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Adezmapimod

CAT: 0804-HY-10256-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-10256-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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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 Number152121-47-6
PubChem CID176155
IUPAC Name4-[4-(4-fluorophenyl)-2-(4-methylsulfinylphenyl)-1H-imidazol-5-yl]pyridine
Molecular FormulaC21H16FN3OS
Molecular Weight377.4
XLogP3.2
Topological Polar Surface Area77.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Heavy Atom Count27
Formal Charge0
Complexity500
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
2D structure of Sb-203580
CAS: 152121-47-6
CID: 176155
Formula: C21H16FN3OS
MW: 377.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight377.4
XLogP33.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass377.09981148
Monoisotopic Mass377.09981148
Topological Polar Surface Area77.9 Ų
Heavy Atom Count27
Formal Charge0
Complexity500
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
BUP20653-01Adezmapimod
C16092-100mgAdezmapimod (SB203580)
E4791-100mgAdezmapimod hydrochloride
A10824-500Adezmapimod (SB-203580) 500mg
A10824-50Adezmapimod (SB-203580) 50mg

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