CTW0415

CTW0415
Identifiers
	IUPAC name (2S,4R)-N-[(2S)-2,3-dihydroxypropyl]-4-phenylpiperidine-2-carboxamide;
CAS Number	2772105-16-3;
PubChem CID	156010013;
ChemSpider	123962189;
ChEMBL	ChEMBL4633717;
Chemical and physical data
Formula	C15H22N2O3
Molar mass	278.352 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN[C@@H](C[C@@H]1C2=CC=CC=C2)C(=O)NC[C@@H](CO)O;
	InChI InChI=1S/C15H22N2O3/c18-10-13(19)9-17-15(20)14-8-12(6-7-16-14)11-4-2-1-3-5-11/h1-5,12-14,16,18-19H,6-10H2,(H,17,20)/t12-,13+,14+/m1/s1; Key:OQMSTMCQUFBTSL-RDBSUJKOSA-N;

CTW0415 is an experimental drug from the piperidine family, which acts as a selective positive allosteric modulator of the 5-HT_2C receptor, with higher potency than older drugs such as VA012. Structure-activity relationship studies showed that small variations to chain length and side chain substitution could lead to preferential binding for either 5-HT_2C or the related 5-HT_2A receptor, which subsequently led to the discovery of the related 5-HT_2A selective positive allosteric modulator CTW0404.^[1]^[2]^[3]

References

^ Wold EA, Garcia EJ, Wild CT, Miszkiel JM, Soto CA, Chen J, et al. (July 2020). "Discovery of 4-Phenylpiperidine-2-Carboxamide Analogues as Serotonin 5-HT_2C Receptor-Positive Allosteric Modulators with Enhanced Drug-like Properties". Journal of Medicinal Chemistry. 63 (14): 7529–7544. doi:10.1021/acs.jmedchem.9b01953. PMC 8434884. PMID 32567857.
^ Zamora JC, Merritt CR, Bolinger AA, Fox RG, Wild CT, Wold EA, et al. (2024). "Serendipitous Discovery of Novel 5-HT2AR Positive Allosteric Modulators (PAMs) Derived From 5-HT2CR PAM Scaffolds". The Journal of Pharmacology and Experimental Therapeutics. 389: 87. doi:10.1124/jpet.087.985400.
^ WO 2023/023287, Zhou J, Cunningham KA, Bolinger AA, Anastasio NC, "Novel heterocyclic compounds as serotonin (5-ht) 5-ht2a and 5-ht2c receptor positive allosteric modulators.", published 22 February 2024, assigned to The Board of Regents of the University of Texas System

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[1] Wold EA, Garcia EJ, Wild CT, Miszkiel JM, Soto CA, Chen J, et al. (July 2020). "Discovery of 4-Phenylpiperidine-2-Carboxamide Analogues as Serotonin 5-HT_2C Receptor-Positive Allosteric Modulators with Enhanced Drug-like Properties". Journal of Medicinal Chemistry. 63 (14): 7529–7544. doi:10.1021/acs.jmedchem.9b01953. PMC 8434884. PMID 32567857.

[Zamora_2024-2] Zamora JC, Merritt CR, Bolinger AA, Fox RG, Wild CT, Wold EA, et al. (2024). "Serendipitous Discovery of Novel 5-HT2AR Positive Allosteric Modulators (PAMs) Derived From 5-HT2CR PAM Scaffolds". The Journal of Pharmacology and Experimental Therapeutics. 389: 87. doi:10.1124/jpet.087.985400.

[3] WO 2023/023287, Zhou J, Cunningham KA, Bolinger AA, Anastasio NC, "Novel heterocyclic compounds as serotonin (5-ht) 5-ht2a and 5-ht2c receptor positive allosteric modulators.", published 22 February 2024, assigned to The Board of Regents of the University of Texas System

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