Anthralin: Historical and current perspectives

Ashton, Richard; André, P; Lowe, Nicholas J.; Whitefield, M.

doi:10.1016/s0190-9622(83)70125-8

Cited by 114 publications

(47 citation statements)

References 119 publications

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“…Psoriasis has been treated for over 70 years with anthralin, the synthetic substitute of chrysarobin [1]. Although anthralin displays effective therapeutic properties, the use of the drug is often limited by severe inflammation of perilesional, uninvolved skin.…”

Section: Introductionmentioning

confidence: 99%

Antioxidants attenuate anthralin-induced skin inflammation in BALB/c mice: role of specific proinflammatory cytokines

Lange

Germolec

Foley

et al. 1998

Journal of Leukocyte Biology

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Anthralin is the most common therapeutic agent among a small number of pro-oxidant, 9-anthrones effective in the topical treatment of psoriasis. However, the usefulness of this drug is diminished by toxic side effects, including skin irritation and inflammation. The activities of anthralin are believed to be mediated by the generation of reactive oxygen intermediates and anthrone radicals produced in the skin. In this study, the dermal inflammatory response to anthralin was determined using a mouse ear swelling test. Maximum ear swelling induced by anthralin coincided with the elevation of cytokine mRNA expression in the skin, including interleukin-6, granulocyte-macrophage colony-stimulating factor, macrophage inflammatory protein-2, and tumor necrosis factor ␣ at 24 h post challenge. The role of free radical generation in ear swelling and cytokine modulation were examined by systemic administration of cell permeable and impermeable antioxidants before anthralin challenge. Superoxide dismutase and ␣-tocopherol acetate, but not the glutathione precursor N-acetyl cysteine, were effective inhibitors of anthralininduced ear swelling and cytokine elevation. Maximum inflammatory cell infiltration occurred 72-96 h post anthralin challenge and was also reduced by antioxidants. These data suggest that oxidative stress, generated at the site of anthralin treatment, alters the expression of dermal chemokines and other cytokines resulting in the recruitment of inflammatory cells. Systemic antioxidant administration may provide opportunities for therapeutic intervention against anthralin-associated toxicities.

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Section: Introductionmentioning

confidence: 99%

Antioxidants attenuate anthralin-induced skin inflammation in BALB/c mice: role of specific proinflammatory cytokines

Lange

Germolec

Foley

et al. 1998

Journal of Leukocyte Biology

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“…Several of these groups have been isolated in a free state. Anthralin was first synthesized in 1916 and since then, anthralin and its various derivatives have been used extensively as an antipsoriatic drugs 4,5 . Regarding the medicinal and chemical importance of anthralin, it was decided to carry out the following objectives in this research: (i) isolation of anthralin from the rhubarb roots by maceration and Soxhlet extraction methods using various polar and non-polar solvents and finally (ii) confirmation of the chemical structure of anthralin by various spectroscopic methods.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Identification of Anthralin From the Roots of Rhubarb Plant (Rheum palmatum)

Ashnagar

Naseri

Nasab

2007

E-Journal of Chemistry

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Anthralin is medically and chemically an important compound which can be found in rhubarb roots. Anthralin and anthralin derivatives have been used as antipsoriatic drugs. In this research, pure anthralin was isolated from the rhubarb roots by maceration and Soxhlet extraction methods in various polar and non-polar solvents.Successive TLC and column chromatography on silica gel with chloroform as the mobile phase afforded two distinct fractions with R f = 0.54 and 0.61. The 1 HNMR, 13 CNMR, IR, UV and MS spectra showed that the fraction with R f = 0.61 was anthralin. In both methods, methanol was found to be the most suitable solvent for extraction.

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“…This drug readily undergoes oxidation to a range of degradation products, including danthron and dithranol dimmer, which are thought to contribute to the undesired effects and are inactive or less active in terms of anti-psoriatic potency (Thoma, Holzmann, 1998;Mahrle, 1997). Dithranol has a yellow color, while its oxidation products are brown to black (Ashton, Andre, Lowe, 1983;Wiegrebe, Plumier, Mayer, 1985). So, the color can be a good parameter to study the stability of new formulations.…”

Section: Introductionmentioning

confidence: 99%

Use of solid dispersions to increase stability of dithranol in topical formulations

Estanqueiro

Conceição

Amaral

et al. 2014

Braz. J. Pharm. Sci.

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The present study was planned to improve the stability of dithranol using solid dispersions (SD). Two different SD at a 1:9 ratio of dithranol/excipient were prepared: one of them using glyceryl behenate as excipient and the other using a mixture of argan oil with stearic acid (1:8 ratio) as excipient. Pure dithranol and SD of dithranol were incorporated in an oil-in-water cream and in a hydrophobic ointment in a drug/ dermatological base ratio of 1:10. The physical and mechanical properties of semisolid formulations incorporating the pure drug and the developed SD were evaluated through rheological and textural analysis. To evaluate the stability, L*a*b* color space parameters of SD and semisolid formulations, and pH of hydrophilic formulations were determined at defined times, during one month. Each sample was stored at different conditions namely, light exposure (room temperature), high temperature exposition (37 °C) (protected from light) and protected from light (room temperature). Despite higher values of firmness and adhesiveness, hydrophobic ointment exhibited the best rheological features compared to the oil-in-water cream, namely a shear-thinning behavior and high thixotropy. These formulations have also presented more stability, with minor changes in L*a*b* color space parameters. The results of this study indicate that is possible to conclude that the developed SD contributed to the increased stability of dithranol.Uniterms: Dithranol/stability. Topical formulations/development. Solid dispersions/preparation. Stearic acid. Glyceryl behenate. Argan oil.Este trabalho teve como objetivo aumentar a estabalidade do ditranol através da preparação de dispersões sólidas (DS). Prepararam-se duas DS diferentes em proporção de 1:9 de ditranol/excipiente: em uma das DS utilizou-se beenato de glicerila como excipiente e na outra se utilizou mistura de óleo de argan com ácido esteárico (razão 1:8). Posteriormente, efetuou-se a incorporação de ditranol puro e das DS contendo este fármaco num creme hidrófilo ou óleo-água (O/A) e em pomada hidrófoba, na proporção 1:10 (fármaco ou respetivas DS/base dermatológica). As propriedades físicas e mecânicas das formulações semissólidas incorporando fármaco ou as respetivas DS previamente desenvolvidas, foram avaliadas através da análise do comportamento reológico e das propriedades de textura. Para avaliar a estabilidade, os parâmetros do espaço de cor L*a*b* das DS e das formulações semissólidas e o pH das preparações hidrófilas foram determinados em períodos de tempo definidos, durante um mês para cada amostra armazenada sob diferentes condições, especificamente, exposição à luz (à temperatura ambiente), protegidas da luz à temperatura elevada (37 °C) e protegidas da luz (temperatura ambiente). Embora tenham apresentado valores de firmeza e de adesividade mais elevados, as pomadas hidrófobas apresentaram melhores características reológicas do que os cremes óleo-água. Além disso, as pomadas hidrófobas também apresentaram melhor estabilidade, com pequenas alterações nos parâ...

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Anthralin: Historical and current perspectives

Cited by 114 publications

References 119 publications

Antioxidants attenuate anthralin-induced skin inflammation in BALB/c mice: role of specific proinflammatory cytokines

Antioxidants attenuate anthralin-induced skin inflammation in BALB/c mice: role of specific proinflammatory cytokines

Isolation and Identification of Anthralin From the Roots of Rhubarb Plant (Rheum palmatum)

Use of solid dispersions to increase stability of dithranol in topical formulations

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