SB-258585

SB-258585
Identifiers
IUPAC name
  • 4-Iodo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]benzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
Chemical and physical data
FormulaC18H22IN3O3S
Molar mass487.36 g·mol−1
3D model (JSmol)
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
 ☒NcheckY (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

  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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