U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14ClN
Molecular Weight 195.689
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LORCASERIN

SMILES

C[C@H]1CNCCC2=C1C=C(Cl)C=C2

InChI

InChIKey=XTTZERNUQAFMOF-QMMMGPOBSA-N
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

HIDE SMILES / InChI
Molecular Formula C11H14ClN
Molecular Weight 195.689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://www.eisai.com/news/news201464.html

Lorcaserin, currently marketed under the trade name Belviq and previously Lorqess during development, is a weight-loss drug developed by Arena Pharmaceuticals. Lorcaserin is a selective 5-HT2C receptor agonist, and in vitro testing of the drug showed reasonable selectivity for 5-HT2C over other related targets. 5-HT2C receptors are located almost exclusively in the brain, and can be found in the choroid plexus, cortex, hippocampus, cerebellum, amygdala, thalamus, and hypothalamus. The activation of 5-HT2C receptors in the hypothalamus is supposed to activate proopiomelanocortin (POMC) production and consequently promote weight loss through satiety. This hypothesis is supported by clinical trials and other studies. While it is generally thought that 5-HT2C receptors help to regulate appetite as well as mood, and endocrine secretion, the exact mechanism of appetite regulation is not yet known. Lorcaserin has shown 100x selectivity for 5-HT2C versus the closely related 5-HT2B receptor, and 17x selectivity over the 5-HT2A receptor

CNS Activity

CNS Active
3897
Curator's Comment: Lorcaserin acts at 5-HT2C receptors in the central nervous system (CNS), particularly the hypothalamus, to reduce appetite

Originator

Arena Pharmaceuticals
15
Curator's Comment: Discovered and developed by Arena Pharmaceuticals, Inc.

Approval Year

2012
614
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2637
 15.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8307
Belviq

Approved Use

Indicated as an adjunct to a reduced-calorie diet and increased physical activity for chronic weight management in adults with an initial body mass index (BMI) of 30 kg/m^2 or greater (obese) or 27 kg/m^2 or greater (overweight) in the presence of at least one weight-related comorbid condition, (e.g., hypertension, dyslipidemia, type 2 diabetes)

Launch Date

1.34075515E12
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:65353
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65353
ChemicalBook
CB61011744
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61011744
ZINC
ZINC000006733300
http://zinc15.docking.org/substances/ZINC000006733300
PubMed

PubMed

TitleDatePubMed
Recent advancements in drug treatment of obesity.
2012 Oct
The new weight-loss drugs, lorcaserin and phentermine-topiramate: slim pickings?
2014 Apr
Nonincretin drugs in later-stage development.
2014 Jan
Drug safety evaluation of naltrexone/bupropion for the treatment of obesity.
2014 Jun
[Cutting-edge of medicine; the prospects of novel anti-obesity drugs].
2014 Mar 10
Patents

Patents

07704993
4
08168782
4
08404675
4
08501935
4
08802845
4
20070142357
4
US2010331312
5
US2014213579
4
US8168782
4

Sample Use Guides

In Vivo Use Guide
One tablet of 10 mg twice daily
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Radioligand binding assays for human and rat 5-HT2A, 5-HT2B, and 5-HT2C receptors were developed using the 5-HT2 agonist [125I] DOI asadioligand.
Lorcaserin was evaluated for its ability to inhibit neurotransmitter uptake into rat brain synaptosomes. Lorcaserin weakly inhibited norepinephrine (EC50 = 2500 nM), serotonin (EC50 = 1400 nM), and dopamine (EC50 = 12,000 nM) uptake.
Substance Class Chemical
Created
by admin
on Fri Dec 16 17:51:26 UTC 2022
Edited
by admin
on Fri Dec 16 17:51:26 UTC 2022
Record UNII
637E494O0Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LORCASERIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
LORCASERIN [MI]
Common Name English
lorcaserin [INN]
Common Name English
LORCASERIN [VANDF]
Common Name English
(1R)-8-CHLORO-1-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE
Systematic Name English
1H-3-BENZAZEPINE, 8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-, (1R)-
Systematic Name English
Lorcaserin [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 828021
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
WHO-ATC A08AA11
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
FDA ORPHAN DRUG 758920
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
LIVERTOX NBK548834
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
NCI_THESAURUS C47794
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
WHO-VATC QA08AA11
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
NDF-RT N0000185010
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
FDA ORPHAN DRUG 565816
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
DEA NO. 1625
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
Code System Code Type Description
DAILYMED
637E494O0Z
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
NDF-RT
N0000185009
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY Serotonin 2c Receptor Agonists [MoA]
ChEMBL
CHEMBL360328
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
HSDB
8128
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
MESH
C506658
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
NDF-RT
N0000182137
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
CHEBI
65353
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
WIKIPEDIA
LORCASERIN
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
INN
8765
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
PUBCHEM
11658860
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
EVMPD
SUB34935
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
NCI_THESAURUS
C76102
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
DRUG CENTRAL
4374
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
RXCUI
1300701
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY RxNorm
FDA UNII
637E494O0Z
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
EPA CompTox
DTXSID3048659
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
CAS
616202-92-7
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
MERCK INDEX
M6908
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY Merck Index
IUPHAR
2941
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
DRUG BANK
DB04871
Created by admin on Fri Dec 16 17:51:27 UTC 2022 , Edited by admin on Fri Dec 16 17:51:27 UTC 2022
PRIMARY
Related Record Type Details
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B17
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
5-HYDROXYTRYPTAMINE RECEPTOR 2C
TARGET -> AGONIST
Ki
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A9
METABOLIC ENZYME -> SUBSTRATE
HUMAN SULFOTRANSFERASE 2A1
METABOLIC ENZYME -> SUBSTRATE
ESTROGEN SULFOTRANSFERASE
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
5-HYDROXYTRYPTAMINE RECEPTOR 2C
TARGET -> AGONIST
EC50
5-HYDROXYTRYPTAMINE RECEPTOR 2B
OFF TARGET->WEAK AGONIST
EC50
CYTOCHROME P450 1A1
METABOLIC ENZYME -> SUBSTRATE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> NON-INHIBITOR
ARYL SULFOTRANSFERASE 2
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2A6
METABOLIC ENZYME -> SUBSTRATE
Structure of LORCASERIN HYDROCHLORIDE, ADSORBED ON SILICON DIOXIDE (1:2 W/W)
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B15
METABOLIC ENZYME -> SUBSTRATE
Structure of LORCASERIN HYDROCHLORIDE HEMIHYDRATE
SALT/SOLVATE -> PARENT
5-HYDROXYTRYPTAMINE RECEPTOR 2A
OFF-TARGET->AGONIST
Ki
CYTOCHROME P450 2E1
METABOLIC ENZYME -> SUBSTRATE
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B7
METABOLIC ENZYME -> SUBSTRATE
5-HYDROXYTRYPTAMINE RECEPTOR 2A
OFF TARGET->WEAK AGONIST
EC50
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> NON-SUBSTRATE
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
Structure of LORCASERIN HYDROCHLORIDE ANHYDROUS
SALT/SOLVATE -> PARENT
5-HYDROXYTRYPTAMINE RECEPTOR 2B
OFF TARGET->WEAK AGONIST
Ki
Related Record Type Details
Structure of (2S,3S,4S,5R)-6-(((5R)-7-CHLORO-5-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPIN-1-YL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Structure of (2S,3S,4S,5R)-6-(((5R)-7-CHLORO-5-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPIN-8-YL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Structure of 1-HYDROXY LORCASERIN
METABOLITE INACTIVE -> PARENT
MINOR
URINE
Structure of (2S,3S,4S,5R)-6-(((5R)-7-CHLORO-5-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPIN-6-YL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Structure of (2S,3S,4S,5R)-6-(((5R)-7-CHLORO-5-METHYL-2-OXO-4,5-DIHYDRO-1H-3-BENZAZEPIN-3-YL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
M8 (1-carboxyl glucuronide) was excreted in urine greater than 10% of dose, but it was a minor metabolite in plasma.
URINE
Structure of ((5R)-7-CHLORO-5-METHYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPIN-8-YL) HYDROGEN SULFATE
METABOLITE -> PARENT
MINOR
PLASMA
Structure of LORCASERIN N-HYDROXY
METABOLITE -> PARENT
Structure of LORCASERIN N-CARBAMOYL GLUCURONIDE
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
Structure of LORCASERIN SULFAMATE
METABOLITE INACTIVE -> PARENT
MINOR
URINE
Structure of (2S,3S,4S,5R)-6-(((5R)-7-CHLORO-5-METHYL-1,2,4,5-TETRAHYDRO-3-BENZAZEPIN-3-YL)OXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Structure of LORCASERIN N-GLUCURONIDE
METABOLITE INACTIVE -> PARENT
MINOR
PLASMA; URINE
Structure of (5R)-7-CHLORO-2,3,4,5-TETRAHYDRO-5-METHYL-1H-3-BENZAZEPIN-1-OL
METABOLITE -> PARENT
Structure of LORCASERIN 7-HYDROXY
METABOLITE -> PARENT
Related Record Type Details
Structure of LORCASERIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Single Dose Administration

Tmax PHARMACOKINETIC Single Dose Administration

NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966