U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H19Cl2NO3S
Molecular Weight 460.373
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TICOLUBANT

SMILES

OC(=O)\C=C\C1=NC(CSC2=C(Cl)C=CC=C2Cl)=CC=C1OCCC3=CC=CC=C3

InChI

InChIKey=ZJLFOOWTDISDIO-ZRDIBKRKSA-N
InChI=1S/C23H19Cl2NO3S/c24-18-7-4-8-19(25)23(18)30-15-17-9-11-21(20(26-17)10-12-22(27)28)29-14-13-16-5-2-1-3-6-16/h1-12H,13-15H2,(H,27,28)/b12-10+

HIDE SMILES / InChI
Ticolubant (also known as SB-209247) is a pyridine derivative patented by SmithKline Beckman Corp. as an anti-inflammatory leukotriene B4 receptor antagonist. Ticolubant displays high affinity for the human neutrophil LTB4 receptor, blocks LTB4-induced Ca2+ mobilization, and demonstrates potent oral and topical antiinflammatory activity in a murine model of dermal inflammation. However, Ticolubant did not show significant oral activity in a murine model of inflammation. Development of Ticolubant was discontinued when administration to beagle dogs for 28 days was associated with non-dose-dependant inflammatory hepatopathy, with minimal hepatocellular necrosis being observed in the more severe cases

Approval Year

PubMed

PubMed

TitleDatePubMed
Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): relation to species differences in hepatotoxicity.
2005 Feb
Patents

Patents

Sample Use Guides

dog 60 to 1000 mg/kg/day for 28 days.
Route of Administration: Oral
Name Type Language
TICOLUBANT
INN   USAN  
INN   USAN  
Official Name English
(E)-6-[[(2,6-Dichlorophenyl)thio]methyl]-3-(phenethyloxy)-2-pyridineacrylic acid
Systematic Name English
2-PROPENOIC ACID, 3-(6(((2,6-DICHLOROPHENYL)THIO)METHYL)-3-(2-PHENYLETHOXY)-2-PYRIDINYL)-, (E)-
Common Name English
SB-209247
Code English
ticolubant [INN]
Common Name English
TICOLUBANT [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C308
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C81669
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
CAS
154413-61-3
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
PUBCHEM
6441619
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL90214
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
FDA UNII
C1FRU4800P
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
INN
7570
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
SMS_ID
100000082187
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
MESH
C093304
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY
EVMPD
SUB11029MIG
Created by admin on Fri Dec 15 15:45:48 GMT 2023 , Edited by admin on Fri Dec 15 15:45:48 GMT 2023
PRIMARY