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Flupenthixol dihydrochloride

Antipsychotic drug,exhibits antagonistic activity at dopamine D1-5 receptors CAS# 2413-38-9

Flupenthixol dihydrochloride

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Chemical structure

Flupenthixol dihydrochloride

3D structure

Chemical Properties of Flupenthixol dihydrochloride

Cas No. 2413-38-9 SDF Download SDF
PubChem ID 5282483 Appearance Powder
Formula C23H27Cl2F3N2OS M.Wt 507.44
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 83.3 mg/mL (164.16 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-[4-[(3Z)-3-[2-(trifluoromethyl)thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol;dihydrochloride
SMILES C1CN(CCN1CCC=C2C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F)CCO.Cl.Cl
Standard InChIKey IOVDQEIIMOZNNA-MHKBYHAFSA-N
Standard InChI InChI=1S/C23H25F3N2OS.2ClH/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29;;/h1-2,4-8,16,29H,3,9-15H2;2*1H/b18-5-;;
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Flupenthixol dihydrochloride

DescriptionAntipsychotic drug. Exhibits antagonistic activity at dopamine D1-5 receptors. Used in schizophrenia treatment.

Flupenthixol dihydrochloride Dilution Calculator

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Flupenthixol dihydrochloride Molarity Calculator

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Preparing Stock Solutions of Flupenthixol dihydrochloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9707 mL 9.8534 mL 19.7068 mL 39.4135 mL 49.2669 mL
5 mM 0.3941 mL 1.9707 mL 3.9414 mL 7.8827 mL 9.8534 mL
10 mM 0.1971 mL 0.9853 mL 1.9707 mL 3.9414 mL 4.9267 mL
50 mM 0.0394 mL 0.1971 mL 0.3941 mL 0.7883 mL 0.9853 mL
100 mM 0.0197 mL 0.0985 mL 0.1971 mL 0.3941 mL 0.4927 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Flupenthixol dihydrochloride

MIC: 10-100 μg/mL in most of the strains

Flupenthixol, introduced in 1965 by Lundbeck, marketed under brand names such asDepixol.Flupenthixolis atypical antipsychoticdrugof thethioxantheneclass. In addition to single drug preparations, flupenthixol is also available asflupentixol/melitracen, which is acombination product.

In vitro: The minimum inhibitory concentration of flupenthixol was determined by the National Committee for Clinical Laboratory Standards agar dilution method. MICs ranged from 10–100 μg/mL for most of the strains, whilst some strains were inhibited at even lower concentrations. The mode of action of flupenthixol was found to be bacteriostatic against Staphylococcus aureus and Vibrio cholerae [1].

In vivo: In the in vivo experiments, flupenthixol was able to contribute significant protection to a Swiss strain of white mice challenged with 50 median lethal dose of a mouse-virulent strain at a drug concentration of 15 μg/mouse. Moreover, flupenthixol reduced remarkably the number of viable bacteria in organs and blood of mice treated with flupenthixol [1].

Clinical trial: An clinical trial was carried out to evaluate the effectiveness and side-effects of flupenthixol treatment. The results showed that symptoms of depression, worrying, withdrawal, as well as psychomotor retardation were improved significantly with flupenthixol. Thus, it was concluded that schizophrenic patients characterized by depressive symptoms might more benefit to the flupenthixol treatment [2].

References:
[1] Jeyaseeli L,Gupta AD,Asok Kumar K,Mazumdar K,Dutta NK,Dastidar SG.  Antimicrobial potentiality of the thioxanthene flupenthixol through extensive in vitro and in vivo experiments. Int J Antimicrob Agents.2006 Jan;27(1):58-62.
[2] Kong DS,Yeo SH.  An open clinical trial with the long-acting neuroleptics flupenthixol decanoate and fluphenazine decanoate in the maintenance treatment of schizophrenia. Pharmatherapeutica.1989;5(6):371-9.

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References on Flupenthixol dihydrochloride

Flupenthixol dihydrochloride decomposition in aqueous solution.[Pubmed:423084]

J Pharm Sci. 1979 Feb;68(2):169-71.

Flupenthixol dihydrochloride in aqueous solution oxidized to trifluoromethylthioxanthone, ethanol, and piperazine via aldehydic and epoxidic intermediates in the presence of air. The formation rate of trifluoromethylthioxanthone increased with increases in pH and oxygen concentration. Buffer ions also affected the decomposition rate. Micelle formation by the drug markedly influenced its oxidation rate.

Depression in general practice: a comparison of flupenthixol dihydrochloride and dothiepin hydrochloride.[Pubmed:2272193]

Curr Med Res Opin. 1990;12(3):191-7.

A single-blind, parallel group, general practice study was carried out in 153 patients with mild to moderate depression to compare the efficacy and tolerability of Flupenthixol dihydrochloride and dothiepin hydrochloride. Patients were allocated at random to receive single daily doses of either 1 mg flupenthixol in the morning or 75 mg dothiepin in the evening, and this dose could be doubled at the end of 2 weeks in the event of inadequate response. Assessments were made on entry and after 1, 2, 4 and 6 weeks of treatment using the Hamilton Depression Rating Scale, a 4-point severity scale and an unwanted symptoms checklist. The results showed that both treatments significantly improved the patients' condition over 6 weeks, and there was a significant difference in favour of flupenthixol at end-point. Both drugs were well tolerated, although persistence of anticholinergic side-effects in the dothiepin group resulted in a trend favouring flupenthixol. One patient in the flupenthixol group attempted suicide by overdose but made a complete recovery.

Description

Flupentixol dihydrochloride, a thioxanthene drug, is used in therapy of schizophrenia as well as in anxiolytic and depressive disorders.

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