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| Targets |
Tioxolone targets carbonic anhydrase (CA), a metalloenzyme that catalyzes the reversible hydration of carbon dioxide. It is a potent inhibitor of carbonic anhydrase I with a Ki of 91 nM. The compound binds in the active site of CA II and is cleaved via a zinc-hydroxide mechanism, forming 4-mercaptobenzene-1, which may contribute to its inhibitory activity. By inhibiting carbonic anhydrase, Tioxolone can modulate various physiological processes, including pH regulation, fluid secretion, and cell proliferation. This mechanism underlies its cytostatic and anti-inflammatory activities.
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| ln Vitro |
Tioxolone is reported to possess cytostatic, antipsoriatic, antibacterial and anti-mycotic properties. Tioxolone is also added to some cosmetics (e.g. hair shampoos and skin cleansers), due to claims for its oil-regulating and antibacterial properties. The three-dimensional framework of Tioxolone is further stabilized by π-π interactions between the oxathiolone and benzene rings in partially overlapping molecules.
In vitro, Tioxolone is reported to possess cytostatic, antipsoriatic, antibacterial, and anti-mycotic properties. It exhibits anti-leishmanial, antitumor, and anti-inflammatory activities. As a carbonic anhydrase inhibitor, its activity has been characterized in enzyme assays using purified CA I, where it demonstrates a Ki of 91 nM. Its antibacterial and antifungal activities have been confirmed in antimicrobial susceptibility tests. The compound's ability to inhibit cell proliferation has been demonstrated in various cell-based assays, supporting its potential as a cytostatic agent. |
| ln Vivo |
Tioxolone, a Benzoxathiol derivatives, has been used in the local therapy of psoriasis vulgaris and acne, and also reported to have anti-bacterial, anti-mycotic, and cytostatic properties. |
| Enzyme Assay |
Non-cellular enzyme assays for Tioxolone typically involve measuring its inhibition of carbonic anhydrase (CA) activity. These assays use purified CA I or CA II enzyme and a spectrophotometric or fluorometric substrate, such as 4-nitrophenyl acetate, to measure the rate of enzymatic reaction in the presence of varying concentrations of Tioxolone. The compound's ability to inhibit CA is assessed by determining the inhibition constant (Ki). Such assays are essential for characterizing its mechanism as a carbonic anhydrase inhibitor and for quantifying its potency.
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| Cell Assay |
In vitro cell-based assays for Tioxolone are conducted using various cell lines to assess its cytostatic, anti-inflammatory, and antibacterial activities. For example, its ability to inhibit cell proliferation can be assessed in cancer cell lines using MTT or similar assays. Its anti-inflammatory activity can be evaluated by measuring the production of inflammatory cytokines in activated immune cells. Antibacterial and antifungal activities are assessed using standard broth microdilution or agar diffusion methods against pathogenic microorganisms. These assays are crucial for confirming its mechanism of action and for identifying its therapeutic potential.
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| Animal Protocol |
In vivo animal studies for Tioxolone are typically conducted in animal models of acne or psoriasis to evaluate its topical efficacy. The compound is applied topically to the affected skin area, and its effects on inflammation, sebum production, and skin lesions are assessed. Its systemic absorption and safety are also evaluated in these studies. However, specific detailed protocols are not extensively documented in standard summaries. Its efficacy in treating psoriasis and acne has been established in clinical settings, supporting its use as a topical therapeutic agent.
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| ADME/Pharmacokinetics |
Tioxolone has a molecular weight of 168.17 g/mol and is a small, lipophilic molecule. It is incorporated into topical formulations such as shampoos and skin cleansers due to its sebum-regulating and antibacterial properties. Its pharmacokinetic properties are characterized by low systemic absorption when applied topically, minimizing the risk of systemic side effects. As a carbonic anhydrase inhibitor, it is expected to be metabolized in the skin and excreted locally. Its topical use is well-established in cosmetic and therapeutic applications.
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| Toxicity/Toxicokinetics |
Tioxolone is generally considered safe for topical use at recommended concentrations. It has been used in cosmetics and topical therapeutic products with a favorable safety profile. However, comprehensive toxicological data are limited, as it is primarily a research compound and cosmetic ingredient. As with all chemicals, appropriate safety precautions should be taken when handling Tioxolone. It is not intended for systemic use and is available as a research compound for studying carbonic anhydrase inhibition and related biological activities.
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| References |
Acta Crystallogr C.2004 Jun;60(Pt 6):o395-6;Exp Mol Med.2011 May 31;43(5):313-21.
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| Additional Infomation |
Tioxolone is a 1,3-benzoxythiocyclopentene with a hydroxyl substituent at the 6-position. It has anti-seborrheic activity.
Tioxolone (Thioxolone) is a benzoxathiol derivative and a potent inhibitor of carbonic anhydrase I with a Ki of 91 nM. It exhibits cytostatic, antipsoriatic, anti-acne, antibacterial, and anti-mycotic properties. It is used topically for the treatment of acne and psoriasis and is incorporated into cosmetics for its sebum-regulating and antibacterial effects. Tioxolone is not an approved systemic drug and is available as a research compound for studying carbonic anhydrase biology and dermatological applications. |
| Molecular Formula |
C7H4O3S
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| Molecular Weight |
168.17
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| Exact Mass |
167.988
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| CAS # |
4991-65-5
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| Related CAS # |
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| PubChem CID |
72139
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
377.8±44.0 °C at 760 mmHg
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| Melting Point |
158-160 °C(lit.)
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| Flash Point |
182.3±28.4 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.718
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| LogP |
1.77
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
183
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
SLYPOVJCSQHITR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H4O3S/c8-4-1-2-6-5(3-4)10-7(9)11-6/h1-3,8H
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| Chemical Name |
6-hydroxy-1,3-benzoxathiol-2-one
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.87 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 (14.87 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (14.87 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.9464 mL | 29.7318 mL | 59.4636 mL | |
| 5 mM | 1.1893 mL | 5.9464 mL | 11.8927 mL | |
| 10 mM | 0.5946 mL | 2.9732 mL | 5.9464 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.
Calculation results
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.
(2) Be sure to add the solvent(s) in order.
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