PF-3644022
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MedKoo CAT#: 532465

CAS#: 1276121-88-0

Description: PF-3644022 is a potent, ATP-competitive inhibitor of mitogen-activated protein kinase (MAPK)-activated protein kinase-2 (MK2) (IC50 = 5.2 nM; Ki = 3 nM). PF-3644022 inhibits tumor necrosis factor α (TNFα) production in U937 monocytic cells and peripheral blood mononuclear cells (PBMCs) (IC50 = 160 nM).

Chemical Structure

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PF-3644022
CAS# 1276121-88-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 532465
Name: PF-3644022
CAS#: 1276121-88-0
Chemical Formula: C21H18N4OS
Exact Mass: 374.12
Molecular Weight: 374.462
Elemental Analysis: C, 67.36; H, 4.85; N, 14.96; O, 4.27; S, 8.56

Price and Availability

Size Price Availability Quantity
5mg USD 250 2 Weeks
10mg USD 450 2 Weeks
50mg USD 1150 2 Weeks
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Synonym: PF-3644022; PF 3644022; PF3644022.

IUPAC/Chemical Name: (15R)-15-methyl-5-(6-methylpyridin-3-yl)-11-thia-6,14,17-triazatetracyclo[8.8.0.0^{2,7}.0^{12,18}]octadeca-1(10),2,4,6,8,12(18)-hexaen-13-one

InChi Key: CMWRPDHVGMHLSZ-GFCCVEGCSA-N

InChi Code: InChI=1S/C21H18N4OS/c1-11-3-4-13(10-22-11)15-6-5-14-16(25-15)7-8-17-18(14)19-20(27-17)21(26)24-12(2)9-23-19/h3-8,10,12,23H,9H2,1-2H3,(H,24,26)/t12-/m1/s1

SMILES Code: O=C1C2=C(C3=C(S2)C=CC4=NC(C5=CC=C(C)N=C5)=CC=C34)NC[C@@H](C)N1

Appearance: Solid powder

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: >2 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

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: PF-3644022 is a potent, selective, orally active and ATP-competitive MAPKAPK2 (MK2) inhibitor with an IC50 of 5.2 nM and a Ki of 3 nM.
In vitro activity: PF-3644022 is a potent freely reversible ATP-competitive compound that inhibits MK2 activity (K(i) = 3 nM) with good selectivity when profiled against 200 human kinases. In the human U937 monocytic cell line or peripheral blood mononuclear cells, PF-3644022 potently inhibits TNFalpha production with similar activity (IC(50) = 160 nM). PF-3644022 blocks TNFalpha and IL-6 production in LPS-stimulated human whole blood with IC(50) values of 1.6 and 10.3 microM, respectively. Inhibition of TNFalpha in U937 cells and blood correlates closely with inhibition of phospho-heat shock protein 27, a target biomarker of MK2 activity. Reference: J Pharmacol Exp Ther. 2010 Jun;333(3):797-807. https://pubmed.ncbi.nlm.nih.gov/20237073/
In vivo activity: Western blot and Real-time PCR showed that the expressions of iNOS and Arg-1 in the compressed spinal cord of twy/twy mice were significantly higher than those of the control group. After treatment with PF-3644022, the expression of Arg1 was increased while that of iNOS decreased. Realtime PCR revealed the increased expressions of inflammation related factors (such as IL-1β, NF-κB, TNF-α, MK2) and pro-apoptotic gene (Bax) except the decreased expression of anti-apoptotic gene (Bcl-2). Nevertheless, such increases were vanished after treatment of PF-3644022 except an increased expression of Bcl-2. The BMS score showed a reduced motor function of the twy/twy mice. The motor function was enhanced again with the treatment of PF-3644022. Reference: Ann Palliat Med. 2021 Feb;10(2):1304-1312. https://pubmed.ncbi.nlm.nih.gov/33040559/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.9 117.19

Preparing Stock Solutions

The following data is based on the product molecular weight 374.46 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.

Recalculate based on batch purity %
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. Mourey RJ, Burnette BL, Brustkern SJ, Daniels JS, Hirsch JL, Hood WF, Meyers MJ, Mnich SJ, Pierce BS, Saabye MJ, Schindler JF, South SA, Webb EG, Zhang J, Anderson DR. A benzothiophene inhibitor of mitogen-activated protein kinase-activated protein kinase 2 inhibits tumor necrosis factor alpha production and has oral anti-inflammatory efficacy in acute and chronic models of inflammation. J Pharmacol Exp Ther. 2010 Jun;333(3):797-807. doi: 10.1124/jpet.110.166173. Epub 2010 Mar 17. PMID: 20237073. 2. Yu L, Song H, Fang X, Hu Y. Role of MK2 signaling pathway mediating microglia/macrophages polarization in chronic compression injury of cervical spinal cord. Ann Palliat Med. 2021 Feb;10(2):1304-1312. doi: 10.21037/apm-20-396. Epub 2020 Sep 24. PMID: 33040559. 3. Song H, Fang X, Wen M, Yu F, Gao K, Sun C, Wang Z. Role of MK2 signaling pathway in the chronic compression of cervical spinal cord. Am J Transl Res. 2015 Nov 15;7(11):2355-63. PMID: 26807183; PMCID: PMC4697715.
In vitro protocol: 1. Mourey RJ, Burnette BL, Brustkern SJ, Daniels JS, Hirsch JL, Hood WF, Meyers MJ, Mnich SJ, Pierce BS, Saabye MJ, Schindler JF, South SA, Webb EG, Zhang J, Anderson DR. A benzothiophene inhibitor of mitogen-activated protein kinase-activated protein kinase 2 inhibits tumor necrosis factor alpha production and has oral anti-inflammatory efficacy in acute and chronic models of inflammation. J Pharmacol Exp Ther. 2010 Jun;333(3):797-807. doi: 10.1124/jpet.110.166173. Epub 2010 Mar 17. PMID: 20237073.
In vivo protocol: 1. Yu L, Song H, Fang X, Hu Y. Role of MK2 signaling pathway mediating microglia/macrophages polarization in chronic compression injury of cervical spinal cord. Ann Palliat Med. 2021 Feb;10(2):1304-1312. doi: 10.21037/apm-20-396. Epub 2020 Sep 24. PMID: 33040559. 2. Song H, Fang X, Wen M, Yu F, Gao K, Sun C, Wang Z. Role of MK2 signaling pathway in the chronic compression of cervical spinal cord. Am J Transl Res. 2015 Nov 15;7(11):2355-63. PMID: 26807183; PMCID: PMC4697715.

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1: Song H, Fang X, Wen M, Yu F, Gao K, Sun C, Wang Z. Role of MK2 signaling pathway in the chronic compression of cervical spinal cord. Am J Transl Res. 2015 Nov 15;7(11):2355-63. eCollection 2015. PubMed PMID: 26807183; PubMed Central PMCID: PMC4697715.

2: Mourey RJ, Burnette BL, Brustkern SJ, Daniels JS, Hirsch JL, Hood WF, Meyers MJ, Mnich SJ, Pierce BS, Saabye MJ, Schindler JF, South SA, Webb EG, Zhang J, Anderson DR. A benzothiophene inhibitor of mitogen-activated protein kinase-activated protein kinase 2 inhibits tumor necrosis factor alpha production and has oral anti-inflammatory efficacy in acute and chronic models of inflammation. J Pharmacol Exp Ther. 2010 Jun;333(3):797-807. doi: 10.1124/jpet.110.166173. Epub 2010 Mar 17. PubMed PMID: 20237073.