Description
Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation. It increases apoptosis and inhibits proliferation of normal human keratinocytes (NHKs) when used at a concentration of 2.5 μM. It also decreases the mitochondrial membrane potential, increases cytochrome
c release, and induces perinuclear mitochondrial clustering in NHKs when used at a concentration of 5 μM. Anthralin (0.25 μM) decreases the expression of β-defensin-2 and S100 calcium-binding protein A9 (S100A9) and increases the expression of IL-6 and IL-8 in IL-17A- and IL-22-stimulated NHKs. It also inhibits leukotriene B
4 (LTB
4; ) production, stimulated by the calcium ionophore A23187 , from human neutrophils (IC
50 = 7 μM). Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.
Chemical Properties
Yellow Crystalline Solid
Indications
Anthralin (Anthra-Derm) is a potent reducing agent
whose mechanism of action is unknown. It is approved
for the treatment of psoriasis and also may be helpful in
alopecia areata. The major toxicities are discoloration
of skin, hair, and nails and irritant dermatitis.
Definition
ChEBI: An anthracene compound derived by the substitution of -OH groups for hydrogen at C-1 and C-8, and with an oxo group at C-9.
brand name
Anthra-Derm (Dermik); DrithoCreme
(Dermik); Drithoscalp (Dermik); Lasan (Stiefel).
General Description
Lemon yellow leaflets or plates or an orange powder. Melting point 176-181°C. No odor or taste. Insoluble in water. Moderately toxic by ingestion, inhalation and skin absorption. Used as a treatment for psoriasis.
Air & Water Reactions
Unstable in air when in alkaline solution. Insoluble in water.
Reactivity Profile
ANTHRALIN reacts as a weak acid. Soluble in aqueous bases. May react with strong oxidizing agents. May be sensitive to light and moisture .
Hazard
Very irritating. Do not use on scalp or near eyes.
Fire Hazard
Flash point data are not available for ANTHRALIN; however, ANTHRALIN is probably combustible.
Side effects
Anthralin's side effects include pruritus, erythema, scaling,
folliculitis, and lymphadenopathy. Staining of skin and clothes can also be an issue.
References
[1] JULIA HOLSTEIN. Anthralin modulates the expression pattern of cytokeratins and antimicrobial peptides by psoriatic keratinocytes[J]. Journal of dermatological science, 2017, 87 3: Pages 236-245. DOI:
10.1016/j.jdermsci.2017.06.007[2] ALISON MCGILL. The anti-psoriatic drug anthralin accumulates in keratinocyte mitochondria, dissipates mitochondrial membrane potential, and induces apoptosis through a pathway dependent on respiratory competent mitochondria.[J]. FASEB Journal, 2005, 19 8: 1012-1014. DOI:
10.1096/fj.04-2664fje[3] SCHRDER J M. Anthralin (1,8-Dihydroxyanthrone) Is a Potent Inhibitor of Leukotriene Production and LTB4-ω Oxidation by Human Neutrophils[J]. Journal of Investigative Dermatology, 1986, 87 5: Pages 624-629. DOI:
10.1111/1523-1747.ep12456188[4] LIREN TANG. Old Wine in New Bottles: Reviving Old Therapies for Alopecia Areata Using Rodent Models[J]. Journal of Investigative Dermatology Symposium Proceedings, 2003, 8 2: Pages 212-216. DOI:
10.1046/j.1087-0024.2003.00812.x
