Synonym
SB-203580 hydrochloride; SB-203580 HCl; SB-203580; RWJ-64809; RWJ 64809; RWJ64809; Adezmapimod; SB203850; SB-203850; SB 203850
IUPAC/Chemical Name
4-[4-(4-fluorophenyl)-2-[4-(methylsulfinyl)phenyl]-1H-imidazol-5-yl]-pyridine, monohydrochloride
InChi Key
WOSGGXINSLMASH-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H16FN3OS.ClH/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);1H
SMILES Code
O=S(C)C(C=C1)=CC=C1C(N2)=NC(C3=CC=NC=C3)=C2C4=CC=C(F)C=C4.Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
SB-203580 HCl is a selective and ATP-competitive p38 MAPK inhibitor with IC50s of 50 nM and 500 nM for SAPK2a/p38 and SAPK2b/p38β2, respectively. SB-203580 HC inhibits LCK, GSK3β and PKBα with IC50s of 100-500-fold higher than that for SAPK2a/p38.
In vitro activity:
In human lung adenocarcinoma (A549) cells, SB-203580 pretreatment enhanced resveratrol-induced apoptosis by accelerating the intrinsic apoptotic pathway, involving Bax activation, mitochondrial membrane potential loss, and activation of caspase-9 and -3. The combination of SB-203580 and resveratrol activated the extrinsic apoptotic pathway, marked by FasL cleavage and caspase-8 activation. This suggests a synergistic effect, providing a potential alternative therapeutic approach for human lung cancer.
Reference: J Biochem Mol Toxicol. 2012 Jul;26(7):251-7. https://pubmed.ncbi.nlm.nih.gov/22644961/
In vivo activity:
In a murine model of acute long injury, SB-203580 protected against inflammatory responses and lung injury by inhibiting lung edema and downregulating proinflammatory mediators in LPS‑induced lung injury.
Reference: Mol Med Rep. 2020 Aug;22(2):1656-1662. https://pubmed.ncbi.nlm.nih.gov/32626961/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
10.4 |
25.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
413.89
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Han X, Chen H, Zhou J, Steed H, Postovit LM, Fu Y. Pharmacological Inhibition of p38 MAPK by SB203580 Increases Resistance to Carboplatin in A2780cp Cells and Promotes Growth in Primary Ovarian Cancer Cells. Int J Mol Sci. 2018 Jul 26;19(8):2184. doi: 10.3390/ijms19082184. PMID: 30049957; PMCID: PMC6121386.
2. Li H, Wang X, Chen T, Qu J. p38 inhibitor SB203580 sensitizes the resveratrol-induced apoptosis in human lung adenocarcinoma (A549) cells. J Biochem Mol Toxicol. 2012 Jul;26(7):251-7. doi: 10.1002/jbt.21413. Epub 2012 May 29. PMID: 22644961.
3. Li G, Dai Y, Tan J, Zou J, Nie X, Yang Z, Zhao J, Yang X, Chen J. SB203580 protects against inflammatory response and lung injury in a mouse model of lipopolysaccharide‑induced acute lung injury. Mol Med Rep. 2020 Aug;22(2):1656-1662. doi: 10.3892/mmr.2020.11214. Epub 2020 Jun 4. PMID: 32626961.
4. Gao X, Li N, Zhang J. SB203580, a p38MAPK inhibitor, attenuates olfactory dysfunction by inhibiting OSN apoptosis in AR mice (activation and involvement of the p38 mitogen-activated protein kinase in olfactory sensory neuronal apoptosis of OVA-induced allergic rhinitis). Brain Behav. 2019 Jun;9(6):e01295. doi: 10.1002/brb3.1295. Epub 2019 Apr 30. PMID: 31041850; PMCID: PMC6577615.
In vitro protocol:
1. Han X, Chen H, Zhou J, Steed H, Postovit LM, Fu Y. Pharmacological Inhibition of p38 MAPK by SB203580 Increases Resistance to Carboplatin in A2780cp Cells and Promotes Growth in Primary Ovarian Cancer Cells. Int J Mol Sci. 2018 Jul 26;19(8):2184. doi: 10.3390/ijms19082184. PMID: 30049957; PMCID: PMC6121386.
2. Li H, Wang X, Chen T, Qu J. p38 inhibitor SB203580 sensitizes the resveratrol-induced apoptosis in human lung adenocarcinoma (A549) cells. J Biochem Mol Toxicol. 2012 Jul;26(7):251-7. doi: 10.1002/jbt.21413. Epub 2012 May 29. PMID: 22644961.
In vivo protocol:
1. Li G, Dai Y, Tan J, Zou J, Nie X, Yang Z, Zhao J, Yang X, Chen J. SB203580 protects against inflammatory response and lung injury in a mouse model of lipopolysaccharide‑induced acute lung injury. Mol Med Rep. 2020 Aug;22(2):1656-1662. doi: 10.3892/mmr.2020.11214. Epub 2020 Jun 4. PMID: 32626961.
2. Gao X, Li N, Zhang J. SB203580, a p38MAPK inhibitor, attenuates olfactory dysfunction by inhibiting OSN apoptosis in AR mice (activation and involvement of the p38 mitogen-activated protein kinase in olfactory sensory neuronal apoptosis of OVA-induced allergic rhinitis). Brain Behav. 2019 Jun;9(6):e01295. doi: 10.1002/brb3.1295. Epub 2019 Apr 30. PMID: 31041850; PMCID: PMC6577615.
1. Roux, P.P., and Blenis, J. ERK and p38 MAPK-activated protein kinases: A family of protein kinases with diverse biological functions. Microbiology and Molecular Biology Reviews 68(2), 320-344 (2004).
2. Cuenda, A., Rouse, J., Doza, Y.N., et al. SB 203580 is a specific inhibitor of a MAP kinase homologue which is stimulated by cellular stresses and interleukin-1. FEBS Letters 364, 229-233 (1995).
3. Lali, F.V., Hunt, A.E., Turner, S.J., 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. The Journal of Biological Chemisty 275(10), 7395-7402 (2008).
