Lurasidone

Identification

Summary

Lurasidone is an atypical antipsychotic used to treat schizophrenia and depressive episodes associated with bipolar I disorder.

Brand Names
Latuda
Generic Name
Lurasidone
DrugBank Accession Number
DB08815
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 492.676
Monoisotopic: 492.255897106
Chemical Formula
C28H36N4O2S
Synonyms
  • Lurasidona
  • Lurasidone
  • Lurasidonum
External IDs
  • SM-13496

Pharmacology

Indication

Treatment of schizophrenia.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
A5-hydroxytryptamine receptor 2A
antagonist
Humans
U5-hydroxytryptamine receptor 7
antagonist
Humans
U5-hydroxytryptamine receptor 1A
antagonist
Humans
UAlpha-2C adrenergic receptor
antagonist
Humans
UAlpha-2A adrenergic receptorNot AvailableHumans
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.

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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Lurasidone is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Lurasidone can be increased when it is combined with Abametapir.
AbirateroneThe metabolism of Lurasidone can be decreased when combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Lurasidone.
AcebutololLurasidone may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Lurasidone.
AcemetacinThe risk or severity of hypertension can be increased when Lurasidone is combined with Acemetacin.
AcenocoumarolThe risk or severity of adverse effects can be increased when Lurasidone is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Lurasidone.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Lurasidone.
Interactions
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Food Interactions
  • Avoid alcohol. The effects of alcohol could be made worse while taking Lurasidone.
  • Avoid grapefruit products. Grapefruit and grapefruit juice may affect the amount of Lurasidone in your blood.
  • Take with food. The manufacturer recommends co-administration with at least 350 calories.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Lurasidone hydrochlorideO0P4I5851I367514-88-3NEKCRUIRPWNMLK-SCIYSFAVSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LatudaTablet, film coated120 mg/1OralSunovion Pharmaceuticals Inc.2012-04-26Not applicableUS flag
LatudaTablet, film coated37 mgOralAziende Chimiche Riunite Angelini Francesco S.P.A.2020-12-16Not applicableEU flag
LatudaTablet, film coated74 mgOralAziende Chimiche Riunite Angelini Francesco S.P.A.2020-12-16Not applicableEU flag
LatudaTablet80 mgOralSunovion2012-09-05Not applicableCanada flag
LatudaTablet, film coated80 mg/1OralBushu Pharmaceutical, LTD.2010-10-28Not applicableUS flag
LatudaTablet, film coated18.5 mgOralAziende Chimiche Riunite Angelini Francesco S.P.A.2020-12-16Not applicableEU flag
LatudaTablet, film coated40 mg/1OralSunovion Pharmaceuticals Inc.2010-10-28Not applicableUS flag63402 0304 30 nlmimage10 2c3e1650
LatudaTablet, film coated80 mg/1OralREMEDYREPACK INC.2021-02-02Not applicableUS flag
LatudaTablet, film coated37 mgOralAziende Chimiche Riunite Angelini Francesco S.P.A.2020-12-16Not applicableEU flag
LatudaTablet, film coated74 mgOralAziende Chimiche Riunite Angelini Francesco S.P.A.2020-12-16Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Lurasidone HydrochlorideTablet, film coated120 mg/1OralAlembic Pharmaceuticals Inc.2021-05-12Not applicableUS flag
Lurasidone HydrochlorideTablet, coated40 mg/1OralAmneal Pharmaceuticals LLC2019-01-032019-02-18US flag
Lurasidone HydrochlorideTablet, film coated40 mg/1OralTorrent Pharmaceuticals Limited2018-12-28Not applicableUS flag
Lurasidone HydrochlorideTablet, film coated40 mg/1OralAlembic Pharmaceuticals Inc.2021-05-12Not applicableUS flag
Lurasidone HydrochlorideTablet, film coated40 mg/1OralAlembic Pharmaceuticals Limited2021-05-12Not applicableUS flag
Lurasidone HydrochlorideTablet, coated80 mg/1OralAmneal Pharmaceuticals LLC2019-01-032019-02-18US flag
Lurasidone HydrochlorideTablet, film coated80 mg/1OralAlembic Pharmaceuticals Limited2021-05-12Not applicableUS flag
Lurasidone HydrochlorideTablet, film coated120 mg/1OralTorrent Pharmaceuticals Limited2018-12-28Not applicableUS flag
Lurasidone HydrochlorideTablet, film coated80 mg/1OralAlembic Pharmaceuticals Inc.2021-05-12Not applicableUS flag
Lurasidone HydrochlorideTablet, film coated20 mg/1OralTorrent Pharmaceuticals Limited2018-12-28Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
LURALEPLurasidone (40 mg) + Lurasidone (80 mg)Tablet, coatedOralMSN LABS AMERICAS S A S2020-12-092025-12-29Colombia flag
LURALEPLurasidone (40 mg) + Lurasidone (80 mg)Tablet, coatedOralMSN LABS AMERICAS S A S2020-12-092025-12-29Colombia flag

Categories

ATC Codes
N05AE05 — Lurasidone
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-benzothiazole / 1,2-thiazolamine / 2-pyrrolidone / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aromatic monoterpenoid / Azacycle / Azole / Benzenoid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-arylpiperazine, dicarboximide, bridged compound, 1,2-benzisothiazole (CHEBI:70735)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
22IC88528T
CAS number
367514-87-2
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

References

General References
  1. 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. [Article]
  2. 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. [Article]
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
FDA label
Download (452 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceDepression, Bipolar1
4CompletedTreatmentPsychosis1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenia1
4CompletedTreatmentSchizophrenia3
4Not Yet RecruitingTreatmentSchizophrenia1
4Unknown StatusTreatmentSchizophrenia1
4WithdrawnTreatmentBipolar 1 Disorder / Bipolar Disorder (BD) / Bipolar Disorder, Type II / Bipolar Spectrum Disorder / Mania1
3CompletedTreatmentAutism, Early Infantile1
3CompletedTreatmentAutism, Early Infantile / Depression, Bipolar / Schizophrenia1
3CompletedTreatmentBipolar 1 Disorder4

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral40 mg
TabletOral120 mg
TabletOral20 mg
TabletOral60 mg
TabletOral80 mg
Tablet, film coatedOral120 mg/1
Tablet, film coatedOral18.5 MG
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral37 MG
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral60 mg/1
Tablet, film coatedOral74 MG
Tablet, film coatedOral80 mg/1
Tablet, coatedOral20 mg
Tablet, coatedOral
Tablet, coatedOral120 mg/1
Tablet, coatedOral20 mg/1
Tablet, coatedOral40 mg/1
Tablet, coatedOral60 mg/1
Tablet, coatedOral80 mg/1
Tablet, coatedOral40 mg
Tablet, film coatedOral40 mg
Tablet, coatedOral80 mg
Tablet, film coatedOral80 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9174975Yes2015-11-032026-12-25US flag
US9259423Yes2016-02-162031-11-23US flag
US8729085Yes2014-05-202026-11-26US flag
US5532372Yes1996-07-022019-01-02US flag
US8883794Yes2014-11-112026-11-26US flag
USRE45573Yes2015-06-232025-12-23US flag
US9555027No2017-01-312026-05-26US flag
US9815827No2017-11-142024-02-20US flag
US9827242No2017-11-282031-05-23US flag
US9907794No2018-03-062026-05-26US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00789 mg/mLALOGPS
logP5.25ALOGPS
logP4.56ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)8.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area56.75 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity139.33 m3·mol-1ChemAxon
Polarizability56.26 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9907
Caco-2 permeable+0.5257
P-glycoprotein substrateSubstrate0.6029
P-glycoprotein inhibitor IInhibitor0.6713
P-glycoprotein inhibitor IIInhibitor0.73
Renal organic cation transporterInhibitor0.5487
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.5922
CYP450 1A2 substrateNon-inhibitor0.677
CYP450 2C9 inhibitorInhibitor0.6714
CYP450 2D6 inhibitorNon-inhibitor0.8292
CYP450 2C19 inhibitorInhibitor0.7439
CYP450 3A4 inhibitorNon-inhibitor0.7835
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8126
Ames testNon AMES toxic0.6477
CarcinogenicityNon-carcinogens0.8986
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.4051 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6636
hERG inhibition (predictor II)Inhibitor0.5858
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]

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
  1. 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. [Article]
  2. Lurasidone HCl FDA Label [Link]

Drug created on July 24, 2011 17:04 / Updated on October 19, 2021 07:39