ContaminantDB: Loxapine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (33)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:49 UTC

Update Date

2026-05-14 16:37:50 UTC

Accession Number

CHEM002188

Identification

Common Name

Loxapine

Class

Small Molecule

Description

Loxapine is only found in individuals that have used or taken this drug. It is an antipsychotic agent used in schizophrenia. Loxapine is a dopamine antagonist, and also a serotonin 5-HT2 blocker. The exact mode of action of Loxapine has not been established, however changes in the level of excitability of subcortical inhibitory areas have been observed in several animal species in association with such manifestations of tranquilization as calming effects and suppression of aggressive behavior.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Antipsychotic Agent
Dopamine Antagonist
Drug
Ether
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Chloro-11-(4-methyl-1-piperazinyl)dibenz[b,F][1,4]oxazepine	ChEBI
Cloxazepine	ChEBI
Loxapina	ChEBI
Loxapinum	ChEBI
Oxilapine	ChEBI
Adasuve	Kegg
Loxapine hydrochloride	HMDB
Loxapine succinate	HMDB
Loxipine maleate	HMDB
Loxapine monohydrochloride	HMDB
Loxapinsuccinate	HMDB
Succinate, loxapine	HMDB
Hydrochloride, loxapine	HMDB
Loxipine succinate	HMDB
Loxitane	HMDB
2-Chloro-11-(4-methyl-1-piperazinyl)-dibenz(b,F)(1,4)oxazepine	HMDB
Maleate, loxipine	HMDB

Chemical Formula

C₁₈H₁₈ClN₃O

Average Molecular Mass

327.808 g/mol

Monoisotopic Mass

327.114 g/mol

CAS Registry Number

1977-10-2

IUPAC Name

13-chloro-10-(4-methylpiperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene

Traditional Name

loxapine

SMILES

CN1CCN(CC1)C1=NC2=CC=CC=C2OC2=C1C=C(Cl)C=C2

InChI Identifier

InChI=1S/C18H18ClN3O/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

InChI Key

XJGVXQDUIWGIRW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazepines

Sub Class

Dibenzoxazepines

Direct Parent

Dibenzoxazepines

Alternative Parents

Substituents

Dibenzoxazepine
Diaryl ether
N-methylpiperazine
N-alkylpiperazine
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Benzenoid
Imidolactam
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Carboxylic acid amidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Amidine
Amine
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzoxazepine (CHEBI:50841 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

dopaminergic antagonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	109-111°C
Boiling Point	Not Available
Solubility	1.03e-01 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.18	ALOGPS
logP	3.46	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	7.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	28.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	95.11 m³·mol⁻¹	ChemAxon
Polarizability	34.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r5-8094000000-3f11548f145e2cd0d2a5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00ai-0149000000-d463f8ddf4248264d132	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-01r6-0930000000-4798aec046d747300d80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00ai-0149000000-d463f8ddf4248264d132	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01r6-0930000000-4798aec046d747300d80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-0092000000-d36334adec23dfc827b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-13c7c5980fa375485ea6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0029000000-ee11b761132aadb447f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9250000000-cdb8e78cf5fd1fd059b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-71d4c9395b89ad9fc22a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0039000000-ca6576c997e0e1af0ab2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006y-3491000000-40caba03e0caacbf4b76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-1f57d14978e5410155ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0019000000-171a44896a8b8aa67151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0090000000-8f9b474f4d539ce49d69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-f859e2aff8bfc6f7a27b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0039000000-568c941d47f67e7c6c41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-5091000000-1f13f155778e72cff118	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-7590000000-118f30ca0699bf2b3d2e	Spectrum

Toxicity Profile

Route of Exposure

Oral, Intramuscular. Systemic bioavailability of the parent drug was only about one third that after an equivalent intramuscular dose (25 mg base) in male volunteers.

Mechanism of Toxicity

Loxapine is a dopamine antagonist, and also a serotonin 5-HT2 blocker. The exact mode of action of Loxapine has not been established, however changes in the level of excitability of subcortical inhibitory areas have been observed in several animal species in association with such manifestations of tranquilization as calming effects and suppression of aggressive behavior.

Metabolism

Hepatic Route of Elimination: Metabolites are excreted in the urine in the form of conjugates and in the feces unconjugated. Half Life: Oral-4 hours

Toxicity Values

LD₅₀=65 mg/kg (Orally in mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the management of the manifestations of psychotic disorders such as schizophrenia

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

LD₅₀=65 mg/kg (Orally in mice)

Treatment

The treatment of overdosage is essentially symptomatic and supportive. Early gastric lavage and extended dialysis might be expected to be beneficial. Centrally-acting emetics may have little effect because of the antiemetic action of loxapine. In addition, emesis should be avoided because of the possibility of aspiration of vomitus. Avoid analeptics, such as pentylenetetrazol, which may cause convulsions. Severe hypotension might be expected to respond to the administration of levarterenol or phenylephrine. Epinephrine should not be used since its use in a patient with partial adrenergic blockade may further lower the blood pressure. Severe extrapyramidal reactions should be treated with anticholinergic antiparkinson agents or diphenhydramine hydrochloride, and anticonvulsant therapy should be initiated as indicated. Additional measures include oxygen and intravenous fluids. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB00408

HMDB ID

HMDB0014552

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID