Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H18ClN3O |
Molecular Weight | 327.808 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC1)C2=NC3=C(OC4=C2C=C(Cl)C=C4)C=CC=C3
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 | 327.808 |
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 |
---|---|---|
Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography. | 1991 Mar 8 |
|
Inhibition of glucose transport in PC12 cells by the atypical antipsychotic drugs risperidone and clozapine, and structural analogs of clozapine. | 2001 Dec 27 |
|
Treatment of the special patient with schizophrenia. | 2001 Jun |
|
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine. | 2002 Nov |
|
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 |
|
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. | 2003 Mar |
|
Differential effects of atypical and typical antipsychotic drugs on N-methyl-D-aspartate- and electrically evoked responses in the pyramidal cells of the rat medial prefrontal cortex. | 2003 May |
|
Effects of some antidepressant drugs on tryptaminergic responses of the rat jejunum. | 2003 Oct |
|
Neuroleptic malignant syndrome: case report and discussion. | 2003 Sep 2 |
|
Differential inverse agonist efficacies of SB-258719, SB-258741 and SB-269970 at human recombinant serotonin 5-HT7 receptors. | 2004 Jul 14 |
|
Treatment-refractory schizophrenia. | 2004 Mar |
|
Minimally effective doses of conventional antipsychotic medications used to treat aggression, self-injurious and destructive behaviors in mentally retarded adults. | 2005 Feb |
|
Chlorpromazine and loxapine reduce interleukin-1beta and interleukin-2 release by rat mixed glial and microglial cell cultures. | 2005 Jan |
|
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs. | 2005 May |
|
Time to discontinuation of atypical versus typical antipsychotics in the naturalistic treatment of schizophrenia. | 2006 Feb 21 |
|
[Therapeutics approach of adult patients with acute and chronic psychotic states: REALITE survey]. | 2006 Jul-Aug |
|
[Clinical and socio-demographic profile of patients with schizophrenia according to the antipsychotic treatment prescribed]. | 2006 May-Jun |
|
Correlations between weight changes and lipid profile changes in schizophrenic patients after antipsychotics therapy. | 2007 Jan-Feb |
|
Pharmacological causes of hyperprolactinemia. | 2007 Oct |
|
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 |
|
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 |
|
Hospitalization risk associated with typical and atypical antipsychotic use in community-dwelling elderly patients. | 2008 Oct |
|
The association between class of antipsychotic and rates of hospitalization: results of a retrospective analysis of data from the 2005 Medicare current beneficiary survey. | 2009 Dec |
|
Neuroanatomical, neurochemical, and neurodevelopmental basis of obsessive-compulsive symptoms in schizophrenia. | 2009 Jan |
|
Spectroscopic and electrochemical analysis of psychotropic drugs. | 2009 Jan |
|
Bacitracin-sensitive aminopeptidase(s) degradation of methionine(5)-enkephalin by human brain putamen and hippocampus preparations: inhibition by phenothiazine drugs. | 2009 Nov-Dec |
|
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 |
|
[Catatonia in a 14 year-old girl: treatment with clorazepam and carbamazepine, a 10-year follow-up]. | 2010 Feb |
|
An overview of Indian research in schizophrenia. | 2010 Jan |
|
Pharmacological interventions for borderline personality disorder. | 2010 Jun 16 |
|
Identifying unexpected therapeutic targets via chemical-protein interactome. | 2010 Mar 8 |
|
Chem2Bio2RDF: a semantic framework for linking and data mining chemogenomic and systems chemical biology data. | 2010 May 17 |
|
In vitro identification of the human cytochrome p450 enzymes involved in the oxidative metabolism of loxapine. | 2011 Oct |
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
Thu Jul 06 00:49:30 UTC 2023
by
admin
on
Thu Jul 06 00:49:30 UTC 2023
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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 |
NBK548875
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NCI_THESAURUS |
C29710
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EMA ASSESSMENT REPORTS |
ADASUVE (AUTHORIZED: SCHIZOPHRENIA)
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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 Thu Jul 06 00:49:30 UTC 2023 , Edited by admin on Thu Jul 06 00:49:30 UTC 2023
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Code System | Code | Type | Description | ||
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LOXAPINE
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LER583670J
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1977-10-2
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6475
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3964
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217-835-3
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3111
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205
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DB00408
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1613
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DTXSID7023229
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LER583670J
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2610
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C61816
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M6915
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D008152
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CHEMBL831
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100000092266
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50841
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Loxapine
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SUB08607MIG
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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 |