Iloperidone

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofBipolar disorder with manic or mixed episodes•••••••••••••••••
Management ofSchizophrenia•••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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

TargetActionsOrganism
A5-hydroxytryptamine receptor 2A
antagonist
Humans
AD(2) dopamine receptor
antagonist
Humans
U5-hydroxytryptamine receptor 1A
antagonist
Humans
U5-hydroxytryptamine receptor 2C
antagonist
Humans
U5-hydroxytryptamine receptor 6
antagonist
Humans
U5-hydroxytryptamine receptor 7
antagonist
Humans
UAlpha-1A adrenergic receptor
antagonist
Humans
UAlpha-2A adrenergic receptor
antagonist
Humans
UAlpha-2B adrenergic receptor
antagonist
Humans
UAlpha-2C adrenergic receptor
antagonist
Humans
UBeta-1 adrenergic receptor
antagonist
Humans
UBeta-2 adrenergic receptor
antagonist
Humans
UD(1A) dopamine receptor
antagonist
Humans
UD(3) dopamine receptor
antagonist
Humans
UD(4) dopamine receptor
antagonist
Humans
UD(1B) dopamine receptor
antagonist
Humans
UHistamine H1 receptor
antagonist
Humans
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

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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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Toxicity

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/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*3Not AvailableC alleleEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableC alleleEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor 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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Iloperidone is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Iloperidone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Iloperidone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Iloperidone can be decreased when combined with Abiraterone.
AcalabrutinibThe 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

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Product Images
International/Other Brands
Fanapta / Fiapta / Zomaril
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FanaptTablet8 mg/1OralNovartis2009-10-012017-08-31US flag
FanaptTablet2 mg/1OralNovartis2009-10-012017-08-31US flag
FanaptTablet8 mg/1OralREMEDYREPACK INC.2019-02-13Not applicableUS flag
FanaptTablet8 mg/1OralVanda Pharmaceuticals Inc.2018-09-24Not applicableUS flag
FanaptTablet6 mg/1OralVanda Pharmaceuticals Inc.2016-07-01Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
IloperidoneTablet8 mg/1OralMylan Pharmaceuticals Inc.2017-03-20Not applicableUS flag
IloperidoneTablet2 mg/1OralMylan Pharmaceuticals Inc.2017-03-20Not applicableUS flag
IloperidoneTablet10 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2019-07-22Not applicableUS flag
IloperidoneTablet4 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2019-07-22Not applicableUS flag
IloperidoneTablet12 mg/1OralMylan Pharmaceuticals Inc.2017-03-20Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FanaptIloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1)KitOralVanda Pharmaceuticals Inc.2015-12-01Not applicableUS flag
FanaptIloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1)KitOralNovartis2009-10-012017-08-31US flag
FanaptIloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1)KitOralVanda Pharmaceuticals Inc.2018-09-24Not applicableUS flag
FanaptIloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1)KitOralVanda Pharmaceuticals Inc.2015-12-01Not applicableUS flag
FanaptIloperidone (1 mg/1) + Iloperidone (2 mg/1) + Iloperidone (4 mg/1) + Iloperidone (6 mg/1)KitOralNovartis2009-10-012017-08-31US flag

Categories

ATC Codes
N05AX14 — Iloperidone
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. FDA Approved Drug Products: FANAPT (iloperidone) tablets, for oral use (April 2024) [Link]
  7. Cayman Chemical: Iloperidone MSDS [Link]
Human Metabolome Database
HMDB0253402
KEGG Drug
D02666
PubChem Compound
71360
PubChem Substance
175426913
ChemSpider
64459
BindingDB
50034043
RxNav
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
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableCompletedNot AvailableBipolar Disorder (BD)1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableSchizophrenia1somestatusstop reasonjust information to hide
4CompletedTreatmentBipolar Disorder (BD)1somestatusstop reasonjust information to hide
4CompletedTreatmentHealthy Volunteers (HV)1somestatusstop reasonjust information to hide
4CompletedTreatmentMajor Depressive Disorder (MDD)1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOral
TabletOral1 mg/1
TabletOral10 mg/1
TabletOral12 mg/1
TabletOral2 mg/1
TabletOral4 mg/1
TabletOral6 mg/1
TabletOral8 mg/1
Kit; tabletOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
USRE39198No2006-07-182016-11-15US flag
US8586610No2013-11-192027-11-02US flag
US9074255No2015-07-072030-12-17US flag
US9072742No2015-07-072031-01-16US flag
US9074256No2015-07-072031-02-10US flag
US9157121No2015-10-132030-04-05US flag
US9138432No2015-09-222025-09-30US flag
US8999638No2015-04-072030-10-28US flag
US9074254No2015-07-072031-12-28US flag
US8652776No2014-02-182030-08-31US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0304 mg/mLALOGPS
logP4.26ALOGPS
logP3.22Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)16.14Chemaxon
pKa (Strongest Basic)8.53Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area64.8 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity116.65 m3·mol-1Chemaxon
Polarizability46.51 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9848
Caco-2 permeable+0.5513
P-glycoprotein substrateSubstrate0.6668
P-glycoprotein inhibitor IInhibitor0.8242
P-glycoprotein inhibitor IIInhibitor0.9268
Renal organic cation transporterInhibitor0.5726
CYP450 2C9 substrateNon-substrate0.9051
CYP450 2D6 substrateSubstrate0.892
CYP450 3A4 substrateSubstrate0.7409
CYP450 1A2 substrateNon-inhibitor0.6111
CYP450 2C9 inhibitorNon-inhibitor0.5061
CYP450 2D6 inhibitorNon-inhibitor0.886
CYP450 2C19 inhibitorInhibitor0.6257
CYP450 3A4 inhibitorInhibitor0.6777
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9008
Ames testNon AMES toxic0.6314
CarcinogenicityNon-carcinogens0.8699
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7862 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6563
hERG inhibition (predictor II)Inhibitor0.7945
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0059-1591700000-642ca68996469c31b6b8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-4021900000-ab31026932091a9915b4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0570-0028900000-15066990dfc7f86a01bc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-6394600000-d5801e726980fe64eb77
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-0029100000-a209dd04359c8577472f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0393200000-1e5847694a9957044dac
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0171-2795300000-b31482103943b36c1dfa
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-195.1035
predicted
DeepCCS 1.0 (2019)
[M+H]+197.4615
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.49661
predicted
DeepCCS 1.0 (2019)

Targets

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insights 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). 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). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors (PubMed:28129538). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538). Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores (PubMed:18703043, PubMed:28129538). 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
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
  1. 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]
  2. Hesselink JM: Iloperidone (Novartis). IDrugs. 2002 Jan;5(1):84-90. [Article]
  3. 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]
  4. 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]
  5. 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]
Details
2. D(2) dopamine receptor
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
  1. 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]
  2. Hesselink JM: Iloperidone (Novartis). IDrugs. 2002 Jan;5(1):84-90. [Article]
  3. 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]
  4. 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). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores. Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism. Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior. Plays a role in the response to anxiogenic stimuli
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
  1. 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]
  2. 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]
  3. 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). 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). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and down-stream signaling cascades and promotes the release of Ca(2+) ions from intracellular stores. Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelacortin neurons and the release of CRH that then regulates the release of corticosterone. Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress. Plays a role in insulin sensitivity and glucose homeostasis
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
  1. 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
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 is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs (By similarity). Controls pyramidal neurons migration during corticogenesis, through the regulation of CDK5 activity (By similarity). Is an activator of TOR 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
  1. 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]
  2. 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
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 is mediated by G proteins that stimulate adenylate cyclase
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
  1. 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
  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. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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]
Details
13. D(1A) dopamine receptor
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
  1. 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]
  2. 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
  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. 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
  1. 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]
  2. 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
  1. 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]
Details
17. Histamine H1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
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
  1. 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]
  2. 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
  1. 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]
  2. 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]
  3. 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
  1. 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]
  2. 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]
  3. 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