SB-258585

SB-258585
Identifiers
	IUPAC name 4-Iodo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzenesulfonamide;
CAS Number	209480-63-7 ;
PubChem CID	3248571;
IUPHAR/BPS	3232;
ChemSpider	2498938 ;
UNII	54BP69J53F;
ChEMBL	ChEMBL60264 ;
CompTox Dashboard (EPA)	DTXSID801026944 ;
Chemical and physical data
Formula	C18H22IN3O3S
Molar mass	487.36 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C3CN(C)CCN3c1cc(ccc1OC)NS(=O)(=O)c2ccc(I)cc2;
	InChI InChI=1S/C18H22IN3O3S/c1-21-9-11-22(12-10-21)17-13-15(5-8-18(17)25-2)20-26(23,24)16-6-3-14(19)4-7-16/h3-8,13,20H,9-12H2,1-2H3 ; Key:BDHMSYNBSBZCAF-UHFFFAOYSA-N ;
	(what is this?) (verify)

SB-258585 is a drug which is used in scientific research. It acts as a potent, selective and orally active 5-HT₆ receptor antagonist, with a Ki of 8.9nM.^[1] It is used in its ¹²⁵I radiolabelled form to map the distribution of 5-HT₆ receptors in the brain.^[2]^[3]

SB-258585 and other 5-HT₆ antagonists show nootropic effects in animal studies,^[4]^[5] as well as antidepressant and anxiolytic effects,^[6] and have been proposed as potential novel treatments for cognitive disorders such as schizophrenia and Alzheimer's disease.

References

^ Hirst WD, Minton JA, Bromidge SM, Moss SF, Latter AJ, Riley G, et al. (August 2000). "Characterization of [(125)I]-SB-258585 binding to human recombinant and native 5-HT(6) receptors in rat, pig and human brain tissue". British Journal of Pharmacology. 130 (7): 1597–605. doi:10.1038/sj.bjp.0703458. PMC 1572217. PMID 10928963.
^ Roberts JC, Reavill C, East SZ, Harrison PJ, Patel S, Routledge C, Leslie RA (April 2002). "The distribution of 5-HT(6) receptors in rat brain: an autoradiographic binding study using the radiolabelled 5-HT(6) receptor antagonist [(125)I]SB-258585". Brain Research. 934 (1): 49–57. doi:10.1016/S0006-8993(02)02360-0. PMID 11937069. S2CID 140209933.
^ East SZ, Burnet PW, Leslie RA, Roberts JC, Harrison PJ (September 2002). "5-HT6 receptor binding sites in schizophrenia and following antipsychotic drug administration: autoradiographic studies with [125I]SB-258585". Synapse. 45 (3): 191–9. doi:10.1002/syn.10097. PMID 12112397. S2CID 25909618.
^ Stean TO, Hirst WD, Thomas DR, Price GW, Rogers D, Riley G, et al. (April 2002). "Pharmacological profile of SB-357134: a potent, selective, brain penetrant, and orally active 5-HT(6) receptor antagonist". Pharmacology, Biochemistry, and Behavior. 71 (4): 645–54. doi:10.1016/S0091-3057(01)00742-0. PMID 11888556. S2CID 34925312.
^ Loiseau F, Dekeyne A, Millan MJ (January 2008). "Pro-cognitive effects of 5-HT6 receptor antagonists in the social recognition procedure in rats: implication of the frontal cortex". Psychopharmacology. 196 (1): 93–104. doi:10.1007/s00213-007-0934-5. PMID 17922111. S2CID 35795618.
^ Wesołowska A, Nikiforuk A, Stachowicz K (September 2007). "Anxiolytic-like and antidepressant-like effects produced by the selective 5-HT6 receptor antagonist SB-258585 after intrahippocampal administration to rats". Behavioural Pharmacology. 18 (5–6): 439–46. doi:10.1097/FBP.0b013e3282d28f9c. PMID 17762512. S2CID 20105974.

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[1] Hirst WD, Minton JA, Bromidge SM, Moss SF, Latter AJ, Riley G, et al. (August 2000). "Characterization of [(125)I]-SB-258585 binding to human recombinant and native 5-HT(6) receptors in rat, pig and human brain tissue". British Journal of Pharmacology. 130 (7): 1597–605. doi:10.1038/sj.bjp.0703458. PMC 1572217. PMID 10928963.

[2] Roberts JC, Reavill C, East SZ, Harrison PJ, Patel S, Routledge C, Leslie RA (April 2002). "The distribution of 5-HT(6) receptors in rat brain: an autoradiographic binding study using the radiolabelled 5-HT(6) receptor antagonist [(125)I]SB-258585". Brain Research. 934 (1): 49–57. doi:10.1016/S0006-8993(02)02360-0. PMID 11937069. S2CID 140209933.

[3] East SZ, Burnet PW, Leslie RA, Roberts JC, Harrison PJ (September 2002). "5-HT6 receptor binding sites in schizophrenia and following antipsychotic drug administration: autoradiographic studies with [125I]SB-258585". Synapse. 45 (3): 191–9. doi:10.1002/syn.10097. PMID 12112397. S2CID 25909618.

[4] Stean TO, Hirst WD, Thomas DR, Price GW, Rogers D, Riley G, et al. (April 2002). "Pharmacological profile of SB-357134: a potent, selective, brain penetrant, and orally active 5-HT(6) receptor antagonist". Pharmacology, Biochemistry, and Behavior. 71 (4): 645–54. doi:10.1016/S0091-3057(01)00742-0. PMID 11888556. S2CID 34925312.

[5] Loiseau F, Dekeyne A, Millan MJ (January 2008). "Pro-cognitive effects of 5-HT6 receptor antagonists in the social recognition procedure in rats: implication of the frontal cortex". Psychopharmacology. 196 (1): 93–104. doi:10.1007/s00213-007-0934-5. PMID 17922111. S2CID 35795618.

[6] Wesołowska A, Nikiforuk A, Stachowicz K (September 2007). "Anxiolytic-like and antidepressant-like effects produced by the selective 5-HT6 receptor antagonist SB-258585 after intrahippocampal administration to rats". Behavioural Pharmacology. 18 (5–6): 439–46. doi:10.1097/FBP.0b013e3282d28f9c. PMID 17762512. S2CID 20105974.

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v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol