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Details

Stereochemistry ACHIRAL
Molecular Formula C19H18N2O4S
Molecular Weight 370.422
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TETOMILAST

SMILES

CCOC1=CC=C(C=C1OCC)C2=NC(=CS2)C3=NC(=CC=C3)C(O)=O

InChI

InChIKey=XDBHURGONHZNJF-UHFFFAOYSA-N
InChI=1S/C19H18N2O4S/c1-3-24-16-9-8-12(10-17(16)25-4-2)18-21-15(11-26-18)13-6-5-7-14(20-13)19(22)23/h5-11H,3-4H2,1-2H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C19H18N2O4S
Molecular Weight 370.422
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Otsuka Pharmaceutical Co developed tetomilast, a thiazole derivative for the treatment of inflammatory bowel disease and chronic obstructive pulmonary disease. Tetomilast acts as a selective inhibitor of phosphodiesterase-4 results in increased intracellular levels of cyclic adenosine monophosphate (cAMP), and subsequent anti-inflammatory effects. Specifically, the release of pro-inflammatory mediators including TNF-a and IL-12 is suppressed, and there is stimulation of the release of anti-inflammatory mediators including IL-10 and prostaglandin E2. Unfortunately, tetomilast clinical trials in patients with ulcerative colitis failed to demonstrate superior efficacy compared to mesalamine and further development of tetomilast was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
OPC-6535, a superoxide anion production inhibitor, attenuates acute lung injury.
1997 Sep
OPC-compounds prevent oxidant-induced carbonylation and depolymerization of the F-actin cytoskeleton and intestinal barrier hyperpermeability.
2001 Feb 1
A practical synthesis of 3,4-diethoxybenzthioamide based on Friedel-Crafts reaction with potassium thiocyanate in methanesulfonic acid.
2002 Sep 2
Effects of OPC-6535 on lipopolysaccharide-induced acute liver injury in the rat: involvement of superoxide and tumor necrosis factor-alpha from hepatic macrophages.
2003 Nov
Gateways to clinical trials.
2004 Dec
Medical therapy for ulcerative colitis: the state of the art and beyond.
2004 Dec
Digestive Disease Week 2004. Bowel inflammation.
2004 Jun
Tetomilast.
2005 Jun
A randomized, placebo-controlled, phase II study of tetomilast in active ulcerative colitis.
2007 Jan
Gateways to clinical trials.
2007 Sep
Tetomilast suppressed production of proinflammatory cytokines from human monocytes and ameliorated chronic colitis in IL-10-deficient mice.
2008 Nov
Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking?
2008 Oct
Phosphodiesterase 4 inhibitors in inflammatory bowel disease: a comprehensive review.
2010
Tetomilast: new promise for phosphodiesterase-4 inhibitors?
2012 Dec
Patents

Sample Use Guides

50 mg/day for 8 weeks
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:52:34 UTC 2023
Edited
by admin
on Fri Dec 15 16:52:34 UTC 2023
Record UNII
S6RXB5KF56
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TETOMILAST
INN   WHO-DD  
INN  
Official Name English
tetomilast [INN]
Common Name English
6-(2-(3,4-DIETHOXYPHENYL)-1,3-THIAZOL-4-YL)PYRIDINE-2-CARBOXYLIC ACID
Systematic Name English
OPC-6535
Code English
2-PYRIDINECARBOXYLIC ACID, 6-(2-(3,4-DIETHOXYPHENYL)-4-THIAZOLYL)-
Common Name English
Tetomilast [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
Code System Code Type Description
SMS_ID
300000034425
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
PUBCHEM
3025803
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL332750
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
NCI_THESAURUS
C90922
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID00163149
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
MESH
C108965
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
CAS
145739-56-6
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
FDA UNII
S6RXB5KF56
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
DRUG BANK
DB05298
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
INN
8430
Created by admin on Fri Dec 15 16:52:34 UTC 2023 , Edited by admin on Fri Dec 15 16:52:34 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY