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Identification
- Summary
Iloperidone is an atypical antipsychotic agent used to treat schizophrenia and manic or mixed episodes associated with bipolar I disorder in adults.
- Brand Names
- Fanapt
- Generic Name
- Iloperidone
- DrugBank Accession Number
- DB04946
- Background
Iloperidone is a benzisoxazole 5 and an atypical antipsychotic agent that was first approved by the FDA on May 6, 2009.1 It is considered to be a second-generation antipsychotic drug 4 with multiple receptor binding profile, although it shows high affinity towards 5-HT2A and dopamine D2 receptors.3 Iloperidone is currently used to treat schizophrenia and manic or mixed episodes associated with bipolar disorder.6
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Iloperidone (DB04946)
- Weight
- Average: 426.4806
Monoisotopic: 426.195485567 - Chemical Formula
- C24H27FN2O4
- Synonyms
- 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1- piperidinyl]propoxy]-3-methoxyphenyl]ethanone
- 4'-(3-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino)propoxy)-3'-methoxyacetophenone
- Iloperidona
- Iloperidone
- Ilopéridone
- Iloperidonum
- External IDs
- HP 873
- HP-873
- HP873
- ILO 522
- ILO-522
- ILO522
Pharmacology
- Indication
Iloperidone is indicated for the treatment of schizophrenia in adults.6
It is also used for the acute treatment of manic or mixed episodes associated with bipolar I disorder in adults.6
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Bipolar disorder with manic or mixed episodes •••••••••••• ••••• Management of Schizophrenia •••••••••••• ••••• - Contraindications & Blackbox Warnings
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Iloperidone binds to various receptors. It exhibits the highest affinity for dopamine D2 receptors, serotonin 5-HT2A receptors, and α1-adrenergic receptors.2,6
Due to its α1 adrenergic antagonism, iloperidone may produce hypotension. It can also prolong the QTc interval.6
- Mechanism of action
The exact mechanism of action of iloperidone in schizophrenia and bipolar I disorder has not been fully elucidated. It is believed that the drug mechanism of action may be related to its antagonism at the dopamine D2 and 5-HT2A receptors.6
Target Actions Organism A5-hydroxytryptamine receptor 2A antagonistHumans AD(2) dopamine receptor antagonistHumans U5-hydroxytryptamine receptor 1A antagonistHumans U5-hydroxytryptamine receptor 2C antagonistHumans U5-hydroxytryptamine receptor 6 antagonistHumans U5-hydroxytryptamine receptor 7 antagonistHumans UAlpha-1A adrenergic receptor antagonistHumans UAlpha-2A adrenergic receptor antagonistHumans UAlpha-2B adrenergic receptor antagonistHumans UAlpha-2C adrenergic receptor antagonistHumans UBeta-1 adrenergic receptor antagonistHumans UBeta-2 adrenergic receptor antagonistHumans UD(1A) dopamine receptor antagonistHumans UD(3) dopamine receptor antagonistHumans UD(4) dopamine receptor antagonistHumans UD(1B) dopamine receptor antagonistHumans UHistamine H1 receptor antagonistHumans - Absorption
Iloperidone is well-absorbed following oral administration.6 Oral bioavailability is approximately 36% in humans.1 The relative availability of the tablet formulation compared to the oral solution is 96%.6 The Tmax is two to four hours with single dosing and 1.5 hours with multiple dosing.1
A high-fat meal can delay the Tmax of iloperidone and its active metabolite, P88, by one and two hours, respectively; however, food has negligible effects on drug Cmax and AUC.6
- Volume of distribution
The apparent volume of distribution ranges from 1340 L to 2800 L.6
- Protein binding
Iloperidone is about 95% bound to serum proteins.1 At therapeutic concentrations, the unbound fraction of iloperidone and its metabolites (P88 and P95) in plasma is about 3% and 8%, respectively.6
- Metabolism
Iloperidone is mainly metabolized in the liver.6 It primarily undergoes three major biotransformation pathways: carbonyl reduction to produce P88, CYP2D6-mediated hydroxylation to produce P95, and CYP3A4-mediated O-demethylation to produce P89.1
P88 and P95 are the two major metabolites. P95 represents 47.9% of the AUC of iloperidone and its metabolites in plasma at steady-state for extensive metabolizers (EM) and 25% for poor metabolizers (PM). P88 is an active metabolite with an in vitro receptor binding profile that is comparable to the parent drug: It accounts for 19.5% and 34% of total plasma exposure in EM and PM, respectively.6
Hover over products below to view reaction partners
- Route of elimination
The main route of elimination is renal.1 About 58.2% and 45.1% of the drug were found in urine in extensive metabolizers (EM) and poor metabolizers (PM), respectively. Feces accounted for 19.9% (EM) to 22.1% (PM) of the dosed radioactivity.6
- Half-life
The observed mean elimination half-lives for iloperidone, P88, and P95 in CYP2D6 extensive metabolizers (EM) are 18, 26, and 23 hours, respectively. The mean half-lives of iloperidone, P88, and P95 in CYP2D6 poor metabolizers (PM) are 33, 37, and 31 hours, respectively.6
- Clearance
Iloperidone has an apparent clearance of 47 to 102 L/h.6
- Adverse Effects
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The intraperitoneal lowest published toxic dose (TDLo) is 0.03 mg/kg in rats.7
In pre-marketing trials, there were eight cases of accidental or intentional overdose of iloperidone from doses ranging from 48 mg to 576 mg taken once and 292 mg taken over three days. There were no deaths from overdose. The largest confirmed single ingestion of iloperidone was 576 mg; however, no adverse physical effects were reported for this patient. The next largest confirmed ingestion of iloperidone was 438 mg over four days: This patient experienced extrapyramidal symptoms and a QTc interval of 507 msec with no cardiac sequelae. In general, reported signs and symptoms were those resulting from an exaggeration of the known pharmacological effects of iloperidone, including drowsiness, sedation, tachycardia, and hypotension. There is no known antidote for iloperidone overdose; thus, treatment should be supportive.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2D6 CYP2D6*3 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*4 Not Available C allele Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*5 Not Available Whole-gene deletion Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*6 Not Available 1707delT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*7 Not Available 2935A>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*8 Not Available 1758G>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*11 Not Available 883G>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*12 Not Available 124G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*13 Not Available CYP2D7/2D6 hybrid gene structure Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*14A Not Available 1758G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*15 Not Available 137insT, 137_138insT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*19 Not Available 2539_2542delAACT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*20 Not Available 1973_1974insG Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*21 Not Available 2573insC Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*31 Not Available -1770G>A / -1584C>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*36 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*38 Not Available 2587_2590delGACT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*40 Not Available 1863_1864ins(TTT CGC CCC)2 Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*42 Not Available 3259_3260insGT Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*44 Not Available 2950G>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*47 Not Available 100C>T / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*51 Not Available -1584C>G / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*56 Not Available 3201C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*57 Not Available 100C>T / 310G>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*62 Not Available 4044C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*68A Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*68B Not Available Similar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4. Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*69 Not Available 2988G>A / -1426C>T … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*92 Not Available 1995delC Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*100 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2D6 CYP2D6*101 Not Available -1426C>T / -1235A>G … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details
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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Iloperidone is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Iloperidone can be increased when it is combined with Abametapir. Abatacept The metabolism of Iloperidone can be increased when combined with Abatacept. Abiraterone The metabolism of Iloperidone can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Iloperidone can be decreased when combined with Acalabrutinib. - Food Interactions
- Avoid excessive or chronic alcohol consumption. Alcohol may worsen the CNS effects of iloperidone, such as dizziness.
- Take with or without food. A high-fat meals may delay the Tmax of iloperidone and its metabolites, without significantly changing the Cmax or AUC.
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 Images
- International/Other Brands
- Fanapta / Fiapta / Zomaril
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Fanapt Tablet 2 mg/1 Oral Vanda Pharmaceuticals Inc. 2024-06-11 Not applicable US 
Fanapt Tablet 1 mg/1 Oral Vanda Pharmaceuticals Inc. 2016-05-01 Not applicable US Fanapt Tablet 12 mg/1 Oral Vanda Pharmaceuticals Inc. 2016-10-15 Not applicable US Fanapt Tablet 12 mg/1 Oral Novartis 2009-10-01 2017-08-31 US Fanapt Tablet 8 mg/1 Oral Vanda Pharmaceuticals Inc. 2015-09-15 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Iloperidone Tablet 4 mg/1 Oral Taro Pharmaceuticals U.S.A., Inc. 2019-07-22 Not applicable US Iloperidone Tablet 12 mg/1 Oral Mylan Pharmaceuticals Inc. 2017-03-20 Not applicable US Iloperidone Tablet 6 mg/1 Oral Mylan Pharmaceuticals Inc. 2017-03-20 Not applicable US Iloperidone Tablet 8 mg/1 Oral Taro Pharmaceuticals U.S.A., Inc. 2019-07-22 Not applicable US Iloperidone Tablet 1 mg/1 Oral Mylan Pharmaceuticals Inc. 2017-03-20 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fanapt Iloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1) Kit Oral Vanda Pharmaceuticals Inc. 2018-09-24 Not applicable US Fanapt Iloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1) Kit Oral Vanda Pharmaceuticals Inc. 2015-12-01 Not applicable US Fanapt Iloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1) Kit Oral Novartis 2009-10-01 2017-08-31 US Fanapt Iloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1) Kit Oral Vanda Pharmaceuticals Inc. 2018-09-24 Not applicable US Fanapt Iloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1) Kit Oral Novartis 2009-10-01 2017-08-31 US
Categories
- ATC Codes
- N05AX14 — Iloperidone
- Drug Categories
- Adrenergic alpha-1 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 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Highest Risk QTc-Prolonging Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Hyperglycemia-Associated Agents
- Nervous System
- Neurotoxic agents
- Psycholeptics
- Psychotropic Drugs
- QTc Prolonging Agents
- Schizophrenia
- 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 5-HT2C Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Alkyl-phenylketones
- Alternative Parents
- Acetophenones / Benzisoxazoles / Phenoxy compounds / Anisoles / Methoxybenzenes / Benzoyl derivatives / Aryl alkyl ketones / Alkyl aryl ethers / Aralkylamines / Piperidines show 10 more
- Substituents
- Acetophenone / Alkyl aryl ether / Alkyl-phenylketone / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl fluoride / Aryl halide show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- piperidines, organofluorine compound, tertiary amino compound, aromatic ether, methyl ketone, aromatic ketone, monoamine, 1,2-benzoxazoles (CHEBI:65173)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- VPO7KJ050N
- CAS number
- 133454-47-4
- InChI Key
- XMXHEBAFVSFQEX-UHFFFAOYSA-N
- InChI
- InChI=1S/C24H27FN2O4/c1-16(28)18-4-7-21(23(14-18)29-2)30-13-3-10-27-11-8-17(9-12-27)24-20-6-5-19(25)15-22(20)31-26-24/h4-7,14-15,17H,3,8-13H2,1-2H3
- IUPAC Name
- 1-(4-{3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy}-3-methoxyphenyl)ethan-1-one
- SMILES
- COC1=C(OCCCN2CCC(CC2)C2=NOC3=C2C=CC(F)=C3)C=CC(=C1)C(C)=O
References
- Synthesis Reference
- US5364866
- General References
- Citrome L: Iloperidone: chemistry, pharmacodynamics, pharmacokinetics and metabolism, clinical efficacy, safety and tolerability, regulatory affairs, and an opinion. Expert Opin Drug Metab Toxicol. 2010 Dec;6(12):1551-64. doi: 10.1517/17425255.2010.531259. Epub 2010 Nov 1. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Jain KK: An assessment of iloperidone for the treatment of schizophrenia. Expert Opin Investig Drugs. 2000 Dec;9(12):2935-43. doi: 10.1517/13543784.9.12.2935. [Article]
- Citrome L: Iloperidone for schizophrenia: a review of the efficacy and safety profile for this newly commercialised second-generation antipsychotic. Int J Clin Pract. 2009 Aug;63(8):1237-48. doi: 10.1111/j.1742-1241.2009.02142.x. [Article]
- Albers LJ, Musenga A, Raggi MA: Iloperidone: a new benzisoxazole atypical antipsychotic drug. Is it novel enough to impact the crowded atypical antipsychotic market? Expert Opin Investig Drugs. 2008 Jan;17(1):61-75. doi: 10.1517/13543784.17.1.61. [Article]
- FDA Approved Drug Products: FANAPT (iloperidone) tablets, for oral use (April 2024) [Link]
- Cayman Chemical: Iloperidone MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0253402
- KEGG Drug
- D02666
- PubChem Compound
- 71360
- PubChem Substance
- 175426913
- ChemSpider
- 64459
- BindingDB
- 50034043
- 73178
- ChEBI
- 65173
- ChEMBL
- CHEMBL14376
- ZINC
- ZINC000001548097
- PharmGKB
- PA161199368
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Iloperidone
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Bipolar Disorder (BD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Schizophrenia 1 somestatus stop reason just information to hide 4 Completed Treatment Bipolar Disorder (BD) 1 somestatus stop reason just information to hide 4 Completed Treatment Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 4 Completed Treatment Major Depressive Disorder (MDD) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral Tablet Oral 1 mg/1 Tablet Oral 10 mg/1 Tablet Oral 12 mg/1 Tablet Oral 2 mg/1 Tablet Oral 4 mg/1 Tablet Oral 6 mg/1 Tablet Oral 8 mg/1 Kit; tablet Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region USRE39198 No 2006-07-18 2016-11-15 US US8586610 No 2013-11-19 2027-11-02 US US9074255 No 2015-07-07 2030-12-17 US US9072742 No 2015-07-07 2031-01-16 US US9074256 No 2015-07-07 2031-02-10 US US9157121 No 2015-10-13 2030-04-05 US US9138432 No 2015-09-22 2025-09-30 US US8999638 No 2015-04-07 2030-10-28 US US9074254 No 2015-07-07 2031-12-28 US US8652776 No 2014-02-18 2030-08-31 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0304 mg/mL ALOGPS logP 4.26 ALOGPS logP 3.22 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 16.14 Chemaxon pKa (Strongest Basic) 8.53 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 64.8 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 116.65 m3·mol-1 Chemaxon Polarizability 46.51 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9848 Caco-2 permeable + 0.5513 P-glycoprotein substrate Substrate 0.6668 P-glycoprotein inhibitor I Inhibitor 0.8242 P-glycoprotein inhibitor II Inhibitor 0.9268 Renal organic cation transporter Inhibitor 0.5726 CYP450 2C9 substrate Non-substrate 0.9051 CYP450 2D6 substrate Substrate 0.892 CYP450 3A4 substrate Substrate 0.7409 CYP450 1A2 substrate Non-inhibitor 0.6111 CYP450 2C9 inhibitor Non-inhibitor 0.5061 CYP450 2D6 inhibitor Non-inhibitor 0.886 CYP450 2C19 inhibitor Inhibitor 0.6257 CYP450 3A4 inhibitor Inhibitor 0.6777 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9008 Ames test Non AMES toxic 0.6314 Carcinogenicity Non-carcinogens 0.8699 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7862 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6563 hERG inhibition (predictor II) Inhibitor 0.7945
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.1035 predictedDeepCCS 1.0 (2019) [M+H]+ 197.4615 predictedDeepCCS 1.0 (2019) [M+Na]+ 204.49661 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895, PubMed:21645528, PubMed:22300836, PubMed:35084960, PubMed:38552625). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538, PubMed:35084960). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:28129538, PubMed:35084960). HTR2A is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:28129538, PubMed:35084960). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538, PubMed:35084960). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Kongsamut S, Roehr JE, Cai J, Hartman HB, Weissensee P, Kerman LL, Tang L, Sandrasagra A: Iloperidone binding to human and rat dopamine and 5-HT receptors. Eur J Pharmacol. 1996 Dec 19;317(2-3):417-23. [Article]
- Hesselink JM: Iloperidone (Novartis). IDrugs. 2002 Jan;5(1):84-90. [Article]
- Kalkman HO, Subramanian N, Hoyer D: Extended radioligand binding profile of iloperidone: a broad spectrum dopamine/serotonin/norepinephrine receptor antagonist for the management of psychotic disorders. Neuropsychopharmacology. 2001 Dec;25(6):904-14. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase (PubMed:21645528). Positively regulates postnatal regression of retinal hyaloid vessels via suppression of VEGFR2/KDR activity, downstream of OPN5 (By similarity)
- Specific Function
- dopamine binding
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Kongsamut S, Roehr JE, Cai J, Hartman HB, Weissensee P, Kerman LL, Tang L, Sandrasagra A: Iloperidone binding to human and rat dopamine and 5-HT receptors. Eur J Pharmacol. 1996 Dec 19;317(2-3):417-23. [Article]
- Hesselink JM: Iloperidone (Novartis). IDrugs. 2002 Jan;5(1):84-90. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:37935376, PubMed:37935377, PubMed:8138923, PubMed:8393041). Also functions as a receptor for various drugs and psychoactive substances (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:38552625, PubMed:8138923, PubMed:8393041). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:8138923, PubMed:8393041). HTR1A is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission: signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores (PubMed:33762731, PubMed:35610220). Beta-arrestin family members regulate signaling by mediating both receptor desensitization and resensitization processes (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the response to anxiogenic stimuli (PubMed:18476671, PubMed:20363322, PubMed:20945968)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Bobo WV: Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. [Article]
- Kalkman HO, Subramanian N, Hoyer D: Extended radioligand binding profile of iloperidone: a broad spectrum dopamine/serotonin/norepinephrine receptor antagonist for the management of psychotic disorders. Neuropsychopharmacology. 2001 Dec;25(6):904-14. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:12970106, PubMed:18703043, PubMed:19057895, PubMed:29398112, PubMed:7895773). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:19057895, PubMed:29398112). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:18703043, PubMed:29398112). HTR2C is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:29398112). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:29398112). Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelanocortin neurons and the release of CRH that then regulates the release of corticosterone (By similarity). Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress (By similarity). Plays a role in insulin sensitivity and glucose homeostasis (By similarity)
- Specific Function
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51804.645 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone and a mitogen (PubMed:35714614, PubMed:36989299, PubMed:37327704, PubMed:8522988). Also has a high affinity for tricyclic psychotropic drugs (By similarity). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:35714614). HTR6 is coupled to G(s) G alpha proteins and mediates activation of adenylate cyclase activity (PubMed:35714614, PubMed:37327704). Controls pyramidal neurons migration during corticogenesis, through the regulation of CDK5 activity (By similarity). Is an activator of mTOR signaling (PubMed:23027611)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR6
- Uniprot ID
- P50406
- Uniprot Name
- 5-hydroxytryptamine receptor 6
- Molecular Weight
- 46953.625 Da
References
- Bobo WV: Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone and a mitogen (PubMed:35714614, PubMed:8226867). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:35714614, PubMed:8226867). HTR7 is coupled to G(s) G alpha proteins and mediates activation of adenylate cyclase activity (PubMed:35714614)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR7
- Uniprot ID
- P34969
- Uniprot Name
- 5-hydroxytryptamine receptor 7
- Molecular Weight
- 53554.43 Da
References
- Bobo WV: Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes
- Specific Function
- alpha1-adrenergic receptor activity
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 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. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
- Specific Function
- alpha-1B adrenergic receptor binding
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 50646.17 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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 clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
- Specific Function
- alpha2-adrenergic receptor activity
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49953.145 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins
- Specific Function
- alpha-2A adrenergic receptor binding
- Gene Name
- ADRA2C
- Uniprot ID
- P18825
- Uniprot Name
- Alpha-2C adrenergic receptor
- Molecular Weight
- 49521.585 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling. Involved in the regulation of sleep/wake behaviors (PubMed:31473062)
- Specific Function
- alpha-2A adrenergic receptor binding
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51222.97 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase
- Specific Function
- arrestin family protein binding
- Gene Name
- DRD1
- Uniprot ID
- P21728
- Uniprot Name
- D(1A) dopamine receptor
- Molecular Weight
- 49292.765 Da
References
- Bobo WV: Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
- Specific Function
- dopamine neurotransmitter receptor activity, coupled via Gi/Go
- Gene Name
- DRD3
- Uniprot ID
- P35462
- Uniprot Name
- D(3) dopamine receptor
- Molecular Weight
- 44194.315 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. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Activated by dopamine, but also by epinephrine and norepinephrine, and by numerous synthetic agonists and drugs (PubMed:16423344, PubMed:27659709, PubMed:29051383, PubMed:9003072). Agonist binding triggers signaling via G proteins that inhibit adenylyl cyclase (PubMed:16423344, PubMed:27659709, PubMed:29051383, PubMed:7512953, PubMed:7643093). Modulates the circadian rhythm of contrast sensitivity by regulating the rhythmic expression of NPAS2 in the retinal ganglion cells (By similarity)
- Specific Function
- dopamine binding
- Gene Name
- DRD4
- Uniprot ID
- P21917
- Uniprot Name
- D(4) dopamine receptor
- Molecular Weight
- 43900.84 Da
References
- Bobo WV: Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase
- Specific Function
- dopamine binding
- Gene Name
- DRD5
- Uniprot ID
- P21918
- Uniprot Name
- D(1B) dopamine receptor
- Molecular Weight
- 52950.5 Da
References
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Bobo WV: Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults. Expert Rev Clin Pharmacol. 2013 Jan;6(1):61-91. doi: 10.1586/ecp.12.70. [Article]
- Rado JT, Janicak PG: Long-term efficacy and safety of iloperidone: an update. Neuropsychiatr Dis Treat. 2014 Feb 26;10:409-15. doi: 10.2147/NDT.S37824. eCollection 2014. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Mutlib AE, Klein JT: Application of liquid chromatography/mass spectrometry in accelerating the identification of human liver cytochrome P450 isoforms involved in the metabolism of iloperidone. J Pharmacol Exp Ther. 1998 Sep;286(3):1285-93. [Article]
- Citrome L: Iloperidone: chemistry, pharmacodynamics, pharmacokinetics and metabolism, clinical efficacy, safety and tolerability, regulatory affairs, and an opinion. Expert Opin Drug Metab Toxicol. 2010 Dec;6(12):1551-64. doi: 10.1517/17425255.2010.531259. Epub 2010 Nov 1. [Article]
- FDA Approved Drug Products: FANAPT (iloperidone) tablets, for oral use (April 2024) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Mutlib AE, Klein JT: Application of liquid chromatography/mass spectrometry in accelerating the identification of human liver cytochrome P450 isoforms involved in the metabolism of iloperidone. J Pharmacol Exp Ther. 1998 Sep;286(3):1285-93. [Article]
- Citrome L: Iloperidone: chemistry, pharmacodynamics, pharmacokinetics and metabolism, clinical efficacy, safety and tolerability, regulatory affairs, and an opinion. Expert Opin Drug Metab Toxicol. 2010 Dec;6(12):1551-64. doi: 10.1517/17425255.2010.531259. Epub 2010 Nov 1. [Article]
- FDA Approved Drug Products: FANAPT (iloperidone) tablets, for oral use (April 2024) [Link]
Drug created at October 21, 2007 22:23 / Updated at August 26, 2024 19:24