C16 (drug)

C16 (drug)

Identifiers
IUPAC name 6,8-Dihydro-8-(1H-imidazol-5-ylmethylene)-7H-pyrrolo[2,3-g]benzothiazol-7-one
CAS Number	608512-97-6
PubChem (CID)	6490494
ChemSpider	4990932
ECHA InfoCard	100.211.648
Chemical and physical data
Formula	C13H8N4OS
Molar mass	268.293 g/mol
3D model (Jmol)	Interactive image
SMILES c4ncnc4\C=C3\c2c1scnc1ccc2NC3=O O=C\1Nc4c(C/1=C\c2cncn2)c3scnc3cc4
InChI InChI=1S/C13H8N4OS/c18-13-8(3-7-4-14-5-15-7)11-9(17-13)1-2-10-12(11)19-6-16-10/h1-6H,(H,14,15)(H,17,18)/b8-3- Key:VFBGXTUGODTSPK-BAQGIRSFSA-N

C16 or PKRi is a drug which acts as a selective inhibitor of the enzyme double-stranded RNA-dependent protein kinase (PKR). It has been shown to effectively inhibit PKR function in vivo and has neuroprotective and nootropic effects in animal studies.^{[1][2][3][4][5][6]}

See also

• S-17092

References

1. Jammi NV, Whitby LR, Beal PA. Small molecule inhibitors of the RNA-dependent protein kinase. Biochemical and Biophysical Research Communications. 2003 Aug 15;308(1):50-7. PMID 12890478
2. Shimazawa M, Hara H. Inhibitor of double stranded RNA-dependent protein kinase protects against cell damage induced by ER stress. Neuroscience Letters. 2006 Dec 6;409(3):192-5. PMID 17055645
3. Ingrand, S.; Barrier, L.; Lafay-Chebassier, C.; Fauconneau, B.; Page, G. N.; Hugon, J. (2007). "The oxindole/imidazole derivative C16 reduces in vivo brain PKR activation". FEBS Letters. 581 (23): 4473–4478. doi:10.1016/j.febslet.2007.08.022. PMID 17761171.
4. Chen, H. M.; Wang, L.; d'Mello, S. R. (2008). "A chemical compound commonly used to inhibit PKR, {8-(imidazol-4-ylmethylene)-6H-azolidino[5,4-g] benzothiazol-7-one}, protects neurons by inhibiting cyclin-dependent kinase". European Journal of Neuroscience. 28 (10): 2003–2016. doi:10.1111/j.1460-9568.2008.06491.x. PMC 3320856. PMID 19046382.
5. Couturier J, Morel M, Pontcharraud R, Gontier V, Fauconneau B, Paccalin M, Page G. Interaction of double-stranded RNA-dependent protein kinase (PKR) with the death receptor signaling pathway in amyloid beta (Abeta)-treated cells and in APPSLPS1 knock-in mice. Journal of Biological Chemistry. 2010 Jan 8;285(2):1272-82. PMID 19889624
6. Zhu PJ, Huang W, Kalikulov D, Yoo JW, Placzek AN, Stoica L, Zhou H, Bell JC, Friedlander MJ, Krnjevic K, Noebels JL, Costa-Mattioli M (2011). "Suppression of PKR Promotes Network Excitability and Enhanced Cognition by Interferon-γ-Mediated Disinhibition". Cell. 147 (6): 1384–1396. doi:10.1016/j.cell.2011.11.029. PMC 3569515. PMID 22153080.