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{{Short description|Chemical compound}} |
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{{cs1 config|name-list-style=vanc}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 447993852 |
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| verifiedrevid = 449588534 |
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| IUPAC_name = ''N''-{''trans''-4-cyclohexyl}quinoline-4-carboxamide |
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| IUPAC_name = ''N''-<nowiki/>{''trans''-4-cyclohexyl}quinoline-4-carboxamide |
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| image = SB277011A.png |
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| image = SB2770112DACS.svg |
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| width = 260 |
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| width = 250px |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|EPA}} |
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| CAS_number = |
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| CAS_number = 215803-78-4 |
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| PubChem = 5311096 |
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| PubChem = 5311096 |
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| IUPHAR_ligand = 143 |
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| IUPHAR_ligand = 143 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 85606 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4470626 |
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| UNII = CHW57ND47C |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=28 | H=30 | N=4 | O=1 |
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| C=28 | H=30 | N=4 | O=1 |
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| molecular_weight = 438.563 g/mol |
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| smiles = c4cccc1c4nccc1C(=O)NC3CCC(CC3)CCN(CCc2c5)Cc2ccc5C#N |
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| smiles = c4cccc1c4nccc1C(=O)NC3CCC(CC3)CCN(CCc2c5)Cc2ccc5C#N |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C28H30N4O/c29-18-21-5-8-23-19-32(16-13-22(23)17-21)15-12-20-6-9-24(10-7-20)31-28(33)26-11-14-30-27-4-2-1-3-25(26)27/h1-5,8,11,14,17,20,24H,6-7,9-10,12-13,15-16,19H2,(H,31,33) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = OLWRVVHPJFLNPW-UHFFFAOYSA-N |
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'''SB-277,011A''' is a drug which acts as a potent and selective ] ] ],<ref>{{cite journal | last1 = Stemp | first1 = G | last2 = Ashmeade | first2 = T | last3 = Branch | first3 = CL | last4 = Hadley | first4 = MS | last5 = Hunter | first5 = AJ | last6 = Johnson | first6 = CN | last7 = Nash | first7 = DJ | last8 = Thewlis | first8 = KM | last9 = Vong | first9 = AK | title = Design and synthesis of trans-N-4-2-(6-cyano-1,2,3, 4-tetrahydroisoquinolin-2-yl)ethylcyclohexyl-4-quinolinecarboxamide (SB-277011): A potent and selective dopamine D(3) receptor antagonist with high oral bioavailability and CNS penetration in the rat | journal = Journal of medicinal chemistry | volume = 43 | issue = 9 | pages = 1878–85 | year = 2000 | pmid = 10794704 | doi=10.1021/jm000090i}}</ref> which is around 80-100x selective for D<sub>3</sub> over D<sub>2</sub>,<ref>{{cite journal | last1 = Southam | first1 = E | last2 = Lloyd | first2 = A | last3 = Jennings | first3 = CA | last4 = Cluderay | first4 = JE | last5 = Cilia | first5 = J | last6 = Gartlon | first6 = JE | last7 = Jones | first7 = DN | title = Effect of the selective dopamine D3 receptor antagonist SB-277011-A on regional c-Fos-like expression in rat forebrain | journal = Brain research | volume = 1149 | pages = 50–7 | year = 2007 | pmid = 17382304 | doi = 10.1016/j.brainres.2007.02.051 }}</ref> and lacks any ] activity.<ref>{{cite journal | last1 = Reavill | first1 = C | last2 = Taylor | first2 = SG | last3 = Wood | first3 = MD | last4 = Ashmeade | first4 = T | last5 = Austin | first5 = NE | last6 = Avenell | first6 = KY | last7 = Boyfield | first7 = I | last8 = Branch | first8 = CL | last9 = Cilia | first9 = J | title = Pharmacological actions of a novel, high-affinity, and selective human dopamine D(3) receptor antagonist, SB-277011-A | journal = The Journal of pharmacology and experimental therapeutics | volume = 294 | issue = 3 | pages = 1154–65 | year = 2000 | pmid = 10945872 }}</ref> |
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'''SB-277,011A''' is a drug which acts as a potent and selective ] ] ],<ref>{{cite journal | vauthors = Stemp G, Ashmeade T, Branch CL, Hadley MS, Hunter AJ, Johnson CN, Nash DJ, Thewlis KM, Vong AK, Austin NE, Jeffrey P, Avenell KY, Boyfield I, Hagan JJ, Middlemiss DN, Reavill C, Riley GJ, Routledge C, Wood M | display-authors = 6 | title = Design and synthesis of trans-N-cyclohexyl]-4-quinolinecarboxamide (SB-277011): A potent and selective dopamine D(3) receptor antagonist with high oral bioavailability and CNS penetration in the rat | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 9 | pages = 1878–85 | date = May 2000 | pmid = 10794704 | doi = 10.1021/jm000090i }}</ref> which is around 80–100{{nbsp}}times selective for D<sub>3</sub> over D<sub>2</sub>,<ref>{{cite journal | vauthors = Southam E, Lloyd A, Jennings CA, Cluderay JE, Cilia J, Gartlon JE, Jones DN | title = Effect of the selective dopamine D3 receptor antagonist SB-277011-A on regional c-Fos-like expression in rat forebrain | journal = Brain Research | volume = 1149 | pages = 50–7 | date = May 2007 | pmid = 17382304 | doi = 10.1016/j.brainres.2007.02.051 | s2cid = 12557234 }}</ref> and lacks any ] activity.<ref>{{cite journal | vauthors = Reavill C, Taylor SG, Wood MD, Ashmeade T, Austin NE, Avenell KY, Boyfield I, Branch CL, Cilia J, Coldwell MC, Hadley MS, Hunter AJ, Jeffrey P, Jewitt F, Johnson CN, Jones DN, Medhurst AD, Middlemiss DN, Nash DJ, Riley GJ, Routledge C, Stemp G, Thewlis KM, Trail B, Vong AK, Hagan JJ | display-authors = 6 | title = Pharmacological actions of a novel, high-affinity, and selective human dopamine D(3) receptor antagonist, SB-277011-A | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 294 | issue = 3 | pages = 1154–65 | date = September 2000 | pmid = 10945872 }}</ref> |
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SB-277,011A is used in the study of ] to ] drugs such as ]<ref>{{cite journal | last1 = Le Foll | first1 = B | last2 = Schwartz | first2 = JC | last3 = Sokoloff | first3 = P | title = Disruption of nicotine conditioning by dopamine D(3) receptor ligands | journal = Molecular psychiatry | volume = 8 | issue = 2 | pages = 225–30 | year = 2003 | pmid = 12610655 | doi = 10.1038/sj.mp.4001202 }}</ref> and ].<ref>{{cite journal | last1 = Vorel | first1 = SR | last2 = Ashby Jr | first2 = CR | last3 = Paul | first3 = M | last4 = Liu | first4 = X | last5 = Hayes | first5 = R | last6 = Hagan | first6 = JJ | last7 = Middlemiss | first7 = DN | last8 = Stemp | first8 = G | last9 = Gardner | first9 = EL | title = Dopamine D3 receptor antagonism inhibits cocaine-seeking and cocaine-enhanced brain reward in rats | journal = Journal of Neuroscience | volume = 22 | issue = 21 | pages = 9595–603 | year = 2002 | pmid = 12417684 }}</ref><ref>{{cite journal | last1 = Di Ciano | first1 = P | last2 = Underwood | first2 = RJ | last3 = Hagan | first3 = JJ | last4 = Everitt | first4 = BJ | title = Attenuation of cue-controlled cocaine-seeking by a selective D3 dopamine receptor antagonist SB-277011-A | journal = Neuropsychopharmacology | volume = 28 | issue = 2 | pages = 329–38 | year = 2003 | pmid = 12589386 | doi = 10.1038/sj.npp.1300148 }}</ref> Where cocaine reduces the threshold for brain electrical self-stimulation in rats, an indication of cocaine's ] effects, SB-277,011A completely reverses this effect. It may thus be useful in the treatment of addiction to nicotine and cocaine,<ref>{{cite journal | last1 = Andreoli | first1 = M | last2 = Tessari | first2 = M | last3 = Pilla | first3 = M | last4 = Valerio | first4 = E | last5 = Hagan | first5 = JJ | last6 = Heidbreder | first6 = CA | title = Selective antagonism at dopamine D3 receptors prevents nicotine-triggered relapse to nicotine-seeking behavior | journal = Neuropsychopharmacology | volume = 28 | issue = 7 | pages = 1272–80 | year = 2003 | pmid = 12700694 | doi = 10.1038/sj.npp.1300183 }}</ref><ref>{{cite journal | last1 = Ross | first1 = JT | last2 = Corrigall | first2 = WA | last3 = Heidbreder | first3 = CA | last4 = Lesage | first4 = MG | title = Effects of the selective dopamine D3 receptor antagonist SB-277011A on the reinforcing effects of nicotine as measured by a progressive-ratio schedule in rats | journal = European journal of pharmacology | volume = 559 | issue = 2-3 | pages = 173–9 | year = 2007 | pmid = 17303116 | doi = 10.1016/j.ejphar.2007.01.004 }}</ref><ref>{{cite journal | last1 = Xi | first1 = ZX | last2 = Gilbert | first2 = J | last3 = Campos | first3 = AC | last4 = Kline | first4 = N | last5 = Ashby Jr | first5 = CR | last6 = Hagan | first6 = JJ | last7 = Heidbreder | first7 = CA | last8 = Gardner | first8 = EL | title = Blockade of mesolimbic dopamine D3 receptors inhibits stress-induced reinstatement of cocaine-seeking in rats | journal = Psychopharmacology | volume = 176 | issue = 1 | pages = 57–65 | year = 2004 | pmid = 15083257 | doi = 10.1007/s00213-004-1858-y }}</ref> and is also being investigated for potential uses in the treatment of other drug addictions, such as addiction to ]<ref>{{cite journal | last1 = Ashby Jr | first1 = CR | last2 = Paul | first2 = M | last3 = Gardner | first3 = EL | last4 = Heidbreder | first4 = CA | last5 = Hagan | first5 = JJ | title = Acute administration of the selective D3 receptor antagonist SB-277011A blocks the acquisition and expression of the conditioned place preference response to heroin in male rats | journal = Synapse | volume = 48 | issue = 3 | pages = 154–6 | year = 2003 | pmid = 12645041 | doi = 10.1002/syn.10188 }}</ref> and ].<ref>{{cite journal | last1 = Thanos | first1 = PK | last2 = Katana | first2 = JM | last3 = Ashby Jr | first3 = CR | last4 = Michaelides | first4 = M | last5 = Gardner | first5 = EL | last6 = Heidbreder | first6 = CA | last7 = Volkow | first7 = ND | title = The selective dopamine D3 receptor antagonist SB-277011-A attenuates ethanol consumption in ethanol preferring (P) and non-preferring (NP) rats | journal = Pharmacology, biochemistry, and behavior | volume = 81 | issue = 1 | pages = 190–7 | year = 2005 | pmid = 15894078 | doi = 10.1016/j.pbb.2005.03.013 }}</ref><ref>{{cite journal | last1 = Vengeliene | first1 = V | last2 = Leonardi-Essmann | first2 = F | last3 = Perreau-Lenz | first3 = S | last4 = Gebicke-Haerter | first4 = P | last5 = Drescher | first5 = K | last6 = Gross | first6 = G | last7 = Spanagel | first7 = R | title = The dopamine D3 receptor plays an essential role in alcohol-seeking and relapse | journal = The FASEB journal : official publication of the Federation of American Societies for Experimental Biology | volume = 20 | issue = 13 | pages = 2223–33 | year = 2006 | pmid = 17077299 | doi = 10.1096/fj.06-6110com }}</ref><ref>{{cite journal | last1 = Heidbreder | first1 = CA | last2 = Andreoli | first2 = M | last3 = Marcon | first3 = C | last4 = Hutcheson | first4 = DM | last5 = Gardner | first5 = EL | last6 = Ashby Jr | first6 = CR | title = Evidence for the role of dopamine D3 receptors in oral operant alcohol self-administration and reinstatement of alcohol-seeking behavior in mice | journal = ] | volume = 12 | issue = 1 | pages = 35–50 | year = 2007 | pmid = 17407496 | doi = 10.1111/j.1369-1600.2007.00051.x }}</ref> |
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SB-277,011A is used in the study of ] to ] drugs such as ]<ref>{{cite journal | vauthors = Le Foll B, Schwartz JC, Sokoloff P | title = Disruption of nicotine conditioning by dopamine D(3) receptor ligands | journal = Molecular Psychiatry | volume = 8 | issue = 2 | pages = 225–30 | date = February 2003 | pmid = 12610655 | doi = 10.1038/sj.mp.4001202 | doi-access = free }}</ref> and ].<ref>{{cite journal | vauthors = Vorel SR, Ashby CR, Paul M, Liu X, Hayes R, Hagan JJ, Middlemiss DN, Stemp G, Gardner EL | display-authors = 6 | title = Dopamine D3 receptor antagonism inhibits cocaine-seeking and cocaine-enhanced brain reward in rats | journal = The Journal of Neuroscience | volume = 22 | issue = 21 | pages = 9595–603 | date = November 2002 | pmid = 12417684 | pmc = 6758043 | doi = 10.1523/JNEUROSCI.22-21-09595.2002 }}</ref><ref>{{cite journal | vauthors = Di Ciano P, Underwood RJ, Hagan JJ, Everitt BJ | title = Attenuation of cue-controlled cocaine-seeking by a selective D3 dopamine receptor antagonist SB-277011-A | journal = Neuropsychopharmacology | volume = 28 | issue = 2 | pages = 329–38 | date = February 2003 | pmid = 12589386 | doi = 10.1038/sj.npp.1300148 | doi-access = free }}</ref> Where cocaine reduces the threshold for brain electrical self-stimulation in rats, an indication of cocaine's ] effects, SB-277,011A completely reverses this effect. It may thus be useful in the treatment of addiction to nicotine and cocaine,<ref>{{cite journal | vauthors = Andreoli M, Tessari M, Pilla M, Valerio E, Hagan JJ, Heidbreder CA | title = Selective antagonism at dopamine D3 receptors prevents nicotine-triggered relapse to nicotine-seeking behavior | journal = Neuropsychopharmacology | volume = 28 | issue = 7 | pages = 1272–80 | date = July 2003 | pmid = 12700694 | doi = 10.1038/sj.npp.1300183 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Ross JT, Corrigall WA, Heidbreder CA, LeSage MG | title = Effects of the selective dopamine D3 receptor antagonist SB-277011A on the reinforcing effects of nicotine as measured by a progressive-ratio schedule in rats | journal = European Journal of Pharmacology | volume = 559 | issue = 2–3 | pages = 173–9 | date = March 2007 | pmid = 17303116 | doi = 10.1016/j.ejphar.2007.01.004 }}</ref><ref>{{cite journal | vauthors = Xi ZX, Gilbert J, Campos AC, Kline N, Ashby CR, Hagan JJ, Heidbreder CA, Gardner EL | display-authors = 6 | title = Blockade of mesolimbic dopamine D3 receptors inhibits stress-induced reinstatement of cocaine-seeking in rats | journal = Psychopharmacology | volume = 176 | issue = 1 | pages = 57–65 | date = October 2004 | pmid = 15083257 | pmc = 3726040 | doi = 10.1007/s00213-004-1858-y }}</ref> and is also being investigated for potential uses in the treatment of other drug addictions, such as addiction to ]<ref>{{cite journal | vauthors = Ashby CR, Paul M, Gardner EL, Heidbreder CA, Hagan JJ | title = Acute administration of the selective D3 receptor antagonist SB-277011A blocks the acquisition and expression of the conditioned place preference response to heroin in male rats | journal = Synapse | volume = 48 | issue = 3 | pages = 154–6 | date = June 2003 | pmid = 12645041 | doi = 10.1002/syn.10188 | s2cid = 26458149 }}</ref> and ].<ref>{{cite journal | vauthors = Thanos PK, Katana JM, Ashby CR, Michaelides M, Gardner EL, Heidbreder CA, Volkow ND | title = The selective dopamine D3 receptor antagonist SB-277011-A attenuates ethanol consumption in ethanol preferring (P) and non-preferring (NP) rats | journal = Pharmacology, Biochemistry, and Behavior | volume = 81 | issue = 1 | pages = 190–7 | date = May 2005 | pmid = 15894078 | doi = 10.1016/j.pbb.2005.03.013 | s2cid = 15406751 }}</ref><ref>{{cite journal | vauthors = Vengeliene V, Leonardi-Essmann F, Perreau-Lenz S, Gebicke-Haerter P, Drescher K, Gross G, Spanagel R | title = The dopamine D3 receptor plays an essential role in alcohol-seeking and relapse | journal = FASEB Journal | volume = 20 | issue = 13 | pages = 2223–33 | date = November 2006 | pmid = 17077299 | doi = 10.1096/fj.06-6110com | doi-access = free | s2cid = 9431585 }}</ref><ref>{{cite journal | vauthors = Heidbreder CA, Andreoli M, Marcon C, Hutcheson DM, Gardner EL, Ashby CR | title = Evidence for the role of dopamine D3 receptors in oral operant alcohol self-administration and reinstatement of alcohol-seeking behavior in mice | journal = Addiction Biology | volume = 12 | issue = 1 | pages = 35–50 | date = March 2007 | pmid = 17407496 | doi = 10.1111/j.1369-1600.2007.00051.x | s2cid = 25984106 }}</ref> |
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Another potential application for SB-277,011A is in the treatment of ],<ref>{{cite journal | last1 = Joyce | first1 = JN | last2 = Millan | first2 = MJ | title = Dopamine D3 receptor antagonists as therapeutic agents | journal = Drug discovery today | volume = 10 | issue = 13 | pages = 917–25 | year = 2005 | pmid = 15993811 | doi = 10.1016/S1359-6446(05)03491-4 }}</ref> and it may be particularly useful in treating ] patients who are both schizophrenic and addicted to drugs.<ref>{{cite journal | last1 = Jahnke | first1 = U | title = Experimental pharmacotherapeutics for schizophrenia and addiction | journal = IDrugs : the investigational drugs journal | volume = 11 | issue = 1 | pages = 7–9 | year = 2008 | pmid = 18175251 }}</ref> However it may worsen side effects such as ] in patients who are already prescribed ] drugs.<ref>{{cite journal | last1 = Malik | first1 = P | last2 = Andersen | first2 = MB | last3 = Peacock | first3 = L | title = The effects of dopamine D3 agonists and antagonists in a nonhuman primate model of tardive dyskinesia | journal = Pharmacology, biochemistry, and behavior | volume = 78 | issue = 4 | pages = 805–10 | year = 2004 | pmid = 15301939 | doi = 10.1016/j.pbb.2004.05.019 }}</ref> |
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Another potential application for SB-277,011A is in the treatment of ],<ref>{{cite journal | vauthors = Joyce JN, Millan MJ | title = Dopamine D3 receptor antagonists as therapeutic agents | journal = Drug Discovery Today | volume = 10 | issue = 13 | pages = 917–25 | date = July 2005 | pmid = 15993811 | doi = 10.1016/S1359-6446(05)03491-4 }}</ref> and it may be particularly useful in treating ] patients who are both schizophrenic and addicted to drugs.<ref>{{cite journal | vauthors = Jahnke U | title = Experimental pharmacotherapeutics for schizophrenia and addiction | journal = IDrugs | volume = 11 | issue = 1 | pages = 7–9 | date = January 2008 | pmid = 18175251 }}</ref> However it may worsen side effects such as ] in patients who are already prescribed ] drugs.<ref>{{cite journal | vauthors = Malik P, Andersen MB, Peacock L | title = The effects of dopamine D3 agonists and antagonists in a nonhuman primate model of tardive dyskinesia | journal = Pharmacology, Biochemistry, and Behavior | volume = 78 | issue = 4 | pages = 805–10 | date = August 2004 | pmid = 15301939 | doi = 10.1016/j.pbb.2004.05.019 | s2cid = 19410897 }}</ref> |
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==References== |
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== See also == |
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* ] |
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{{reflist|2}} |
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* ] |
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== References == |
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{{Dopaminergics}} |
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{{Reflist|32em}} |
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{{Dopamine receptor modulators}} |
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