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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

Molecular Formula C22H26FN3O2
Molecular Weight 383.4591
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19556450

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL

Sample Use Guides

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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:23 UTC 2023
Edited
by admin
on Fri Dec 15 16:13:23 UTC 2023
Record UNII
F2DQF16BXE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOSMAPIMOD
INN   USAN  
USAN   INN  
Official Name English
GW-856553X
Code English
GSKAHAB
Code English
GW856553X
Code English
FTX1821
Code English
LOSMAPIMOD [USAN]
Common Name English
Losmapimod [WHO-DD]
Common Name English
6-(5-((CYCLOPROPYLAMINO)CARBONYL)-3-FLUORO-2-METHYLPHENYL)-N-(2,2-DIMETHYLPROPYL)-3-PYRIDINECARBOXAMIDE
Systematic Name English
3-PYRIDINECARBOXAMIDE, 6-(5-((CYCLOPROPYLAMINO)CARBONYL)-3-FLUORO-2-METHYLPHENYL)-N-(2,2-DIMETHYLPROPYL)-
Systematic Name English
FTX-1821
Code English
losmapimod [INN]
Common Name English
GW856553
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2149
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
FDA ORPHAN DRUG 721919
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
Code System Code Type Description
PUBCHEM
11552706
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
NCI_THESAURUS
C96532
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
CAS
585543-15-3
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
FDA UNII
F2DQF16BXE
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL1088752
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
DRUG BANK
DB12270
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID30974109
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
INN
9118
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
WIKIPEDIA
LOSMAPIMOD
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
SMS_ID
100000175049
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
USAN
UU-47
Created by admin on Fri Dec 15 16:13:23 UTC 2023 , Edited by admin on Fri Dec 15 16:13:23 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY