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Latest revision as of 20:48, 5 April 2024 edit undoحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Heterocyclic compounds with 2 rings using HotCat |
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{{Short description|Chemical compound}} |
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{{drugbox | |
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{{Drugbox |
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| IUPAC_name = ''N''-{5-dec-8-yl)pentanoyl] -2,4-dimethoxyphenyl}-4-(trifluoromethyl)benzenesulfonamide |
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| Verifiedfields = changed |
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| image = RS-102,221_structure.png |
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| verifiedrevid = 407718072 |
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| width = 250 |
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| IUPAC_name = ''N''-{5-dec-8-yl)pentanoyl] -2,4-dimethoxyphenyl}-4-(trifluoromethyl)benzenesulfonamide |
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| CAS_number = 185376-97-0 |
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| image = RS-102221.svg |
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| synonyms = <small>RS-102,221; 8--1,3,8-triazaspirodecane-2,4-dione</small> |
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| width = 250 |
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| ATC_prefix = |
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<!--Clinical data--> |
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| PubChem = 3693566 |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 185376-97-0 |
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| ATC_prefix = |
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| PubChem = 3693566 |
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| IUPHAR_ligand = 187 |
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| IUPHAR_ligand = 187 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| C = 27 | H = 33 | F = 3 | N = 4 | O = 7 | S = 1 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| molecular_weight = 614.632 g/mol |
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| ChEMBL = 88402 |
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| smiles = c4cc(C(F)(F)F)ccc4S(=O)(=O)Nc(c(OC)cc2OC)cc2C(=O)CCCCN(CC3)CCC13NC(=O)NC1=O |
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| bioavailability = |
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| ChemSpiderID = 2925610 |
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<!--Chemical data--> |
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| metabolism = |
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| C=27 | H=33 | F=3 | N=4 | O=7 | S=1 |
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| smiles = c4cc(C(F)(F)F)ccc4S(=O)(=O)Nc(c(OC)cc2OC)cc2C(=O)CCCCN(CC3)CCC13NC(=O)NC1=O |
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| excretion = |
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| StdInChI = 1S/C27H31F3N4O7S/c1-40-22-16-23(41-2)20(33-42(38,39)18-8-6-17(7-9-18)27(28,29)30)15-19(22)21(35)5-3-4-12-34-13-10-26(11-14-34)24(36)31-25(37)32-26/h6-9,15-16,33H,3-5,10-14H2,1-2H3,(H2,31,32,36,37) |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| StdInChIKey = HZZZZODVDSHQRG-UHFFFAOYSA-N |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| synonyms = <small>RS-102,221; 8--1,3,8-triazaspirodecane-2,4-dione</small> |
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| pregnancy_category= |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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'''RS-102,221''' is a drug developed by ], which was one of the first compounds discovered that acts as a potent and selective ] at the ] ] ], with around 100x selectivity over the closely related ] and ] receptors.<ref>Bonhaus DW, Weinhardt KK, Taylor M, DeSouza A, McNeeley PM, Szczepanski K, Fontana DJ, Trinh J, Rocha CL, Dawson MW, Flippin LA, Eglen RM. RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist. ''Neuropharmacology''. 1997 Apr-May;36(4-5):621-9. PMID 9225287</ref> It has ] effects in animal studies,<ref>Kuznetsova EG, Amstislavskaya TG, Shefer EA, Popova NK. Effect of 5-HT2C receptor antagonist RS 102221 on mouse behavior. ''Bulletin of Experimental Biology and Medicine''. 2006 Jul;142(1):76-9. PMID 17369908</ref> increases the effectiveness of ] antidepressants,<ref>Cremers TI, Giorgetti M, Bosker FJ, Hogg S, Arnt J, Mørk A, Honig G, Bøgesø KP, Westerink BH, den Boer H, Wikstrom HV, Tecott LH. Inactivation of 5-HT(2C) receptors potentiates consequences of serotonin reuptake blockade. ''Neuropsychopharmacology''. 2004 Oct;29(10):1782-9. PMID 15138437</ref> and shows a complex interaction with ], increasing some effects but decreasing others, reflecting a role for the 5-HT<sub>2C</sub> receptor in regulation of the ] signalling system in the brain.<ref>Filip M, Cunningham KA. Serotonin 5-HT(2C) receptors in nucleus accumbens regulate expression of the hyperlocomotive and discriminative stimulus effects of cocaine. ''Pharmacology, Biochemistry and Behaviour''. 2002 Apr;71(4):745-56. PMID 11888566</ref><ref>Filip M, Cunningham KA. Hyperlocomotive and discriminative stimulus effects of cocaine are under the control of serotonin(2C) (5-HT(2C)) receptors in rat prefrontal cortex. ''Journal of Pharmacology and Experimental Therapeutics''. 2003 Aug;306(2):734-43. PMID 12721337</ref><ref>Morita K, Hamamoto M, Arai S, Kitayama S, Irifune M, Kawahara M, Kihira K, Dohi T. Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities. ''Brain Research''. 2005 Sep 28;1057(1-2):153-60. PMID 16125150</ref><ref>Dremencov E, Weizmann Y, Kinor N, Gispan-Herman I, Yadid G. Modulation of dopamine transmission by 5HT2C and 5HT3 receptors: a role in the antidepressant response. ''Current Drug Targets''. 2006 Feb;7(2):165-75. PMID 16475958</ref> |
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'''RS-102221''' is a drug developed by ], which was one of the first compounds discovered that acts as a potent and selective ] at the ] ] ], with around 100× selectivity over the closely related ] and ] receptors.<ref>{{cite journal | vauthors = Bonhaus DW, Weinhardt KK, Taylor M, DeSouza A, McNeeley PM, Szczepanski K, Fontana DJ, Trinh J, Rocha CL, Dawson MW, Flippin LA, Eglen RM | display-authors = 6 | title = RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist | journal = Neuropharmacology | volume = 36 | issue = 4–5 | pages = 621–9 | pmid = 9225287 | doi = 10.1016/s0028-3908(97)00049-x | year = 1997 | s2cid = 24930608 }}</ref> It has ] effects in animal studies,<ref>{{cite journal | vauthors = Kuznetsova EG, Amstislavskaya TG, Shefer EA, Popova NK | title = Effect of 5-HT2C receptor antagonist RS 102221 on mouse behavior | journal = Bulletin of Experimental Biology and Medicine | volume = 142 | issue = 1 | pages = 76–9 | date = July 2006 | pmid = 17369908 | doi = 10.1007/s10517-006-0296-8 | s2cid = 36424571 }}</ref> increases the effectiveness of ] antidepressants,<ref>{{cite journal | vauthors = Cremers TI, Giorgetti M, Bosker FJ, Hogg S, Arnt J, Mørk A, Honig G, Bøgesø KP, Westerink BH, den Boer H, Wikstrom HV, Tecott LH | display-authors = 6 | title = Inactivation of 5-HT(2C) receptors potentiates consequences of serotonin reuptake blockade | journal = Neuropsychopharmacology | volume = 29 | issue = 10 | pages = 1782–9 | date = October 2004 | pmid = 15138437 | doi = 10.1038/sj.npp.1300474 | doi-access = free }}</ref> and shows a complex interaction with ], increasing some effects but decreasing others, reflecting a role for the 5-HT<sub>2C</sub> receptor in regulation of the ] signalling system in the brain.<ref>{{cite journal | vauthors = Filip M, Cunningham KA | title = Serotonin 5-HT(2C) receptors in nucleus accumbens regulate expression of the hyperlocomotive and discriminative stimulus effects of cocaine | journal = Pharmacology, Biochemistry, and Behavior | volume = 71 | issue = 4 | pages = 745–56 | date = April 2002 | pmid = 11888566 | doi = 10.1016/s0091-3057(01)00741-9 | s2cid = 292398 }}</ref><ref>{{cite journal | vauthors = Filip M, Cunningham KA | title = Hyperlocomotive and discriminative stimulus effects of cocaine are under the control of serotonin(2C) (5-HT(2C)) receptors in rat prefrontal cortex | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 306 | issue = 2 | pages = 734–43 | date = August 2003 | pmid = 12721337 | doi = 10.1124/jpet.102.045716 | s2cid = 8338748 }}</ref><ref>{{cite journal | vauthors = Morita K, Hamamoto M, Arai S, Kitayama S, Irifune M, Kawahara M, Kihira K, Dohi T | display-authors = 6 | title = Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities | journal = Brain Research | volume = 1057 | issue = 1–2 | pages = 153–60 | date = September 2005 | pmid = 16125150 | doi = 10.1016/j.brainres.2005.07.049 | s2cid = 30437231 | url = http://ir.lib.hiroshima-u.ac.jp/files/public/0/115/20141016115526561231/Brain-Res_1057-1-2_153-160_2005-9-28.pdf }}</ref><ref>{{cite journal | vauthors = Dremencov E, Weizmann Y, Kinor N, Gispan-Herman I, Yadid G | title = Modulation of dopamine transmission by 5HT2C and 5HT3 receptors: a role in the antidepressant response | journal = Current Drug Targets | volume = 7 | issue = 2 | pages = 165–75 | date = February 2006 | pmid = 16475958 | doi = 10.2174/138945006775515491 }}</ref> |
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== See also == |
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{{pharm-stub}} |
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* ] |
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== References == |
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== References == |
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{{reflist}} |
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{{Reflist|2}} |
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{{Serotonergics}} |
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{{Serotonergics}} |
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