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Details

Stereochemistry ACHIRAL
Molecular Formula C19H15ClN2O4S2
Molecular Weight 434.916
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LANIFIBRANOR

SMILES

OC(=O)CCCC1=CC2=CC(Cl)=CC=C2N1S(=O)(=O)C3=CC4=C(C=C3)N=CS4

InChI

InChIKey=OQDQIFQRNZIEEJ-UHFFFAOYSA-N
InChI=1S/C19H15ClN2O4S2/c20-13-4-7-17-12(8-13)9-14(2-1-3-19(23)24)22(17)28(25,26)15-5-6-16-18(10-15)27-11-21-16/h4-11H,1-3H2,(H,23,24)

HIDE SMILES / InChI

Molecular Formula C19H15ClN2O4S2
Molecular Weight 434.916
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

IVA-337 (LANIFIBRANOR), an indole sulfonamide derivative, is a pan peroxisome proliferator-activated receptor (PPAR) agonist. It is under investigation in Phase 2 clinical trials for non-alcoholic steatohepatitis, non-alcoholic fatty liver disease, and type 2 diabetes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q07869
Gene ID: 5465.0
Gene Symbol: PPARA
Target Organism: Homo sapiens (Human)
Target ID: Q03181|||Q9BUD4
Gene ID: 5467.0
Gene Symbol: PPARD
Target Organism: Homo sapiens (Human)
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Pan-PPAR agonist IVA337 is effective in experimental lung fibrosis and pulmonary hypertension.
2017 Nov
Design, Synthesis, and Evaluation of a Novel Series of Indole Sulfonamide Peroxisome Proliferator Activated Receptor (PPAR) α/γ/δ Triple Activators: Discovery of Lanifibranor, a New Antifibrotic Clinical Candidate.
2018 Mar 22

Sample Use Guides

800 mg/day.
Route of Administration: Oral
LANIFIBRANOR (IVA-337) is a pan peroxisome proliferator-activated receptor (PPAR) agonist with EC50s of 1.5, 0.87 and 0.21 uM for human PPARa, PPARb and PPARg, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 12:04:13 UTC 2023
Edited
by admin
on Sat Dec 16 12:04:13 UTC 2023
Record UNII
28Q8AG0PYL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LANIFIBRANOR
INN  
INN  
Official Name English
Lanifibranor [WHO-DD]
Common Name English
lanifibranor [INN]
Common Name English
1H-INDOLE-2-BUTANOIC ACID, 1-(6-BENZOTHIAZOLYLSULFONYL)-5-CHLORO-
Systematic Name English
IVA-337
Code English
5-CHLORO-1-((6-BENZOTHIAZOLYL)SULFONYL)-1H-INDOLE-2-BUTANOIC ACID
Systematic Name English
4-(1-(1,3-BENZOTHIAZOL-6-YLSULFONYL)-5-CHLORO-INDOL-2-YL)BUTANOIC ACID
Systematic Name English
IVA337
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 470315
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
EU-Orphan Drug EU/3/14/1361
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
Code System Code Type Description
DRUG BANK
DB14801
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
FDA UNII
28Q8AG0PYL
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
EVMPD
SUB184623
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
EU-Orphan Drug
EU/3/14/1362(POSITIVE)
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY On 19 November 2014, orphan designation (EU/3/14/1362) was granted by the European Commission to Inventiva, France, for 1-(6-benzothiazolylsulfonyl)-5-chloro-1H-indole-2-butanoic acid for the treatment of idiopathic pulmonary fibrosis.
NCI_THESAURUS
C166556
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
INN
10474
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
PUBCHEM
68677842
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
CAS
927961-18-0
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
SMS_ID
100000170566
Created by admin on Sat Dec 16 12:04:13 UTC 2023 , Edited by admin on Sat Dec 16 12:04:13 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
TARGET -> AGONIST
AGONIST
EC50
TARGET -> AGONIST
AGONIST
EC50
Related Record Type Details
ACTIVE MOIETY
RESULTS: In mice, IVA337 was associated with decreased extracellular matrix (ECM) deposition and reduced expression of phosphorylated SMAD2/3-intracellular effector of transforming growth factor (TGF)-.BETA.1. Although the antifibrotic effect of pan PPAR was similar to that of PPAR.GAMMA. agonist alone, a significant downregulation of several markers of inflammation was associated with IVA337. Despite its anti-inflammatory and antifibrotic properties, IVA337 did not interfere with wound closure. In vitro effects of IVA337 included attenuation of transcription of ECM genes and alteration of canonical and non-canonical TGF-.BETA. signalling pathways. CONCLUSIONS: These findings indicate that simultaneous activation of all three PPAR isoforms exerts a dampening effect on inflammation and fibrosis, making IVA337 a potentially effective therapeutic candidate in the treatment of fibrotic diseases including SSc.