U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C18H18ClN3O.ClH
Molecular Weight 364.269
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOXAPINE HYDROCHLORIDE

SMILES

Cl.CN1CCN(CC1)C2=NC3=C(OC4=C2C=C(Cl)C=C4)C=CC=C3

InChI

InChIKey=JSXBVMKACNEMKY-UHFFFAOYSA-N
InChI=1S/C18H18ClN3O.ClH/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18;/h2-7,12H,8-11H2,1H3;1H

HIDE SMILES / InChI

Molecular Formula C18H18ClN3O
Molecular Weight 327.808
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25859275

Loxapine is a dibenzoxazepine tricyclic antipsychotic agent, available for oral and inhalatory administration, classified as a typical antipsychotic. Loxapine acts as an antagonist at central serotonin and dopamine receptors. Adasuve (loxapine inhalation powder) is a prescription medicine that is used to treat acute agitation in adults with schizophrenia or bipolar I disorder.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21728
Gene ID: 1812.0
Gene Symbol: DRD1
Target Organism: Homo sapiens (Human)
18.0 nM [Ki]
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
10.0 nM [Ki]
Target ID: P35462
Gene ID: 1814.0
Gene Symbol: DRD3
Target Organism: Homo sapiens (Human)
21.0 nM [Ki]
Target ID: P21917
Gene ID: 1815.0
Gene Symbol: DRD4
Target Organism: Homo sapiens (Human)
9.0 nM [Ki]
Target ID: P35367
Gene ID: 3269.0
Gene Symbol: HRH1
Target Organism: Homo sapiens (Human)
15.0 nM [Ki]
Target ID: P11229
Gene ID: 1128.0
Gene Symbol: CHRM1
Target Organism: Homo sapiens (Human)
117.0 nM [Ki]
Target ID: P08913
Gene ID: 150.0
Gene Symbol: ADRA2A
Target Organism: Homo sapiens (Human)
250.0 nM [Ki]
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
2.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOXITANE

Approved Use

Loxapine Capsules, USP are indicated for the treatment of schizophrenia. The efficacy of loxapine in schizophrenia was established in clinical studies which enrolled newly hospitalized and chronically hospitalized acutely ill schizophrenic patients as subjects.

