U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ANTHRALIN

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

HIDE SMILES / InChI

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

Description
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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A new animal model for contact dermatitis: the hairless guinea pig.
1992 Mar
Dithranol: recent views on its mechanism of action.
2001 Mar-Apr
[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
[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
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
Successful treatment of recalcitrant psoriasis with a combination of infliximab and hydroxyurea.
2003 Dec
[Dithranol in the treatment of scalp psoriasis].
2003 Sep
Characterization of humic substances by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2004
A technique for obtaining matrix-assisted laser desorption/ionization time-of-flight mass spectra of poorly soluble and insoluble aromatic polyamides.
2004 Apr 1
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
Established treatments of psoriasis.
2004 Jun
Dithranol in an emulsifying oil base (bio-wash-oil) for the treatment of psoriasis of the scalp.
2004 Mar-Apr
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
Physiological variation in the erythemal response to ultraviolet radiation and photoadaptation.
2004 Nov
Optimal management of severe plaque form of psoriasis.
2005
The effect of treatment on quality of life in psoriasis patients.
2005
Profile of clinical efficacy and safety of topical tacalcitol.
2005 Apr
Importance of solubility in the sample preparation of poly(ethylene terephthalate) for MALDI TOFMS.
2005 Feb 1
[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
Dithranol irritation in psoriasis treatment: a study of 68 inpatients.
2005 Mar
Characterization of some synthetic Ru and Ir complexes by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
2005 May
Analysis of poly(oxyethylene) and poly(oxypropylene) triblock copolymers by MALDI-TOF mass spectrometry.
2005 May 15
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
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
Fluorescent sensing of transition metal ions based on the encapsulation of dithranol in a polymeric core shell architecture.
2005 Sep 28
Alefacept modifies long-term disease severity and improves the response to other treatments.
2005 Sep-Oct
Treatment of childhood psoriasis.
2006
Comparison of growth-inhibitory agents by fluorescence imaging of human skin re-epithelialization in vitro.
2006
Interleukin 6 and 8 levels in plasma and fibroblast cultures in psoriasis.
2006
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
The expression of keratinocyte growth factor receptor (FGFR2-IIIb) correlates with the high proliferative rate of HaCaT keratinocytes.
2006 Aug
Significant parameters in the optimization of MALDI-TOF-MS for synthetic polymers.
2006 Feb
Apoptosis in physiological and pathological skin: implications for therapy.
2006 Jun
Quality of life in patients with psoriasis.
2006 Jun 6
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
Identification of avarol derivatives as potential antipsoriatic drugs using an in vitro model for keratinocyte growth and differentiation.
2006 Nov 17
Dithranol abolishes UCH-L1 immunoreactivity in the nerve fibers of the rat orofacial skin.
2006 Nov 22
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
Defensive components in insect eggs: are anthraquinones produced during egg development?
2006 Sep
Psoriasis of the face and flexures.
2007
Plasma interleukin-18 and dendritic cells in males with psoriasis vulgaris.
2007
A randomized, double-blind, vehicle-controlled study of a novel liposomal dithranol formulation in psoriasis.
2007
Exanthematous infantile psoriasis.
2007 Aug
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version).
2007 Jun
Charge-remote fragmentation of lithiated fatty acids on a TOF-TOF instrument using matrix-ionization.
2007 Nov
Optimized sample preparation for MALDI mass spectrometry analysis of protected synthetic peptides.
2008 Apr
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
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
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
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

Patents

Sample Use Guides

Unknown
Route of Administration: Topical
In Vitro Use Guide
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
by admin
on Sat Dec 16 15:54:38 GMT 2023
Edited
by admin
on Sat Dec 16 15:54:38 GMT 2023
Record UNII
U8CJK0JH5M
Record Status Validated (UNII)
Record Version
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Name Type Language
ANTHRALIN
MI   USP   USP-RS   VANDF  
Common Name English
DRITHOSCALP
Brand Name English
PSORIACIDE
Brand Name English
NSC-629313
Code English
ANTHRALIN [MI]
Common Name English
9(10H)-ANTHRACENONE, 1,8-DIHYDROXY-
Systematic Name English
DEROBIN
Brand Name English
ANTHRALIN [VANDF]
Common Name English
PSORIACID-STIFT
Brand Name English
ANTHRA-DERM
Brand Name English
CHRYSODERMOL
Brand Name English
DITHRANOL [EP IMPURITY]
Common Name English
dithranol [INN]
Common Name English
ANTHRALIN [USP-RS]
Common Name English
DRITHOCREME
Brand Name English
DITHRANOL [WHO-IP]
Common Name English
ANTHRADERM
Brand Name English
PSODADRATE
Brand Name English
BATIDROL
Brand Name English
CIGNOLIN
Brand Name English
DITHRANOL [IARC]
Common Name English
DITHRANOL [MART.]
Common Name English
NSC-43970
Code English
ANTHRALIN [USP MONOGRAPH]
Common Name English
Dithranol [WHO-DD]
Common Name English
DITHRANOL
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
DITHRANOL [EP MONOGRAPH]
Common Name English
BATRIDOL
Brand Name English
CIGTHRANOL
Brand Name English
LASAN
Brand Name English
1,8-Dihydroxy-9-anthrone
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29708
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
WHO-VATC QD05AC01
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
WHO-VATC QD05AC51
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 13.4
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
WHO-ATC D05AC51
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
WHO-ATC D05AC01
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
Code System Code Type Description
RXCUI
873
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY RxNorm
NSC
43970
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
NSC
629313
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
SMS_ID
100000081858
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PRIMARY
INN
83
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
RS_ITEM_NUM
1039006
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
DRUG BANK
DB11157
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
CHEBI
37510
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
CAS
1143-38-0
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ANTHRALIN
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
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.
FDA UNII
U8CJK0JH5M
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
PUBCHEM
2202
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
DRUG CENTRAL
226
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
NCI_THESAURUS
C28827
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID7024538
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
EVMPD
SUB06332MIG
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
CHEBI
2756
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
MESH
D000875
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
WIKIPEDIA
DITHRANOL
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
ChEMBL
CHEMBL46469
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
MERCK INDEX
m1946
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
214-538-0
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
DAILYMED
U8CJK0JH5M
Created by admin on Sat Dec 16 15:54:39 GMT 2023 , Edited by admin on Sat Dec 16 15:54:39 GMT 2023
PRIMARY
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