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Details

Stereochemistry ACHIRAL
Molecular Formula C18H18ClN3O.C4H6O4
Molecular Weight 445.8968
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOXAPINE SUCCINATE

SMILES

CN1CCN(CC1)C2=Nc3ccccc3Oc4ccc(cc42)Cl.C(CC(=O)O)C(=O)O

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)

HIDE SMILES / InChI

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

Molecular Formula C4H6O4
Molecular Weight 118.0882
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOXITANE

Approved Use

Loxapine 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 Date

1.62518401E11
Primary
Adasuve

Approved Use

Schizophrenia

Launch Date

1.3559616E12
Primary
Adasuve

Approved Use

Bipolar I disorder

Launch Date

1.3559616E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Lack of enhanced effect of antipsychotics combined with fluvoxamine on acetylcholine release in rat prefrontal cortex.
2006 Dec
[Therapeutics approach of adult patients with acute and chronic psychotic states: REALITE survey].
2006 Jul-Aug
Systematic review of antipsychotics for the treatment of hospital-associated delirium in medically or surgically ill patients.
2006 Nov
Loxapine treatment in an autistic child with aggressive behavior: therapeutic challenges.
2006 Oct
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
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
Clozapine: Current perspective.
2007 Oct
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
Safety and efficacy of antipsychotic drugs for the behavioral and psychological symptoms of dementia.
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
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
[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
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
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
In vitro identification of the human cytochrome p450 enzymes involved in the oxidative metabolism of loxapine.
2011 Oct
Patents

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:03:07 UTC 2021
Edited
by admin
on Fri Jun 25 21:03:07 UTC 2021
Record UNII
X59SG0MRYU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOXAPINE SUCCINATE
MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
LOXAPINE SUCCINATE [USP-RS]
Common Name English
LOXAPINE SUCCINATE [USP MONOGRAPH]
Common Name English
LOXAPINE SUCCINATE [ORANGE BOOK]
Common Name English
LOXAPINE SUCCINATE [MART.]
Common Name English
NSC-759578
Code English
CL 71563
Code English
LOXAPINE SUCCINATE [VANDF]
Common Name English
LOXAPINE SUCCINATE [USAN]
Common Name English
CL-71563
Code English
LOXAPINE SUCCINATE [WHO-DD]
Common Name English
LOXAPINE SUCCINATE [MI]
Common Name English
LOXITANE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
Code System Code Type Description
MERCK INDEX
M6915
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
248-682-0
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
USP_CATALOG
1370702
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY USP-RS
EPA CompTox
27833-64-3
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
EVMPD
SUB02977MIG
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
NCI_THESAURUS
C47590
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
CAS
27833-64-3
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
DRUG BANK
DBSALT001194
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
PUBCHEM
71399
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
ChEMBL
CHEMBL831
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
RXCUI
6476
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY RxNorm
FDA UNII
X59SG0MRYU
Created by admin on Fri Jun 25 21:03:07 UTC 2021 , Edited by admin on Fri Jun 25 21:03:07 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY