Lorcaserin hydrochlorideProduct ingredient for Lorcaserin

Name
Lorcaserin hydrochloride
Drug Entry
Lorcaserin

Lorcaserin (previously APD-356), a highly selective 5HT2C receptor agonist, is used for the treatment of obesity. It has been shown to reduce body weight and food intake in animal models of obesity, and it is thought that targeting the 5HT2C receptor may alter body weight by regulating satiety. Lorcaserin is marketed as a salt form called Belviq, which is lorcaserin hydrochloride.

In February 2020, the FDA issued a Drug Safety Communication requesting the manufacturer of Belviq (lorcaserin hydrochloride tablets, 10 mg) and Belviq XR (lorcaserin hydrochloride extended-release tablets, 20 mg) to voluntarily withdraw these products from the U.S. market, and the company has submitted a request to voluntarily withdraw the drug. This decision was based on the results of a clinical trial assessing the risk of heart-related problems that found that patients treated with lorcaserin may have a higher risk of cancer.3,4

Accession Number
DBSALT000111
Structure
Synonyms
(1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride / Lorcaserin HCl / Lorcaserin hydrochloride anhydrous
External IDs
APD-356 / APD356
UNII
0QJF08GDPE
CAS Number
846589-98-8
Weight
Average: 232.15
Monoisotopic: 231.058154899
Chemical Formula
C11H15Cl2N
InChI Key
ITIHHRMYZPNGRC-QRPNPIFTSA-N
InChI
InChI=1S/C11H14ClN.ClH/c1-8-7-13-5-4-9-2-3-10(12)6-11(8)9;/h2-3,6,8,13H,4-5,7H2,1H3;1H/t8-;/m0./s1
IUPAC Name
(1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
SMILES
Cl.[H][C@]1(C)CNCCC2=C1C=C(Cl)C=C2
PubChem Compound
11673085
ChemSpider
9847815
ChEBI
65350
ChEMBL
CHEMBL2095211
Wikipedia
Lorcaserin
Predicted Properties
PropertyValueSource
Water Solubility0.0709 mg/mLALOGPS
logP3ALOGPS
logP2.83Chemaxon
logS-3.4ALOGPS
pKa (Strongest Basic)10.12Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area12.03 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity56.65 m3·mol-1Chemaxon
Polarizability21.51 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon