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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Topical
In Vitro Use Guide
Highly purified human monocytes (MO) were incubated with anthralin (0.01-1.0 um/ml).
Substance Class Chemical
Record UNII
U8CJK0JH5M
Record Status Validated (UNII)
Record Version