Fenobam

Fenobam
	1-(3-hlorofenil)-3-(3-metil-5-okso-4H-imidazol-2-il)ureja
Identifikacija
CAS registarski broj	57653-26-6
PubChem	162834
MeSH	fenobam
ChEMBL	CHEMBL239800
IUPHAR ligand	1434
Jmol-3D slike	Slika 1
SMILES
	CN1CC(=O)N=C1NC(=O)NC2=CC(=CC=C2)Cl
InChI
	InChI=1S/C11H11ClN4O2/c1-16-6-9(17)14-10(16)15-11(18)13-8-4-2-3-7(12)5-8/h2-5H,6H2,1H3,(H2,13,14,15,17,18) ; Kod: DWPQODZAOSWNHB-UHFFFAOYSA-N
Svojstva
Molekulska formula	C11H11ClN4O2
Molarna masa	266,684
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Fenobam je imidazolni derivat razvijen tokom kasnih 1970-tih kao anksiolitski lek sa svojevremeno nepoznatim molekulskim ciljem u mozgu. Naknadno, je utvrđeno da fenobam deluje potentan i selektivan negativni alosterni modulator metabotropnog glutamatnog receptora mGluR₅.^[4]^[5] On je korišten kao vodeće jedinjenje za razvoj niza novijih mGluR₅ antagonista.^[6]^[7]^[8]^[9]

Hemija

Fenobam se može pripremiti u dva koraka iz kreatina.^[10]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Porter RH, Jaeschke G, Spooren W et al. (November 2005). „Fenobam: a clinically validated nonbenzodiazepine anxiolytic is a potent, selective, and noncompetitive mGlu5 receptor antagonist with inverse agonist activity”. J. Pharmacol. Exp. Ther. 315 (2): 711–21. DOI:10.1124/jpet.105.089839. PMID 16040814.
↑ Marino, MJ; Conn, PJ (2006). „Glutamate-based therapeutic approaches: Allosteric modulators of metabotropic glutamate receptors”. Current opinion in pharmacology 6 (1): 98–102. DOI:10.1016/j.coph.2005.09.006. PMID 16368268.
↑ Wållberg, A; Nilsson, K; Osterlund, K; Peterson, A; Elg, S; Raboisson, P; Bauer, U; Hammerland, LG et al. (2006). „Phenyl ureas of creatinine as mGluR5 antagonists. A structure-activity relationship study of fenobam analogues”. Bioorganic & medicinal chemistry letters 16 (5): 1142–5. DOI:10.1016/j.bmcl.2005.11.092. PMID 16380255.
↑ Ceccarelli, SM; Jaeschke, G; Buettelmann, B; Huwyler, J; Kolczewski, S; Peters, JU; Prinssen, E; Porter, R et al. (2007). „Rational design, synthesis, and structure-activity relationship of benzoxazolones: New potent mglu5 receptor antagonists based on the fenobam structure”. Bioorganic & medicinal chemistry letters 17 (5): 1302–6. DOI:10.1016/j.bmcl.2006.12.006. PMID 17189691.
↑ Jaeschke, G; Porter, R; Büttelmann, B; Ceccarelli, SM; Guba, W; Kuhn, B; Kolczewski, S; Huwyler, J et al. (2007). „Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists”. Bioorganic & medicinal chemistry letters 17 (5): 1307–11. DOI:10.1016/j.bmcl.2006.12.033. PMID 17196387.
↑ Gichinga, Moses G.; Olson, Jeremy P.; Butala, Elizabeth; Navarro, Hernán A.; Gilmour, Brian P.; Mascarella, S. Wayne; Carroll, F. Ivy (2011). „Synthesis and Evaluation of Metabotropic Glutamate Receptor Subtype 5 Antagonists Based on Fenobam”. ACS Medicinal Chemistry Letters 2 (12): 882–884. DOI:10.1021/ml200162f. PMC 3328804. PMID 22523618.
↑ Rasmussen, C. R.; 1976, U.S. Patent 3.983.135.

Vanjske veze

Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid16040814-4] Porter RH, Jaeschke G, Spooren W et al. (November 2005). „Fenobam: a clinically validated nonbenzodiazepine anxiolytic is a potent, selective, and noncompetitive mGlu5 receptor antagonist with inverse agonist activity”. J. Pharmacol. Exp. Ther. 315 (2): 711–21. DOI:10.1124/jpet.105.089839. PMID 16040814.

[5] Marino, MJ; Conn, PJ (2006). „Glutamate-based therapeutic approaches: Allosteric modulators of metabotropic glutamate receptors”. Current opinion in pharmacology 6 (1): 98–102. DOI:10.1016/j.coph.2005.09.006. PMID 16368268.

[6] Wållberg, A; Nilsson, K; Osterlund, K; Peterson, A; Elg, S; Raboisson, P; Bauer, U; Hammerland, LG et al. (2006). „Phenyl ureas of creatinine as mGluR5 antagonists. A structure-activity relationship study of fenobam analogues”. Bioorganic & medicinal chemistry letters 16 (5): 1142–5. DOI:10.1016/j.bmcl.2005.11.092. PMID 16380255.

[7] Ceccarelli, SM; Jaeschke, G; Buettelmann, B; Huwyler, J; Kolczewski, S; Peters, JU; Prinssen, E; Porter, R et al. (2007). „Rational design, synthesis, and structure-activity relationship of benzoxazolones: New potent mglu5 receptor antagonists based on the fenobam structure”. Bioorganic & medicinal chemistry letters 17 (5): 1302–6. DOI:10.1016/j.bmcl.2006.12.006. PMID 17189691.

[8] Jaeschke, G; Porter, R; Büttelmann, B; Ceccarelli, SM; Guba, W; Kuhn, B; Kolczewski, S; Huwyler, J et al. (2007). „Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists”. Bioorganic & medicinal chemistry letters 17 (5): 1307–11. DOI:10.1016/j.bmcl.2006.12.033. PMID 17196387.

[9] Gichinga, Moses G.; Olson, Jeremy P.; Butala, Elizabeth; Navarro, Hernán A.; Gilmour, Brian P.; Mascarella, S. Wayne; Carroll, F. Ivy (2011). „Synthesis and Evaluation of Metabotropic Glutamate Receptor Subtype 5 Antagonists Based on Fenobam”. ACS Medicinal Chemistry Letters 2 (12): 882–884. DOI:10.1021/ml200162f. PMC 3328804. PMID 22523618.

[10] Rasmussen, C. R.; 1976, U.S. Patent 3.983.135.

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