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Details

Stereochemistry ACHIRAL
Molecular Formula C22H26FN3O2
Molecular Weight 383.4591
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOSMAPIMOD

SMILES

CC1=C(F)C=C(C=C1C2=CC=C(C=N2)C(=O)NCC(C)(C)C)C(=O)NC3CC3

InChI

InChIKey=KKYABQBFGDZVNQ-UHFFFAOYSA-N
InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)

HIDE SMILES / InChI

Description

Losmapimod (GW856553, GSK-AHAB) is a selective, potent, and orally active p38 MAPK (p38α and p38β isoforms) inhibitor that acts by competing for the kinase ATP binding site. GlaxoSmithKline (GSK) is developing oral losmapimod for the treatment of acute coronary syndromes (phase III), chronic obstructive pulmonary disease (phase II) and primary focal segmental glomerulosclerosis (phase II). Oral losmapimod was in phase II development for the treatment of rheumatoid arthritis and major depressive disorder; however, it appears that development for these indications has been discontinued. No further development was reported for atherosclerosis, dyslipidaemia and neuropathic pain.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
8.1 null [pKi]
7.6 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Oral losmapimod 2.5 - 20 mg twice daily. A single IV infusion of losmapimod (3 mg) may potentially serve as an initial loading dose in acute coronary syndrome as rapid exposure is achieved.
Route of Administration: Other
In Vitro Use Guide
0.1 and 1 nM Losmapimod (GW856553) synergistically increased the inhibitory effect of dexamethasone on LPS-induced CXCL8 release in peripheral blood mononuclear cells from patients with chronic obstructive pulmonary disease