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 ;
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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

^ 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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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
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^N Key:BDHMSYNBSBZCAF-UHFFFAOYSA-N^N
^NY (what is this?) (verify)