Crebinostat

Crebinostat
Clinical data
Drug class	Histone deacetylase inhibitor; Cognitive enhancer
ATC code	None;
Identifiers
	IUPAC name N'-hydroxy-N-[(E)-(4-phenylphenyl)methylideneamino]heptanediamide;
PubChem CID	25118059;
ChemSpider	58863792;
ChEBI	CHEBI:125541;
ChEMBL	ChEMBL3759982;
Chemical and physical data
Formula	C20H23N3O3
Molar mass	353.422 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C2=CC=C(C=C2)/C=N/NC(=O)CCCCCC(=O)NO;
	InChI InChI=1S/C20H23N3O3/c24-19(9-5-2-6-10-20(25)23-26)22-21-15-16-11-13-18(14-12-16)17-7-3-1-4-8-17/h1,3-4,7-8,11-15,26H,2,5-6,9-10H2,(H,22,24)(H,23,25)/b21-15+; Key:AEIVDBATQVVQFS-RCCKNPSSSA-N;

Crebinostat is a histone deacetylase (HDAC) inhibitor and possible cognitive enhancer.^[1]^[2]^[3]

It specifically inhibits the class I HDAC1, HDAC2, and HDAC3, the class IIb HDAC6, and weakly the class I HDAC8, with no significant inhibition of the class IIa HDAC4, HDAC5, HDAC7, or HDAC9.^[1] The drug has been found to robustly activate CREB-mediated transcription and to upregulate brain-derived neurotrophic factor (BDNF) expression and increase synaptogenesis.^[1] It has been found to enhance memory in rodents.^[1]^[3] The pharmacokinetics of crebinostat have been studied in rodents.^[1]

Crebinostat was first described in the scientific literature by 2013.^[1] It was identified via screening of a library of over 1,200 compounds designed to target HDACs.^[1] There is interest in crebinostat as a potential novel cognitive enhancer in humans.^[1]^[2] Subsequent to the development of crebinostat, an analogue known as neurinostat with improved properties was discovered and described.^[2]

References

1 2 3 4 5 6 7 8 Fass DM, Reis SA, Ghosh B, Hennig KM, Joseph NF, Zhao WN, Nieland TJ, Guan JS, Kuhnle CE, Tang W, Barker DD, Mazitschek R, Schreiber SL, Tsai LH, Haggarty SJ (January 2013). "Crebinostat: a novel cognitive enhancer that inhibits histone deacetylase activity and modulates chromatin-mediated neuroplasticity". Neuropharmacology. 64: 81–96. doi:10.1016/j.neuropharm.2012.06.043. PMC 3447535. PMID 22771460.
1 2 3 Ghosh B, Zhao WN, Reis SA, Patnaik D, Fass DM, Tsai LH, Mazitschek R, Haggarty SJ (February 2016). "Dissecting structure-activity-relationships of crebinostat: Brain penetrant HDAC inhibitors for neuroepigenetic regulation". Bioorg Med Chem Lett. 26 (4): 1265–1271. doi:10.1016/j.bmcl.2016.01.022. PMC 4753070. PMID 26804233.
1 2 Dama D, Sharma SK (May 2024). "Crebinostat facilitates memory formation". Biochem Biophys Res Commun. 710: 149872. doi:10.1016/j.bbrc.2024.149872. PMID 38593621.{{cite journal}}: CS1 maint: article number as page number (link)

[FassReisGhosh2013-1] 1 2 3 4 5 6 7 8 Fass DM, Reis SA, Ghosh B, Hennig KM, Joseph NF, Zhao WN, Nieland TJ, Guan JS, Kuhnle CE, Tang W, Barker DD, Mazitschek R, Schreiber SL, Tsai LH, Haggarty SJ (January 2013). "Crebinostat: a novel cognitive enhancer that inhibits histone deacetylase activity and modulates chromatin-mediated neuroplasticity". Neuropharmacology. 64: 81–96. doi:10.1016/j.neuropharm.2012.06.043. PMC 3447535. PMID 22771460.

[GhoshZhaoReis2016-2] 1 2 3 Ghosh B, Zhao WN, Reis SA, Patnaik D, Fass DM, Tsai LH, Mazitschek R, Haggarty SJ (February 2016). "Dissecting structure-activity-relationships of crebinostat: Brain penetrant HDAC inhibitors for neuroepigenetic regulation". Bioorg Med Chem Lett. 26 (4): 1265–1271. doi:10.1016/j.bmcl.2016.01.022. PMC 4753070. PMID 26804233.

[DamaSharma2024-3] 1 2 Dama D, Sharma SK (May 2024). "Crebinostat facilitates memory formation". Biochem Biophys Res Commun. 710: 149872. doi:10.1016/j.bbrc.2024.149872. PMID 38593621.{{cite journal}}: CS1 maint: article number as page number (link)

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[2]

[3]

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Crebinostat

See also

References