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Losmapimod (Standard)

CAT: 0804-HY-10402R-02Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-10402R-02Size:10 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Losmapimod (Standard) is the analytical standard of Losmapimod. This product is intended for research and analytical applications. Losmapimod (GSK-AHAB) is a selective, potent, and orally active p38 MAPK inhibitor with pKis of 8.1 and 7.6 for p38α and p38β, respectively[1].
CAS Number
585543-15-3
Product Name Alternative
GSK-AHAB (Standard) ; GW856553X (Standard) ; SB856553 (Standard)
UNSPSC
12352005
Target
Autophagy; p38 MAPK; Reference Standards
Related Pathways
Autophagy; MAPK/ERK Pathway; Others
Field of Research
Inflammation/Immunology; Cancer
Smiles
CC1=C(C2=NC=C(C(NCC(C)(C)C)=O)C=C2)C=C(C(NC3CC3)=O)C=C1F
Molecular Formula
C22H26FN3O2
Molecular Weight
383.46
References & Citations
[1]Willette RN, et al. Differential effects of p38 mitogen-activated protein kinase and cyclooxygenase 2 inhibitors in a model of cardiovascular disease. J Pharmacol Exp Ther. 2009 Sep;330 (3) :964-70.|[2]Zhang XM, et al. Suppression of mitochondrial fission in experimental cerebral ischemia: The potential neuroprotective target of p38 MAPK inhibition. Neurochem Int. 2015 Nov;90:1-8.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Losmapimod

Losmapimod is a secondary carboxamide resulting from the formal condensation of the carboxy group of 6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]pyridine-3-carboxylic acid with the amino group of neopentylamine. It is a potent p38alpha/beta mitogen activated protein kinase inhibitor which was previously in clinical trials for the treatment of facioscapulohumeral muscular dystrophy trial now discontinued due to not achieving its primary endpoint. It has a role as a nootropic agent, an anti-inflammatory agent, a cardioprotective agent and an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor. It is a secondary carboxamide, a member of benzamides, a pyridinecarboxamide, a member of toluenes, a phenylpyridine, a member of cyclopropanes and a member of monofluorobenzenes.

CAS Number585543-15-3
PubChem CID11552706
IUPAC Name6-[5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl]-N-(2,2-dimethylpropyl)pyridine-3-carboxamide
Molecular FormulaC22H26FN3O2
Molecular Weight383.5
XLogP3.8
Topological Polar Surface Area71.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Heavy Atom Count28
Formal Charge0
Complexity573
SMILES
CC1=C(C=C(C=C1F)C(=O)NC2CC2)C3=NC=C(C=C3)C(=O)NCC(C)(C)C
InChI
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)
InChIKey
KKYABQBFGDZVNQ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Losmapimod
CAS: 585543-15-3
CID: 11552706
Formula: C22H26FN3O2
MW: 383.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight383.5
XLogP33.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass383.20090524
Monoisotopic Mass383.20090524
Topological Polar Surface Area71.1 Ų
Heavy Atom Count28
Formal Charge0
Complexity573
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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