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
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
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 |
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 |
---|---|---|
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 |
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 23:52:23 UTC 2023
by
admin
on
Wed Jul 05 23:52:23 UTC 2023
|
Record UNII |
376MYL4MAL
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |