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

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14ClN.ClH
Molecular Weight 232.15
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LORCASERIN HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=ITIHHRMYZPNGRC-QRPNPIFTSA-N
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

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Recent advancements in drug treatment of obesity.
2012 Oct
The new weight-loss drugs, lorcaserin and phentermine-topiramate: slim pickings?
2014 Apr
Drug safety evaluation of naltrexone/bupropion for the treatment of obesity.
2014 Jun
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 Fri Dec 15 15:41:11 UTC 2023
Edited
by admin
on Fri Dec 15 15:41:11 UTC 2023
Record UNII
0QJF08GDPE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LORCASERIN HYDROCHLORIDE ANHYDROUS
DASH  
Common Name English
LORCASERIN HYDROCHLORIDE
MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Preferred Name English
1H-3-BENZAZEPINE, 8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-, HYDROCHLORIDE (1:1), (1R)-
Systematic Name English
APD-356
Code English
LORCASERIN HYDROCHLORIDE [VANDF]
Common Name English
LORCASERIN HYDROCHLORIDE [MI]
Common Name English
LORCASERIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
LORCASERIN HYDROCHLORIDE [USAN]
Common Name English
Lorcaserin hydrochloride [WHO-DD]
Common Name English
APD356
Code English
LORQESS
Brand Name English
1H-3-BENZAZEPINE, 8-CHLORO-2,3,4,5-TETRAHYDRO-1-METHYL-, HYDROCHLORIDE, (1R)-
Systematic Name English
(1R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride
Systematic Name English
LORCASERIN HCL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
Code System Code Type Description
DRUG BANK
DBSALT000111
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
FDA UNII
0QJF08GDPE
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
MERCK INDEX
m6908
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY Merck Index
DAILYMED
0QJF08GDPE
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
SMS_ID
100000128163
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
NCI_THESAURUS
C76103
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
RXCUI
1808546
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
ALTERNATIVE
RXCUI
1300700
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID60233650
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
EVMPD
SUB34927
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
CAS
846589-98-8
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
PUBCHEM
11673085
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
USAN
RR-89
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
CHEBI
65350
Created by admin on Fri Dec 15 15:41:11 UTC 2023 , Edited by admin on Fri Dec 15 15:41:11 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY