Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H10O3 |
| Molecular Weight | 226.2274 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C2C(=O)C3=C(O)C=CC=C3CC2=CC=C1
InChI
InChIKey=NUZWLKWWNNJHPT-UHFFFAOYSA-N
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
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4d624774-3618-423c-89bd-492f4795ad19Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Dithranol
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4d624774-3618-423c-89bd-492f4795ad19
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Dithranol
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. The terms dithranol and anthralin are sometimes used synonymously. Anthralin cream is a topical antimitotic. It works by slowing the reproduction of skin cells, 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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Analysis of rosin and modified rosin esters in adhesives by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). | 2008-04-07 |
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| Optimized sample preparation for MALDI mass spectrometry analysis of protected synthetic peptides. | 2008-04 |
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| A comparison of twice-daily calcipotriol ointment with once-daily short-contact dithranol cream therapy: quality-of-life outcomes of a randomized controlled trial of supervised treatment of psoriasis in a day-care setting. | 2008-02 |
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| Separation and preconcentration of ultra trace amounts of beryllium in water samples using mixed micelle-mediated extraction and determination by inductively coupled plasma-atomic emission spectrometry. | 2008-01-28 |
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| Trans-synaptic regulation of calmodulin gene expression after experimentally induced orofacial inflammation and subsequent corticosteroid treatment in the principal sensory and motor trigeminal nuclei of the rat. | 2008-01 |
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| Charge-remote fragmentation of lithiated fatty acids on a TOF-TOF instrument using matrix-ionization. | 2007-11 |
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| Dithranol: recent views on its mechanism of action. | 2007-08-01 |
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| Exanthematous infantile psoriasis. | 2007-08 |
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| German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). | 2007-06 |
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| Psoriasis of the face and flexures. | 2007 |
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| Plasma interleukin-18 and dendritic cells in males with psoriasis vulgaris. | 2007 |
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| A randomized, double-blind, vehicle-controlled study of a novel liposomal dithranol formulation in psoriasis. | 2007 |
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| Dithranol abolishes UCH-L1 immunoreactivity in the nerve fibers of the rat orofacial skin. | 2006-11-22 |
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| Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation. | 2006-11-17 |
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| 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. | 2006-10 |
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| Defensive components in insect eggs: are anthraquinones produced during egg development? | 2006-09 |
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| The expression of keratinocyte growth factor receptor (FGFR2-IIIb) correlates with the high proliferative rate of HaCaT keratinocytes. | 2006-08 |
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| Quality of life in patients with psoriasis. | 2006-06-06 |
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| Apoptosis in physiological and pathological skin: implications for therapy. | 2006-06 |
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| Solvent-free MALDI-MS: developmental improvements in the reliability and the potential of MALDI in the analysis of synthetic polymers and giant organic molecules. | 2006-05 |
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| Significant parameters in the optimization of MALDI-TOF-MS for synthetic polymers. | 2006-02 |
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| Treatment of childhood psoriasis. | 2006 |
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| Comparison of growth-inhibitory agents by fluorescence imaging of human skin re-epithelialization in vitro. | 2006 |
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| Interleukin 6 and 8 levels in plasma and fibroblast cultures in psoriasis. | 2006 |
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| Quantitative analysis of an oligomeric hindered amine light stabilizer in polypropylene by matrix-assisted laser desorption/ionization mass spectrometry using a solid sampling technique. | 2006 |
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| Serum levels of TNF-alpha, IFN-gamma, IL-6, IL-8, IL-12, IL-17, and IL-18 in patients with active psoriasis and correlation with disease severity. | 2005-10-24 |
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| MALDI TOF mass study on oligomerization of Pd(OAc)2(L)2 (L = pyridine derivatives): relevance to Pd black formation in Pd-catalyzed air oxidation of alcohols. | 2005-10-13 |
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| Fluorescent sensing of transition metal ions based on the encapsulation of dithranol in a polymeric core shell architecture. | 2005-09-28 |
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| Alefacept modifies long-term disease severity and improves the response to other treatments. | 2005-06-17 |
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| [Health economic aspects of psoriasis therapy. Is inpatient topical treatment of plaque-type psoriasis in this age of biologics still appropriate from both medical and economic viewpoints?]. | 2005-06 |
