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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=CC2=C(C=C1)C(NC(N)=O)=C(O2)C(=O)C3=CC=C(Cl)C=C3Cl

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Sample Use Guides

In Vivo Use Guide
Single dose 10 mg/kg
Route of Administration: Oral
Substance Class Chemical
Record UNII
GDK3KY5FCU
Record Status Validated (UNII)
Record Version