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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Lurasidone
- Accession Number
- DB08815
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Lurasidone is an atypical antipsychotic developed by Dainippon Sumitomo Pharma. It was approved by the U.S. Food and Drug Administration (FDA) for treatment of schizophrenia on October 29, 2010 and is currently pending approval for the treatment of bipolar disorder in the United States.
- Structure
Structure for Lurasidone (DB08815)
- Synonyms
- Lurasidona
- Lurasidone
- Lurasidonum
- External IDs
- SM-13496
- Product Ingredients
Ingredient UNII CAS InChI Key Lurasidone hydrochloride O0P4I5851I 367514-88-3 NEKCRUIRPWNMLK-SCIYSFAVSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataLatuda Tablet, film coated 60 mg/1 Oral REMEDYREPACK INC. 2019-01-23 Not applicable US 
Latuda Tablet, film coated 20 mg/1 Oral REMEDYREPACK INC. 2019-01-24 Not applicable US Latuda Tablet 20 mg Oral Sunovion 2014-04-09 Not applicable Canada 
Latuda Tablet, film coated 120 mg/1 Oral REMEDYREPACK INC. 2019-03-06 Not applicable US Latuda Tablet 60 mg Oral Sunovion 2014-03-14 Not applicable Canada Latuda Tablet, film coated 80 mg/1 Oral Bushu Pharmaceutical, LTD. 2010-10-28 Not applicable US Latuda Tablet 120 mg Oral Sunovion 2012-09-06 Not applicable Canada Latuda Tablet, film coated 40 mg/1 Oral Bushu Pharmaceutical, LTD. 2010-10-28 Not applicable US Latuda Tablet 80 mg Oral Sunovion 2012-09-05 Not applicable Canada Latuda Tablet 40 mg Oral Sunovion 2012-09-06 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataLurasidone Hydrochloride Tablet, coated 120 mg/1 Oral Amneal Pharmaceuticals LLC 2019-01-03 2019-02-18 US Lurasidone Hydrochloride Tablet, coated 80 mg/1 Oral Amneal Pharmaceuticals LLC 2019-01-03 2019-02-18 US Lurasidone Hydrochloride Tablet, coated 60 mg/1 Oral Amneal Pharmaceuticals LLC 2019-01-03 2019-02-18 US Lurasidone Hydrochloride Tablet, coated 40 mg/1 Oral Amneal Pharmaceuticals LLC 2019-01-03 2019-02-18 US Lurasidone Hydrochloride Tablet, coated 20 mg/1 Oral Amneal Pharmaceuticals LLC 2019-01-03 2019-02-18 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Categories
- Adrenergic Agents
- Adrenergic alpha-2 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Antidepressive Agents
- Antipsychotic Agents
- Antipsychotic Agents (Second Generation [Atypical])
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Heterocyclic Compounds, Fused-Ring
- Hyperglycemia-Associated Agents
- Indole Derivatives
- Isoindoles
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Potential QTc-Prolonging Agents
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Antagonists
- Serotonin 5-HT1A Receptor Antagonists
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Sulfur Compounds
- Thiazoles
- Tranquilizing Agents
- UNII
- 22IC88528T
- CAS number
- 367514-87-2
- Weight
- Average: 492.676
Monoisotopic: 492.255897106 - Chemical Formula
- C28H36N4O2S
- InChI Key
- PQXKDMSYBGKCJA-CVTJIBDQSA-N
- InChI
- InChI=1S/C28H36N4O2S/c33-27-24-18-9-10-19(15-18)25(24)28(34)32(27)17-21-6-2-1-5-20(21)16-30-11-13-31(14-12-30)26-22-7-3-4-8-23(22)35-29-26/h3-4,7-8,18-21,24-25H,1-2,5-6,9-17H2/t18-,19+,20-,21-,24+,25-/m0/s1
- IUPAC Name
- (1R,2S,6R,7S)-4-{[(1R,2R)-2-{[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]methyl}cyclohexyl]methyl}-4-azatricyclo[5.2.1.0^{2,6}]decane-3,5-dione
- SMILES
- [H][C@@]12[C@H]3CC[C@H](C3)[C@]1([H])C(=O)N(C[C@@H]1CCCC[C@H]1CN1CCN(CC1)C1=NSC3=CC=CC=C13)C2=O
Pharmacology
- Indication
Treatment of schizophrenia.
