PF-4800567

PF-4800567
Identifiers
	IUPAC name 3-(3-chloro-phenoxymethyl)-1-(tetrahydro-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine;
CAS Number	1188296-52-7;
PubChem CID	53472153;
IUPHAR/BPS	8050;
ChemSpider	26325201;
ChEBI	CHEBI:87237;
CompTox Dashboard (EPA)	DTXSID20703849 ;
Chemical and physical data
Formula	C17H18ClN5O2
Molar mass	359.81 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c4c(Cl)cccc4OCc(c1c3N)nn(c1ncn3)C2CCOCC2;
	InChI InChI=1S/C17H18ClN5O2/c18-11-2-1-3-13(8-11)25-9-14-15-16(19)20-10-21-17(15)23(22-14)12-4-6-24-7-5-12/h1-3,8,10,12H,4-7,9H2,(H2,19,20,21); Key:AUMDBEHGJRZSOO-UHFFFAOYSA-N;

PF-4800567 is a drug developed by Pfizer which acts as a selective inhibitor of the enzyme Casein kinase 1 epsilon (CK1-ε), and has mainly been used in the study of the casein kinase 1 enzymes in the regulation of circadian rhythm,^[1]^[2] as well as showing potential neuroprotective effects.^[3] While this research has shown that circadian rhythm is modulated primarily by the alternate isoform CK1-δ rather than CK1-ε,^[4] both PF-4800567 and the related non-selective CK1-δ/ε inhibitor PF-670462 were found in animal studies to enhance responses to certain drugs of abuse such as methamphetamine and fentanyl, which suggests a role for CK1-ε in negative regulation of sensitivity to stimulant and opioid drugs.^[5]^[6]

References

^ Walton KM, Fisher K, Rubitski D, Marconi M, Meng QJ, Sládek M, et al. (August 2009). "Selective inhibition of casein kinase 1 epsilon minimally alters circadian clock period". The Journal of Pharmacology and Experimental Therapeutics. 330 (2): 430–9. doi:10.1124/jpet.109.151415. PMID 19458106. S2CID 26565986.
^ Meng QJ, Maywood ES, Bechtold DA, Lu WQ, Li J, Gibbs JE, et al. (August 2010). "Entrainment of disrupted circadian behavior through inhibition of casein kinase 1 (CK1) enzymes". Proceedings of the National Academy of Sciences of the United States of America. 107 (34): 15240–5. Bibcode:2010PNAS..10715240M. doi:10.1073/pnas.1005101107. PMC 2930590. PMID 20696890.
^ Perez DI, Gil C, Martinez A (November 2011). "Protein kinases CK1 and CK2 as new targets for neurodegenerative diseases". Medicinal Research Reviews. 31 (6): 924–54. doi:10.1002/med.20207. hdl:10261/87060. PMID 20577972. S2CID 206251000.
^ Etchegaray JP, Yu EA, Indic P, Dallmann R, Weaver DR (April 2010). Yamazaki S (ed.). "Casein kinase 1 delta (CK1delta) regulates period length of the mouse suprachiasmatic circadian clock in vitro". PLOS ONE. 5 (4): e10303. Bibcode:2010PLoSO...510303E. doi:10.1371/journal.pone.0010303. PMC 2858662. PMID 20421981.
^ Bryant CD, Graham ME, Distler MG, Munoz MB, Li D, Vezina P, et al. (May 2009). "A role for casein kinase 1 epsilon in the locomotor stimulant response to methamphetamine". Psychopharmacology. 203 (4): 703–11. doi:10.1007/s00213-008-1417-z. PMC 2729782. PMID 19050854.
^ Bryant CD, Parker CC, Zhou L, Olker C, Chandrasekaran RY, Wager TT, et al. (March 2012). "Csnk1e is a genetic regulator of sensitivity to psychostimulants and opioids". Neuropsychopharmacology. 37 (4): 1026–35. doi:10.1038/npp.2011.287. PMC 3280656. PMID 22089318.

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[1] Walton KM, Fisher K, Rubitski D, Marconi M, Meng QJ, Sládek M, et al. (August 2009). "Selective inhibition of casein kinase 1 epsilon minimally alters circadian clock period". The Journal of Pharmacology and Experimental Therapeutics. 330 (2): 430–9. doi:10.1124/jpet.109.151415. PMID 19458106. S2CID 26565986.

[2] Meng QJ, Maywood ES, Bechtold DA, Lu WQ, Li J, Gibbs JE, et al. (August 2010). "Entrainment of disrupted circadian behavior through inhibition of casein kinase 1 (CK1) enzymes". Proceedings of the National Academy of Sciences of the United States of America. 107 (34): 15240–5. Bibcode:2010PNAS..10715240M. doi:10.1073/pnas.1005101107. PMC 2930590. PMID 20696890.

[3] Perez DI, Gil C, Martinez A (November 2011). "Protein kinases CK1 and CK2 as new targets for neurodegenerative diseases". Medicinal Research Reviews. 31 (6): 924–54. doi:10.1002/med.20207. hdl:10261/87060. PMID 20577972. S2CID 206251000.

[4] Etchegaray JP, Yu EA, Indic P, Dallmann R, Weaver DR (April 2010). Yamazaki S (ed.). "Casein kinase 1 delta (CK1delta) regulates period length of the mouse suprachiasmatic circadian clock in vitro". PLOS ONE. 5 (4): e10303. Bibcode:2010PLoSO...510303E. doi:10.1371/journal.pone.0010303. PMC 2858662. PMID 20421981.

[5] Bryant CD, Graham ME, Distler MG, Munoz MB, Li D, Vezina P, et al. (May 2009). "A role for casein kinase 1 epsilon in the locomotor stimulant response to methamphetamine". Psychopharmacology. 203 (4): 703–11. doi:10.1007/s00213-008-1417-z. PMC 2729782. PMID 19050854.

[6] Bryant CD, Parker CC, Zhou L, Olker C, Chandrasekaran RY, Wager TT, et al. (March 2012). "Csnk1e is a genetic regulator of sensitivity to psychostimulants and opioids". Neuropsychopharmacology. 37 (4): 1026–35. doi:10.1038/npp.2011.287. PMC 3280656. PMID 22089318.

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Identifiers

IUPAC name 3-(3-chloro-phenoxymethyl)-1-(tetrahydro-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
CAS Number	1188296-52-7
PubChem CID	53472153
IUPHAR/BPS	8050
ChemSpider	26325201
ChEBI	CHEBI:87237
CompTox Dashboard (EPA)	DTXSID20703849
Chemical and physical data
Formula	C₁₇H₁₈ClN₅O₂
Molar mass	359.81 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c4c(Cl)cccc4OCc(c1c3N)nn(c1ncn3)C2CCOCC2
InChI InChI=1S/C17H18ClN5O2/c18-11-2-1-3-13(8-11)25-9-14-15-16(19)20-10-21-17(15)23(22-14)12-4-6-24-7-5-12/h1-3,8,10,12H,4-7,9H2,(H2,19,20,21) Key:AUMDBEHGJRZSOO-UHFFFAOYSA-N