Fenobam
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| Nazivi | |
|---|---|
| IUPAC naziv
1-(3-hlorofenil)-3-(3-metil-5-okso-4H-imidazol-2-il)ureja
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| Identifikacija | |
3D model (Jmol)
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| ECHA InfoCard | 100.165.052 |
| MeSH | fenobam |
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| Svojstva | |
| C11H11ClN4O2 | |
| Molarna masa | 266,684 |
Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa). | |
 verifikuj (šta je   ?)
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| Reference infokutije | |
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.[3][4] On je korišten kao vodeće jedinjenje za razvoj niza novijih mGluR5 antagonista.[5][6][7][8]
Hemija
[уреди | уреди извор]Fenobam se može pripremiti u dva koraka iz kreatina.[9]
Reference
[уреди | уреди извор]- ^ 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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.
- ^ 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.
- ^ Porter RH; Jaeschke G; Spooren W; et al. (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. PMID 16040814. doi:10.1124/jpet.105.089839.
- ^ Marino, MJ; Conn, PJ (2006). „Glutamate-based therapeutic approaches: Allosteric modulators of metabotropic glutamate receptors”. Current opinion in pharmacology. 6 (1): 98—102. PMID 16368268. doi:10.1016/j.coph.2005.09.006.
- ^ 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. PMID 16380255. doi:10.1016/j.bmcl.2005.11.092.
- ^ 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. PMID 17189691. doi:10.1016/j.bmcl.2006.12.006.
- ^ 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. PMID 17196387. doi:10.1016/j.bmcl.2006.12.033.
- ^ 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. PMC 3328804
. PMID 22523618. doi:10.1021/ml200162f.
- ^ Rasmussen, C. R.; 1976, U.S. Patent 3.983.135.
