3DChem.com - Chemistry, Structures & 3D Molecules a visual and interactive website showcasing the beautiful world of chemistry

Dithranol (Molecule of the Month for March 2019)

Anthralin, Drithocreme, Dithrocream, Zithranol-RR, Micanol, Psorlin, Dritho-Scalp, Anthraforte, Anthranol and Anthrascalp



Dithranol or anthralin is a Hydroxyanthrone, anthracene derivative, medicine applied to the skin of people with psoriasis. It is available as creams, ointment or pastes. Dithranol has a slower onset of action in controlling psoriasis, typically several weeks, compared to glucocorticoid steroids, but is without the potential for rebound reaction on withdrawal. It cannot be used on the face or genitalia. There is some tentative evidence that anthralin might be useful for alopecia areata.

It temporarily stains the skin a yellowy-brown and permanently stains clothing fabrics and other materials such as ceramic sinks. It may cause a local burning sensation and irritation; this may be minimised by careful attention to the details of treatment and only gradually stepping up through the strengths of dithranol formulations. The surrounding skin can be protected using soft white paraffin and the treated area is covered with tube gauze.

Dithranol accumulates in mitochondria where it interferes with the supply of energy to the cell, probably by the oxidation of dithranol releasing free radicals. This impedes DNA replication and so slows the excessive cell division that occurs in psoriatic plaques.

Formal Chemical Name (IUPAC)
1,8-Dihydroxyanthracen-9(10H)-one

References

https://en.wikipedia.org/wiki/Dithranol

Picture of Dithranol 3D model

click on the picture of  Dithranol above to interact
with the 3D model of the
Dithranol structure
(this will open a new browser window)

Picture of Dithranol

C14 H10 O3



Update by Karl Harrison
(Molecule of the Month for March 2019 )

Stacks Image 34 All the images on this web site are are made available with a Creative Commons Attribution license and so can be used as long as the attribution © Karl Harrison 3DChem.com is written with the image. High resolution images and illustrations are available on request.