Identification
- Summary
Anthralin is an anthracene used to treat stable plaque psoriasis.
- Brand Names
- Drithocreme, Zithranol, Zithranol-RR
- Generic Name
- Anthralin
- DrugBank Accession Number
- DB11157
- Background
Anthralin (1,8‐dihydroxy‐9anthrone, dithranol) is an older anti-psoriatic agent that was first synthesized as a derivative of chrysarobin, obtained from the araroba tree in Brazil over 100 years ago. Adverse effects of anthralin include irritation and discoloration of the skin 2.
This specific property of the molecule inspired workers to study details of its pharmacology. It is important to consider that the drug is relatively innocuous, yet effective, and systemic side effects have not been observed with this anthralin, in contrast to a wide variety of systemic and topical therapies for psoriasis 9.
Anthralin is also known as dithranol. It is a main active ingredient in topical skin formulations for the treatment of psoriasis. Various formulations of the drug are available, including solutions, foams, and shampoos 13. The chemical structure of anthralin allows for dual solubility, permitting the compound to be absorbed well through the epidermis 1.
Anthralin has also been studied in the treatment of warts, showing promising results 3. Salicylic acid is frequently added to anthralin to augment the stability of anthralin and to increase its penetration and efficacy 13.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Anthralin (DB11157)
- Weight
- Average: 226.231
Monoisotopic: 226.062994182 - Chemical Formula
- C14H10O3
- Synonyms
- Anthralin
- Dithranol
- Ditranol
- External IDs
- NSC-43970
- NSC-629313
Pharmacology
- Indication
Stable plaque psoriasis of the skin and scalp 8.
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 10.
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- Contraindications & Blackbox Warnings
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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 10.
- Mechanism of action
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 13. In vitro studies demonstrate that anthralin prolongs the prophase component of mitosis for keratinocytes and leukocytes 7. 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 14. In vivo studies demonstrate that anthralin blocks DNA synthesis and can increase the release of reactive oxygen species 7.
Anthralin is believed to normalize the rate of epidermal cell proliferation and keratinization by reducing the mitotic activity of the epidermal hyperplasia in psoriasis 13.
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 8, 13.
Recent studies suggest that its ability to prevent T-lymphocyte activation and normalize keratinocyte differentiation may occur by a direct effect on mitochondria 4.
Target Actions Organism AKeratin, type II cytoskeletal 2 epidermal antagonistHumans AKeratin, type I cytoskeletal 12 antagonistHumans UC-Jun-amino-terminal kinase-interacting protein 1 agonistHumans - 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 7.
- Volume of distribution
Not Available
- Protein binding
Not Available
- 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 7, 8.
Anthralin does not inhibit hepatic microsomal enzyme activity 8.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Some mild adverse effects include alterations in nail coloring, hair coloring, increase in photosensitivity, and skin irritation 8.
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 12.
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 13.
There is no current evidence of any long-term anthralin toxicity related either to skin exposure or to systemic issues 12. 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 7. Anthralin is classified as FDA pregnancy risk category C drug 13. 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 8.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dritho-creme Hp Cream 1 g/100g Topical Summers Laboratories Inc 2013-01-01 Not applicable US 
Zithranol Shampoo 1 g/100g Topical Elorac, Inc. 2012-03-05 Not applicable US Zithranol-RR Cream .012 g/1g Topical Elorac, Inc. 2009-07-09 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anthraforte 1 Ointment 1% Ointment 1 % Topical Medican Technologies Inc. 1984-12-31 2014-09-02 Canada 
Anthraforte 2 Ointment 2% Ointment 2 % Topical Medican Technologies Inc. 1984-12-31 2014-09-02 Canada Anthranol Cream 0.1% Cream 0.1 % Topical Medican Technologies Inc. 1982-12-31 2014-09-02 Canada Anthranol Cream 0.2% Cream 0.2 % Topical Medican Technologies Inc. 1982-12-31 2014-09-02 Canada Anthranol Cream 0.4% Cream 0.4 % Topical Medican Technologies Inc. 1982-12-31 2000-06-30 Canada Anthrascalp Lotion 0.4% Lotion 0.4 % Topical Medican Technologies Inc. 1987-12-31 2014-09-02 Canada Micanol 3% Cream Cream 3 % Topical Canderm G.P. 1998-09-01 2004-07-30 Canada Micanol Cream Cream 1 % Topical Canderm G.P. 1998-05-06 2004-07-30 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image PSORAKS 30 GR FORT KREM Anthralin (0.5 %) + Salicylic acid (0.2 %) Cream Topical KURTSAN İLAÇLARI A.Ş. 2020-08-14 Not applicable Turkey 
PSORAKS 30 GR KREM Anthralin (0.25 %) + Salicylic acid (0.2 %) Cream Topical KURTSAN İLAÇLARI A.Ş. 2020-08-14 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dritho-creme Hp Anthralin (1 g/100g) Cream Topical Summers Laboratories Inc 2013-01-01 Not applicable US Zithranol Anthralin (1 g/100g) Shampoo Topical Elorac, Inc. 2012-03-05 Not applicable US Zithranol-RR Anthralin (.012 g/1g) Cream Topical Elorac, Inc. 2009-07-09 Not applicable US
