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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/01/14 05:11:09」(JST)
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Dithranol
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Systematic (IUPAC) name |
1,8-dihydroxy-9,10-dihydroanthracen-9-one |
Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy cat. |
B2 (AU) |
Legal status |
P (UK) |
Routes |
topical |
Pharmacokinetic data |
Bioavailability |
0%, trace amounts metabolites |
Protein binding |
0% |
Metabolism |
absorbed and oxidised within the skin |
Half-life |
n/a |
Excretion |
n/a |
Identifiers |
CAS number |
1143-38-0 Y |
ATC code |
D05AC01 |
PubChem |
CID 2202 |
ChemSpider |
2117 Y |
UNII |
U8CJK0JH5M Y |
KEGG |
D00233 Y |
ChEBI |
CHEBI:37510 Y |
ChEMBL |
CHEMBL46469 Y |
Chemical data |
Formula |
C14H10O3 |
Mol. mass |
226.227 g/mol |
SMILES
- O=C2c1c(O)cccc1Cc3c2c(O)ccc3
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InChI
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InChI=1S/C14H10O3/c15-10-5-1-3-8-7-9-4-2-6-11(16)13(9)14(17)12(8)10/h1-6,15-16H,7H2 Y
Key:NUZWLKWWNNJHPT-UHFFFAOYSA-N Y
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Y (what is this?) (verify)
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Dithranol (INN) or Anthralin (USAN and former BAN) is a Hydroxyanthrone, anthracene derivative, medicine applied to the skin of people with psoriasis. It is available as creams, ointment or pastes in 0.1 to 2% strengths (Drithocreme, Dithrocream, Zithranol-RR, Micanol, Psorlin, Dritho-Scalp, Anthraforte, Anthranol and Anthrascalp). The terms dithranol and anthralin are sometimes used synonymously.
Contents
- 1 Pharmacology
- 2 Clinical considerations
- 3 Side effects
- 4 References
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Pharmacology
Dithranol accumulates in mitochondria where it interferes with the supply of energy to the cell, probably by the oxidation of dithranol releasing free radicals. This impedes DNA replication and so slows the excessive cell division that occurs in psoriatic plaques. In addition Dithranol may act by reducing the elevated levels of cGMP that occurs in psoriasis. (citations?)
Anthralin is a synthetic compound whose precise mechanism of anti-psoriatic action is not yet fully understood. However, numerous studies have demonstrated anti-proliferative and anti-inflammatory effects of anthralin on psoriatic and normal skin. The anti-proliferative effects of anthralin appear to result from both an inhibition of DNA synthesis as well as from its strong reducing properties. Recently, anthralin’s effectiveness as an anti-psoriatic agent has also been in part attributed to its abilities to induce lipid peroxidation and reduce levels of endothelial adhesion molecules which are markedly elevated in psoriatic patients. Unlike retinoids and PUVA, anthralin does not inhibit liver microsomal enzyme activity; consequently, the likelihood of adverse drug interactions is greatly reduced when other agents are administered concomitantly with anthralin. (citations?)
More dithranol penetrates into impaired skin in 30 minutes than into intact skin during about 16 hours. For this reason weaker 0.1-0.5% preparations are applied over night, but stronger 1-2% products are applied for between 30 minutes and one hour depending upon the formulation.
Clinical considerations
Dithranol has a slower onset of action in controlling psoriasis, typically several weeks, compared to glucocorticoid steroids, but is without the potential for rebound reaction on withdrawal. It cannot be used on the face or genitalia.
Side effects
It temporarily stains the skin a yellowy-brown and permanently stains clothing fabrics. It may cause a local burning sensation and irritation; this may be minimised by careful attention to the details of treatment and only gradually stepping up through the strengths of dithranol formulations. The surrounding skin can be protected using soft white paraffin and the treated area is covered with tube gauze.
References
- Anthralin Treatment of Psoriasis The Skin Site
- British National Formulary 45 March 2003
Antipsoriatics (D05)
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Topical |
Tars
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Antracens
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Psoralens
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Other
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- Fumaric acid
- vitamin D (Calcipotriol
- Calcipotriol/betamethasone
- Calcitriol
- Tacalcitol)
- Tazarotene
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Systemic |
Psoralens
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- Trioxysalen
- Methoxsalen
- Bergapten
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Retinoids
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (i/b/d/q/u/r/p/m/k/v/f)/cong/tumr (n/e/d), sysi/epon
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proc, drug (D2/3/4/5/8/11)
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UpToDate Contents
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English Journal
- Exploring the mode of action of dithranol therapy for psoriasis: a metabolomic analysis using HaCaT cells.
- Hollywood KA1, Winder CL, Dunn WB, Xu Y, Broadhurst D, Griffiths CE, Goodacre R.
- Molecular bioSystems.Mol Biosyst.2015 Jul 14;11(8):2198-209. doi: 10.1039/c4mb00739e.
- Psoriasis is a common, immune-mediated inflammatory skin disease characterized by red, heavily scaled plaques. The disease affects over one million people in the UK and causes significant physical, psychological and societal impact. There is limited understanding regarding the exact pathogenesis of
- PMID 26018604
- Efficacy and safety of diphenylcyclopropenone alone or in combination with anthralin in the treatment of chronic extensive alopecia areata: a retrospective case series.
- Durdu M1, Özcan D2, Baba M3, Seçkin D2.
- Journal of the American Academy of Dermatology.J Am Acad Dermatol.2015 Apr;72(4):640-50. doi: 10.1016/j.jaad.2015.01.008. Epub 2015 Feb 1.
- BACKGROUND: Some patients with chronic extensive alopecia areata (AA) may be refractory to topical immunotherapy. Combination therapy is recommended for such patients. Efficacy and safety of a combination therapy with diphenylcyclopropenone (DPCP) and anthralin in chronic extensive AA is unknown.OBJ
- PMID 25653027
- An update on topical therapies for mild-moderate psoriasis.
- van de Kerkhof PC1.
- Dermatologic clinics.Dermatol Clin.2015 Jan;33(1):73-7. doi: 10.1016/j.det.2014.09.006.
- Topical therapies are the mainstream treatment of psoriasis because most patients have mild disease. First-line treatments are vitamin D derivatives and corticosteroids. These treatments are usually given in combination schedules. For topical treatments the selection of the most appropriate vehicle
- PMID 25412784
Japanese Journal
- Inhibition of the Nuclear Factor-κB Signaling Pathway by Leflunomide or Triptolide also Inhibits the Anthralin-Induced Inflammatory Response but Does Not Affect Keratinocyte Growth Inhibition(Molecular and Cell Biology)
- Feng Hua,Li Xin-Yu,Zheng Jia-Run [他],GAO Ji Wei,XU Lan Fang,TANG Mei Yu
- Biological and Pharmaceutical Bulletin 28(9), 1597-1602, 2005-09-01
- … We performed this study to determine the relationship between activation of nuclear factor (NF)-κB and inhibition of keratinocyte growth by anthralin, which not only might be useful for a better understanding of the role of NF-κB in the pathogenesis of psoriasis, but also indicate whether the inflammatory reaction induced by anthralin is inseparable from its antipsoriatic activity. …
- NAID 110003666474
- A Novel Liposomal Formulation of Dithranol for Psoriasis : Preliminary Results
- AGARWAL Ravindra,SARASWAT Abir,KAUR Inderjeet,KATARE Om Prakash,KUMAR Bhushan
- Journal of dermatology 29(8), 529-532, 2002-08-01
- NAID 10016261973
- Topical Anthralin for Psoriasis Vulgaris : Evaluation of 70 Japanese Patients
- YAMAMOTO Toshiyuki,MATSUUCHI Mizue,IRIMAJIRI Junya,OTOYAMA Kazunobu,NISHIOKA Kiyoshi
- Journal of dermatology 27(7), 482-485, 2000-07-01
- NAID 10016194474
Related Links
- Consumer information about the medication ANTHRALIN - TOPICAL, includes side effects, drug interactions, recommended dosages, and storage information. Read more about the prescription drug ANTHRALIN - TOPICAL. ...
- Easy to read patient leaflet for anthralin cream. Includes indications, proper use, special instructions, precautions, and possible side effects. ... If OVERDOSE is suspected: Contact 1-800-222-1222 (the American Association of ...
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[★]
- 英
- anthralin
- 同
- ジトラノール dithranol