-
Systematic Name English
(2S)-2-METHOXY-3-(4-(3-(4-PHENOXYPHENOXY)PROPOXY)PHENYL)PROPANOATE SODIUM
Systematic Name English
Code System Code Type Description
CAS
477981-15-0
Created by admin on Fri Dec 15 15:25:41 GMT 2023 , Edited by admin on Fri Dec 15 15:25:41 GMT 2023
PRIMARY
PUBCHEM
58822574
Created by admin on Fri Dec 15 15:25:41 GMT 2023 , Edited by admin on Fri Dec 15 15:25:41 GMT 2023
PRIMARY
FDA UNII
9EPC7SXH23
Created by admin on Fri Dec 15 15:25:41 GMT 2023 , Edited by admin on Fri Dec 15 15:25:41 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE