anthralin

Summary

Summary: An anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS.

Top Publications

  1. Peus D, Beyerle A, Vasa M, Pott M, Meves A, Pittelkow M. Antipsoriatic drug anthralin induces EGF receptor phosphorylation in keratinocytes: requirement for H(2)O(2) generation. Exp Dermatol. 2004;13:78-85 pubmed
    Even though anthralin is a well-established topical therapeutic agent for psoriasis, little is known about its effects and biochemical mechanisms of signal transduction...
  2. Sasmaz S, Arican O. Comparison of azelaic acid and anthralin for the therapy of patchy alopecia areata: a pilot study. Am J Clin Dermatol. 2005;6:403-6 pubmed
    ..and safety of azelaic acid treatment in patients with patchy alopecia areata (AA) in comparison with anthralin (dithranol) treatment...
  3. Lau W, White A, Heard C. Topical delivery of a naproxen-dithranol co-drug: in vitro skin penetration, permeation, and staining. Pharm Res. 2010;27:2734-42 pubmed publisher
    ..Topical delivery of Nap-DTH not only improves the delivery of naproxen and dithranol, but also reduces unwanted effects of the parent moieties, in particular the skin staining, which is a major issue concerning the use of dithranol. ..
  4. Matsumoto K, Kawai S, Chignell C, Utsumi H. Location of anthralin radical generation in mouse skin by UV-A irradiation: an estimation using microscopic EPR spectral-spatial imaging. Magn Reson Med. 2006;55:738-42 pubmed
    In vivo location of the anthralin radical generated in mouse skin by ultraviolet A (UV-A) irradiation was estimated by microscopic electron paramagnetic resonance (EPR) spectral-spatial imaging...
  5. McGill A, Frank A, Emmett N, Turnbull D, Birch Machin M, Reynolds N. The anti-psoriatic drug anthralin accumulates in keratinocyte mitochondria, dissipates mitochondrial membrane potential, and induces apoptosis through a pathway dependent on respiratory competent mitochondria. FASEB J. 2005;19:1012-4 pubmed
    b>Anthralin is a potent topical drug, inducing clearance of psoriatic plaques. Anthralin disrupts mitochondrial function and structure, but its mechanism of action remains undefined...
  6. Kemeny L, Csato M, Braquet P, Dobozy A. Effect of BN 52021, a platelet activating factor antagonist, on dithranol-induced inflammation. Br J Dermatol. 1990;122:539-44 pubmed
    ..Pretreatment of the skin with 0.45% BN 52021 ointment significantly suppressed the decrease in capillary resistance, rise in skin temperature and increase in skin-fold thickness produced by dithranol. ..
  7. Stein Gold L. Topical Therapies for Psoriasis: Improving Management Strategies and Patient Adherence. Semin Cutan Med Surg. 2016;35:S36-44; quiz S45 pubmed publisher
    ..Topical treatments for psoriasis include corticosteroids, vitamin D derivatives, tazarotene, anthralin, tacrolimus, pimecrolimus, and newer formulations of tar...
  8. Sticherling M. [Children and adolescents with psoriasis. What therapy is recommended?]. Hautarzt. 2012;63:192-201 pubmed publisher
    ..Rehabilitative measures in mountain and seaside areas are reasonable for maintaining improvement and helping patient learn to deal with disease. ..
  9. Strohal R, Puig L, Chouela E, Tsai T, Melin J, Freundlich B, et al. The efficacy and safety of etanercept when used with as-needed adjunctive topical therapy in a randomised, double-blind study in subjects with moderate-to-severe psoriasis (the PRISTINE trial). J Dermatolog Treat. 2013;24:169-78 pubmed publisher
    ..More potent topical medications were used electively in <25% of subjects in each group. ..

More Information

Publications62

  1. Archid R, Duerr H, Patzelt A, Philipp S, Röwert Huber H, Ulrich M, et al. Relationship between Histological and Clinical Course of Psoriasis: A Pilot Investigation by Reflectance Confocal Microscopy during Goeckerman Treatment. Skin Pharmacol Physiol. 2016;29:47-54 pubmed publisher
    ..Further investigations of a large group of patients are needed to evaluate the potential of RCM findings as successor of the PASI in the monitoring of psoriasis. ..
  2. van de Kerkhof P, Van Der Valk P, Swinkels O, Kucharekova M, De Rie M, de Vries H, et al. A comparison of twice-daily calcipotriol ointment with once-daily short-contact dithranol cream therapy: a randomized controlled trial of supervised treatment of psoriasis vulgaris in a day-care setting. Br J Dermatol. 2006;155:800-7 pubmed
  3. Saraswat A, Agarwal R, Kaur I, Katare O, Kumar B. Fabric-staining properties and washability of a novel liposomal dithranol formulation. J Dermatolog Treat. 2002;13:119-22 pubmed
    ..The liposomal gel due to its superior staining properties may potentially increase the acceptability of dithranol amongst psoriasis patients. ..
  4. Endzweig Gribetz C, Brady C, Lynde C, Sibbald D, Lebwohl M. Drug interactions in psoriasis: the pros and cons of combining topical psoriasis therapies. J Cutan Med Surg. 2002;6:12-6 pubmed
  5. Gupta S, Tewatia P, Misri J, Singh R. Molecular Modeling of Cloned Bacillus subtilis Keratinase and Its Insinuation in Psoriasis Treatment Using Docking Studies. Indian J Microbiol. 2017;57:485-491 pubmed publisher
    ..90 kcal/mol), Fluticasone (- 38.53 kcal/mol), Desonide (- 32.23 kcal/mol), Anthralin (- 38.04 kcal/mol), Calcipotreine (- 21.55 kcal/mol) and Mometasone (- 28...
  6. Rundhaug J, Pavone A, Kim E, Fischer S. The effect of cyclooxygenase-2 overexpression on skin carcinogenesis is context dependent. Mol Carcinog. 2007;46:981-92 pubmed
    ..DMBA) only, as well as a two-stage protocol using DMBA plus an unrelated tumor promoter, anthralin. In addition, the responses of transgenic and wild-type mice to TPA in terms of induction of proliferation and ..
  7. Tremblay J, Bissonnette R. Topical agents for the treatment of psoriasis, past, present and future. J Cutan Med Surg. 2002;6:8-11 pubmed
  8. van de Kerkhof P, Franssen M. Psoriasis of the scalp. Diagnosis and management. Am J Clin Dermatol. 2001;2:159-65 pubmed
    ..Management of scalp psoriasis requires long term strategies in order to reach an optimal improvement of the condition, while avoiding the adverse effects associated with the long term use of treatments. ..
  9. Zachariae H, Zachariae R, Blomqvist K, Davidsson S, Molin L, Mørk C, et al. Treatment of psoriasis in the Nordic countries: a questionnaire survey from 5739 members of the psoriasis associations data from the Nordic Quality of Life Study. Acta Derm Venereol. 2001;81:116-21 pubmed
    ..6% had taken such medication during the last week. The results of the study suggest that different treatment patterns should be taken into consideration when discussing the prognosis of psoriasis in different countries. ..
  10. Nimmo J, Gawkrodger D, O Docherty C, Going S, Percy Robb I, Hunter J. Plasma 5-S-cysteinyldopa as an index of melanogenesis. Br J Dermatol. 1988;118:487-95 pubmed
    ..The value of plasma 5-S-CD in the follow-up of patients with malignant melanoma does not seem to be invalidated by unavoidable exposure of the subjects to sunlight in a temperate climate such as that of South East Scotland. ..
  11. Guenther U, Smirnova I, Neubert R. Hydrophilic silica aerogels as dermal drug delivery systems--dithranol as a model drug. Eur J Pharm Biopharm. 2008;69:935-42 pubmed publisher
    ..Dithranol adsorbed on hydrophilic silica aerogels exhibited superior penetration behaviour compared to that of the standard ointment (dithranol in white soft paraffin). ..
  12. Kemeny L, Gross E, Arenberger P, Ruzicka T. Dithranol-induced down-regulation of 12(S)-hydroxyeicosatetraenoic acid [12(S)-HETE] receptors in a human epidermal cell line. Arch Dermatol Res. 1991;283:333-6 pubmed
    ..The down-regulation of 12(S)-HETE receptors on epidermal cells by dithranol may contribute to its antipsoriatic action. ..
  13. Swinkels O, Prins M, Kucharekova M, de Boo T, Gerritsen M, Van Der Valk P, et al. Combining lesional short-contact dithranol therapy of psoriasis with a potent topical corticosteroid. Br J Dermatol. 2002;146:621-6 pubmed
    ..Intermittent addition of clobetasol-17-propionate ointment enhanced the antipsoriatic efficacy of short-contact, high-dose dithranol therapy in terms of clearing capacity and treatment duration, without shortening remission duration. ..
  14. Baturay N, Trombetta L. Cocarcinogenic and tumor-promoting capabilities of anthralin. Arch Dermatol Res. 1988;280:443-50 pubmed
    ..b>Anthralin, and antipsoriatic agent, acts as a tumor promoter for Balb/c-3T3 mouse embryo cell cultures that were ..
  15. Ghorpade A. Accentuated Blaschko-linear manifestation of psoriasis. Eur J Dermatol. 2008;18:196-7 pubmed publisher
  16. Kouam S, Khan S, Krohn K, Ngadjui B, Kapche D, Yapna D, et al. Alpha-glucosidase inhibitory anthranols, kenganthranols A-C, from the stem bark of Harungana madagascariensis. J Nat Prod. 2006;69:229-33 pubmed
    ..Some isolated compounds (3-5, 7-11) were evaluated for their alpha-glucosidase inhibition activity. Compounds 3, 4, 8, and 11 showed significant activity, whereas compounds 7, 9, and 10 were inactive in this test...
  17. Agarwal R, Katare O, Vyas S. Preparation and in vitro evaluation of liposomal/niosomal delivery systems for antipsoriatic drug dithranol. Int J Pharm. 2001;228:43-52 pubmed
    ..13 microg/cm(2)/h) and niosomes (7.78 microg/cm(2)/h) as compared with the cream base (4.10 microg/cm(2)/h). ..
  18. Gotter B, Faubel W, Neubert R. Photothermal imaging in 3D surface analysis of membrane drug delivery. Eur J Pharm Biopharm. 2010;74:26-32 pubmed publisher
  19. Peus D, Beyerle A, Rittner H, Pott M, Meves A, Weyand C, et al. Anti-psoriatic drug anthralin activates JNK via lipid peroxidation: mononuclear cells are more sensitive than keratinocytes. J Invest Dermatol. 2000;114:688-92 pubmed
    b>Anthralin is a widely used, topical therapy for psoriasis. Anti-proliferative and anti-inflammatory properties of anthralin have been identified...
  20. Zalewska A, Wyczółkowska J, Dziankowska Bartkowiak B, Sysa Jedrzejowska A. Interleukin 4 plasma levels in psoriasis vulgaris patients. Med Sci Monit. 2004;10:CR156-62 pubmed
    ..05). Our data seem to support the hypothesis of the existence of immunologically distinct psoriasis subtypes. ..
  21. Torchia D, Schachner L. Bilateral treatment for alopecia areata. Pediatr Dermatol. 2010;27:415-6 pubmed publisher
    A 4-year-old, otherwise healthy white girl was referred for a 15-month history of alopecia areata. Anthralin 0.1% cream was prescribed for the left side of the scalp, while corticosteroids for the right side...
  22. Kemeny L, Csato M, Dobozy A. Pharmacological studies on dithranol-induced irritative dermatitis in mice. Arch Dermatol Res. 1989;281:362-5 pubmed
    ..The results provide evidence of the coinvolvement of PAF, prostaglandins, histamine, and reactive oxygen radicals in dithranol-induced irritative dermatitis in mice. ..
  23. Ummenhofer B. [Reader's letter on Norbert Haas, Andrea Wulff-Woesten,W. Sterry and H. Meffert. The treatment of psoriasis capillitii with dithranol. JDDG 2003, 1:688-693]. J Dtsch Dermatol Ges. 2003;1:1002-3; author reply 1003 pubmed
  24. Jiaravuthisan M, Sasseville D, Vender R, Murphy F, Muhn C. Psoriasis of the nail: anatomy, pathology, clinical presentation, and a review of the literature on therapy. J Am Acad Dermatol. 2007;57:1-27 pubmed
    ..Therefore, until better-documented evidence validating the treatment options emerges within the literature, clinicians and patients are left with a vague and relatively unproven approach to psoriatic nail disease. ..
  25. Ummenhofer B. [Comment on the letter and response regarding "Treatment of psoriasis capilliti with Dethranol]. J Dtsch Dermatol Ges. 2004;2:156 pubmed
  26. MacDonald Hull S, Wood M, Hutchinson P, Sladden M, Messenger A. Guidelines for the management of alopecia areata. Br J Dermatol. 2003;149:692-9 pubmed
  27. Jantke M, Bertsch H, Schön M, Fuchs T. [Treatment of disseminated granuloma annulare with anthralin]. Hautarzt. 2011;62:935-9 pubmed publisher
    ..should always be assessed critically and reserved for patients who are severely affected and in whom treatment approaches with few side effects such as local application of anthralin do not suffice to achieve a satisfactory effect.
  28. Muller K, Reindl H, Breu K. Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation. Bioorg Med Chem Lett. 2001;11:47-50 pubmed
    Heterocyclic substituted derivatives of the antipsoriatic anthralin were synthesized and evaluated in vitro for their antiproliferative action against keratinocytes and their ability to induce keratinocyte differentiation...
  29. Ceović R, Pasic A, Lipozencic J, Murat Susić S, Skerlev M, Husar K, et al. Treatment of childhood psoriasis. Acta Dermatovenerol Croat. 2006;14:261-4 pubmed
    ..All these therapeutic options can be used as monotherapy or in various combinations. ..
  30. Li D, Li X, Wang B. Natural anthraquinone derivatives from a marine mangrove plant-derived endophytic fungus Eurotium rubrum: structural elucidation and DPPH radical scavenging activity. J Microbiol Biotechnol. 2009;19:675-80 pubmed
    ..Their structures were elucidated on the basis of spectroscopic analysis. All of the isolated compounds were evaluated for 1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging activity. ..
  31. Sticherling M, Augustin M, Boehncke W, Christophers E, Domm S, Gollnick H, et al. Therapy of psoriasis in childhood and adolescence - a German expert consensus. J Dtsch Dermatol Ges. 2011;9:815-23 pubmed publisher
    ..In any case the therapy has to be individually planned and decided together with the patients and their parents to gain maximal safety, comfort and success. ..
  32. Yamamoto T, Nishioka K. Alteration of the expression of Bcl-2, Bcl-x, Bax, Fas, and Fas ligand in the involved skin of psoriasis vulgaris following topical anthralin therapy. Skin Pharmacol Appl Skin Physiol. 2003;16:50-8 pubmed
    b>Anthralin (dithranol) is frequently used for the treatment of psoriasis. However, the mode of action of anthralin has not been completely elucidated as yet...
  33. Raevskaya A, Gorbunova S, Savvateeva M, Severin S, Kirpichnikov M. Effect of anthralin on cell viability in human prostate adenocarcinoma. Bull Exp Biol Med. 2012;153:361-3 pubmed
    ..Selective cytotoxic action of anthralin, an inhibitor of hepsin activity, on human adenocarcinoma cells was demonstrated in comparison with other tumor ..
  34. Raza K, Katare O, Setia A, Bhatia A, Singh B. Improved therapeutic performance of dithranol against psoriasis employing systematically optimized nanoemulsomes. J Microencapsul. 2013;30:225-36 pubmed publisher
    Despite marked antipsoriatic activity of dithranol (anthralin), the drug is quite infrequently employed in therapeutic practice owing to its strong propensity to cause skin problems like irritation, erythema and peeling, and potential ..
  35. Kirkup M, Sabroe R, Kavanagh G, Downs A, Sansom J, de Berker D, et al. Twice-daily vs. once-daily inpatient dithranol for psoriasis. Clin Exp Dermatol. 2002;27:695-9 pubmed
    ..once-daily regimes of dithranol (anthralin) in Lassar's paste...
  36. Terrier P, Buchmann W, Cheguillaume G, Desmazières B, Tortajada J. Analysis of poly(oxyethylene) and poly(oxypropylene) triblock copolymers by MALDI-TOF mass spectrometry. Anal Chem. 2005;77:3292-300 pubmed
    ..The combination of MALDI-TOF MS with separations techniques and NMR brings precious complementary information. ..
  37. Blazso G, Gabor M. Effects of prostaglandin antagonist phloretin derivatives on mouse ear edema induced with different skin irritants. Prostaglandins. 1995;50:161-8 pubmed
    ..The inhibition of the ear edema by the phloretin derivatives was: dithranol > croton oil > capsaicin > arachidonic acid. This probably reflects the different contributions of prostaglandins to the inflammation. ..
  38. Holstein J, Fehrenbacher B, Brück J, Müller Hermelink E, Schäfer I, Carevic M, et al. Anthralin modulates the expression pattern of cytokeratins and antimicrobial peptides by psoriatic keratinocytes. J Dermatol Sci. 2017;87:236-245 pubmed publisher
    ..include modern targeted therapies using anti-cytokine antibodies and traditional non-targeted treatments like anthralin (dithranol)...
  39. Bendkowski W, Hadas E, Swietochowska E, Wielkoszyński T, Ostrowska Z, Szapska B. [Influence of dithranol therapy on clinical status and serum calcitonin concentrations in patients with common psoriasis]. Pol Merkur Lekarski. 2002;13:481-3 pubmed
    ..After a 14-day dithranol therapy a significant calcitonin concentration decrease as well as clinical effects were observed in the investigated group. ..
  40. Czerwinska M, Sikora A, Szajerski P, Zielonka J, Adamus J, Marcinek A, et al. Anthralin: primary products of its redox reactions. J Org Chem. 2006;71:5312-9 pubmed
    One-electron reduction significantly enhances the ability of anthralin, 1, to act as a hydrogen atom donor...
  41. Farkas A, Kemeny L, Szony B, Bata Csorgo Z, Pivarcsi A, Kiss M, et al. Dithranol upregulates IL-10 receptors on the cultured human keratinocyte cell line HaCaT. Inflamm Res. 2001;50:44-9 pubmed
    ..Since the interleukin-10 receptor expression of keratinocytes in psoriatic lesional skin is downregulated, the dithranol induced upregulation of the receptor in our model system might help to reveal the therapeutic action of the drug. ..
  42. Alexandrescu D, Kauffman C, Dasanu C. The cutaneous epidermal growth factor network: Can it be translated clinically to stimulate hair growth?. Dermatol Online J. 2009;15:1 pubmed
    ..A better characterization of the individual roles pertaining to the EGF family ligands and receptors, has the potential provide new strategies for the management of hair loss. ..
  43. Bruner C, Feldman S, Ventrapragada M, Fleischer A. A systematic review of adverse effects associated with topical treatments for psoriasis. Dermatol Online J. 2003;9:2 pubmed
    ..Since clearance is not a realistic expectation, reasonable goals should be set as excessive use of topical treatments may increase the risk of both cutaneous and systemic side effects. ..
  44. Gyulai R, Kemeny L. [The immunology of psoriasis: from basic research to the bedside]. Orv Hetil. 2006;147:2213-20 pubmed
  45. Strauss R, Bäte J, Pring D. Connubial contact dermatitis: an unusual pregnancy dermatosis. Acta Derm Venereol. 2003;83:316 pubmed
  46. De Jager M, de Jong E, van de Kerkhof P, Seyger M. Efficacy and safety of treatments for childhood psoriasis: a systematic literature review. J Am Acad Dermatol. 2010;62:1013-30 pubmed publisher
    ..A rough summary of the proposed algorithm is as follows: first, calcipotriene with/without topical corticosteroids, followed by dithranol. Methotrexate is considered to be the systemic treatment of choice. ..
  47. Ronpirin C, Tencomnao T. Dithranol downregulates expression of Id1 mRNA in human keratinocytes in vitro. Genet Mol Res. 2012;11:3290-7 pubmed publisher
    ..However, the normalized Id1 protein levels were not significantly affected. The molecular mechanisms underlying this finding should be investigated further to help determine the therapeutic action of this drug. ..
  48. Haas N, Wulff Woesten A, Sterry W, Meffert H. [Dithranol in the treatment of scalp psoriasis]. J Dtsch Dermatol Ges. 2003;1:688-93 pubmed
    ..in 1979, summarize our subsequent experience and present a recent comparative study paying special attention to side effects, practical notes, and patient comfort and satisfaction. ..
  49. Trimpin S, Rouhanipour A, Az R, Räder H, Mullen K. New aspects in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry: a universal solvent-free sample preparation. Rapid Commun Mass Spectrom. 2001;15:1364-73 pubmed
    ..Additionally, this contribution provides new insight regarding the analyte/matrix preorganization for the desorption step which now appears to be independent of crystallinity. ..
  50. Kowalzick L. Clinical experience with topical calcitriol (1,25-dihydroxyvitamin D3) in psoriasis. Br J Dermatol. 2001;144 Suppl 58:21-5 pubmed
    ..Finally, two studies confirm that calcitriol 3 microg g(-1) ointment can be used safely in patients with psoriasis of the head and confirm the high level of clinical efficacy achieved with this compound. ..
  51. Prins M, Swinkels O, Bouwhuis S, de Gast M, Bouwman Boer Y, van der Valk P, et al. Dithranol in a cream preparation: disperse or dissolve?. Skin Pharmacol Appl Skin Physiol. 2000;13:273-9 pubmed
    ..Besides, it will be less expensive to prepare. We advise to use this formulation for short-contact treatment. ..
  52. Muller K, Reindl H. Cornified envelope formation by anthralin, simple analogues, and related anthracenones. Arch Pharm (Weinheim). 2001;334:86-92 pubmed
    The ability of the antipsoriatic anthralin to induce HaCaT keratinocyte differentiation was investigated and correlated with its potency to inhibit proliferation of keratinocytes...
  53. Prins M, Krabbe P, Swinkels Q, De Boo T, van de Kerkhof P, van der Valk P. The effect of treatment on quality of life in psoriasis patients. Acta Derm Venereol. 2005;85:304-10 pubmed
    ..At the end of the study HRQoL became comparable for all treatment groups. All three treatments led to substantial improvement in HRQoL; however, patients treated by short contact treatment or UVB showed a better HRQoL than inpatients. ..