lorcaserin   Click here for help

GtoPdb Ligand ID: 2941

Synonyms: APD-356 | Belviq®
Approved drug
lorcaserin is an approved drug (FDA (2012))
Compound class: Synthetic organic
Comment: Lorcaserin is a selective, orally available and CNS active serotonin 2C receptor agonist that modulates appetite [2-3,5-6]. Cardiovascular safety in obese/overweight patients was reported by Bohula et al. (2018) [1].
Clinical formulations contain lorcaserin hydrochloride (PubChem CID 11673085).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 12.03
Molecular weight 195.08
XLogP 2.45
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES Clc1ccc2c(c1)C(C)CNCC2
Isomeric SMILES Clc1ccc2c(c1)[C@@H](C)CNCC2
InChI InChI=1S/C11H14ClN/c1-8-7-13-5-4-9-2-3-10(12)6-11(8)9/h2-3,6,8,13H,4-5,7H2,1H3/t8-/m0/s1
InChI Key XTTZERNUQAFMOF-QMMMGPOBSA-N
References
1. Bohula EA, Wiviott SD, McGuire DK, Inzucchi SE, Kuder J, Im K, Fanola CL, Qamar A, Brown C, Budaj A et al.. (2018)
Cardiovascular Safety of Lorcaserin in Overweight or Obese Patients.
N Engl J Med, 379 (12): 1107-1117. DOI: 10.1056/NEJMoa1808721 [PMID:30145941]
2. Halford JC. (2010)
Lorcaserin--not a new weapon in the battle with appetite.
Nat Rev Endocrinol, 6 (12): 663-4. [PMID:21102648]
3. Jia J, Xiong L, Chen S. (2010)
Trial of lorcaserin for weight management.
N Engl J Med, 363 (25): 2468-9; author reply 2469-70. [PMID:21158670]
4. Smith B, Smith J. (2005)
5HT2C receptor modulators.
Patent number: US6953787 B2. Assignee: Arena Pharmaceuticals, Inc.. Priority date: 12/04/2002. Publication date: 11/10/2005.
5. Thomsen WJ, Grottick AJ, Menzaghi F, Reyes-Saldana H, Espitia S, Yuskin D, Whelan K, Martin M, Morgan M, Chen W et al.. (2008)
Lorcaserin, a novel selective human 5-hydroxytryptamine2C agonist: in vitro and in vivo pharmacological characterization.
J Pharmacol Exp Ther, 325 (2): 577-87. [PMID:18252809]
6. von Haehling S. (2010)
Trial of lorcaserin for weight management.
N Engl J Med, 363 (25): 2468; author reply 2469-70. [PMID:21158671]