SB-699551

SB-699551
Identifiers
	IUPAC name 3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-([(2-phenylethyl)amino]methyl)-4-biphenylyl)methyl]propanamide;
CAS Number	791789-61-2 ;
PubChem CID	11168182;
ChemSpider	9343277;
Chemical and physical data
Formula	C34H45N3O
Molar mass	511.739 g/mol
3D model (Jmol)	Interactive image;
	SMILES C2CCCC2CCC(=O)N(CCN(C)C)Cc(cc3)ccc3-c(cc1)ccc1CNCCc4ccccc4 ;
	InChI InChI=1S/C34H45N3O/c1-36(2)24-25-37(34(38)21-16-28-10-6-7-11-28)27-31-14-19-33(20-15-31)32-17-12-30(13-18-32)26-35-23-22-29-8-4-3-5-9-29/h3-5,8-9,12-15,17-20,28,35H,6-7,10-11,16,21-27H2,1-2H3 ; Key:SEQAMPXQRKYYQF-UHFFFAOYSA-N ;
(verify)

SB-699551 is a drug which was the first compound developed to act as a selective antagonist for the serotonin receptor 5-HT_5A, with selectivity of around 100x over other serotonin receptor subtypes.^[1] The function of the 5-HT_5A receptor remains poorly defined, but SB-699551 was found to modulate serotonin release from neurons, suggesting it acts as a presynaptic inhibitory autoreceptor similar to the 5-HT_1B and 5-HT_1D receptors.^[2] Multiple therapeutic roles have been suggested for 5-HT_5A ligands due to the presence of this receptor in several areas of the brain, but research is still at an early stage,^[3] with one possible application being the currently difficult to treat negative symptoms of schizophrenia.^[4]

References[edit]

^ Corbett, DF; Heightman, TD; Moss, SF; Bromidge, SM; Coggon, SA; Longley, MJ; Roa, AM; Williams, JA; Thomas, DR (2005). "Discovery of a potent and selective 5-ht5A receptor antagonist by high-throughput chemistry". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4014–8. doi:10.1016/j.bmcl.2005.06.024. PMID 16002289.
^ Thomas DR, Soffin EM, Roberts C, Kew JN, de la Flor RM, Dawson LA, Fry VA, Coggon SA, Faedo S, Hayes PD, Corbett DF, Davies CH, Hagan JJ. SB-699551-A (3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-{[(2-phenylethyl)amino]methyl}-4-biphenylyl)methyl]propanamide dihydrochloride), a novel 5-ht5A receptor-selective antagonist, enhances 5-HT neuronal function: Evidence for an autoreceptor role for the 5-ht5A receptor in guinea pig brain. Neuropharmacology. 2006 Sep;51(3):566-77. PMID 16846620
^ Thomas, DR (2006). "5-ht5A receptors as a therapeutic target". Pharmacology & therapeutics. 111 (3): 707–14. doi:10.1016/j.pharmthera.2005.12.006. PMID 16516972.
^ Nikiforuk A, Hołuj M, Kos T, Popik P. The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia. Neuropharmacology. 2016 Jun;105:351-60. doi: 10.1016/j.neuropharm.2016.01.035. PMID 26826431

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[1] Corbett, DF; Heightman, TD; Moss, SF; Bromidge, SM; Coggon, SA; Longley, MJ; Roa, AM; Williams, JA; Thomas, DR (2005). "Discovery of a potent and selective 5-ht5A receptor antagonist by high-throughput chemistry". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4014–8. doi:10.1016/j.bmcl.2005.06.024. PMID 16002289.

[2] Thomas DR, Soffin EM, Roberts C, Kew JN, de la Flor RM, Dawson LA, Fry VA, Coggon SA, Faedo S, Hayes PD, Corbett DF, Davies CH, Hagan JJ. SB-699551-A (3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-{[(2-phenylethyl)amino]methyl}-4-biphenylyl)methyl]propanamide dihydrochloride), a novel 5-ht5A receptor-selective antagonist, enhances 5-HT neuronal function: Evidence for an autoreceptor role for the 5-ht5A receptor in guinea pig brain. Neuropharmacology. 2006 Sep;51(3):566-77. PMID 16846620

[3] Thomas, DR (2006). "5-ht5A receptors as a therapeutic target". Pharmacology & therapeutics. 111 (3): 707–14. doi:10.1016/j.pharmthera.2005.12.006. PMID 16516972.

[4] Nikiforuk A, Hołuj M, Kos T, Popik P. The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia. Neuropharmacology. 2016 Jun;105:351-60. doi: 10.1016/j.neuropharm.2016.01.035. PMID 26826431

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SB-699551

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Identifiers

IUPAC name 3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-([(2-phenylethyl)amino]methyl)-4-biphenylyl)methyl]propanamide
CAS Number	791789-61-2^Y
PubChem CID	11168182
ChemSpider	9343277
Chemical and physical data
Formula	C₃₄H₄₅N₃O
Molar mass	511.739 g/mol
3D model (Jmol)	Interactive image
SMILES C2CCCC2CCC(=O)N(CCN(C)C)Cc(cc3)ccc3-c(cc1)ccc1CNCCc4ccccc4
InChI InChI=1S/C34H45N3O/c1-36(2)24-25-37(34(38)21-16-28-10-6-7-11-28)27-31-14-19-33(20-15-31)32-17-12-30(13-18-32)26-35-23-22-29-8-4-3-5-9-29/h3-5,8-9,12-15,17-20,28,35H,6-7,10-11,16,21-27H2,1-2H3 Key:SEQAMPXQRKYYQF-UHFFFAOYSA-N
(verify)