General
Preferred name
ANTHRALIN
Synonyms
1,8,9-trihydroxyanthracene ()
cignoline ()
Dithranol ()
Anthralin, cignoline, 1,8,9-trihydroxyanthracene ()
Dithrocream Fte ()
Dithrocream Hp ()
Cigthranol ()
Drithocreme ()
NSC-43970 ()
Anthra-derm ()
Stie-Lasan ()
Psoradrate ()
Psoriacid-stift ()
Micanol ()
Cignolin ()
Dithrocream ()
Psorin ()
Psodadrate ()
Anthraderm ()
Batidrol ()
Ditranol ()
NSC-629313 ()
Derobin ()
Batridol ()
Chrysodermol ()
Lasan ()
Psoriacide ()
Antraderm ()
Drithoscalp ()
Psorin Fte ()
Alphodith ()
P&D ID
PD002470
CAS
480-22-8
1143-38-0
Tags
available
drug
Approved by
FDA
Drug Status
approved
investigational
Max Phase
2.0
Drug indication
psoriasis
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Anthralin is a natural anthraquinone derivative, anti-psoriatic and anti-inflammatory agent. It controls skin growth by reducing the synthesis of DNA and the mitotic activity in the hyperplastic epidermis, normalizing the rate of cell proliferation and keratinization [L1936].
MOA Anthralin inhibits the proliferation of keratinocytes (epidermal skin cells), prevents the action of T-cells, and promotes cell differentiation, likely through mitochondrial dysfunction. In addition, the production of free radicals may contribute to its anti-psoriatic effect [L1979]. In vitro studies demonstrate that anthralin prolongs the prophase component of mitosis for keratinocytes and leukocytes [L1932]. Prophase is the first step of mitosis, the process separating the duplicated genetic material carried in the nucleus of a parent cell into two identical daughter cells [L1980]. In vivo studies demonstrate that anthralin blocks DNA synthesis and can increase the release of reactive oxygen species [L1932].; ; Anthralin is believed to normalize the rate of epidermal cell proliferation and keratinization by reducing the mitotic activity of the epidermal hyperplasia in psoriasis [L1979].; ; ; Anti-proliferative and anti-inflammatory effects of anthralin have been demonstrated on both psoriatic and healthy skin. The anti-proliferative effects of anthralin are thought to be due to a combination of inhibition of DNA synthesis and its strong reducing properties. The effectiveness of anthralin as an anti-psoriatic agent is partly owed to its ability to promote lipid peroxidation and reduce the concentration of endothelial adhesion molecules, which are found to be elevated in psoriatic patients [L1933], [L1979].; ; Recent studies suggest that its ability to prevent T-lymphocyte activation and normalize keratinocyte differentiation may occur by a direct effect on mitochondria [A32313].
INDICATION Stable plaque psoriasis of the skin and scalp [L1933].; ; It is also used topically in the management of psoriasis, dermatoses, and alopecia areata. Anthralin is also used in biomedical research due to its effect on EGFR autophosphorylation [L1936].
TOXICITY Some mild adverse effects include alterations in nail coloring, hair coloring, increase in photosensitivity, and skin irritation [L1933].; ; The most common side effects of anthralin are skin irritation and staining of nearby skin, nails, clothing, and other objects that come in contact with the treated patient. The incidence of irritation of psoriatic/surrounding healthy skin is higher in patients who leave anthralin on the skin without rinsing than in those who use short-contact therapy of 2 hours or less, followed by rinsing [L1939].; ; If the psoriatic plaques are well circumscribed, the surrounding normal skin may be protected by the use of a coating agent such as zinc oxide ointment. Anthralin should be applied cautiously to the face and intertriginous areas due to the risk of severe skin irritation [L1979].; ; There is no current evidence of any long-term anthralin toxicity related either to skin exposure or to systemic issues [L1939].; Some long-term studies in mice have demonstrated anthralin to be tumorigenic in mouse skin. This carcinogenic potential has not been thoroughly evaluated. Tumorigenic and carcinogenic effects of anthralin have not been observed in humans at this time [L1932]. Anthralin is classified as FDA pregnancy risk category C drug [L1979]. It is not known if anthralin can cause fetal harm when administered during gestation. Because of the lack of evidential human data, anthralin should be used during pregnancy only when clearly required [L1933].
METABOLISM Anthralin is administered topically. Although the extent of systemic absorption after topical application has not been determined, no traces of anthraquinone metabolites were detected in the urine of treated subjects in a limited clinical study of anthralin cream [L1932], [L1933].; ; Anthralin does not inhibit hepatic microsomal enzyme activity [L1933].
ABSORPTION Anthralin penetrates damaged skin and psoriatic lesions faster and to a greater extent than normal skin, likely due to increased vascularity of psoriatic lesions [L1932].; ; ; ;
DESCRIPTION Dithranol (Anthralin) is an anthraquinone derivative, with potent anti-psoriatic effects. Dithranol can inhibit DNA replication and repair[1][2].
PRICE 29
DESCRIPTION Dithranol is a hydroxyanthrone, anthracene derivative, medicine applied to the skin of people with psoriasis. (BOC Sciences Bioactive Compounds)
DESCRIPTION Anthralin is a natural anthraquinone derivative, anti-psoriatic and anti-inflammatory agent. It inhibits the proliferation of keratinocytes (epidermal skin cells), prevents the action of T-cells, and promotes cell differentiation, likely through mitochondrial dysfunction. It is used to treat stable plaque psoriasis. (Enamine Bioactive Compounds)
DESCRIPTION Dithranol (cignoline) is an anthracene derivative that disrupts MITOCHONDRIA function and structure and is used for the treatment of DERMATOSES, especially PSORIASIS. It may cause FOLLICULITIS. (TargetMol Bioactive Compound Library)
Cell lines
5
Organisms
0
Compound Sets
19
BOC Sciences Bioactive Compounds
dithranol-cas-1143-38-0-item-84-290998
Cayman Chemical Bioactives
28371
ChEMBL Drugs
CHEMBL46469
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB11157
DrugBank Approved Drugs
DB11157
DrugCentral
226
DrugCentral Approved Drugs
226
DrugMatrix
Enamine Bioactive Compounds
EBC-26240
EU-OPENSCREEN Bioactive Compound Library
EOS100395
MedChem Express Bioactive Compound Library
HY-B0738
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
dithranol
TargetMol Bioactive Compound Library
T1068
The Spectrum Collection
External IDs
42
Properties
(calculated by RDKit )
Molecular Weight
226.06
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
2
Rotatable Bonds
0
Ring Count
3
Aromatic Ring Count
2
cLogP
2.23
TPSA
57.53
Fraction CSP3
0.07
Chiral centers
0.0
Largest ring
6.0
QED
0.62
Structural alerts
2
aggregator (Aggregator Advisor)
Aggregators
aggregator (ZINC)
Aggregators
Related compounds
Custom attributes
(extracted from source data)
Target
DNA/RNA Synthesis
Indication
psoriasis
MOA
DNA synthesis inhibitor
Pathway
Cell Cycle/Checkpoint
DNA Damage/DNA Repair
Cell Cycle/DNA Damage
Source data