Chemistry: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 ;
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 ;
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Short description: Chemical compound

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

↑ "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. August 2000. doi:10.1038/sj.bjp.0703458. PMID 10928963.
↑ "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. April 2002. doi:10.1016/S0006-8993(02)02360-0. PMID 11937069.
↑ "5-HT6 receptor binding sites in schizophrenia and following antipsychotic drug administration: autoradiographic studies with [125I]SB-258585". Synapse 45 (3): 191–9. September 2002. doi:10.1002/syn.10097. PMID 12112397.
↑ "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. April 2002. doi:10.1016/S0091-3057(01)00742-0. PMID 11888556.
↑ "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. January 2008. doi:10.1007/s00213-007-0934-5. PMID 17922111.
↑ "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. September 2007. doi:10.1097/FBP.0b013e3282d28f9c. PMID 17762512.

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[1] "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. August 2000. doi:10.1038/sj.bjp.0703458. PMID 10928963.

[2] "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. April 2002. doi:10.1016/S0006-8993(02)02360-0. PMID 11937069.

[3] "5-HT6 receptor binding sites in schizophrenia and following antipsychotic drug administration: autoradiographic studies with [125I]SB-258585". Synapse 45 (3): 191–9. September 2002. doi:10.1002/syn.10097. PMID 12112397.

[4] "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. April 2002. doi:10.1016/S0091-3057(01)00742-0. PMID 11888556.

[5] "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. January 2008. doi:10.1007/s00213-007-0934-5. PMID 17922111.

[6] "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. September 2007. doi:10.1097/FBP.0b013e3282d28f9c. PMID 17762512.

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v t e Piperazines
Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	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 Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil 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 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine 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 Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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Identifiers

IUPAC name 4-Iodo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzenesulfonamide
CAS Number	209480-63-7^Y
PubChem CID	3248571
IUPHAR/BPS	3232
ChemSpider	2498938^N
UNII	54BP69J53F
ChEMBL	ChEMBL60264^N
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^N Key:BDHMSYNBSBZCAF-UHFFFAOYSA-N^N
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