AZD9272

AZD 9272
Identifiers
	IUPAC name 3-fluoro-5-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile;
CAS Number	327056-26-8 ;
PubChem CID	9838729;
IUPHAR/BPS	6439;
ChemSpider	8014449;
UNII	54SQ9B412I;
ChEMBL	ChEMBL2164551;
Chemical and physical data
Formula	C14H6F2N4O
Molar mass	284.226 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#Cc1cc(cc(F)c1)c1nc(no1)c1ncc(F)cc1;
	InChI InChI=1S/C14H6F2N4O/c15-10-1-2-12(18-7-10)13-19-14(21-20-13)9-3-8(6-17)4-11(16)5-9/h1-5,7H; Key:RBSPCALDSNXWEP-UHFFFAOYSA-N;

AZD 9272 is a drug which acts as a selective antagonist for the metabotropic glutamate receptor subtype mGluR5.^[1] It was unsuccessful in human trials as an analgesic,^[2] but continues to be widely used in research especially as its radiolabelled forms.^[3]^[4]^[5]^[6]

References

^ Raboisson P, Breitholtz-Emanuelsson A, Dahllöf H, Edwards L, Heaton WL, Isaac M, et al. (November 2012). "Discovery and characterization of AZD9272 and AZD6538-Two novel mGluR5 negative allosteric modulators selected for clinical development". Bioorganic & Medicinal Chemistry Letters. 22 (22): 6974–6979. doi:10.1016/j.bmcl.2012.08.100. PMID 23046966.
^ Kalliomäki J, Huizar K, Kågedal M, Hägglöf B, Schmelz M (November 2013). "Evaluation of the effects of a metabotropic glutamate receptor 5-antagonist on electrically induced pain and central sensitization in healthy human volunteers". European Journal of Pain. 17 (10): 1465–1471. doi:10.1002/j.1532-2149.2013.00327.x. PMID 23650072. S2CID 26095267.
^ Swedberg MD, Raboisson P (August 2014). "AZD9272 and AZD2066: selective and highly central nervous system penetrant mGluR5 antagonists characterized by their discriminative effects". The Journal of Pharmacology and Experimental Therapeutics. 350 (2): 212–222. doi:10.1124/jpet.114.215137. PMID 24876235. S2CID 29315210.
^ Varnäs K, Juréus A, Finnema SJ, Johnström P, Raboisson P, Amini N, et al. (June 2018). "The metabotropic glutamate receptor 5 radioligand [¹¹C]AZD9272 identifies unique binding sites in primate brain". Neuropharmacology. 135: 455–463. doi:10.1016/j.neuropharm.2018.03.039. PMID 29608920.
^ Varnäs K, Cselényi Z, Arakawa R, Nag S, Stepanov V, Moein MM, et al. (January 2020). "The pro-psychotic metabotropic glutamate receptor compounds fenobam and AZD9272 share binding sites with monoamine oxidase-B inhibitors in humans". Neuropharmacology. 162: 107809. doi:10.1016/j.neuropharm.2019.107809. PMID 31589885.
^ Nag S, Varnäs K, Arakawa R, Jahan M, Schou M, Farde L, Halldin C (April 2020). "Synthesis, Biodistribution, and Radiation Dosimetry of a Novel mGluR5 Radioligand: ¹⁸F-AZD9272". ACS Chemical Neuroscience. 11 (7): 1048–1057. doi:10.1021/acschemneuro.9b00680. PMC 7309225. PMID 32167745.

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[1] Raboisson P, Breitholtz-Emanuelsson A, Dahllöf H, Edwards L, Heaton WL, Isaac M, et al. (November 2012). "Discovery and characterization of AZD9272 and AZD6538-Two novel mGluR5 negative allosteric modulators selected for clinical development". Bioorganic & Medicinal Chemistry Letters. 22 (22): 6974–6979. doi:10.1016/j.bmcl.2012.08.100. PMID 23046966.

[2] Kalliomäki J, Huizar K, Kågedal M, Hägglöf B, Schmelz M (November 2013). "Evaluation of the effects of a metabotropic glutamate receptor 5-antagonist on electrically induced pain and central sensitization in healthy human volunteers". European Journal of Pain. 17 (10): 1465–1471. doi:10.1002/j.1532-2149.2013.00327.x. PMID 23650072. S2CID 26095267.

[3] Swedberg MD, Raboisson P (August 2014). "AZD9272 and AZD2066: selective and highly central nervous system penetrant mGluR5 antagonists characterized by their discriminative effects". The Journal of Pharmacology and Experimental Therapeutics. 350 (2): 212–222. doi:10.1124/jpet.114.215137. PMID 24876235. S2CID 29315210.

[4] Varnäs K, Juréus A, Finnema SJ, Johnström P, Raboisson P, Amini N, et al. (June 2018). "The metabotropic glutamate receptor 5 radioligand [¹¹C]AZD9272 identifies unique binding sites in primate brain". Neuropharmacology. 135: 455–463. doi:10.1016/j.neuropharm.2018.03.039. PMID 29608920.

[5] Varnäs K, Cselényi Z, Arakawa R, Nag S, Stepanov V, Moein MM, et al. (January 2020). "The pro-psychotic metabotropic glutamate receptor compounds fenobam and AZD9272 share binding sites with monoamine oxidase-B inhibitors in humans". Neuropharmacology. 162: 107809. doi:10.1016/j.neuropharm.2019.107809. PMID 31589885.

[6] Nag S, Varnäs K, Arakawa R, Jahan M, Schou M, Farde L, Halldin C (April 2020). "Synthesis, Biodistribution, and Radiation Dosimetry of a Novel mGluR5 Radioligand: ¹⁸F-AZD9272". ACS Chemical Neuroscience. 11 (7): 1048–1057. doi:10.1021/acschemneuro.9b00680. PMC 7309225. PMID 32167745.

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See also

References