Synonym
Loxapine Succinate; Loxapine succinate salt; Loxapac; Cloxazepin; Daxolin; Maleate, Loxipine; Oxilapine; Succinate, Loxapine;
IUPAC/Chemical Name
butanedioic acid;8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine
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)
SMILES Code
CN1CCN(CC1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl.C(CC(=O)O)C(=O)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Loxapine succinate is an orally active dopamine inhibitor, 5-HT receptor antagonist and also a dibenzoxazepine anti-psychotic agent.
In vitro activity:
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.
Reference: Eur Neuropsychopharmacol. 2005 Jan;15(1):23-30. https://pubmed.ncbi.nlm.nih.gov/15572270/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
67.28 |
| DMSO |
73.0 |
163.71 |
| DMSO:PBS (pH 7.2) (1:9) |
0.1 |
0.22 |
| Ethanol |
3.5 |
7.85 |
| Water |
2.5 |
5.61 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
445.90
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Labuzek K, Kowalski J, Gabryel B, Herman ZS. Chlorpromazine and loxapine reduce interleukin-1beta and interleukin-2 release by rat mixed glial and microglial cell cultures. Eur Neuropsychopharmacol. 2005 Jan;15(1):23-30. doi: 10.1016/j.euroneuro.2004.04.002. PMID: 15572270.
2. Singh AN, Barlas C, Singh S, Franks P, Mishra RK. A neurochemical basis for the antipsychotic activity of loxapine: interactions with dopamine D1, D2, D4 and serotonin 5-HT2 receptor subtypes. J Psychiatry Neurosci. 1996 Jan;21(1):29-35. PMID: 8580115; PMCID: PMC1188731.
In vitro protocol:
1. Labuzek K, Kowalski J, Gabryel B, Herman ZS. Chlorpromazine and loxapine reduce interleukin-1beta and interleukin-2 release by rat mixed glial and microglial cell cultures. Eur Neuropsychopharmacol. 2005 Jan;15(1):23-30. doi: 10.1016/j.euroneuro.2004.04.002. PMID: 15572270.
2. Singh AN, Barlas C, Singh S, Franks P, Mishra RK. A neurochemical basis for the antipsychotic activity of loxapine: interactions with dopamine D1, D2, D4 and serotonin 5-HT2 receptor subtypes. J Psychiatry Neurosci. 1996 Jan;21(1):29-35. PMID: 8580115; PMCID: PMC1188731.
1: Bhardwaj RM, Johnston BF, Oswald ID, Florence AJ. A complementary experimental
and computational study of loxapine succinate and its monohydrate. Acta
Crystallogr C. 2013 Nov;69(Pt 11):1273-8. doi: 10.1107/S0108270113029363. Epub
2013 Oct 31. PubMed PMID: 24192171.
2: Escande M, Granier F, Gardes JP, Boscredon J, Concina M. [Clinical trial of
loxapine succinate in the treatment of 30 cases of psychotic states]. Ann Med
Psychol (Paris). 1983 Mar;141(3):309-22. French. PubMed PMID: 6357022.
3: Feldman HS. Loxapine succinate as initial treatment of hostile and aggressive
schizophrenic criminal offenders. J Clin Pharmacol. 1982 Aug-Sep;22(8-9):366-70.
PubMed PMID: 7130427.
4: Branchey MH, Lee JH, Simpson GM, Elgart B, Vicencio A. Loxapine succinate as a
neuroleptic agent: evaluation in two populations of elderly psychiatric patients.
J Am Geriatr Soc. 1978 Jun;26(6):263-7. PubMed PMID: 757995.
5: Clark ML, Paredes A, Costiloe JP, Fulkerson FG, Wood F. Evaluation of two dose
levels of loxapine succinate in chronic schizophrenia. Dis Nerv Syst. 1977
Jan;38(1):7-10. PubMed PMID: 318984.
6: Dube KC, Kumar N. Loxapine succinate: a comparative study with chlorpromazine.
Curr Ther Res Clin Exp. 1976 Jun;19(6):653-60. PubMed PMID: 819223.
7: Simpson GM, Branchey MH, Lee JH, Varga E. A two year trial of loxapine
succinate in chronic psychotic patients. Dis Nerv Syst. 1976 May;37(5):305-7.
PubMed PMID: 816626.
8: Moyano CZ. A double-blind comparison of loxitane--loxapine succinate and
trifluoperazine hydrochloride in chronic schizophrenic patients. Dis Nerv Syst.
1975 Jun;36(6):301-4. PubMed PMID: 238810.
9: van der Velde CD, Kiltie H. Effectiveness of loxapine succinate in acute
schizophrenia: a comparative study with thiothixene. Curr Ther Res Clin Exp. 1975
Jan;17(1):1-12. PubMed PMID: 806422.
10: Charlalmpous KD, Freemesser GF, Smalling KF. A double-blind controlled study
of loxapine succinate in the treatment of anxiety neuroses. J Clin Pharmacol.
1974 Aug-Sep;14(8):464-9. PubMed PMID: 4850200.
11: Claghorn JL. A comparative study of loxapine succinate, librium, and placebo
in neurotic outpatients. Curr Ther Res Clin Exp. 1973 Jan;15(1):8-12. PubMed
PMID: 4631381.
12: Varga E, Simpson GM. Loxapine succinate in the treatment of uncontrollable
destructive behavior. Curr Ther Res Clin Exp. 1971 Dec;13(12):737-42. PubMed
PMID: 5001742.
13: Gershon S, Hekimian LJ, Burdock EI, Kim SS. Antipsychotic properties of
loxapine succinate. Curr Ther Res Clin Exp. 1970 May;12(5):280-5. PubMed PMID:
4986243.
14: Clinical pharmacological trial of loxapine succinate. J Clin Pharmacol J New
Drugs. 1970 May-Jun;10(3):175-81. PubMed PMID: 4910276.
15: James B, McIntyre M, Hannah J. A study of parenteral loxapine succinate in
very disturbed psychotic patients. N Z Med J. 1982 Feb 24;95(702):123-4. PubMed
PMID: 6952119.
16: Zisook S, Click MA Jr. Evaluations of loxapine succinate in the ambulatory
treatment of acute schizophrenic episodes. Int Pharmacopsychiatry.
1980;15(6):365-78. Review. PubMed PMID: 7028656.
17: Cottereau MJ, Poirier MF, Lôo H, Deniker P. [Loxapine succinate: a new
neuroleptic]. Encephale. 1979;5(3):251-67. French. PubMed PMID: 39739.
18: Chouinard G, Annable L, DeMontigny C, Kropsky ML. Loxapine succinate in the
treatment of newly admitted schizophrenic patients. Curr Ther Res Clin Exp. 1977
Jan;21(1):73-9. PubMed PMID: 12921.
19: Nair NP, Decker BL, Schwartz G. Loxapine succinate in the treatment of
chronic schizophrenia. Curr Ther Res Clin Exp. 1976 Dec;20(6):802-9. PubMed PMID:
12919.
20: Mahal AS, Malik SC, Srinivasamurthy U. Evaluation of loxapine succinate as an
anxiolytic in comparison with chlordiazepoxide. Curr Ther Res Clin Exp. 1976
Jul;20(1):84-93. PubMed PMID: 821710.
