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

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

Originator

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
15.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
PubMed

PubMed

TitleDatePubMed
Nonincretin drugs in later-stage development.
2014 Jan
Patents

Sample Use Guides

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 Wed Jul 05 23:10:09 UTC 2023
Edited
by admin
on Wed Jul 05 23:10:09 UTC 2023
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 Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
WHO-ATC A08AA11
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
FDA ORPHAN DRUG 758920
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
LIVERTOX NBK548834
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
NCI_THESAURUS C47794
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
WHO-VATC QA08AA11
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
NDF-RT N0000185010
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
FDA ORPHAN DRUG 565816
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
DEA NO. 1625
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
Code System Code Type Description
DAILYMED
637E494O0Z
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
NDF-RT
N0000185009
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY Serotonin 2c Receptor Agonists [MoA]
ChEMBL
CHEMBL360328
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
HSDB
8128
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
MESH
C506658
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
NDF-RT
N0000182137
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY Cytochrome P450 2D6 Inhibitors [MoA]
CHEBI
65353
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
SMS_ID
100000128165
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
WIKIPEDIA
LORCASERIN
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
INN
8765
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
PUBCHEM
11658860
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
EVMPD
SUB34935
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
NCI_THESAURUS
C76102
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
DRUG CENTRAL
4374
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
RXCUI
1300701
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY RxNorm
FDA UNII
637E494O0Z
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048659
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
CAS
616202-92-7
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
MERCK INDEX
M6908
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY Merck Index
IUPHAR
2941
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
DRUG BANK
DB04871
Created by admin on Wed Jul 05 23:10:09 UTC 2023 , Edited by admin on Wed Jul 05 23:10:09 UTC 2023
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
Ki
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
EC50
OFF TARGET->WEAK AGONIST
EC50
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> NON-INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
OFF-TARGET->AGONIST
Ki
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
OFF TARGET->WEAK AGONIST
EC50
TRANSPORTER -> NON-SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
OFF TARGET->WEAK AGONIST
Ki
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METABOLITE -> PARENT
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METABOLITE -> PARENT
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METABOLITE -> PARENT
M8 (1-carboxyl glucuronide) was excreted in urine greater than 10% of dose, but it was a minor metabolite in plasma.
URINE
METABOLITE -> PARENT
MINOR
PLASMA
METABOLITE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
URINE
METABOLITE INACTIVE -> PARENT
MINOR
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METABOLITE -> PARENT
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METABOLITE INACTIVE -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Single Dose Administration

Tmax PHARMACOKINETIC Single Dose Administration