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;
UNII	3FN59X9DPR;
CompTox Dashboard (EPA)	DTXSID90457468 ;
Chemical and physical data
Formula	C34H45N3O
Molar mass	511.754 g·mol−1
3D model (JSmol)	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] 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,^[2] In animal studies, SB-699551 was found to block cue-mediated responding to LSD, again suggesting an antipsychotic type of activity.^[3] It also reduces the viability of certain types of cancer cells in vitro, suggesting the 5-HT_5A receptor as a possible target for novel chemotherapy drugs.^[4]^[5]

References

^ Thomas DR, Soffin EM, Roberts C, Kew JN, de la Flor RM, Dawson LA, et al. (September 2006). "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. 51 (3): 566–577. doi:10.1016/j.neuropharm.2006.04.019. PMID 16846620. S2CID 543423.
^ Nikiforuk A, Hołuj M, Kos T, Popik P (June 2016). "The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia". Neuropharmacology. 105: 351–360. doi:10.1016/j.neuropharm.2016.01.035. PMID 26826431. S2CID 31557477.
^ Popik P, Krawczyk M, Kuziak A, Bugno R, Hogendorf A, Staroń J, Nikiforuk A (November 2019). "Serotonin type 5A receptor antagonists inhibit D-lysergic acid diethylamide discriminatory cue in rats". Journal of Psychopharmacology. 33 (11): 1447–1455. doi:10.1177/0269881119867603. PMID 31452444. S2CID 201733534.
^ Itsumi M, Shiota M, Sekino Y, Ushijima M, Kashiwagi E, Takeuchi A, et al. (August 2020). "High-throughput screen identifies 5-HT receptor as a modulator of AR and a therapeutic target for prostate cancer". The Prostate. 80 (11): 885–894. doi:10.1002/pros.24022. PMID 32483877. S2CID 219174471.
^ Gwynne WD, Shakeel MS, Girgis-Gabardo A, Kim KH, Ford E, Dvorkin-Gheva A, et al. (August 2020). "Antagonists of the serotonin receptor 5A target human breast tumor initiating cells". BMC Cancer. 20 (1): 724. doi:10.1186/s12885-020-07193-6. PMC 7404930. PMID 32758183.

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[1] Thomas DR, Soffin EM, Roberts C, Kew JN, de la Flor RM, Dawson LA, et al. (September 2006). "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. 51 (3): 566–577. doi:10.1016/j.neuropharm.2006.04.019. PMID 16846620. S2CID 543423.

[2] Nikiforuk A, Hołuj M, Kos T, Popik P (June 2016). "The effects of a 5-HT5A receptor antagonist in a ketamine-based rat model of cognitive dysfunction and the negative symptoms of schizophrenia". Neuropharmacology. 105: 351–360. doi:10.1016/j.neuropharm.2016.01.035. PMID 26826431. S2CID 31557477.

[3] Popik P, Krawczyk M, Kuziak A, Bugno R, Hogendorf A, Staroń J, Nikiforuk A (November 2019). "Serotonin type 5A receptor antagonists inhibit D-lysergic acid diethylamide discriminatory cue in rats". Journal of Psychopharmacology. 33 (11): 1447–1455. doi:10.1177/0269881119867603. PMID 31452444. S2CID 201733534.

[pmid32483877-4] Itsumi M, Shiota M, Sekino Y, Ushijima M, Kashiwagi E, Takeuchi A, et al. (August 2020). "High-throughput screen identifies 5-HT receptor as a modulator of AR and a therapeutic target for prostate cancer". The Prostate. 80 (11): 885–894. doi:10.1002/pros.24022. PMID 32483877. S2CID 219174471.

[pmid32758183-5] Gwynne WD, Shakeel MS, Girgis-Gabardo A, Kim KH, Ford E, Dvorkin-Gheva A, et al. (August 2020). "Antagonists of the serotonin receptor 5A target human breast tumor initiating cells". BMC Cancer. 20 (1): 724. doi:10.1186/s12885-020-07193-6. PMC 7404930. PMID 32758183.

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