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

Details

Stereochemistry ACHIRAL
Molecular Formula C17H12Cl2N2O6S
Molecular Weight 443.258
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIRIMILAST

SMILES

CS(=O)(=O)OC1=CC=C2C(OC(C(=O)C3=C(Cl)C=C(Cl)C=C3)=C2NC(N)=O)=C1

InChI

InChIKey=YPFLFUJKZDAXRA-UHFFFAOYSA-N
InChI=1S/C17H12Cl2N2O6S/c1-28(24,25)27-9-3-5-11-13(7-9)26-16(14(11)21-17(20)23)15(22)10-4-2-8(18)6-12(10)19/h2-7H,1H3,(H3,20,21,23)

HIDE SMILES / InChI

Molecular Formula C17H12Cl2N2O6S
Molecular Weight 443.258
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Lirimilast is representative of a new structural class of PDE4 inhibitors, the benzofurans. It it is highly selective type 4 cyclic nucleotide phosphodiesterase inhibitor. Lirimilast inhibited human inflammatory cell functions that previously were reported to be sensitive to PDE4 inhibitors. It showed some selectivity for neutrophil and eosinophil functions over those of monocytes and T lymphocytes when compared to cilomilast and other reference PDE4 inhibitors. Lirimilast exhibited a broad profile of anti-inflammatory activity in animal models of COPD and asthma. Lirimilast produced emesis in primates. 1 week of treatment with the selective PDE4 inhibitor lirimilast does not affect FEV1 and sputum cell numbers in patients with asthma or chronic obstructive pulmonary disease (COPD). However, such treatment does seem to reduce levels of albumin and eosinophil cationic protein in sputum samples obtained from patients with COPD.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Phosphodiesterase 4 inhibitors for the treatment of COPD.
2002 May
Efficacy of the novel phosphodiesterase-4 inhibitor BAY 19-8004 on lung function and airway inflammation in asthma and chronic obstructive pulmonary disease (COPD).
2003
Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking?
2008 Oct

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Guinea pig data
Single dose 10 mg/kg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:37:24 GMT 2023
Edited
by admin
on Fri Dec 15 16:37:24 GMT 2023
Record UNII
GDK3KY5FCU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIRIMILAST
INN   WHO-DD  
INN  
Official Name English
Lirimilast [WHO-DD]
Common Name English
2-(2,4-DICHLOROBENZOYL)-3-UREIDOBENZOFURAN-6-YL METHANESULPHONATE
Systematic Name English
2-(2,4-DICHLOROBENZOYL)-3-UREIDOBENZOFURAN-6-YL METHANESULFONATE
Systematic Name English
lirimilast [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
Code System Code Type Description
CAS
329306-27-6
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
INN
8091
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
FDA UNII
GDK3KY5FCU
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL1922282
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
NCI_THESAURUS
C82304
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID70186582
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
PUBCHEM
6433118
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
SMS_ID
300000036970
Created by admin on Fri Dec 15 16:37:24 GMT 2023 , Edited by admin on Fri Dec 15 16:37:24 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY