Dithranol (Anthralin)
(Synonyms: 蒽林; Anthralin) 目录号 : GC31684An anthrone inhibitor of keratinocyte proliferation
Cas No.:1143-38-0
Sample solution is provided at 25 µL, 10mM.
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Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation.1 It increases apoptosis and inhibits proliferation of normal human keratinocytes (NHKs) when used at a concentration of 2.5 μM. It also decreases the mitochondrial membrane potential, increases cytochrome c release, and induces perinuclear mitochondrial clustering in NHKs when used at a concentration of 5 μM.2 Anthralin (0.25 μM) decreases the expression of β-defensin-2 and S100 calcium-binding protein A9 (S100A9) and increases the expression of IL-6 and IL-8 in IL-17A- and IL-22-stimulated NHKs.1 It also inhibits leukotriene B4 production, stimulated by the calcium ionophore A23187 , from human neutrophils (IC50 = 7 μM).3 Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.4
1.Holstein, J., Fehrenbacher, B., Brück, J., et al.Anthralin modulates the expression pattern of cytokeratins and antimicrobial peptides by psoriatic keratinocytesJ. Dermatol. Sci.87(3)236-245(2017) 2.McGill, A., Frank, A., Emmett, N., et al.The anti-psoriatic drug anthralin accumulates in keratinocyte mitochondria, dissipates mitochondrial membrane potential, and induces apoptosis through a pathway dependent on respiratory competent mitochondriaFASEB J.19(8)1012-1014(2005) 3.Schr?der, J.M.Anthralin (1,8-dihydroxyanthrone) is a potent inhibitor of leukotriene production and LTB4-ω oxidation by human neutrophilsJ. Invest. Dermatol.87(5)624-629(1986) 4.Tang, L., Sundberg, J.P., Liu, H., et al.Old wine in new bottles: Reviving old therapies for alopecia areata using rodent modelsJ. Invest. Dermatol. Symp. Proc.8(2)212-216(2003)
Cas No. | 1143-38-0 | SDF | |
别名 | 蒽林; Anthralin | ||
Canonical SMILES | O=C1C2=C(C=CC=C2O)CC3=CC=CC(O)=C13 | ||
分子式 | C14H10O3 | 分子量 | 226.23 |
溶解度 | DMSO : ≥ 10 mg/mL (44.20 mM);Water : < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 4.4203 mL | 22.1014 mL | 44.2028 mL |
5 mM | 0.8841 mL | 4.4203 mL | 8.8406 mL |
10 mM | 0.442 mL | 2.2101 mL | 4.4203 mL |
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Anthralin/dithranol in dermatology
Anthralin (1,8-dihydroxy-9anthrone, dithranol) was first synthesized as a derivative of chrysarobin, prepared from the araroba tree in Brazil over a century ago. Drawbacks to the use of anthralin include irritation and discoloration of the skin. This property of the molecule prompted workers to investigate details of its pharmacology, mode of action, and indications. The major point of this article is to highlight and revisit these aspects for pertinent future use. Therefore, it is worthwhile to consider that the drug is relatively innocuous, yet effective, and is devoid of any systemic side effects in contrast to a wide variety of systemic and topical therapies available for psoriasis and other dermatoses.
[Dithranol]
Anthralin
Dithranol
Dithranol (anthralin)-induced skin irritation in C57BL/6, NMRI and SENCAR mice
Dithranol-induced skin irritation was compared in C57BL/6, NMRI and SENCAR mice, the strains representing different sensitivity to tumour promotion. Skin irritation was assessed using ear thickness and skin weight measurements, visual estimation of back skin irritation and histopathology. Both single and repeated applications of dithranol caused a delayed skin irritation resulting in the maximal response between 7-11 days after the beginning of the treatment. Contrary to the findings with 12-O-tetradecanoyl-phorbol-13-acetate (TPA), C57BL/6 mice were the most sensitive and SENCAR mice the most resistant to the dithranol-induced skin irritation up to 30 days from the beginning of the treatment. NMRI mice were intermediate. Differences were found in the ear swelling, epidermal hyperplasia, amount of inflammatory cell infiltrate and skin ulceration. During repeated treatment of about 40 days, however, the responsiveness of SENCAR mice increased over that of C57BL/6 and NMRI mice. SENCAR mice had also more epidermal hyperplasia than the other strains at the end of the 74 day period of 3 times weekly applications. The magnitude of epidermal hyperplasia after long term treatment seems to correlate with the sensitivity to tumor promotion in the different mouse strains.