アントラリン、ジトラノール
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/03/11 06:46:36」(JST)
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Dithranol
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| Clinical data |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy
category |
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Routes of
administration |
topical |
| ATC code |
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| Legal status |
| Legal status |
- UK: P (Pharmacy medicines)
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| Pharmacokinetic data |
| Bioavailability |
0%, trace amounts metabolites |
| Protein binding |
0% |
| Metabolism |
absorbed and oxidised within the skin |
| Biological half-life |
n/a |
| Excretion |
n/a |
| Identifiers |
IUPAC name
- 1,8-dihydroxy-9,10-dihydroanthracen-9-one
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| CAS Number |
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| PubChem CID |
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| ChemSpider |
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| UNII |
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| KEGG |
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| ChEBI |
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| ChEMBL |
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| ECHA InfoCard |
100.013.216 |
| Chemical and physical data |
| Formula |
C14H10O3 |
| Molar mass |
226.227 g/mol |
| 3D model (Jmol) |
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| Melting point |
178 °C (352 °F) |
SMILES
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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
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Key:NUZWLKWWNNJHPT-UHFFFAOYSA-N Y
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| (verify) |
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 Medical uses
- 2 Side effects
- 3 Pharmacology
- 4 References
Medical uses
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. There is some tentative evidence that anthralin might be useful for alopecia areata.[1]
Side effects
It temporarily stains the skin a yellowy-brown and permanently stains clothing fabrics and other materials such as ceramic sinks. 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.
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.[citation needed]
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.[citation needed]
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.
References
- ^ Shapiro, J (Dec 2013). "Current treatment of alopecia areata.". The journal of investigative dermatology. Symposium proceedings / the Society for Investigative Dermatology, Inc. [and] European Society for Dermatological Research. 16 (1): S42–4. doi:10.1038/jidsymp.2013.14. PMID 24326551.
- Anthralin Treatment of Psoriasis The Skin Site
- British National Formulary 45 March 2003
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Drugs used for psoriasis (D05)
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| Topical |
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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 |
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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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UpToDate Contents
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English Journal
- Monooxygenase Substrates Mimic Flavin to Catalyze Cofactorless Oxygenations.
- Machovina MM1, Usselman RJ1, DuBois JL2.
- The Journal of biological chemistry.J Biol Chem.2016 Aug 19;291(34):17816-28. doi: 10.1074/jbc.M116.730051. Epub 2016 Jun 15.
- Members of the antibiotic biosynthesis monooxygenase family catalyze O2-dependent oxidations and oxygenations in the absence of any metallo- or organic cofactor. How these enzymes surmount the kinetic barrier to reactions between singlet substrates and triplet O2 is unclear, but the reactions have b
- PMID 27307041
- Health economic analyses of psoriasis management: a systematic literature search.
- Gutknecht M1, Krensel M2, Augustin M2.
- Archives of dermatological research.Arch Dermatol Res.2016 Jul 19. [Epub ahead of print]
- In the course of the chronic skin disease psoriasis, where a variety of treatment interventions is available, a strong growth of health economic studies comparing treatment costs and benefits can be noticed. The objective was to identify health economic evaluations of psoriasis treatments that have
- PMID 27435415
- [Psoriasis in special localizations].
- Schmieder A1, Peitsch WK2.
- Der Hautarzt; Zeitschrift für Dermatologie, Venerologie, und verwandte Gebiete.Hautarzt.2016 Jun;67(6):454-63. doi: 10.1007/s00105-016-3806-2.
- A large proportion of patients with plaque psoriasis suffer from psoriatic lesions of the scalp, nails, and intertrigines. These locations can also be soley or predominantly affected. Scalp psoriasis, nail psoriasis, and inverse psoriasis are often perceived as particularly stigmatizing. Involvemen
- PMID 27215754
Japanese Journal
- マトリックス支援レーザー脱離イオン化飛行時間型質量分析法による脂肪族系石油樹脂の分析
- 雲岡 義雄
- 分析化学 57(7), 539-542, 2008-07-05
- 代表的な脂肪族系石油樹脂であるエスコレッツ1202を以下のマトリックスとトリフロロ酢酸銀を使用して,マトリックス支援レーザー脱離イオン化飛行時間型質量分析装置で分析し,最適分析条件を求めた.試みたマトリックスはジトラノール,ピレン,trans,trans-1,4-ジフェニル-1,3-ブタジエン,9-ニトロアントラセン,アントラセン,2,5-ジヒドロキシ安息香酸,レチノイン酸,3-インドールアクリル …
- NAID 110006825846
- マトリックス支援レーザー脱離イオン化飛行時間型質量分析法による芳香族石油樹脂とクマロン樹脂の分析
- 雲岡 義雄
- 質量分析 = Mass spectroscopy 56(2), 41-48, 2008-04-01
- … The optimum analytical method uses dithranol as a matrix with silver trifluoroacetate as a cationizing agent. …
- NAID 10021086520
Related Links
- Pharmacology [edit source | edit] 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 ...
- Sigma-Aldrich offers Fluka-10608, Dithranol for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Other Notes Matrix substance for MALDI-MS (matrix-assisted laser ...
★リンクテーブル★
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- 英
- anthralin
- 同
- ジトラノール dithranol