SB-258719

SB-258719
Identifiers
	IUPAC name (1R)-3,N-dimethyl-N-[1-methyl-3-(4-methylpiperidin-1-yl)propyl]benzenesulfonamide;
CAS Number	195199-95-2 ;
PubChem CID	5312148;
IUPHAR/BPS	281;
ChemSpider	4471578 ;
ChEMBL	ChEMBL12264 ;
Chemical and physical data
Formula	C18H32N2O2S
Molar mass	340.53 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccc(C)cc1S(=O)(=O)N(C)C(C)CCN(CC2)CCC2C;
	InChI InChI=1S/C18H30N2O2S/c1-15-8-11-20(12-9-15)13-10-17(3)19(4)23(21,22)18-7-5-6-16(2)14-18/h5-7,14-15,17H,8-13H2,1-4H3/t17-/m1/s1 ; Key:AGVNHDNTFYHZNL-QGZVFWFLSA-N ;
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SB-258719 is a drug developed by GlaxoSmithKline which acts as a selective 5-HT₇ receptor partial inverse agonist,[1] and was the first such ligand identified for 5-HT₇.[2] Its use in research has mainly been in demonstrating the potential use for 5-HT₇ agonists as potential novel analgesics, due to the ability of SB-258719 to block the analgesic effects of a variety of 5-HT₇ agonists across several different testing models.[3][4][5][6]

References

Mahé C, Loetscher E, Feuerbach D, Müller W, Seiler MP, Schoeffter P (July 2004). "Differential inverse agonist efficacies of SB-258719, SB-258741 and SB-269970 at human recombinant serotonin 5-HT7 receptors". European Journal of Pharmacology. 495 (2–3): 97–102. doi:10.1016/j.ejphar.2004.05.033. PMID 15249157.
Forbes IT, Dabbs S, Duckworth DM, Jennings AJ, King FD, Lovell PJ, et al. (February 1998). "(R)-3,N-dimethyl-N-[1-methyl-3-(4-methyl-piperidin-1-yl) propyl]benzenesulfonamide: the first selective 5-HT7 receptor antagonist". Journal of Medicinal Chemistry. 41 (5): 655–7. doi:10.1021/jm970519e. PMID 9513592.
Brenchat A, Romero L, García M, Pujol M, Burgueño J, Torrens A, et al. (February 2009). "5-HT7 receptor activation inhibits mechanical hypersensitivity secondary to capsaicin sensitization in mice". Pain. 141 (3): 239–47. doi:10.1016/j.pain.2008.11.009. PMID 19118950.
Yanarates O, Dogrul A, Yildirim V, Sahin A, Sizlan A, Seyrek M, et al. (March 2010). "Spinal 5-HT7 receptors play an important role in the antinociceptive and antihyperalgesic effects of tramadol and its metabolite, O-Desmethyltramadol, via activation of descending serotonergic pathways". Anesthesiology. 112 (3): 696–710. doi:10.1097/ALN.0b013e3181cd7920. PMID 20179508.
Brenchat A, Nadal X, Romero L, Ovalle S, Muro A, Sánchez-Arroyos R, et al. (June 2010). "Pharmacological activation of 5-HT7 receptors reduces nerve injury-induced mechanical and thermal hypersensitivity". Pain. 149 (3): 483–94. doi:10.1016/j.pain.2010.03.007. PMID 20399562.
Brenchat A, Ejarque M, Zamanillo D, Vela JM, Romero L (August 2011). "Potentiation of morphine analgesia by adjuvant activation of 5-HT7 receptors". Journal of Pharmacological Sciences. 116 (4): 388–91. doi:10.1254/jphs.11039sc. PMID 21778664.

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[pmid15249157-1] Mahé C, Loetscher E, Feuerbach D, Müller W, Seiler MP, Schoeffter P (July 2004). "Differential inverse agonist efficacies of SB-258719, SB-258741 and SB-269970 at human recombinant serotonin 5-HT7 receptors". European Journal of Pharmacology. 495 (2–3): 97–102. doi:10.1016/j.ejphar.2004.05.033. PMID 15249157.

[pmid9513592-2] Forbes IT, Dabbs S, Duckworth DM, Jennings AJ, King FD, Lovell PJ, et al. (February 1998). "(R)-3,N-dimethyl-N-[1-methyl-3-(4-methyl-piperidin-1-yl) propyl]benzenesulfonamide: the first selective 5-HT7 receptor antagonist". Journal of Medicinal Chemistry. 41 (5): 655–7. doi:10.1021/jm970519e. PMID 9513592.

[pmid19118950-3] Brenchat A, Romero L, García M, Pujol M, Burgueño J, Torrens A, et al. (February 2009). "5-HT7 receptor activation inhibits mechanical hypersensitivity secondary to capsaicin sensitization in mice". Pain. 141 (3): 239–47. doi:10.1016/j.pain.2008.11.009. PMID 19118950.

[pmid20179508-4] Yanarates O, Dogrul A, Yildirim V, Sahin A, Sizlan A, Seyrek M, et al. (March 2010). "Spinal 5-HT7 receptors play an important role in the antinociceptive and antihyperalgesic effects of tramadol and its metabolite, O-Desmethyltramadol, via activation of descending serotonergic pathways". Anesthesiology. 112 (3): 696–710. doi:10.1097/ALN.0b013e3181cd7920. PMID 20179508.

[pmid20399562-5] Brenchat A, Nadal X, Romero L, Ovalle S, Muro A, Sánchez-Arroyos R, et al. (June 2010). "Pharmacological activation of 5-HT7 receptors reduces nerve injury-induced mechanical and thermal hypersensitivity". Pain. 149 (3): 483–94. doi:10.1016/j.pain.2010.03.007. PMID 20399562.

[pmid21778664-6] Brenchat A, Ejarque M, Zamanillo D, Vela JM, Romero L (August 2011). "Potentiation of morphine analgesia by adjuvant activation of 5-HT7 receptors". Journal of Pharmacological Sciences. 116 (4): 388–91. doi:10.1254/jphs.11039sc. PMID 21778664.