Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H18ClN3O |
Molecular Weight | 327.8086 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC1)C2=Nc3ccccc3Oc4ccc(cc42)Cl
InChI
InChIKey=XJGVXQDUIWGIRW-UHFFFAOYSA-N
InChI=1S/C18H18ClN3O/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
Molecular Formula | C18H18ClN3O |
Molecular Weight | 327.8086 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment:: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25859275
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
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
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LOXITANE Approved UseLoxapine 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 Date1.62518401E11 |
|||
Primary | Adasuve Approved UseSchizophrenia Launch Date1.3559616E12 |
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Primary | Adasuve Approved UseBipolar I disorder Launch Date1.3559616E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 66.0 |
no | |||
Page: 20.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 63.0 |
minor | |||
Page: 20.0 |
no | no (co-administration study) Comment: ketoconazole did not affect loxapine transport Page: 20.0 |
||
Page: 20.0 |
yes | |||
Page: 10.0 |
yes | |||
Page: 10.0 |
yes | |||
Page: 20.0 |
yes | |||
Page: 20.0 |
yes | |||
Page: 10.0 |
yes | |||
Page: 20.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 181.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Treatment of the special patient with schizophrenia. | 2001 Jun |
|
[Survey of management methods for patients in a state of agitation at admission and emergency departments in France]. | 2003 Mar-Apr |
|
Induction of hyperglycemia in mice with atypical antipsychotic drugs that inhibit glucose uptake. | 2003 May |
|
A comparison of the effects of loxapine with ziprasidone and thioridazine on the release of dopamine and acetylcholine in the prefrontal cortex and nucleus accumbens. | 2003 May |
|
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 |
|
Transient hyperproinsulinemia during treatment with clozapine and amisulpride. | 2004 Jun |
|
Treatment-refractory schizophrenia. | 2004 Mar |
|
An assessment of quality of sleep and the use of drugs with sedating properties in hospitalized adult patients. | 2004 Mar 24 |
|
Treatment of acute mania--from clinical trials to recommendations for clinical practice. | 2005 Jan |
|
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs. | 2005 May |
|
Contrasting loxapine to its isomer isoloxapine--the critical role of in vivo D2 blockade in determining atypicality. | 2005 Sep 15 |
|
Increasing psychosis in a patient switched from clozaril to generic clozapine. | 2006 Apr |
|
Time to discontinuation of atypical versus typical antipsychotics in the naturalistic treatment of schizophrenia. | 2006 Feb 21 |
|
[Efficacy and adverse reactions of antipsychotics for neuropsychiatric symptoms in dementia: a systematic review]. | 2006 Jul 15 |
|
[Therapeutics approach of adult patients with acute and chronic psychotic states: REALITE survey]. | 2006 Jul-Aug |
|
Adjunctive topiramate in ultradian cycling bipolar disorder: case report with 3-year follow-up. | 2006 Jun |
|
[Clinical and socio-demographic profile of patients with schizophrenia according to the antipsychotic treatment prescribed]. | 2006 May-Jun |
|
Synthesis, characterization, antimicrobial and single crystal X-ray crystallographic studies of some new sulfonyl, 4-chloro phenoxy benzene and dibenzoazepine substituted benzamides. | 2006 Nov |
|
Loxapine treatment in an autistic child with aggressive behavior: therapeutic challenges. | 2006 Oct |
|
Efficacy of typical and atypical antipsychotics for primary and comorbid anxiety symptoms or disorders: a review. | 2006 Sep |
|
Risk of extrapyramidal syndrome in schizophrenic patients treated with antipsychotics: a population-based study. | 2007 Apr |
|
Correlations between weight changes and lipid profile changes in schizophrenic patients after antipsychotics therapy. | 2007 Jan-Feb |
|
Simultaneous determination of methadone, buprenorphine and norbuprenorphine in biological fluids for therapeutic drug monitoring purposes. | 2007 Mar 1 |
|
Simultaneous analysis of classical neuroleptics, atypical antipsychotics and their metabolites in human plasma. | 2007 May |
|
Clozapine: Current perspective. | 2007 Oct |
|
Determination of clozapine and its metabolite, norclozapine in various biological matrices using high-performance liquid chromatography. | 2007 Oct |
|
HPLC analysis of the novel antidepressant duloxetine in human plasma after an original solid-phase extraction procedure. | 2007 Sep 1 |
|
Analysis of the recent antipsychotic aripiprazole in human plasma by capillary electrophoresis and high-performance liquid chromatography with diode array detection. | 2008 Apr 7 |
|
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913). | 2008 Dec 22 |
|
Modifications of antiepileptic drugs for improved tolerability and efficacy. | 2008 Feb 14 |
|
Incorporating clinical guidelines through clinician decision-making. | 2008 Feb 29 |
|
Efficacy and tolerability of second-generation antipsychotics in children and adolescents with schizophrenia. | 2008 Jan |
|
Rapid liquid chromatography/tandem mass spectrometer (LCMS) method for clozapine and its metabolite N-desmethyl clozapine (norclozapine) in human serum. | 2009 |
|
Neuroanatomical, neurochemical, and neurodevelopmental basis of obsessive-compulsive symptoms in schizophrenia. | 2009 Jan |
|
Safety and efficacy of antipsychotic drugs for the behavioral and psychological symptoms of dementia. | 2009 Jan |
|
Finding my faith. | 2009 Jan |
|
Use and safety of antipsychotic drugs during pregnancy. | 2009 May |
|
Psychotic woman with painful abdominal distension. Life-threatening psychotropic drug-induced gastrointestinal hypomotility. | 2009 Nov |
|
Beneficial effects of loxapine on agitation and breathing patterns during weaning from mechanical ventilation. | 2010 |
|
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 |
|
Validation of HPLC-MS/MS methods for analysis of loxapine, amoxapine, 7-OH-loxapine, 8-OH-loxapine and loxapine N-oxide in human plasma. | 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 |
|
Pharmacological interventions for borderline personality disorder. | 2010 Jun 16 |
|
Identifying unexpected therapeutic targets via chemical-protein interactome. | 2010 Mar 8 |
|
4-Nitro-2-phenoxy-aniline. | 2010 May 8 |
|
Olanzapine approved for the acute treatment of schizophrenia or manic/mixed episodes associated with bipolar I disorder in adolescent patients. | 2010 Nov 10 |
|
A 64-week, multicenter, open-label study of aripiprazole effectiveness in the management of patients with schizophrenia or schizoaffective disorder in a general psychiatric outpatient setting. | 2010 Sep 17 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.adasuve.com/PDF/AdasuvePI.pdf http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022549s000lbl.pdf
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 00:09:55 UTC 2021
by
admin
on
Sat Jun 26 00:09:55 UTC 2021
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Record UNII |
LER583670J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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LIVERTOX |
575
Created by
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NCI_THESAURUS |
C29710
Created by
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EMA ASSESSMENT REPORTS |
ADASUVE (AUTHORIZED: SCHIZOPHRENIA)
Created by
admin on Sat Jun 26 00:09:56 UTC 2021 , Edited by admin on Sat Jun 26 00:09:56 UTC 2021
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WHO-VATC |
QN05AH01
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WHO-ATC |
N05AH01
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EMA ASSESSMENT REPORTS |
ADASUVE (AUTHORIZED: BIPOLAR DISORDER)
Created by
admin on Sat Jun 26 00:09:56 UTC 2021 , Edited by admin on Sat Jun 26 00:09:56 UTC 2021
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Code System | Code | Type | Description | ||
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LOXAPINE
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PRIMARY | |||
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1977-10-2
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PRIMARY | |||
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6475
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PRIMARY | RxNorm | ||
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3964
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PRIMARY | |||
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217-835-3
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PRIMARY | |||
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3111
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205
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PRIMARY | |||
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DB00408
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1613
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PRIMARY | |||
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1977-10-2
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PRIMARY | |||
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LER583670J
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PRIMARY | |||
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2610
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PRIMARY | |||
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C61816
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PRIMARY | |||
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M6915
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PRIMARY | Merck Index | ||
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D008152
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CHEMBL831
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Loxapine
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SUB08607MIG
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PRIMARY |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
PLASMA
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE ACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
Mediator: flavanoid monoamine oxidases
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Related Record | Type | Details | ||
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ACTIVE MOIETY |