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MedKoo Cat#: 531001 | Name: Anthralin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Anthralin, also known as Dithranol, is a hepsin activity inhibitor used for treatment of psoriasis Inhibition of hepsin activity suppresses the invasive growth of the tumor. Anthralin exerts a direct effect on keratinocytes and leukocytes. Anthralin significantly prolonged the prophase of mitotic keratinocytes in subtoxic doses and suppressed the expression of keratin 6 mRNA in the immediately suprabasal layer of psoriatic epidermis in vivo. Anthralin also inhibits the transformation of lymphocytes and the release of reactive oxygen species from activated leukocytes, in vitro.

Chemical Structure

Anthralin
Anthralin
CAS#1143-38-0

Theoretical Analysis

MedKoo Cat#: 531001

Name: Anthralin

CAS#: 1143-38-0

Chemical Formula: C14H10O3

Exact Mass: 226.0630

Molecular Weight: 226.23

Elemental Analysis: C, 74.33; H, 4.46; O, 21.22

Price and Availability

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1g USD 250.00 2 Weeks
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Related CAS #
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Synonym
Anthralin; Batridol; Dithranol; NSC 629313; NSC-629313; NSC629313
IUPAC/Chemical Name
1,8-dihydroxyanthracen-9(10H)-one
InChi Key
NUZWLKWWNNJHPT-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C1C2=C(C=CC=C2O)CC3=CC=CC(O)=C13
Appearance
Light yellow to yellow crystalline solid.
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 226.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: 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. Review. PubMed PMID: 25208745. 2: Durdu M, Özcan D, Baba M, Seçkin D. Efficacy and safety of diphenylcyclopropenone alone or in combination with anthralin in the treatment of chronic extensive alopecia areata: a retrospective case series. J Am Acad Dermatol. 2015 Apr;72(4):640-50. doi: 10.1016/j.jaad.2015.01.008. Epub 2015 Feb 1. PubMed PMID: 25653027. 3: Lowe NJ, Ashton RE, Koudsi H, Verschoore M, Schaefer H. Anthralin for psoriasis: short-contact anthralin therapy compared with topical steroid and conventional anthralin. J Am Acad Dermatol. 1984 Jan;10(1):69-72. PubMed PMID: 6693604. 4: Raevskaya AA, Gorbunova SL, Savvateeva MV, Severin SE, Kirpichnikov MP. Effect of anthralin on cell viability in human prostate adenocarcinoma. Bull Exp Biol Med. 2012 Jul;153(3):361-3. PubMed PMID: 22866312. 5: Lawrence CM, Shuster S. Mechanism of anthralin inflammation. 2. Effect of pretreatment with glucocorticoids, anthralin and removal of stratum corneum. Br J Dermatol. 1985 Jul;113(1):117-22. PubMed PMID: 4015968. 6: Kawai S, Matsumoto K, Utsumi H. An EPR method for estimating activity of antioxidants in mouse skin using an anthralin-derived radical model. Free Radic Res. 2010 Mar;44(3):267-74. doi: 10.3109/10715760903456100. PubMed PMID: 20001648. 7: Mahrle G, Bonnekoh B, Wevers A, Hegemann L. Anthralin: how does it act and are there more favourable derivatives? Acta Derm Venereol Suppl (Stockh). 1994;186:83-4. PubMed PMID: 8073848. 8: Ashton RE, Andre P, Lowe NJ, Whitefield M. Anthralin: historical and current perspectives. J Am Acad Dermatol. 1983 Aug;9(2):173-92. Review. PubMed PMID: 6309924. 9: Schulze HJ, Schauder S, Mahrle G, Steigleder GK. Combined tar-anthralin versus anthralin treatment lowers irritancy with unchanged antipsoriatic efficacy. Modifications of short-contact therapy and Ingram therapy. J Am Acad Dermatol. 1987 Jul;17(1):19-24. PubMed PMID: 3611453. 10: Cavey D, Caron JC, Shroot B. Anthralin: chemical instability and glucose-6-phosphate dehydrogenase inhibition. J Pharm Sci. 1982 Sep;71(9):980-3. PubMed PMID: 7131282. 11: Fisher LB, Maibach HI. The effect of anthralin and its derivatives on epidermal cell kinetics. J Invest Dermatol. 1975 May;64(5):338-41. PubMed PMID: 1141709. 12: Lambelet P, Ducret F, Löliger J, Maignan J, Reichert U, Shroot B. The relevance of secondary radicals in the mode of action of anthralin. Free Radic Biol Med. 1990;9(3):183-90. PubMed PMID: 2177025. 13: Müller K, Reindl H. Cornified envelope formation by anthralin, simple analogues, and related anthracenones. Arch Pharm (Weinheim). 2001 Mar;334(3):86-92. PubMed PMID: 11315339. 14: Müller K. Antipsoriatic and proinflammatory action of anthralin. Implications for the role of oxygen radicals. Biochem Pharmacol. 1997 May 9;53(9):1215-21. Review. PubMed PMID: 9214681. 15: Czerwinska M, Sikora A, Szajerski P, Zielonka J, Adamus J, Marcinek A, Piech K, Bednarek P, Bally T. Anthralin: primary products of its redox reactions. J Org Chem. 2006 Jul 7;71(14):5312-9. PubMed PMID: 16808521. 16: Hegemann L, Fruchtmann R, van Rooijen LA, Müller-Peddinghaus R, Mahrle G. The antipsoriatic drug, anthralin, inhibits protein kinase C--implications for its mechanism of action. Arch Dermatol Res. 1992;284(3):179-83. PubMed PMID: 1503504. 17: Müller K, Leukel P, Mayer KK, Wiegrebe W. Modification of DNA bases by anthralin and related compounds. Biochem Pharmacol. 1995 May 26;49(11):1607-13. PubMed PMID: 7786301. 18: Mrowietz U, Falsafi M, Schröder JM, Christophers E. Inhibition of human monocyte functions by anthralin. Br J Dermatol. 1992 Oct;127(4):382-6. PubMed PMID: 1329912. 19: Parslew R, Friedmann PS. The irritancy of anthralin is inhibited by repeat applications of a subirritant concentration. Br J Dermatol. 1999 Sep;141(3):469-74. PubMed PMID: 10583050. 20: Raab W. [Antipsoriatic effect of dithranol (anthralin). 1]. Hautarzt. 1975 Sep;26(9):452-5. German. PubMed PMID: 1184389.