- Associated Conditions
- Pharmacodynamics
Lurasidone is a benzothiazol derivative that is an antagonist and binds with high affinity to Dopamine-2 (D2) (Ki = 0.994 nM), 5-HT2A (Ki = 0.47 nM) receptors, and 5-HT7 receptors (Ki = 0.495 nM). It also binds with moderate affinity to alpha-2C adrenergic receptors (Ki = 10.8 nM) and is a partial agonist at 5-HT1A receptors (Ki = 6.38 nM). Its actions on histaminergic and muscarinic receptors are negligible.
- Mechanism of action
Lurasidone is an atypical antipsychotic that is a D2 and 5-HT2A (mixed serotonin and dopamine activity) to improve cognition. It is thought that antagonism of serotonin receptors can improve negative symptoms of psychoses and reduce the extrapyramidal side effects that are often associated with typical antipsychotics.
Target Actions Organism ADopamine D2 receptor antagonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans U5-hydroxytryptamine receptor 7 antagonistHumans U5-hydroxytryptamine receptor 1A antagonistHumans UAlpha-2C adrenergic receptor antagonistHumans UAlpha-2A adrenergic receptor Not Available Humans - Absorption
Lurasidone is readily absorbed and quickly reaches maximal concentrations (Cmax) within 1-4 hours. When taken with food, there is a two-fold increase in exposure and time to maximal concentration is increased by 0.5-1.5 hours. This occurs regardless of fat or caloric content.
Bioavailability = 9-19%.- Volume of distribution
6173 L
- Protein binding
~99% bound to serum proteins.
- Metabolism
Lurasidone is metabolized by CYP3A4 in which its major active metabolite is referred to as ID-14283 (25% of parent exposure). Its two minor metabolites are referred to as ID14326 and ID11614 which make up 3% and 1% of parent exposure respectively. Its two non-active metabolites are referred to as ID-20219 and ID-20220.
- Route of elimination
Urine (~9%) and feces (~80%)
- Half life
40 mg dose= 18 hours 120 mg - 160 mg dose = 29-37 hours
- Clearance
3902 mL/min
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- 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 Unlock Additional Data(R)-warfarin The risk or severity of adverse effects can be increased when Lurasidone is combined with (R)-warfarin. (S)-Warfarin The risk or severity of adverse effects can be increased when Lurasidone is combined with (S)-Warfarin. 1-benzylimidazole The risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Lurasidone. 2,4-thiazolidinedione The therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Lurasidone. 2,5-Dimethoxy-4-ethylamphetamine The therapeutic efficacy of Lurasidone can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine. 2,5-Dimethoxy-4-ethylthioamphetamine The therapeutic efficacy of Lurasidone can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine. 3,5-Dinitrocatechol The therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Lurasidone. 4-Bromo-2,5-dimethoxyamphetamine The therapeutic efficacy of Lurasidone can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine. 4-Bromo-2,5-dimethoxyphenethylamine The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Lurasidone. 4-hydroxycoumarin The risk or severity of adverse effects can be increased when Lurasidone is combined with 4-hydroxycoumarin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with food. The manufacturer recommends co-administration with at least 350 calories.