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| Analysis of poly(oxyethylene) and poly(oxypropylene) triblock copolymers by MALDI-TOF mass spectrometry. | 2005-05-15 |
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| Characterization of some synthetic Ru and Ir complexes by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2005-05 |
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| Profile of clinical efficacy and safety of topical tacalcitol. | 2005-04 |
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| Dithranol irritation in psoriasis treatment: a study of 68 inpatients. | 2005-03 |
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| Importance of solubility in the sample preparation of poly(ethylene terephthalate) for MALDI TOFMS. | 2005-02-01 |
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| Optimal management of severe plaque form of psoriasis. | 2005 |
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| The effect of treatment on quality of life in psoriasis patients. | 2005 |
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| Physiological variation in the erythemal response to ultraviolet radiation and photoadaptation. | 2004-11 |
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| Effectiveness and side effects of UVB-phototherapy, dithranol inpatient therapy and a care instruction programme of short contact dithranol in moderate to severe psoriasis. | 2004-07-13 |
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| Established treatments of psoriasis. | 2004-06 |
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| A technique for obtaining matrix-assisted laser desorption/ionization time-of-flight mass spectra of poorly soluble and insoluble aromatic polyamides. | 2004-04-01 |
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| Direct analysis of an oligomeric hindered amine light stabilizer in polypropylene materials by MALDI-MS using a solid sampling technique to study its photostabilizing action. | 2004-02-01 |
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| Characterization of humic substances by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2004 |
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| [Reader's letter on Norbert Haas, Andrea Wulff-Woesten, W. Steary and H. Meffert. The treatment of psoriasis capillitii with dithranol. JDDG 2003; 1:688-693]. | 2003-12 |
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| [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]. | 2003-12 |
|
| Optimizing the frequency of outpatient short-contact dithranol treatment used in combination with broadband ultraviolet B for psoriasis: a randomized, within-patient controlled trial. | 2003-12 |
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| Successful treatment of recalcitrant psoriasis with a combination of infliximab and hydroxyurea. | 2003-12 |
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| [Dithranol in the treatment of scalp psoriasis]. | 2003-09 |
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| Dithranol in an emulsifying oil base (bio-wash-oil) for the treatment of psoriasis of the scalp. | 2003-02-24 |
|
| A new animal model for contact dermatitis: the hairless guinea pig. | 1992-03 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9155955
Curator's Comment: Secretion of IL-1 beta immunoreactivity measured by ELISA as well as determination of biological activity of IL-1 using the D10[N4]M-bioassay revealed a slight increase in IL-1 secretion with a maximum at an anthralin concentration of 0.1 ug/ml. Was shown a differential, dose-dependent inhibition of cytokine secretion from human MO by anthralin.
Highly purified human monocytes (MO) were incubated with anthralin (0.01-1.0 um/ml).
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29708
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WHO-VATC |
QD05AC01
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WHO-VATC |
QD05AC51
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WHO-ESSENTIAL MEDICINES LIST |
13.4
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WHO-ATC |
D05AC51
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WHO-ATC |
D05AC01
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873
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43970
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629313
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100000081858
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1143-38-0
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ANTHRALIN
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PRIMARY | Description: A yellow or brownish yellow, crystalline powder.Solubility: Practically insoluble in water; soluble in dichloromethane R; sparingly soluble in acetone R; slightly soluble in ethanol (~750 g/l) TS and ether R.Category: Keratolytic agent.Storage: Dithranol should be kept in a tightly closed container, protected from light.Requirements:Dithranol contains not less than 98.5% and not more than 101.0% of C14H10O3, calculated with reference to the dried substance. | ||
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U8CJK0JH5M
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C28827
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DTXSID7024538
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SUB06332MIG
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2756
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D000875
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DITHRANOL
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CHEMBL46469
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m1946
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214-538-0
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U8CJK0JH5M
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ACTIVE MOIETY