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Loxapine Succinate

Alias: Loxapac; Cloxazepin; Daxolin; Maleate; Loxipine; Loxapine succinate salt; Loxapac; Loxapine, Succinate; Daxolin; Lederle; Oxilapine
Cat No.:V1031 Purity: ≥98%
Loxapine Succinate (Loxapac; Adasuve; Cloxazepin; Daxolin; Oxilapine), the succinate salt ofLoxapine which is a dibenzoxazepine anti-psychotic drug, is a potent D2DR/D4DR inhibitor as well as serotonergic receptor antagonist.
Loxapine Succinate
Loxapine Succinate Chemical Structure CAS No.: 27833-64-3
Product category: 5-HT Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
500mg
1g
2g
5g
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Other Forms of Loxapine Succinate:

  • Loxapine
  • Loxapine HCl
  • Loxapine-d8 (Loxapine-d8; Ketiapine-d8)
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Loxapine Succinate (Loxapac; Adasuve; Cloxazepin; Daxolin; Oxilapine), the succinate salt of Loxapine which is a dibenzoxazepine anti-psychotic drug, is a potent D2DR/D4DR inhibitor as well as serotonergic receptor antagonist. It is a common antipsychotic medication that is mostly used to treat schizophrenia.

Biological Activity I Assay Protocols (From Reference)
Targets
human 5-HT2; Human D4 Receptor; Human D1 Receptor; Human D2Receptor
ln Vitro

In vitro activity: [3H]ketanserin attaches to the 5-HT2 receptor in the human and bovine frontal cortex of the brain in the presence of loxapine, with ki values of 6.2 nM and 6.6 nM, respectively. The potency rank order of loxapine for the different receptors seems to be as follows: 5-HT2≥D4>D1>D2 in the comparative studies of the human membranes.[1] After one or three days of exposure, IL-1beta secretion by LPS-activated mixed glia cultures is decreased by loxapine at concentrations of 0.2 μM, 2 μM, and 20 μM. Moreover, loxapine reduces IL-1beta and IL-2 secretion in LPS-induced microglia cultures at concentrations of 2 μM, 10 μM, and 20 μM. Loxapine reduces IL-2 secretion in mixed glia cultures after 1 and 3 days of exposure.[2]

ln Vivo
Loxapine (5 mg/kg) causes the rat's serotonin (S2) receptor density to drop dramatically (by more than 50%) after four or ten weeks of daily injection. Rat brains treated with loxapine (5 mg/kg) show a significant 47% reduction in serotonin receptor density but no change in dopamine receptor density.[3] In rats, loxapine (0.3 mg/kg s.c.) causes severe catalepsy; two to five hours after injection, the scores reach the cut-off point of 45 s. After clozapine (10 mg/kg s.c.) is administered to treat fully established loxapine-induced catalepsy, the high catalepsy score in rats is lowered to a level that is not statistically different from that of vehicle-treated controls.[4]
Enzyme Assay
Receptor binding assays - dopamine, 5-HT2, NMDA receptors [1]
To perform the receptor binding assays, 0.8 nM of [3H] SCH23390 (Di receptor antagonist), 0.5 nM [3H] spiroperidol (D2 and D4 receptor antagonist), 0.5 nM of [3H] ketanserin (5-HT2 receptor antagonist), and 2.0 nM [3H] MK801 (NMDA receptor antagonist) were incubated with 150 )ig of membrane proteins in a final volume of 1 ml. Nonspecific binding was determined in parallel assays in the presence of 1 jM (+) butaclamol (D2 and D4 assays), 10 jM cis-flupenthixol (Di assays), 2 ,uM methysergide (5-HT2 assays) and 50 jM MK801 (NMDA assays). Assays using [3H] spiroperidol also included 50 nM ketanserin to occlude the presence ofserotonergic sites. For the competition experiments, varying concentrations of loxapine were included in the assay tubes. Incubations forthe Di, D2, 5-HT2 andNMDA receptors were performed at 25°C for 90 min, 25°C for 60 min, 37°C for 15 min and 25°C for 120 min, respectively. D4 receptor binding assays with COS cells were incubated at 22°C for 120 min using the cell binding buffer described in the membrane preparation section. At the end ofthe incubation, the bound and free ligands were separated by rapid filtration on Whatman GF/B filters, which were washed 3 times with 5 ml ofcold filtration buffer: (50 mM Tris-HCL, 1.0 mM EDTA, pH 7.4) for the [3H] spiroperidol and [3H] SCH23390 assays, (50 mM Tris-HCL, pH 7.4) for [3H] ketanserin assays, and (10 mM HEPES, 1 mM EDTA, pH 7.4) for [3H] MK80 1 assays. Bound radioactivity was measured using a Beckman Scintillation Counter (model LS 5000TA).[1]
Cell Assay
The cytokines IL-1beta and IL-2 are released from activated glial cells in the central nervous system and they are able to enhance catecholaminergic neurotransmission. There is no data concerning influence of antipsychotics on glial cell activity. Antipsychotics reaching the brain act not only on neurons but probably also on glial cells. The aim of this study was to evaluate the effect of chlorpromazine and loxapine on release of IL-1beta and IL-2 by mixed glial and microglial cell cultures. Chlorpromazine in concentrations 2 and 20 muM, and loxapine 0.2, 2 and 20 microM reduced IL-1beta secretion by LPS-activated mixed glia cultures after 1 and 3 days of exposure. Chlorpromazine in concentrations of 0.2, 2 and 20 microM reduced the IL-2 secretion in mixed glial cultures after 3 days of exposure. Loxapine in concentrations of 0.2, 2 and 20 microM reduced IL-2 secretion in mixed glia cultures after 1 and 3 days of exposure, and additionally loxapine decreased IL-1beta and IL-2 secretion in LPS-induced microglia cultures in concentrations of 2, 10 and 20 muM. Quinpirole-a D2 dopaminergic agonist increased LPS-induced IL-1beta and IL-2 secretion in mixed glia cultures only in the highest dose of 20 microM. These findings suggest the absence of functional dopamine receptors on cortical microglial cells. Mixed glia cultures deprived of microglia (by shaking and incubating with L-leucine methyl ester) did not release IL-1beta and IL-2. This observation suggests that microglia can be a source of assessed cytokines. Results of the present study support the view that antipsychotics act not only on neurons but also on glial cells. However, the clinical significance of these observations still remains unclear[2].
Animal Protocol
Adult male Wistar rats (150-175 g)
5 mg/kg
Intraperitoneal injection, daily for 4 or 10 weeks
Loxapine (0.3 mg/kg s.c.), olanzapine (10 mg/kg s.c.) and SCH 23390 (R-(+)-chloro-2, 3, 4, 5-tetrahydro-3-methyl-5-phenyl-1-H-3-benzazepine; 1 mg/kg, s.c.), but not clozapine (10 mg/kg, s.c.), induced catalepsy in rats. Co-administration of clozapine (1, 3 and 10 mg/kg s.c.) dose-dependently inhibited loxapine-induced catalepsy. Clozapine (10 mg/kg s.c.) also prevented the induction of catalepsy by olanzapine. In addition, clozapine abolished the catalepsy induced by loxapine when it was administered after the response had fully developed. In contrast, the duration of SCH 23390-induced catalepsy was prolonged by clozapine, indicating that its anti-catalepsy effects against olanzapine and loxapine are unlikely to be caused by muscle relaxation, sedation or stimulation. Since SCH 23390-induced catalepsy is reported to be blocked by scopolamine, dizocilpine (MK-801) or 8-hydroxy-dipropylamino-tetralin, it is unlikely that muscarinic blockade, NMDA ion channel blockade and 5-HT1A receptor agonism, respectively, are involved in clozapine's action, but the mechanism by which clozapine exerts this anti-cataleptic effect remains unknown.[4]
ADME/Pharmacokinetics
Absorption
Systemic bioavailability of the parent drug was only about one third that after an equivalent intramuscular dose (25 mg base) in male volunteers

Route of Elimination
Metabolites are excreted in the urine in the form of conjugates and in the feces unconjugated.

Animal studies with radioactive drug indicate that loxapine and/or its metabolites are widely distributed in body tissues with highest concentrations in brain, lungs, heart, liver, and pancreas. The drug appears in the CSF.

Loxapine is rapidly and almost completely absorbed from the GI tract. The drug is also almost completely absorbed following IM administration.

RAPIDLY & ALMOST COMPLETELY ABSORBED FROM GI TRACT. PEAK LOXAPINE SERUM LEVELS /WITHIN 2 HR, RANGE FROM 0.006 TO 0.013 MCG/ML AFTER/ 25 MG ORAL DOSE...MAJOR /ACTIVE/ METABOLITE IN SERUM IS 8-HYDROXYLOXAPINE /MAX CONCN 0.012-0.038 MCG/ML WITHIN 2-4 HR AFTER ORAL LOXAPINE. HUMAN/

LOXAPINE AND/OR METABOLITES...WIDELY DISTRIBUTED IN BODY TISSUES...HIGHEST CONCN IN BRAIN, LUNGS, HEART, LIVER, & PANCREAS...APPEARS IN CSF...CROSSES PLACENTA...IN MILK OF NURSING MOTHERS /ANIMALS, RADIOACTIVE DRUG/

METABOLITES /7- & 8-HYDROXY-, 7- & 8-HYDROXYDESMETHYLLOXAPINE; N-OXIDES OF LOXAPINE, 7- & 8-HYDROXYLOXAPINE/ EXCRETED IN URINE & FECES. LITTLE OR NO UNMETABOLIZED DRUG...FOUND...METABOLITES /PRIMARILY GLUCURONIDE OR SULFATE CONJUGATES IN URINE, PRIMARILY UNCONJUGATED IN FECES. HUMAN, ORAL/
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Metabolism / Metabolites
Hepatic

RAPIDLY & EXTENSIVELY METABOLIZED IN LIVER BY AROMATIC HYDROXYLATION, N-DEMETHYLATION & N-OXIDATION. MAJOR METABOLITES...8-HYDROXYLOXAPINE, & 7-HYDROXYLOXAPINE WHICH ARE ACTIVE...8-HYDROXYDESMETHYLLOXAPINE, 7-HYDROXYDESMETHYLLOXAPINE & LOXAPINE-N-OXIDE WHICH ARE INACTIVE /HUMAN, ORAL/

SIGNIFICANT AMT OF N-OXIDES OF /7-HYDROXY- & 8-HYDROXYLOXAPINES, METABOLITES FORMED BY HYDROXYLATION & N-OXIDATION/, PRESENT...LOXAPINE METABOLITES ARE EXCRETED IN URINE PRIMARILY AS GLUCURONIDE OR SULFATE CONJUGATES /HUMAN, ORAL/ American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1976

2 METABOLITES: 8-HYDROXYLOXAPINE & 8-HYDROXYAMOXAPINE, INCR ON ORAL MEDICATION.

Loxapine is rapidly and extensively metabolized in the liver by aromatic hydroxylation, N-oxidation. The major metabolites of loxapine are 8-hydroxyloxapine and 7-hydroxyloxapine which are active and 8-hydroxydesmethylloxapine, 7-hydroxydesmethylloxapine, and loxapine N-oxide which are inactive. Significant amounts of the N-oxides of the hydroxyloxapines are also present. McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1890
Loxepine has known human metabolites that include Loxepine N-glucuronide. S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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


Biological Half-Life Oral-4 hours
SERUM LEVELS OF LOXAPINE & METABOLITES DECLINE IN BIPHASIC MANNER. HALF-LIFE DURING 1ST PHASE...5 HR...DURING 2ND PHASE...19 HR. /AFTER SINGLE 25 MG ORAL DOSE, SEDATIVE EFFECT BEGINS IN 20-30 MIN; PEAK EFFECT WITHIN 1.5-3 HR; DURATION APPROX 12 HR. HUMAN/

References

[1]. J Psychiatry Neurosci . 1996 Jan;21(1):29-35.

[2]. Eur Neuropsychopharmacol . 2005 Jan;15(1):23-30.

[3]. Psychiatry Res . 1984 Aug;12(4):277-85.

[4]. Naunyn Schmiedebergs Arch Pharmacol . 1997 Mar;355(3):361-4.