References
- General References
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Tarazi FI, Stahl SM: Iloperidone, asenapine and lurasidone: a primer on their current status. Expert Opin Pharmacother. 2012 Sep;13(13):1911-22. doi: 10.1517/14656566.2012.712114. Epub 2012 Jul 31. [PubMed:22849428]
- External Links
- KEGG Drug
- D04820
- PubChem Compound
- 213046
- PubChem Substance
- 175427100
- ChemSpider
- 184739
- BindingDB
- 85222
- RxNav
- 1040028
- ChEBI
- 70735
- ChEMBL
- CHEMBL1237021
- ZINC
- ZINC000003927822
- PharmGKB
- PA166129557
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Lurasidone
- ATC Codes
- N05AE05 — Lurasidone
- AHFS Codes
- 28:16.08.04 — Atypical Antipsychotics
- FDA label
- Download (452 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Tablet Oral 120 mg Tablet Oral 20 mg Tablet Oral 40 mg Tablet Oral 60 mg Tablet Oral 80 mg Tablet, film coated Oral 120 mg/1 Tablet, film coated Oral 20 mg/1 Tablet, film coated Oral 40 mg/1 Tablet, film coated Oral 60 mg/1 Tablet, film coated Oral 80 mg/1 Tablet, coated Oral 120 mg/1 Tablet, coated Oral 20 mg/1 Tablet, coated Oral 40 mg/1 Tablet, coated Oral 60 mg/1 Tablet, coated Oral 80 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Unlock Additional DataUS9174975 Yes 2015-11-03 2026-12-25 US US9259423 Yes 2016-02-16 2031-11-23 US US8729085 Yes 2014-05-20 2026-11-26 US US5532372 Yes 1996-07-02 2019-01-02 US US8883794 Yes 2014-11-11 2026-11-26 US USRE45573 Yes 2015-06-23 2025-12-23 US US9555027 No 2017-01-31 2026-05-26 US US9815827 No 2017-11-14 2024-02-20 US US9827242 No 2017-11-28 2031-05-23 US US9907794 No 2018-03-06 2026-05-26 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00789 mg/mL ALOGPS logP 5.25 ALOGPS logP 4.56 ChemAxon logS -4.8 ALOGPS pKa (Strongest Basic) 8.5 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 56.75 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 139.33 m3·mol-1 ChemAxon Polarizability 56.26 Å3 ChemAxon Number of Rings 7 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9907 Caco-2 permeable + 0.5257 P-glycoprotein substrate Substrate 0.6029 P-glycoprotein inhibitor I Inhibitor 0.6713 P-glycoprotein inhibitor II Inhibitor 0.73 Renal organic cation transporter Inhibitor 0.5487 CYP450 2C9 substrate Non-substrate 0.7897 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Substrate 0.5922 CYP450 1A2 substrate Non-inhibitor 0.677 CYP450 2C9 inhibitor Inhibitor 0.6714 CYP450 2D6 inhibitor Non-inhibitor 0.8292 CYP450 2C19 inhibitor Inhibitor 0.7439 CYP450 3A4 inhibitor Non-inhibitor 0.7835 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8126 Ames test Non AMES toxic 0.6477 Carcinogenicity Non-carcinogens 0.8986 Biodegradation Not ready biodegradable 0.9959 Rat acute toxicity 2.4051 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6636 hERG inhibition (predictor II) Inhibitor 0.5858
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- N-arylpiperazines
- Alternative Parents
- Aromatic monoterpenoids / Isoindolones / Benzothiazoles / Dialkylarylamines / N-alkylpiperazines / Aminothiazoles / Benzenoids / Pyrrolidine-2-ones / Imidolactams / N-substituted carboxylic acid imides show 11 more
- Substituents
- N-arylpiperazine / Aromatic monoterpenoid / Monoterpenoid / Norbornane monoterpenoid / Isoindolone / 1,2-benzothiazole / Isoindoline / Isoindole or derivatives / Dialkylarylamine / N-alkylpiperazine show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- N-arylpiperazine, dicarboximide, bridged compound, 1,2-benzisothiazole (CHEBI:70735)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
- Gene Name
- HTR7
- Uniprot ID
- P34969
- Uniprot Name
- 5-hydroxytryptamine receptor 7
- Molecular Weight
- 53554.43 Da
References
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- 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. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Protein homodimerization activity
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
- Gene Name
- ADRA2C
- Uniprot ID
- P18825
- Uniprot Name
- Alpha-2C adrenergic receptor
- Molecular Weight
- 49521.585 Da
References
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Tarazi FI, Stahl SM: Iloperidone, asenapine and lurasidone: a primer on their current status. Expert Opin Pharmacother. 2012 Sep;13(13):1911-22. doi: 10.1517/14656566.2012.712114. Epub 2012 Jul 31. [PubMed:22849428]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- George M, Amrutheshwar R, Rajkumar RP, Kattimani S, Dkhar SA: Newer antipsychotics and upcoming molecules for schizophrenia. Eur J Clin Pharmacol. 2013 Aug;69(8):1497-509. doi: 10.1007/s00228-013-1498-4. Epub 2013 Apr 2. [PubMed:23545936]
- Lurasidone HCl FDA Label [Link]
Drug created on July 24, 2011 11:04 / Updated on July 08, 2020 06:59
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