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Details

Stereochemistry ACHIRAL
Molecular Formula C24H27FN2O4
Molecular Weight 426.4806
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ILOPERIDONE

SMILES

COC1=CC(=CC=C1OCCCN2CCC(CC2)C3=NOC4=C3C=CC(F)=C4)C(C)=O

InChI

InChIKey=XMXHEBAFVSFQEX-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Iloperidone, also known as Fanapt, Fanapta, and previously known as Zomaril, is an atypical antipsychotic for the treatment of schizophrenia. Iloperidone shows high affinity and maximal receptor occupancy for dopamine D2 receptors in the caudate nucleus and putamen of the brains of schizophrenic patients. The improvement in cognition is attributed to iloperidone's high affinity for α adrenergic receptors. Iloperidone also binds with high affinity to serotonin 5-HT2a and dopamine 3 receptors. Iloperidone binds with moderate affinity to dopamine D4, serotonin 5-HT6 and 5-HT7, and norepinephrine NEα1 receptors. Furthermore, iloperidone binds with weak affinity to serotonin 5-HT1A, dopamine D1, and histamine H1 receptors. Iloperidone is indicated for the treatment of acute schizophrenia.

CNS Activity

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FANAPT
PubMed

PubMed

TitleDatePubMed
The ratios of serotonin2 and dopamine2 affinities differentiate atypical and typical antipsychotic drugs.
1989
3-[[(Aryloxy)alkyl]piperidinyl]-1,2-benzisoxazoles as D2/5-HT2 antagonists with potential atypical antipsychotic activity: antipsychotic profile of iloperidone (HP 873).
1995 Mar 31
The pharmacological profile of iloperidone, a novel atypical antipsychotic agent.
1995 Sep
Iloperidone binding to human and rat dopamine and 5-HT receptors.
1996 Dec 19
Treatments for chronic psychosis.
2001 Dec
A review of new atypical antipsychotic launches in the United States.
2010 Dec
Iloperidone: chemistry, pharmacodynamics, pharmacokinetics and metabolism, clinical efficacy, safety and tolerability, regulatory affairs, and an opinion.
2010 Dec
New antipsychotic drugs: how do their receptor-binding profiles compare?
2010 Sep
Asenapine, iloperidone and lurasidone: critical appraisal of the most recently approved pharmacotherapies for schizophrenia in adults.
2013 Jan
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
Patents

Sample Use Guides

In Vivo Use Guide
The recommended target dosage is 12 to 24 mg/day administered twice daily. This target dosage range is achieved by daily dosage adjustments, alerting patients to symptoms of orthostatic hypotension, starting at a dose of 1 mg twice daily, then moving to 2 mg, 4 mg, 6 mg, 8 mg, 10 mg, and 12 mg twice daily on Days 2, 3, 4, 5, 6, and 7 respectively, to reach the 12 mg/day to 24 mg/day dose range.
Route of Administration: Oral
In Vitro Use Guide
While pacing the hearts at stimulation cycle lengths of 200 or 250 ms, or during natural sinus rhythm (no external pacing), iloperidone 100 nmol/L prolonged MAPD(90) by respectively 9.2 ± 0.9, 11.2 ± 1.6 and 21.4 ± 2.3 ms.
Name Type Language
ILOPERIDONE
DASH   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ILOPERIDONE [VANDF]
Common Name English
HP-873
Code English
ILOPERIDONE [USAN]
Common Name English
4'-(3-(4-(6-FLUORO-1,2-BENZISOXAZOL-3-YL)PIPERIDINO)PROPOXY)-3'-METHOXYACETOPHENONE
Systematic Name English
ILOPERIDONE [ORANGE BOOK]
Common Name English
ILOPERIDONE [WHO-DD]
Common Name English
ILOPERIDONE [MART.]
Common Name English
HP 873
Code English
ETHANONE, 1-(4-(3-(4-(6-FLUORO-1,2-BENZISOXAZOL-3-YL)-1-PIPERIDINYL)PROPOXY)-3-METHOXYPHENYL)-
Systematic Name English
ILOPERIDONE [INN]
Common Name English
FANAPT
Brand Name English
ILOPERIDONE [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175430
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
LIVERTOX 498
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
WHO-VATC QN05AX14
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
WHO-ATC N05AX14
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
Code System Code Type Description
DRUG BANK
DB04946
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
EVMPD
SUB08135MIG
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
WIKIPEDIA
Iloperidone
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
ChEMBL
CHEMBL14376
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
INN
7045
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
MERCK INDEX
M6211
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY Merck Index
NCI_THESAURUS
C83784
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
LactMed
133454-47-4
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
EPA CompTox
133454-47-4
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
PUBCHEM
71360
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY SWITZERF
CAS
133454-47-4
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
HSDB
133454-47-4
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
RXCUI
73178
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY RxNorm
MESH
C081732
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY
IUPHAR
87
Created by admin on Tue Mar 06 11:15:48 UTC 2018 , Edited by admin on Tue Mar 06 11:15:48 UTC 2018
PRIMARY