Launch Date

1.62518401E11
Primary
Adasuve

Approved Use

Schizophrenia

Launch Date

1.3559616E12
Primary
Adasuve

Approved Use

Bipolar I disorder

Launch Date

1.3559616E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
257 ng/mL
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LOXAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
188 ng × h/mL
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LOXAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.61 h
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LOXAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3.4%
10 mg single, respiratory
dose: 10 mg
route of administration: Respiratory
experiment type: SINGLE
co-administered:
LOXAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Does loxapine have "atypical" properties? Clinical evidence.
1999
Olanzapine-induced tardive dystonia.
1999 Oct
Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.
2000 Oct
Thioridazine for dementia.
2001
Clinically significant drug interactions with agents specific for migraine attacks.
2001
Inhibition of glucose transport in PC12 cells by the atypical antipsychotic drugs risperidone and clozapine, and structural analogs of clozapine.
2001 Dec 27
Loxapine side-effects: 3 case reports of hyperleukocytosis.
2001 Jan-Feb
Re: Neuroleptic malignant syndrome associated with quetiapine.
2001 May
[Body weight changes and psychotropic drug treatment: neuroleptics].
2001 May-Jun
A new class of antiarrhythmic-defibrillatory agents.
2001 Nov 19
[Psychiatric manifestations of lupus erythematosus systemic and Sjogren's syndrome].
2001 Nov-Dec
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.
2001 Oct
Current practices in managing acutely disturbed patients at three hospitals in Rio de Janeiro-Brazil: a prevalence study.
2002
Evidence for impaired cortical inhibition in schizophrenia using transcranial magnetic stimulation.
2002 Apr
[Self-poisoning with Datura stramonium. 3 case reports].
2002 Jan 19
Structure-based enzyme inhibitor design: modeling studies and crystal structure analysis of Pneumocystis carinii dihydrofolate reductase ternary complex with PT653 and NADPH.
2002 Jun
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine.
2002 Nov
TREC-Rio trial: a randomised controlled trial for rapid tranquillisation for agitated patients in emergency psychiatric rooms [ISRCTN44153243].
2002 Oct 16
Human genetic variations in the 5HT2A receptor: a single nucleotide polymorphism identified with altered response to clozapine.
2003 Feb
In vitro human plasma leucine(5)-enkephalin degradation is inhibited by a select number of drugs with the phenothiazine molecule in their chemical structure.
2003 Jan
[Survey of management methods for patients in a state of agitation at admission and emergency departments in France].
2003 Mar-Apr
Interspecies variability and drug interactions of loxapine metabolism in liver microsomes.
2003 Oct-Dec
Differential inverse agonist efficacies of SB-258719, SB-258741 and SB-269970 at human recombinant serotonin 5-HT7 receptors.
2004 Jul 14
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients.
2004 Mar 24
Minimally effective doses of conventional antipsychotic medications used to treat aggression, self-injurious and destructive behaviors in mentally retarded adults.
2005 Feb
Adjunctive topiramate in ultradian cycling bipolar disorder: case report with 3-year follow-up.
2006 Jun
Systematic review of antipsychotics for the treatment of hospital-associated delirium in medically or surgically ill patients.
2006 Nov
Risk of extrapyramidal syndrome in schizophrenic patients treated with antipsychotics: a population-based study.
2007 Apr
Risk of death associated with the use of conventional versus atypical antipsychotic drugs among elderly patients.
2007 Feb 27
HPLC analysis of the novel antidepressant duloxetine in human plasma after an original solid-phase extraction procedure.
2007 Sep 1
Modifications of antiepileptic drugs for improved tolerability and efficacy.
2008 Feb 14
Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients.
2008 Oct
Rapid liquid chromatography/tandem mass spectrometer (LCMS) method for clozapine and its metabolite N-desmethyl clozapine (norclozapine) in human serum.
2009
Safety and efficacy of antipsychotic drugs for the behavioral and psychological symptoms of dementia.
2009 Jan
Current perspectives in the treatment of resistant schizophrenia.
2009 Oct-Dec
In vitro aerosol deposition in the oropharyngeal region for Staccato loxapine.
2010 Aug
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
An overview of Indian research in schizophrenia.
2010 Jan
Simultaneous HPLC determination of 14 tricyclic antidepressants and metabolites in human plasma.
2010 Jan
4-Nitro-2-phenoxy-aniline.
2010 May 8
In vitro identification of the human cytochrome p450 enzymes involved in the oxidative metabolism of loxapine.
2011 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Loxitane (loxapine) capsules are prescribed for schizophrenia in dosage 10 mg twice daily (initial dose, orally) http://www.rxlist.com/loxitane-drug/indications-dosage.htm
Adasuve (loxapine inhalation powder), 10 mg by oral inhalation
Route of Administration: Respiratory
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:52:23 UTC 2023
Edited
by admin
on Wed Jul 05 23:52:23 UTC 2023
Record UNII
376MYL4MAL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOXAPINE HYDROCHLORIDE
MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
Loxapine hydrochloride [WHO-DD]
Common Name English
LOXITANE C
Brand Name English
LOXAPINE HYDROCHLORIDE [MART.]
Common Name English
LOXAPINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
LOXAPINE HCL
Common Name English
LOXAPINE HYDROCHLORIDE [VANDF]
Common Name English
LOXITANE IM
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
NCI_THESAURUS C66883
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL831
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
EVMPD
SUB22686
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
NCI_THESAURUS
C77574
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
PUBCHEM
71400
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
WIKIPEDIA
Loxapine hydrochloride
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
FDA UNII
376MYL4MAL
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
SMS_ID
100000088112
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
DRUG BANK
DBSALT001429
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
CAS
54810-23-0
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID70203304
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY
RXCUI
91138
Created by admin on Wed Jul 05 23:52:23 UTC 2023 , Edited by admin on Wed Jul 05 23:52:23 UTC 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY