Chemistry:SB-399885

SB-399885
Identifiers
	IUPAC name N-(3,5-Dichloro-2-methoxyphenyl)-4-methoxy-3-(1-piperazinyl)benzenesulfonamide;
CAS Number	402713-80-8 ;
PubChem CID	6918649;
IUPHAR/BPS	3241;
ChemSpider	5293842;
ChEMBL	ChEMBL1210710 ;
Chemical and physical data
Formula	C18H21Cl2N3O4S
Molar mass	446.34 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C3CNCCN3c2cc(ccc2OC)S(=O)(=O)Nc(c1OC)cc(Cl)cc1Cl;
	InChI InChI=1S/C18H21Cl2N3O4S/c1-26-17-4-3-13(11-16(17)23-7-5-21-6-8-23)28(24,25)22-15-10-12(19)9-14(20)18(15)27-2/h3-4,9-11,21-22H,5-8H2,1-2H3; Key:ATKZKAYWARYLBW-UHFFFAOYSA-N;
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Short description: Chemical compound

SB-399885 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 9.0nM. SB-399885 and other 5-HT₆ antagonists show nootropic effects in animal studies,^[1]^[2] as well as antidepressant and anxiolytic effects which are comparable to and synergistic with drugs such as imipramine and diazepam,^[3]^[4]^[5] and have been proposed as potential novel treatments for cognitive disorders such as schizophrenia^[6] and Alzheimer's disease.

References

↑ "Oral administration of the 5-HT6 receptor antagonists SB-357134 and SB-399885 improves memory formation in an autoshaping learning task". Pharmacology, Biochemistry, and Behavior 81 (3): 673–82. July 2005. doi:10.1016/j.pbb.2005.05.005. PMID 15964617.
↑ "SB-399885 is a potent, selective 5-HT6 receptor antagonist with cognitive enhancing properties in aged rat water maze and novel object recognition models". European Journal of Pharmacology 553 (1–3): 109–19. December 2006. doi:10.1016/j.ejphar.2006.09.049. PMID 17069795.
↑ "Effects of the brain-penetrant and selective 5-HT6 receptor antagonist SB-399885 in animal models of anxiety and depression". Neuropharmacology 52 (5): 1274–83. April 2007. doi:10.1016/j.neuropharm.2007.01.007. PMID 17320917.
↑ "The anxiolytic-like effect of the selective 5-HT6 receptor antagonist SB-399885: the impact of benzodiazepine receptors". European Journal of Pharmacology 580 (3): 355–60. February 2008. doi:10.1016/j.ejphar.2007.11.022. PMID 18096153.
↑ "The selective 5-HT(6) receptor antagonist SB-399885 enhances anti-immobility action of antidepressants in rats". European Journal of Pharmacology 582 (1–3): 88–93. March 2008. doi:10.1016/j.ejphar.2007.12.013. PMID 18234190.
↑ "5-HT6 receptor antagonist SB-399885 potentiates haloperidol and risperidone-induced dopamine efflux in the medial prefrontal cortex or hippocampus". Brain Research 1134 (1): 70–8. February 2007. doi:10.1016/j.brainres.2006.11.060. PMID 17207474.

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[1] "Oral administration of the 5-HT6 receptor antagonists SB-357134 and SB-399885 improves memory formation in an autoshaping learning task". Pharmacology, Biochemistry, and Behavior 81 (3): 673–82. July 2005. doi:10.1016/j.pbb.2005.05.005. PMID 15964617.

[2] "SB-399885 is a potent, selective 5-HT6 receptor antagonist with cognitive enhancing properties in aged rat water maze and novel object recognition models". European Journal of Pharmacology 553 (1–3): 109–19. December 2006. doi:10.1016/j.ejphar.2006.09.049. PMID 17069795.

[3] "Effects of the brain-penetrant and selective 5-HT6 receptor antagonist SB-399885 in animal models of anxiety and depression". Neuropharmacology 52 (5): 1274–83. April 2007. doi:10.1016/j.neuropharm.2007.01.007. PMID 17320917.

[4] "The anxiolytic-like effect of the selective 5-HT6 receptor antagonist SB-399885: the impact of benzodiazepine receptors". European Journal of Pharmacology 580 (3): 355–60. February 2008. doi:10.1016/j.ejphar.2007.11.022. PMID 18096153.

[5] "The selective 5-HT(6) receptor antagonist SB-399885 enhances anti-immobility action of antidepressants in rats". European Journal of Pharmacology 582 (1–3): 88–93. March 2008. doi:10.1016/j.ejphar.2007.12.013. PMID 18234190.

[6] "5-HT6 receptor antagonist SB-399885 potentiates haloperidol and risperidone-induced dopamine efflux in the medial prefrontal cortex or hippocampus". Brain Research 1134 (1): 70–8. February 2007. doi:10.1016/j.brainres.2006.11.060. PMID 17207474.

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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 N-(3,5-Dichloro-2-methoxyphenyl)-4-methoxy-3-(1-piperazinyl)benzenesulfonamide
CAS Number	402713-80-8^Y
PubChem CID	6918649
IUPHAR/BPS	3241
ChemSpider	5293842
ChEMBL	ChEMBL1210710^N
Chemical and physical data
Formula	C₁₈H₂₁Cl₂N₃O₄S
Molar mass	446.34 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C3CNCCN3c2cc(ccc2OC)S(=O)(=O)Nc(c1OC)cc(Cl)cc1Cl
InChI InChI=1S/C18H21Cl2N3O4S/c1-26-17-4-3-13(11-16(17)23-7-5-21-6-8-23)28(24,25)22-15-10-12(19)9-14(20)18(15)27-2/h3-4,9-11,21-22H,5-8H2,1-2H3 Key:ATKZKAYWARYLBW-UHFFFAOYSA-N
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