Categories
- ATC Codes
- D05AC01 — Dithranol
- D05AC — Antracen derivatives
- D05A — ANTIPSORIATICS FOR TOPICAL USE
- D05 — ANTIPSORIATICS
- D — DERMATOLOGICALS
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Anthracenes
- Sub Class
- Not Available
- Direct Parent
- Anthracenes
- Alternative Parents
- Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Anthracene / Aromatic homopolycyclic compound / Aryl ketone / Hydrocarbon derivative / Ketone / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- anthracenes (CHEBI:37510)
- Affected organisms
- Humans
Chemical Identifiers
- UNII
- U8CJK0JH5M
- CAS number
- 1143-38-0
- InChI Key
- NUZWLKWWNNJHPT-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 1,8-dihydroxy-9,10-dihydroanthracen-9-one
- SMILES
- OC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C2
References
- General References
- Ashton RE, Andre P, Lowe NJ, Whitefield M: Anthralin: historical and current perspectives. J Am Acad Dermatol. 1983 Aug;9(2):173-92. [Article]
- Sehgal VN, Verma P, Khurana A: Anthralin/dithranol in dermatology. Int J Dermatol. 2014 Oct;53(10):e449-60. doi: 10.1111/j.1365-4632.2012.05611.x. Epub 2014 Sep 10. [Article]
- Flindt-Hansen H, Tikjob G, Brandrup F: Wart treatment with anthralin. Acta Derm Venereol. 1984;64(2):177-9. [Article]
- McGill A, Frank A, Emmett N, Turnbull DM, Birch-Machin MA, Reynolds NJ: The anti-psoriatic drug anthralin accumulates in keratinocyte mitochondria, dissipates mitochondrial membrane potential, and induces apoptosis through a pathway dependent on respiratory competent mitochondria. FASEB J. 2005 Jun;19(8):1012-4. doi: 10.1096/fj.04-2664fje. Epub 2005 Mar 31. [Article]
- Diezel W, Meffert H, Sonnichsen N: [Study on the mode of action of dithranol: increased lipid peroxidation and enzyme inhibition]. Dermatologica. 1975;150(3):154-62. [Article]
- Peus D, Beyerle A, Rittner HL, Pott M, Meves A, Weyand C, Pittelkow MR: Anti-psoriatic drug anthralin activates JNK via lipid peroxidation: mononuclear cells are more sensitive than keratinocytes. J Invest Dermatol. 2000 Apr;114(4):688-92. doi: 10.1046/j.1523-1747.2000.00934.x. [Article]
- Anthralin [Link]
- Zithranol, PDR [Link]
- Anthralin/dithranol in dermatology [Link]
- PubChem, Anthralin [Link]
- Zithranol-RR [Link]
- American Academy of Dermatology Recommendations [Link]
- NIH.gov Topical Therapies in psoriasis [Link]
- Prophase Definition [Link]
- External Links
- KEGG Compound
- C06831
- PubChem Compound
- 2202
- PubChem Substance
- 347827926
- ChemSpider
- 2117
- BindingDB
- 50041802
- 873
- ChEBI
- 37510
- ChEMBL
- CHEMBL46469
- ZINC
- ZINC000000001322
- Wikipedia
- Dithranol
- MSDS
- Download (47.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Topical 1 % Ointment Topical 2 % Cream Topical Cream Topical 0.1 % Cream Topical 0.2 % Cream Topical 0.4 % Lotion Topical 0.4 % Cream Topical 1 g/100g Cream Topical 3 % Cream Topical 1 % Cream Topical Shampoo Topical 1 g/100g Cream Topical .012 g/1g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178-182 °C MSDS water solubility not soluble in water MSDS - Predicted Properties
Property Value Source Water Solubility 0.184 mg/mL ALOGPS logP 2.73 ALOGPS logP 4.24 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 8.47 Chemaxon pKa (Strongest Basic) -5.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 64.27 m3·mol-1 Chemaxon Polarizability 23.12 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Mass Spectrum (Electron Ionization) MS splash10-004i-3790000000-74ab4aae2d6ceb313831 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Probably contributes to terminal cornification. Associated with keratinocyte activation, proliferation and keratinization.
- Specific Function
- Cytoskeletal protein binding
- Gene Name
- KRT2
- Uniprot ID
- P35908
- Uniprot Name
- Keratin, type II cytoskeletal 2 epidermal
- Molecular Weight
- 65432.65 Da
References
- McGill A, Frank A, Emmett N, Turnbull DM, Birch-Machin MA, Reynolds NJ: The anti-psoriatic drug anthralin accumulates in keratinocyte mitochondria, dissipates mitochondrial membrane potential, and induces apoptosis through a pathway dependent on respiratory competent mitochondria. FASEB J. 2005 Jun;19(8):1012-4. doi: 10.1096/fj.04-2664fje. Epub 2005 Mar 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Structural molecule activity
- Specific Function
- May play a unique role in maintaining the normal corneal epithelial function. Together with KRT3, essential for the maintenance of corneal epithelium integrity (By similarity).
- Gene Name
- KRT12
- Uniprot ID
- Q99456
- Uniprot Name
- Keratin, type I cytoskeletal 12
- Molecular Weight
- 53510.935 Da
References
- Anthralin/dithranol in dermatology [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Protein kinase inhibitor activity
- Specific Function
- The JNK-interacting protein (JIP) group of scaffold proteins selectively mediates JNK signaling by aggregating specific components of the MAPK cascade to form a functional JNK signaling module. Req...
- Gene Name
- MAPK8IP1
- Uniprot ID
- Q9UQF2
- Uniprot Name
- C-Jun-amino-terminal kinase-interacting protein 1
- Molecular Weight
- 77523.56 Da
References
- Peus D, Beyerle A, Rittner HL, Pott M, Meves A, Weyand C, Pittelkow MR: Anti-psoriatic drug anthralin activates JNK via lipid peroxidation: mononuclear cells are more sensitive than keratinocytes. J Invest Dermatol. 2000 Apr;114(4):688-92. doi: 10.1046/j.1523-1747.2000.00934.x. [Article]
Drug created at December 03, 2015 16:51 / Updated at February 21, 2021 18:52