Identification
- Summary
Lorcaserin is a serotonin 2C receptor agonist used in conjunction with physical activity and calorie restriction for weight loss in obese patients with a body mass index (BMI) of 30 and above, and in overweight patients with weight-related comorbidities.
- Generic Name
- Lorcaserin
- DrugBank Accession Number
- DB04871
- Background
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
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Lorcaserin (DB04871)
- Weight
- Average: 195.69
Monoisotopic: 195.0814772 - Chemical Formula
- C11H14ClN
- Synonyms
- Lorcaserin
- Lorqess
Pharmacology
- Indication
For the treatment of obesity, as an adjunct to a reduced-calorie diet and increased physical activity.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Obesity •••••••••••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Lorcaserin produced a dose-dependent weight loss over a 12-week period by promoting satiety and decreasing food consumption.
- Mechanism of action
Although the exact mechanism is unknown, it is believed to involve the selective activation of 5-HT2C receptors in the anorexigenic pro-opiomelanocortin neurons in the arcuate nucleus of the hypothalamus. This results in decreased food intake and satiety by promoting the release of alpha-melanocortin stimulating hormone, which acts on melanocortin-4 receptors.
Target Actions Organism U5-hydroxytryptamine receptor 2C Not Available Humans - Absorption
Lorcaserin has a peak plasma concentration of about 1.5 - 2 hours, but the bioavailability was not determined.
- Volume of distribution
The volume of distribution was not determined, but lorcaserin distributes to the central nervous system and cerebrospinal fluid.
- Protein binding
Lorcaserin hydrochloride has a plasma protein binding of approximately 70%.
- Metabolism
Lorcaserin has extensive hepatic metabolism producing inactive compounds. Lorcaserin sulfamate (M1) is the major metabolite circulating in the plasma, and N-carbamoyl glucuronide lorcaserin (M5) is the major metabolite in urine. Other minor metabolites that are both excreted in urine are glucuronide or sulfate conjugates.
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- Route of elimination
Lorcaserin is eliminated by hepatic metabolism, and the metabolites are eliminated mostly in the urine (92.3%) and some through feces (2.2%).
- Half-life
The plasma half life is approximately 11 hours.
- Clearance
The clearance value was not determined.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Most common adverse reactions include hypoglycemia (diabetic patients), headache, back pain,fatigue, decrease in lymphocytes,upper respiratory tract infection, and nasopharyngitis. Moreover, the safety and efficacy of coadministration with other weight loss products has not been established, and cardiovascular effects on mortality and morbidity have not been established.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Lorcaserin is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Lorcaserin which could result in a higher serum level. Abametapir The serum concentration of Lorcaserin can be increased when it is combined with Abametapir. Abatacept The metabolism of Lorcaserin can be increased when combined with Abatacept. Abiraterone The serum concentration of Lorcaserin can be increased when it is combined with Abiraterone. - Food Interactions
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Lorcaserin hydrochloride 0QJF08GDPE 846589-98-8 ITIHHRMYZPNGRC-QRPNPIFTSA-N Lorcaserin hydrochloride hemihydrate REV26SR2B4 856681-05-5 WRZCAWKMTLRWPR-VSODYHHCSA-N - International/Other Brands
- Lorqess
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Belviq Tablet 10 mg/1 Oral Eisai Inc. 2012-06-27 2022-04-30 US 
Belviq XR Tablet, film coated, extended release 20 mg/1 Oral Eisai Inc. 2016-07-15 2022-05-31 US
Categories
- ATC Codes
- A08AA11 — Lorcaserin
- Drug Categories
- Alimentary Tract and Metabolism
- Antidepressive Agents
- Antiobesity Preparations, Excl. Diet Products
- Central Nervous System Depressants
- Centrally Acting Antiobesity Products
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 2c Receptor Agonists
- Serotonin 5-HT2 Receptor Agonists
- Serotonin 5-HT2C Receptor Agonists
- Serotonin Agents
- Serotonin Modulators
- Serotonin Receptor Agonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Not Available
- Direct Parent
- Benzazepines
- Alternative Parents
- Azepines / Aralkylamines / Benzenoids / Aryl chlorides / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azepine / Benzazepine / Benzenoid / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organochlorine compound, benzazepine (CHEBI:65353)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 637E494O0Z
- CAS number
- 616202-92-7
- InChI Key
- XTTZERNUQAFMOF-QMMMGPOBSA-N
- 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
- IUPAC Name
- (1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
- SMILES
- C[C@H]1CNCCC2=CC=C(Cl)C=C12
References
- Synthesis Reference
Jandacek RJ: APD-356 (Arena). Curr Opin Investig Drugs. 2005 Oct;6(10):1051-6.
- General References
- Halford JC: Obesity drugs in clinical development. Curr Opin Investig Drugs. 2006 Apr;7(4):312-8. [Article]
- Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, Chen RR, Park DM, Prieto EB, Gallardo CS, Sengupta D, Dosa PI, Covel JA, Ren A, Webb RR, Beeley NR, Martin M, Morgan M, Espitia S, Saldana HR, Bjenning C, Whelan KT, Grottick AJ, Menzaghi F, Thomsen WJ: Discovery and structure-activity relationship of (1R)-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (Lorcaserin), a selective serotonin 5-HT2C receptor agonist for the treatment of obesity. J Med Chem. 2008 Jan 24;51(2):305-13. Epub 2007 Dec 21. [Article]
- Federal Register: Determination That BELVIQ (Lorcaserin Hydrochloride) Tablets, 10 Milligrams, and BELVIQ XR (Lorcaserin Hydrochloride) Extended-Release Tablets, 20 Milligrams, Were Withdrawn From Sale for Reasons of Safety or Effectiveness [Link]
- US Food & Drug Administration: FDA Requests Voluntary Withdrawal of Weight-Loss Medication After Clinical Trial Shows an Increased Occurrence of Cancer [Link]
- External Links
- KEGG Drug
- D06613
- PubChem Compound
- 11658860
- PubChem Substance
- 310264855
- ChemSpider
- 9833595
- BindingDB
- 50161646
- 1300701
- ChEBI
- 65353
- ChEMBL
- CHEMBL360328
- ZINC
- ZINC000006733300
- PDBe Ligand
- T4U
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Lorcaserin
- PDB Entries
- 8dpf / 8dph / 8dpi
- FDA label
- Download (401 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Obesity / Weight Loss 1 4 Completed Treatment Cardiovascular Disease (CVD) / High Cardiovascular Risk / Obesity / Overweight / Type 2 Diabetes Mellitus 1 4 Completed Treatment Chronic Weight Management therapy 1 4 Terminated Other Overweight and Obesity 1 4 Terminated Treatment Obesity 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 10 mg/1 Tablet, film coated, extended release Oral 20 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6953787 No 2005-10-11 2023-04-10 US US7514422 No 2009-04-07 2023-04-10 US US7977329 No 2011-07-12 2023-04-10 US US8207158 No 2012-06-26 2023-04-10 US US8273734 No 2012-09-25 2023-04-10 US US8546379 No 2013-10-01 2023-04-10 US US8367657 No 2013-02-05 2023-04-10 US US8575149 No 2013-11-05 2023-04-10 US US9169213 No 2015-10-27 2032-12-06 US US8999970 No 2015-04-07 2033-02-07 US US8980881 No 2015-03-17 2025-12-20 US US8946207 No 2015-02-03 2024-06-16 US US8168624 No 2012-05-01 2029-04-18 US US8697686 No 2014-04-15 2025-12-20 US US7169401 No 2007-01-30 2023-07-18 US US9770455 No 2017-09-26 2031-08-31 US US10226471 No 2019-03-12 2031-08-31 US US10463676 No 2019-11-05 2031-08-31 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Water solubility is greater than 400 mg/mL. From FDA label. - Predicted Properties
Property Value Source Water Solubility 0.0709 mg/mL ALOGPS logP 3 ALOGPS logP 2.83 Chemaxon logS -3.4 ALOGPS pKa (Strongest Basic) 10.12 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 56.65 m3·mol-1 Chemaxon Polarizability 21.51 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-a0f5c77c22d01408db9a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0900000000-8f86c4702336215e4670 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-69a1754e34631fd859aa Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9300000000-ba9d7590224a519381d1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100000000-c3e738d793f0170ac110 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-3900000000-5e907a09f20ac5028797 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 138.28056 predictedDeepCCS 1.0 (2019) [M+H]+ 141.20586 predictedDeepCCS 1.0 (2019) [M+Na]+ 150.34312 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51820.705 Da
References
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- Curator comments
- Data supporting this interaction are obtained from an in vitro study.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Nadp binding
- Specific Function
- This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
- Gene Name
- FMO1
- Uniprot ID
- Q01740
- Uniprot Name
- Dimethylaniline monooxygenase [N-oxide-forming] 1
- Molecular Weight
- 60310.285 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Usmani KA, Chen WG, Sadeque AJ: Identification of human cytochrome P450 and flavin-containing monooxygenase enzymes involved in the metabolism of lorcaserin, a novel selective human 5-hydroxytryptamine 2C agonist. Drug Metab Dispos. 2012 Apr;40(4):761-71. doi: 10.1124/dmd.111.043414. Epub 2012 Jan 20. [Article]
Drug created at October 20, 2007 10:39 / Updated at February 20, 2024 23:31