SB-258585

SB-258585

Systematic (IUPAC) name
4-Iodo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzenesulfonamide
Identifiers
CAS Number	209480-63-7
PubChem	CID 3248571
IUPHAR/BPS	3232
ChemSpider	2498938
ChEMBL	CHEMBL60264
Chemical data
Formula	C18H22IN3O3S
Molar mass	487.354 g/mol
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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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

1. Hirst, WD; Minton, JA; Bromidge, SM; Moss, SF; Latter, AJ; Riley, G; Routledge, C; Middlemiss, DN; Price, GW (2000). "Characterization of 125I-SB-258585 binding to human recombinant and native 5-HT6 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 (2002). "The distribution of 5-HT(6) receptors in rat brain: an autoradiographic binding study using the radiolabelled 5-HT(6) receptor antagonist (125)ISB-258585". Brain Research 934 (1): 49–57. doi:10.1016/S0006-8993(02)02360-0. PMID 11937069.
3. East, SZ; Burnet, PW; Leslie, RA; Roberts, JC; Harrison, PJ (2002). "5-HT6 receptor binding sites in schizophrenia and following antipsychotic drug administration: autoradiographic studies with 125ISB-258585". Synapse 45 (3): 191–9. doi:10.1002/syn.10097. PMID 12112397.
4. Stean, TO; Hirst, WD; Thomas, DR; Price, GW; Rogers, D; Riley, G; Bromidge, SM; Serafinowska, HT; et al. (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.
5. Loiseau, F; Dekeyne, A; Millan, MJ (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.
6. Wesołowska, A; Nikiforuk, A; Stachowicz, K (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.