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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChemSpiderID InChI1 InChIKey1 SMILES.
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| image = SB334867_structure.png
| image = SB334867_structure.png
| width = 240px
| width = 240px
| ChemSpiderID = 5037182
| InChI1 = 1/C17H13N5O2/c1-10-20-12-5-4-11(9-15(12)24-10)21-17(23)22-14-6-8-18-13-3-2-7-19-16(13)14/h2-9H,1H3,(H2,18,21,22,23)
| InChIKey1 = AKMNUCBQGHFICM-UHFFFAOYAZ
| CAS_number= 249889-64-3
| CAS_number= 249889-64-3
| ATC_prefix=
| ATC_prefix=
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| C=17 | H=13 | N=5 | O=2
| C=17 | H=13 | N=5 | O=2
| molecular_weight = 319.317 g/mol
| molecular_weight = 319.317 g/mol
| smiles = c3cc2nc(C)oc2cc3NC(=O)Nc1ccnc4c1nccc4
| smiles = O=C(Nc1c2ncccc2ncc1)Nc3ccc4nc(oc4c3)C
| bioavailability=
| bioavailability=
| metabolism =
| metabolism =

Revision as of 17:39, 6 November 2010

SB-334867
Identifiers
  • 1-(2-methylbenzoxazol- 6-yl)- 3-[1,5]naphthyridin- 4-yl urea
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.164.490 Edit this at Wikidata
Chemical and physical data
FormulaC17H13N5O2
Molar mass319.317 g/mol g·mol−1
3D model (JSmol)
  • O=C(Nc1c2ncccc2ncc1)Nc3ccc4nc(oc4c3)C

SB-334,867 is a drug which was the first non-peptide antagonist developed that is selective for the orexin receptor subtype OX1, with around 50x selectivity for OX1 over OX2 receptors.[1] It has been shown to produce sedative and anorectic effects in animals,[2] and has been useful in characterising the orexinergic regulation of brain systems involved with appetite and sleep,[3][4][5][6][7][8] as well as other physiological processes.[9][10][11][12] Orexin antagonists have multiple potential clinical applications including the treatment of drug addiction, insomnia, obesity and diabetes.[13][14][15][16][17][18][19]

References

  1. ^ Smart D, Sabido-David C, Brough SJ, Jewitt F, Johns A, Porter RA, Jerman JC. SB-334867-A: the first selective orexin-1 receptor antagonist. British Journal of Pharmacology. 2001 Mar;132(6):1179-82. PMID 11250867
  2. ^ Rodgers RJ, Halford JC, Nunes de Souza RL, Canto de Souza AL, Piper DC, Arch JR, Upton N, Porter RA, Johns A, Blundell JE. SB-334867, a selective orexin-1 receptor antagonist, enhances behavioural satiety and blocks the hyperphagic effect of orexin-A in rats. European Journal of Neuroscience. 2001 Apr;13(7):1444-52. PMID 11298806
  3. ^ Haynes AC, Chapman H, Taylor C, Moore GB, Cawthorne MA, Tadayyon M, Clapham JC, Arch JR. Anorectic, thermogenic and anti-obesity activity of a selective orexin-1 receptor antagonist in ob/ob mice. Regulatory Peptides. 2002 Mar 15;104(1-3):153-9. PMID 11830290
  4. ^ Rodgers RJ, Ishii Y, Halford JC, Blundell JE. Orexins and appetite regulation. Neuropeptides. 2002 Oct;36(5):303-25. PMID 12450737
  5. ^ Bernard R, Lydic R, Baghdoyan HA. Hypocretin-1 causes G protein activation and increases ACh release in rat pons. European Journal of Neuroscience. 2003 Oct;18(7):1775-85. PMID 14622212
  6. ^ Soffin EM, Gill CH, Brough SJ, Jerman JC, Davies CH. Pharmacological characterisation of the orexin receptor subtype mediating postsynaptic excitation in the rat dorsal raphe nucleus. Neuropharmacology. 2004 Jun;46(8):1168-76. PMID 15111023
  7. ^ Thorpe AJ, Kotz CM. Orexin A in the nucleus accumbens stimulates feeding and locomotor activity. Brain Research. 2005 Jul 19;1050(1-2):156-62. PMID 15979595
  8. ^ Frederick-Duus D, Guyton MF, Fadel J. Food-elicited increases in cortical acetylcholine release require orexin transmission. Neuroscience. 2007 Nov 9;149(3):499-507. PMID 17928158
  9. ^ Small CJ, Goubillon ML, Murray JF, Siddiqui A, Grimshaw SE, Young H, Sivanesan V, Kalamatianos T, Kennedy AR, Coen CW, Bloom SR, Wilson CA. Central orexin A has site-specific effects on luteinizing hormone release in female rats. Endocrinology. 2003 Jul;144(7):3225-36. PMID 12810579
  10. ^ D'Anna KL, Gammie SC. Hypocretin-1 dose-dependently modulates maternal behaviour in mice. Journal of Neuroendocrinology. 2006 Aug;18(8):553-66. PMID 16867176
  11. ^ Muschamp JW, Dominguez JM, Sato SM, Shen RY, Hull EM. A role for hypocretin (orexin) in male sexual behavior. Journal of Neuroscience. 2007 Mar 14;27(11):2837-45. PMID 17360905
  12. ^ Eliassi A, Nazari M, Naghdi N. Role of the ventromedial hypothalamic orexin-1 receptors in regulation of gastric acid secretion in conscious rats. Journal of Neuroendocrinology. 2009 Mar;21(3):177-82. PMID 19207823
  13. ^ Smart D, Haynes AC, Williams G, Arch JR. Orexins and the treatment of obesity. European Journal of Pharmacology. 2002 Apr 12;440(2-3):199-212. PMID 12007536
  14. ^ Bingham MJ, Cai J, Deehan MR. Eating, sleeping and rewarding: orexin receptors and their antagonists. Current Opinion in Drug Discovery and Development. 2006 Sep;9(5):551-9. PMID 17002215
  15. ^ Borgland SL, Taha SA, Sarti F, Fields HL, Bonci A. Orexin A in the VTA is critical for the induction of synaptic plasticity and behavioral sensitization to cocaine. Neuron. 2006 Feb 16;49(4):589-601. PMID 16476667
  16. ^ Narita M, Nagumo Y, Hashimoto S, Narita M, Khotib J, Miyatake M, Sakurai T, Yanagisawa M, Nakamachi T, Shioda S, Suzuki T. Direct involvement of orexinergic systems in the activation of the mesolimbic dopamine pathway and related behaviors induced by morphine. Journal of Neuroscience. 2006 Jan 11;26(2):398-405. PMID 16407535
  17. ^ Lawrence AJ, Cowen MS, Yang HJ, Chen F, Oldfield B. The orexin system regulates alcohol-seeking in rats. British Journal of Pharmacology. 2006 Jul;148(6):752-9. PMID 16751790
  18. ^ Sharf R, Sarhan M, Dileone RJ. Orexin mediates the expression of precipitated morphine withdrawal and concurrent activation of the nucleus accumbens shell. Biological Psychiatry. 2008 Aug 1;64(3):175-83. PMID 18423425
  19. ^ Aston-Jones G, Smith RJ, Moorman DE, Richardson KA. Role of lateral hypothalamic orexin neurons in reward processing and addiction. Neuropharmacology. 2009;56 Suppl 1:112-21. PMID 18655797


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