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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
Structure of LOXAPINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

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
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
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 Dec 16 20:09:53 UTC 2022
Edited
by admin
on Fri Dec 16 20:09:53 UTC 2022
Record UNII
376MYL4MAL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOXAPINE HYDROCHLORIDE
MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
Loxapine hydrochloride [WHO-DD]
Common Name English
LOXITANE C
Brand Name English
LOXAPINE HYDROCHLORIDE [MART.]
Common Name English
LOXAPINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
LOXAPINE HCL
Common Name English
LOXAPINE HYDROCHLORIDE [VANDF]
Common Name English
LOXITANE IM
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
NCI_THESAURUS C66883
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
Code System Code Type Description
ChEMBL
CHEMBL831
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
EVMPD
SUB22686
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
NCI_THESAURUS
C77574
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
PUBCHEM
71400
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
WIKIPEDIA
Loxapine hydrochloride
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
FDA UNII
376MYL4MAL
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
DRUG BANK
DBSALT001429
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
CAS
54810-23-0
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
EPA CompTox
DTXSID70203304
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY
RXCUI
91138
Created by admin on Fri Dec 16 20:09:54 UTC 2022 , Edited by admin on Fri Dec 16 20:09:54 UTC 2022
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY