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Revision as of 13:23, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456646299 of page SB-334,867 for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 21:32, 22 January 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Altered volume. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 418106574 | verifiedrevid = 464385140
| IUPAC_name = 1-(2-methylbenzoxazol- 6-yl)- 3-naphthyridin- 4-yl urea | IUPAC_name = 1-(2-methylbenzoxazol-6-yl)-3-naphthyridin-4-yl urea
| image = SB334867_structure.png
| width = 240px | image = SB-334,867.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 249889-64-3 --> | CAS_number = 249889-64-3
| PubChem = 6604926 | PubChem = 6604926
| IUPHAR_ligand = 1703 | IUPHAR_ligand = 1703
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<!--Chemical data--> <!--Chemical data-->
| C=17 | H=13 | N=5 | O=2 | C=17 | H=13 | N=5 | O=2
| molecular_weight = 319.317 g/mol
| smiles = O=C(Nc1c2ncccc2ncc1)Nc3ccc4nc(oc4c3)C | smiles = O=C(Nc1c2ncccc2ncc1)Nc3ccc4nc(oc4c3)C
| InChI = 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)
| InChIKey = AKMNUCBQGHFICM-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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) | StdInChI = 1S/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)
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| StdInChIKey = AKMNUCBQGHFICM-UHFFFAOYSA-N | StdInChIKey = AKMNUCBQGHFICM-UHFFFAOYSA-N
}} }}

'''SB-334867''' is an ]. It was the first non-peptide antagonist developed that is selective for the ] subtype ], with around 50x selectivity for OX<sub>1</sub> over ] receptors.<ref>{{cite journal | vauthors = Smart D, Sabido-David C, Brough SJ, Jewitt F, Johns A, Porter RA, Jerman JC | title = SB-334867-A: the first selective orexin-1 receptor antagonist | journal = British Journal of Pharmacology | volume = 132 | issue = 6 | pages = 1179–82 | date = March 2001 | pmid = 11250867 | pmc = 1572677 | doi = 10.1038/sj.bjp.0703953 }}</ref> It has been shown to produce ] and ] effects in animals,<ref>{{cite journal | vauthors = Rodgers RJ, Halford JC, Nunes de Souza RL, Canto de Souza AL, Piper DC, Arch JR, Upton N, Porter RA, Johns A, Blundell JE | display-authors = 6 | title = SB-334867, a selective orexin-1 receptor antagonist, enhances behavioural satiety and blocks the hyperphagic effect of orexin-A in rats | journal = The European Journal of Neuroscience | volume = 13 | issue = 7 | pages = 1444–52 | date = April 2001 | pmid = 11298806 | doi = 10.1046/j.0953-816x.2001.01518.x | s2cid = 24935644 }}</ref> and has been useful in characterising the orexinergic regulation of brain systems involved with appetite and sleep,<ref>{{cite journal | vauthors = Haynes AC, Chapman H, Taylor C, Moore GB, Cawthorne MA, Tadayyon M, Clapham JC, Arch JR | display-authors = 6 | title = Anorectic, thermogenic and anti-obesity activity of a selective orexin-1 receptor antagonist in ob/ob mice | journal = Regulatory Peptides | volume = 104 | issue = 1–3 | pages = 153–9 | date = March 2002 | pmid = 11830290 | doi = 10.1016/S0167-0115(01)00358-5 | s2cid = 25523175 }}</ref><ref>{{cite journal | vauthors = Rodgers RJ, Ishii Y, Halford JC, Blundell JE | title = Orexins and appetite regulation | journal = Neuropeptides | volume = 36 | issue = 5 | pages = 303–25 | date = October 2002 | pmid = 12450737 | doi = 10.1016/S0143-4179(02)00085-9 | s2cid = 23352886 }}</ref><ref>{{cite journal | vauthors = Bernard R, Lydic R, Baghdoyan HA | title = Hypocretin-1 causes G protein activation and increases ACh release in rat pons | journal = The European Journal of Neuroscience | volume = 18 | issue = 7 | pages = 1775–85 | date = October 2003 | pmid = 14622212 | doi = 10.1046/j.1460-9568.2003.02905.x | url = https://deepblue.lib.umich.edu/bitstream/2027.42/75751/1/j.1460-9568.2003.02905.x.pdf | hdl = 2027.42/75751 | s2cid = 18515164 | hdl-access = free }}</ref><ref>{{cite journal | vauthors = Soffin EM, Gill CH, Brough SJ, Jerman JC, Davies CH | title = Pharmacological characterisation of the orexin receptor subtype mediating postsynaptic excitation in the rat dorsal raphe nucleus | journal = Neuropharmacology | volume = 46 | issue = 8 | pages = 1168–76 | date = June 2004 | pmid = 15111023 | doi = 10.1016/j.neuropharm.2004.02.014 | s2cid = 45872346 }}</ref><ref>{{cite journal | vauthors = Thorpe AJ, Kotz CM | title = Orexin A in the nucleus accumbens stimulates feeding and locomotor activity | journal = Brain Research | volume = 1050 | issue = 1–2 | pages = 156–62 | date = July 2005 | pmid = 15979595 | doi = 10.1016/j.brainres.2005.05.045 | s2cid = 24662237 }}</ref><ref>{{cite journal | vauthors = Frederick-Duus D, Guyton MF, Fadel J | title = Food-elicited increases in cortical acetylcholine release require orexin transmission | journal = Neuroscience | volume = 149 | issue = 3 | pages = 499–507 | date = November 2007 | pmid = 17928158 | doi = 10.1016/j.neuroscience.2007.07.061 | s2cid = 19452926 }}</ref> as well as other physiological processes.<ref>{{cite journal | vauthors = Small CJ, Goubillon ML, Murray JF, Siddiqui A, Grimshaw SE, Young H, Sivanesan V, Kalamatianos T, Kennedy AR, Coen CW, Bloom SR, Wilson CA | display-authors = 6 | title = Central orexin A has site-specific effects on luteinizing hormone release in female rats | journal = Endocrinology | volume = 144 | issue = 7 | pages = 3225–36 | date = July 2003 | pmid = 12810579 | doi = 10.1210/en.2002-0041 | doi-access = free }}</ref><ref>{{cite journal | vauthors = D'Anna KL, Gammie SC | title = Hypocretin-1 dose-dependently modulates maternal behaviour in mice | journal = Journal of Neuroendocrinology | volume = 18 | issue = 8 | pages = 553–66 | date = August 2006 | pmid = 16867176 | pmc = 2275401 | doi = 10.1111/j.1365-2826.2006.01448.x }}</ref><ref>{{cite journal | vauthors = Muschamp JW, Dominguez JM, Sato SM, Shen RY, Hull EM | title = A role for hypocretin (orexin) in male sexual behavior | journal = The Journal of Neuroscience | volume = 27 | issue = 11 | pages = 2837–45 | date = March 2007 | pmid = 17360905 | pmc = 6672590 | doi = 10.1523/JNEUROSCI.4121-06.2007 }}</ref><ref>{{cite journal | vauthors = Eliassi A, Nazari M, Naghdi N | title = Role of the ventromedial hypothalamic orexin-1 receptors in regulation of gastric Acid secretion in conscious rats | journal = Journal of Neuroendocrinology | volume = 21 | issue = 3 | pages = 177–82 | date = March 2009 | pmid = 19207823 | doi = 10.1111/j.1365-2826.2009.01824.x | s2cid = 23781282 }}</ref> The hydrochloride salt of SB-334867 has been demonstrated to be hydrolytically unstable, both in solution and as the solid.<ref>{{cite journal | vauthors = McElhinny CJ, Lewin AH, Mascarella SW, Runyon S, Brieaddy L, Carroll FI | title = Hydrolytic instability of the important orexin 1 receptor antagonist SB-334867: possible confounding effects on in vivo and in vitro studies | journal = Bioorganic & Medicinal Chemistry Letters | volume = 22 | issue = 21 | pages = 6661–4 | date = November 2012 | pmid = 23031594 | doi = 10.1016/j.bmcl.2012.08.109 }}</ref> Orexin antagonists have multiple potential clinical applications including the treatment of drug addiction, insomnia, obesity and diabetes.<ref>{{cite journal | vauthors = Smart D, Haynes AC, Williams G, Arch JR | title = Orexins and the treatment of obesity | journal = European Journal of Pharmacology | volume = 440 | issue = 2–3 | pages = 199–212 | date = April 2002 | pmid = 12007536 | doi = 10.1016/S0014-2999(02)01429-2 }}</ref><ref>{{cite journal | vauthors = Bingham MJ, Cai J, Deehan MR | title = Eating, sleeping and rewarding: orexin receptors and their antagonists | journal = Current Opinion in Drug Discovery & Development | volume = 9 | issue = 5 | pages = 551–9 | date = September 2006 | pmid = 17002215 }}</ref><ref>{{cite journal | vauthors = Borgland SL, Taha SA, Sarti F, Fields HL, Bonci A | title = Orexin A in the VTA is critical for the induction of synaptic plasticity and behavioral sensitization to cocaine | journal = Neuron | volume = 49 | issue = 4 | pages = 589–601 | date = February 2006 | pmid = 16476667 | doi = 10.1016/j.neuron.2006.01.016 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Narita M, Nagumo Y, Hashimoto S, Narita M, Khotib J, Miyatake M, Sakurai T, Yanagisawa M, Nakamachi T, Shioda S, Suzuki T | display-authors = 6 | title = Direct involvement of orexinergic systems in the activation of the mesolimbic dopamine pathway and related behaviors induced by morphine | journal = The Journal of Neuroscience | volume = 26 | issue = 2 | pages = 398–405 | date = January 2006 | pmid = 16407535 | pmc = 6674410 | doi = 10.1523/JNEUROSCI.2761-05.2006 }}</ref><ref>{{cite journal | vauthors = Lawrence AJ, Cowen MS, Yang HJ, Chen F, Oldfield B | title = The orexin system regulates alcohol-seeking in rats | journal = British Journal of Pharmacology | volume = 148 | issue = 6 | pages = 752–9 | date = July 2006 | pmid = 16751790 | pmc = 1617074 | doi = 10.1038/sj.bjp.0706789 }}</ref><ref>{{cite journal | vauthors = Sharf R, Sarhan M, Dileone RJ | title = Orexin mediates the expression of precipitated morphine withdrawal and concurrent activation of the nucleus accumbens shell | journal = Biological Psychiatry | volume = 64 | issue = 3 | pages = 175–83 | date = August 2008 | pmid = 18423425 | pmc = 2529153 | doi = 10.1016/j.biopsych.2008.03.006 }}</ref><ref>{{cite journal | vauthors = Aston-Jones G, Smith RJ, Moorman DE, Richardson KA | title = Role of lateral hypothalamic orexin neurons in reward processing and addiction | journal = Neuropharmacology | volume = 56 | issue = Suppl 1 | pages = 112–21 | year = 2009 | pmid = 18655797 | pmc = 2635332 | doi = 10.1016/j.neuropharm.2008.06.060 }}</ref><ref>{{cite journal | vauthors = Martin-Fardon R, Weiss F | title = Blockade of hypocretin receptor-1 preferentially prevents cocaine seeking: comparison with natural reward seeking | journal = NeuroReport | volume = 25 | issue = 7 | pages = 485–8 | date = May 2014 | pmid = 24407199 | pmc = 3981907 | doi = 10.1097/wnr.0000000000000120 }}</ref>

== References ==
{{reflist}}

{{Hypnotics and sedatives}}
{{Orexin receptor modulators}}

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{{sedative-stub}}