Additional Infomation
Loxapine Succinate is the succinate salt form of loxapine, a tricyclic dibenzoxazepine antipsychotic agent with antiemetic, sedative, anticholinergic, and antiadrenergic actions. Loxapine succinate exerts its actions by blocking the dopamine receptors at postsynaptic receptor sites in the limbic system, cortical system and basal ganglia, thereby reducing the hallucinations and delusions that are associated with schizophrenia. This agent also exerts extrapyramidal side effects.
An antipsychotic agent used in schizophrenia.
See also: Loxapine (has active moiety).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H24CLN3O5
Molecular Weight
445.9
Exact Mass
445.14
Elemental Analysis
C, 59.26; H, 5.43; Cl, 7.95; N, 9.42; O, 17.94
CAS #
27833-64-3
Related CAS #
Loxapine; 1977-10-2; Loxapine hydrochloride; 54810-23-0; Loxapine-d8; 1189455-63-7
PubChem CID
71399
Appearance
White to off-white solid powder
Boiling Point
458.6ºC at 760mmHg
Melting Point
150-152°C
Flash Point
231.1ºC
LogP
3.018
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
4
Heavy Atom Count
31
Complexity
542
Defined Atom Stereocenter Count
0
SMILES
ClC1C([H])=C([H])C2=C(C=1[H])C(=NC1=C([H])C([H])=C([H])C([H])=C1O2)N1C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])C1([H])[H].O([H])C(C([H])([H])C([H])([H])C(=O)O[H])=O
InChi Key
YQZBAXDVDZTKEQ-UHFFFAOYSA-N
InChi Code
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)
Chemical Name
butanedioic acid;8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine
Synonyms
Loxapac; Cloxazepin; Daxolin; Maleate; Loxipine; Loxapine succinate salt; Loxapac; Loxapine, Succinate; Daxolin; Lederle; Oxilapine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 89~100 mg/mL (199.6~224.3 mM)
Water: <1 mg/mL
Ethanol: ~2 mg/mL (~4.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (5.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (5.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2427 mL 11.2133 mL 22.4266 mL
5 mM 0.4485 mL 2.2427 mL 4.4853 mL
10 mM 0.2243 mL 1.1213 mL 2.2427 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
Fasting Study of Loxapine Succinate Capsules 25 mg and Loxitane® Capsules 25 mg
CTID: NCT00648778
Phase: Phase 1
Status: Completed
Date: 2024-04-24
Tolerability and analgesic efficacy of Loxapine in patients with refractory, chemotherapy-induced neuropathic pain
EudraCT: 2014-005440-17
Phase: Phase 2
Status: Prematurely Ended
Date: 2015-09-17
Evaluation de l'intérêt de la loxapine dans le contrôle de l'agitation au cours du sevrage de la ventilation mécanique. Etude randomisée, contrôlée.
EudraCT: 2007-006742-18
Phase: Phase 4
Status: Ongoing
Date: 2010-08-25
Tolerability and Analgesic Efficacy of Loxapine in Patients With Refractory, Chemotherapy-induced Neuropathic Pain
CTID: NCT02820519
Phase: Phase 2
Status: Terminated
Date: 2022-07-01
Observational Study Evaluating the Safety of ADASUVE® in Agitation Associated With Schizophrenia or Bipolar I Disorder
CTID: NCT03513549
Status: Unknown status
Date: 2020-10-19
Family Intervention in Recent Onset Schizophrenia Treatment (FIRST)
CTID: NCT02600741
Status: Completed
Date: 2019-01-23
Inhaled Loxapine vs Intramuscular (IM) Haloperidol + Lorazepam for Agitation
CTID: NCT03110900
Phase: Phase 4
Status: Terminated
Date: 2018-06-11
Staccato Loxapine in Migraine (in Clinic)
CTID: NCT00489476
Phase: Phase 2
Status: Completed
Date: 2017-07-06
Biological Data
  • Loxapine Succinate
    Least-squares mean ΔΔQTcI (predose subtracted individually corrected QT duration compared with placebo) and two-sided 90% CIs, primary analysis model (QT population).Int J Clin Pharmacol Ther. 2015 Nov; 53(11): 963–971.
  • Loxapine Succinate
    Predose subtracted individually corrected QT duration compared with placebo (ΔΔQTcI, msec) vs. loxapine concentrations (ng/mL) and fitted linear regression (ΔΔQTcI = –1.1 + 1.64 (log (loxapine)); p = 0.013).Int J Clin Pharmacol Ther. 2015 Nov; 53(11): 963–971.
  • Loxapine Succinate
    Predose subtracted individually corrected QT duration compared with placebo (ΔΔQTcI, msec) vs. 8-OH-loxapine concentrations (ng/mL) and fitted linear regression (ΔΔQTcI = 1.7 – 0.561 (log (loxapine)); p = not significant).Int J Clin Pharmacol Ther. 2015 Nov; 53(11): 963–971.
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