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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H26O6
Molecular Weight 422.4703
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAVEGLITAZAR

SMILES

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

InChI

InChIKey=OKJHGOPITGTTIM-DEOSSOPVSA-N
InChI=1S/C25H26O6/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)/t24-/m0/s1

HIDE SMILES / InChI
Molecular Formula C25H26O6
Molecular Weight 422.4703
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 1.71 µM [IC50]
Agonist
2752
 0.024 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Neoplastic and non-neoplastic changes in F-344 rats treated with Naveglitazar, a gamma-dominant PPAR alpha/gamma agonist.
2009-10
Allometric prediction of the human pharmacokinetic parameters for naveglitazar.
2008-11-15
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.
2008-02
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
The disposition and metabolism of naveglitazar, a peroxisome proliferator-activated receptor alpha-gamma dual, gamma-dominant agonist in mice, rats, and monkeys.
2007-01
Patents

Patents

20050020684
2
20060040999
3
20060069161
5
JP2006104199A
3

Sample Use Guides

In Vivo Use Guide
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 Use Guide
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 Mon Mar 31 18:24:45 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:45 GMT 2025
Record UNII
Y995M7GM0G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LY-519818
Preferred Name English
NAVEGLITAZAR
INN   USAN  
USAN   INN  
Official Name English
(2S)-2-Methoxy-3-[4-[3-(4-phenoxyphenoxy)propoxy]phenyl]propanoic acid
Systematic Name English
naveglitazar [INN]
Common Name English
BENZENEPROPANOIC ACID, .ALPHA.-METHOXY-4-(3-(4-PHENOXYPHENOXY)PROPOXY), (.ALPHA.S)
Common Name English
LY519818
Code English
LY9818
Code English
NAVEGLITAZAR [USAN]
Common Name English
LY-9818
Code English
Classification Tree Code System Code
NCI_THESAURUS C98233
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
Code System Code Type Description
PUBCHEM
9888484
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
MESH
C517861
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
ChEMBL
CHEMBL181954
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
NCI_THESAURUS
C75191
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
FDA UNII
Y995M7GM0G
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
INN
8472
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
USAN
PP-41
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID70870358
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
DRUG BANK
DB12662
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
CAS
476436-68-7
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
SMS_ID
300000034359
Created by admin on Mon Mar 31 18:24:45 GMT 2025 , Edited by admin on Mon Mar 31 18:24:45 GMT 2025
PRIMARY
Related Record Type Details
Structure of NAVEGLITAZAR SODIUM
SALT/SOLVATE -> PARENT
PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR ALPHA
TARGET -> AGONIST
PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR GAMMA
TARGET -> AGONIST
Related Record Type Details
Structure of NAVEGLITAZAR
ACTIVE MOIETY
NIH
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