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=CC=CC2=C1C(=O)C3=C(O)C=CC=C3C2
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
Molecular Formula | C14H10O3 |
Molecular Weight | 226.2274 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
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A new animal model for contact dermatitis: the hairless guinea pig. | 1992 Mar |
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Dithranol: recent views on its mechanism of action. | 2001 Mar-Apr |
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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 Dec |
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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 Dec |
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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 Dec |
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Successful treatment of recalcitrant psoriasis with a combination of infliximab and hydroxyurea. | 2003 Dec |
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[Dithranol in the treatment of scalp psoriasis]. | 2003 Sep |
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Characterization of humic substances by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2004 |
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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 Apr 1 |
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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 Feb 1 |
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Established treatments of psoriasis. | 2004 Jun |
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Dithranol in an emulsifying oil base (bio-wash-oil) for the treatment of psoriasis of the scalp. | 2004 Mar-Apr |
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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 May-Jun |
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Physiological variation in the erythemal response to ultraviolet radiation and photoadaptation. | 2004 Nov |
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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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Profile of clinical efficacy and safety of topical tacalcitol. | 2005 Apr |
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Importance of solubility in the sample preparation of poly(ethylene terephthalate) for MALDI TOFMS. | 2005 Feb 1 |
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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 Jun |
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Dithranol irritation in psoriasis treatment: a study of 68 inpatients. | 2005 Mar |
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Characterization of some synthetic Ru and Ir complexes by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. | 2005 May |
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Analysis of poly(oxyethylene) and poly(oxypropylene) triblock copolymers by MALDI-TOF mass spectrometry. | 2005 May 15 |
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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 Oct 13 |
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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 Oct 24 |
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Fluorescent sensing of transition metal ions based on the encapsulation of dithranol in a polymeric core shell architecture. | 2005 Sep 28 |
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Alefacept modifies long-term disease severity and improves the response to other treatments. | 2005 Sep-Oct |
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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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The expression of keratinocyte growth factor receptor (FGFR2-IIIb) correlates with the high proliferative rate of HaCaT keratinocytes. | 2006 Aug |
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Significant parameters in the optimization of MALDI-TOF-MS for synthetic polymers. | 2006 Feb |
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Apoptosis in physiological and pathological skin: implications for therapy. | 2006 Jun |
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Quality of life in patients with psoriasis. | 2006 Jun 6 |
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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 May |
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Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation. | 2006 Nov 17 |
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Dithranol abolishes UCH-L1 immunoreactivity in the nerve fibers of the rat orofacial skin. | 2006 Nov 22 |
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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 Oct |
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Defensive components in insect eggs: are anthraquinones produced during egg development? | 2006 Sep |
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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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Exanthematous infantile psoriasis. | 2007 Aug |
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German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). | 2007 Jun |
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Charge-remote fragmentation of lithiated fatty acids on a TOF-TOF instrument using matrix-ionization. | 2007 Nov |
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Optimized sample preparation for MALDI mass spectrometry analysis of protected synthetic peptides. | 2008 Apr |
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Analysis of rosin and modified rosin esters in adhesives by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). | 2008 Apr 7 |
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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 Feb |
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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 Jan |
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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 Jan 28 |
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).
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 15:54:38 GMT 2023
by
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on
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Record UNII |
U8CJK0JH5M
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Record Status |
Validated (UNII)
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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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83
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1039006
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DB11157
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37510
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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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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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