SB-258585

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

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
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
^NY (what is this?)  (verify)

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, 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.
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.
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.
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.
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.