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 |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| minor | ||||
| no | no (co-administration study) Comment: ketoconazole did not affect loxapine transport Page: 20.0 |
|||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors. | 2000 Oct |
|
| Inhibition of glucose transport in PC12 cells by the atypical antipsychotic drugs risperidone and clozapine, and structural analogs of clozapine. | 2001 Dec 27 |
|
| [Body weight changes and psychotropic drug treatment: neuroleptics]. | 2001 May-Jun |
|
| A new class of antiarrhythmic-defibrillatory agents. | 2001 Nov 19 |
|
| 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 |
|
| [Survey of management methods for patients in a state of agitation at admission and emergency departments in France]. | 2003 Mar-Apr |
|
| 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 |
|
| 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 |
|
| JL 13, an atypical antipsychotic: a preclinical review. | 2003 Spring |
|
| 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 |
|
| [Agranulocytosis induced by loxapine in an elderly patient: a case study]. | 2004 Sep-Oct |
|
| 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 |
|
| 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 |
|
| Lack of enhanced effect of antipsychotics combined with fluvoxamine on acetylcholine release in rat prefrontal cortex. | 2006 Dec |
|
| 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 |
|
| Simultaneous analysis of classical neuroleptics, atypical antipsychotics and their metabolites in human plasma. | 2007 May |
|
| Pharmacological causes of hyperprolactinemia. | 2007 Oct |
|
| Modifications of antiepileptic drugs for improved tolerability and efficacy. | 2008 Feb 14 |
|
| Rapid liquid chromatography/tandem mass spectrometer (LCMS) method for clozapine and its metabolite N-desmethyl clozapine (norclozapine) in human serum. | 2009 |
|
| Spectroscopic and electrochemical analysis of psychotropic drugs. | 2009 Jan |
|
| 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 |
|
| [Catatonia in a 14 year-old girl: treatment with clorazepam and carbamazepine, a 10-year follow-up]. | 2010 Feb |
|
| Identifying unexpected therapeutic targets via chemical-protein interactome. | 2010 Mar 8 |
|
| Olanzapine approved for the acute treatment of schizophrenia or manic/mixed episodes associated with bipolar I disorder in adolescent patients. | 2010 Nov 10 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 20:09:53 UTC 2022
by
admin
on
Fri Dec 16 20:09:53 UTC 2022
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| Record UNII |
376MYL4MAL
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C66885
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NCI_THESAURUS |
C66883
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CHEMBL831
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SUB22686
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C77574
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71400
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Loxapine hydrochloride
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376MYL4MAL
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DBSALT001429
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54810-23-0
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DTXSID70203304
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91138
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |