Adezmapimod
CAT: 0804-HY-10256-07Size: 500 mgDry Ice: NoHazardous: No
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Description
Adezmapimod (SB 203580) is a selective and ATP-competitive p38 MAPK inhibitor with IC50s of 50 nM and 500 nM for SAPK2a/p38 and SAPK2b/p38β2, respectively. Adezmapimod inhibits LCK, GSK3β and PKBα with IC50s of 100-500-fold higher than that for SAPK2a/p38. Adezmapimod can inhibit p38 MAPK and lead to the inhibition of downstream HSP27 phosphorylation. Adezmapimod does not disrupt JNK activity and is an autophagy and mitophagy activator[1][2][3].
CAS Number
152121-47-6
Product Name Alternative
SB 203580; RWJ 64809
UNSPSC
12352005
Hazard Statement
H302, H319
Target
Autophagy; HSP; Mitophagy; Organoid; p38 MAPK
Type
Reference compound
Related Pathways
Autophagy; Cell Cycle/DNA Damage; MAPK/ERK Pathway; Metabolic Enzyme/Protease; Stem Cell/Wnt
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology; Cancer
Assay Protocol
https://www.medchemexpress.com/SB-203580.html
Purity
99.96
Solubility
DMSO : 20 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=S(C1=CC=C(C2=NC(C3=CC=C(F)C=C3)=C(C4=CC=NC=C4)N2)C=C1)C
Molecular Formula
C21H16FN3OS
Molecular Weight
377.43
Precautions
H302, H319
References & Citations
[1]Davies SP, et al. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J. 2000 Oct 1;351 (Pt 1) :95-105.|[2]Lali FV, et al. The pyridinyl imidazole inhibitor SB203580 blocks phosphoinositide-dependent protein kinase activity, protein kinase B phosphorylation, and retinoblastoma hyperphosphorylation in interleukin-2-stimulated T cells independently of p38 mitogen-activated protein kinase. J Biol Chem. 2000 Mar 10;275 (10) :7395-402.|[3]Leelahavanichkul K, et al. A role for p38 MAPK in head and neck cancer cell growth and tumor-induced angiogenesis and lymphangiogenesis. Mol Oncol. 2014 Feb;8 (1) :105-18.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
P38 MAPK; p38β
Citation 01
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Chemical Information
Sb-203580
SB 203580 is a member of the class of imidazoles carrying 4-methylsulfinylphenyl, 4-pyridyl and 4-fluorophenyl substituents at positions 2, 4 and 5 respectively. An inhibitor of mitogen-activated protein kinase. It has a role as a geroprotector, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a neuroprotective agent, a Hsp90 inhibitor and an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor. It is a sulfoxide, a member of imidazoles, a member of pyridines and a member of monofluorobenzenes.
| CAS Number | 152121-47-6 |
| PubChem CID | 176155 |
| IUPAC Name | 4-[4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine |
| Molecular Formula | C21H16FN3OS |
| Molecular Weight | 377.4 |
| XLogP | 3.2 |
| Topological Polar Surface Area | 77.9 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 500 |
SMILES
CS(=O)C1=CC=C(C=C1)C2=NC(=C(N2)C3=CC=NC=C3)C4=CC=C(C=C4)F
InChI
InChI=1S/C21H16FN3OS/c1-27(26)18-8-4-16(5-9-18)21-24-19(14-2-6-17(22)7-3-14)20(25-21)15-10-12-23-13-11-15/h2-13H,1H3,(H,24,25)
InChIKey
CDMGBJANTYXAIV-UHFFFAOYSA-N
Chemical Structure
2D Structure
CAS: 152121-47-6
CID: 176155
Formula: C21H16FN3OS
MW: 377.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
| Property | Value |
|---|---|
| Molecular Weight | 377.4 |
| XLogP3 | 3.2 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Exact Mass | 377.09981148 |
| Monoisotopic Mass | 377.09981148 |
| Topological Polar Surface Area | 77.9 Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 500 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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