Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H18ClN3O.C4H6O4 |
Molecular Weight | 445.896 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCC(O)=O.CN1CCN(CC1)C2=NC3=C(OC4=C2C=C(Cl)C=C4)C=CC=C3
InChI
InChIKey=YQZBAXDVDZTKEQ-UHFFFAOYSA-N
InChI=1S/C18H18ClN3O.C4H6O4/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;5-3(6)1-2-4(7)8/h2-7,12H,8-11H2,1H3;1-2H2,(H,5,6)(H,7,8)
Molecular Formula | C4H6O4 |
Molecular Weight | 118.088 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|||
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 |
|
Treatment of the special patient with schizophrenia. | 2001 Jun |
|
Treatment-refractory schizophrenia. | 2004 Mar |
|
Increasing psychosis in a patient switched from clozaril to generic clozapine. | 2006 Apr |
|
Lack of enhanced effect of antipsychotics combined with fluvoxamine on acetylcholine release in rat prefrontal cortex. | 2006 Dec |
|
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 |
|
[Clinical and socio-demographic profile of patients with schizophrenia according to the antipsychotic treatment prescribed]. | 2006 May-Jun |
|
Systematic review of antipsychotics for the treatment of hospital-associated delirium in medically or surgically ill patients. | 2006 Nov |
|
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 |
|
Effect of loxapine on electrical brain activity, intracranial pressure, and middle cerebral artery flow velocity in traumatic brain-injured patients. | 2007 |
|
Risk of extrapyramidal syndrome in schizophrenic patients treated with antipsychotics: a population-based study. | 2007 Apr |
|
Simultaneous determination of the antipsychotic drugs levomepromazine and clozapine and their main metabolites in human plasma by a HPLC-UV method with solid-phase extraction. | 2007 Feb 1 |
|
Risk of death associated with the use of conventional versus atypical antipsychotic drugs among elderly patients. | 2007 Feb 27 |
|
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 |
|
Pharmacological causes of hyperprolactinemia. | 2007 Oct |
|
Determination of clozapine and its metabolite, norclozapine in various biological matrices using high-performance liquid chromatography. | 2007 Oct |
|
Loxapine for schizophrenia. | 2007 Oct 17 |
|
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 |
|
HPLC analysis of the antidepressant trazodone and its main metabolite m-CPP in human plasma. | 2008 Aug 5 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Bacitracin-sensitive aminopeptidase(s) degradation of methionine(5)-enkephalin by human brain putamen and hippocampus preparations: inhibition by phenothiazine drugs. | 2009 Nov-Dec |
|
Current perspectives in the treatment of resistant schizophrenia. | 2009 Oct-Dec |
|
Beneficial effects of loxapine on agitation and breathing patterns during weaning from mechanical ventilation. | 2010 |
|
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 |
|
Pharmacokinetics of loxapine following inhalation of a thermally generated aerosol in healthy volunteers. | 2010 Feb |
|
An overview of Indian research in schizophrenia. | 2010 Jan |
|
Simultaneous HPLC determination of 14 tricyclic antidepressants and metabolites in human plasma. | 2010 Jan |
|
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 |
|
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 |
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
Wed Jul 05 23:04:34 UTC 2023
by
admin
on
Wed Jul 05 23:04:34 UTC 2023
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Record UNII |
X59SG0MRYU
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Record Status |
Validated (UNII)
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Record Version |
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C29710
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |