SB-699551
{{Short description|Chemical compound}}
{{Drugbox
| verifiedrevid = 449560048
| IUPAC_name = 3-cyclopentyl-N-[2-(dimethylamino)ethyl]-N-[(4'-([(2-phenylethyl)amino]methyl)-4-biphenylyl)methyl]propanamide
| image = SB-699,551_structure.png
| width = 240
| tradename =
| legal_status =
| routes_of_administration =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 791789-61-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3FN59X9DPR
| PubChem = 11168182
| ChemSpiderID = 9343277
| C=34 | H=45 | N=3 | O=1
| smiles = C2CCCC2CCC(=O)N(CCN(C)C)Cc(cc3)ccc3-c(cc1)ccc1CNCCc4ccccc4
| StdInChI = 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
| StdInChIKey = SEQAMPXQRKYYQF-UHFFFAOYSA-N
}}
SB-699551 is a drug which was the first compound developed to act as a selective antagonist for the serotonin receptor 5-HT5A, with selectivity of around 100x over other serotonin receptor subtypes.{{cite journal | vauthors = 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 | display-authors = 6 | title = 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 | journal = Neuropharmacology | volume = 51 | issue = 3 | pages = 566–577 | date = September 2006 | pmid = 16846620 | doi = 10.1016/j.neuropharm.2006.04.019 | s2cid = 543423 }} Multiple therapeutic roles have been suggested for 5-HT5A ligands due to the presence of this receptor in several areas of the brain, but research is still at an early stage,{{cite journal | vauthors = Nikiforuk A, Hołuj M, Kos T, Popik P | title = The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia | journal = Neuropharmacology | volume = 105 | pages = 351–360 | date = June 2016 | pmid = 26826431 | doi = 10.1016/j.neuropharm.2016.01.035 | s2cid = 31557477 }} In animal studies, SB-699551 was found to block cue-mediated responding to LSD, again suggesting an antipsychotic type of activity.{{cite journal | vauthors = Popik P, Krawczyk M, Kuziak A, Bugno R, Hogendorf A, Staroń J, Nikiforuk A | title = Serotonin type 5A receptor antagonists inhibit D-lysergic acid diethylamide discriminatory cue in rats | journal = Journal of Psychopharmacology | volume = 33 | issue = 11 | pages = 1447–1455 | date = November 2019 | pmid = 31452444 | doi = 10.1177/0269881119867603 | s2cid = 201733534 }} It also reduces the viability of certain types of cancer cells in vitro, suggesting the 5-HT5A receptor as a possible target for novel chemotherapy drugs.{{cite journal | vauthors = Itsumi M, Shiota M, Sekino Y, Ushijima M, Kashiwagi E, Takeuchi A, Inokuchi J, Kajioka S, Uchiumi T, Eto M | display-authors = 6 | title = High-throughput screen identifies 5-HT receptor as a modulator of AR and a therapeutic target for prostate cancer | journal = The Prostate | volume = 80 | issue = 11 | pages = 885–894 | date = August 2020 | pmid = 32483877 | doi = 10.1002/pros.24022 | s2cid = 219174471 | doi-access = free }}{{cite journal | vauthors = Gwynne WD, Shakeel MS, Girgis-Gabardo A, Kim KH, Ford E, Dvorkin-Gheva A, Aarts C, Isaac M, Al-Awar R, Hassell JA | display-authors = 6 | title = Antagonists of the serotonin receptor 5A target human breast tumor initiating cells | journal = BMC Cancer | volume = 20 | issue = 1 | pages = 724 | date = August 2020 | pmid = 32758183 | pmc = 7404930 | doi = 10.1186/s12885-020-07193-6 | doi-access = free }}