| Identification | More | [Name]
ANTHRALIN | [CAS]
1143-38-0 | [Synonyms]
1,8,9-ANTHRACENETRIOL
1,8-DIHYDROXY-10H-ANTHRACEN-9-ONE
1,8-DIHYDROXY-9(10H)-ANTHRACENONE
1,8-DIHYDROXYANTHRONE
ANTHRALIN
DITHRANOL
DITHRANOL, ANTHRALIN
1,8-dihydroxy-9(10h)-anthracenon
1,8-dihydroxy-anthron
Anthranol
Anthrone, 1,8-dihydroxy-
Batridol
DrithoCreme
Drithoscalp
Psodadrate
batridrol
DithraSal
Psorin
1,8-dihydroxyanthracen-9(10H)-one
9-anthrol | [EINECS(EC#)]
214-538-0 | [Molecular Formula]
C14H10O3 | [MDL Number]
MFCD00053409 | [Molecular Weight]
226.23 | [MOL File]
1143-38-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Crystalline Solid | [Melting point ]
178-181 °C (lit.) | [Boiling point ]
464.1±45.0 °C(Predicted) | [density ]
1.419±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Practically insoluble in water, soluble in methylene chloride, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides. | [form ]
neat | [pka]
7.16±0.20(Predicted) | [color ]
Yellow to Orange to Dark Yellow | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
Insoluble in water. Soluble in acetic acid, chloroform (20 mg/mL), acetone, benzene, solutions of alkali hydroxides, fixed oil. Slightly soluble in 95% ethanol, alcohol, ether, and glacial acetic acid. | [Usage]
Antipsoriatic | [Merck ]
14,684 | [BRN ]
2054360 | [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 | [InChIKey]
NUZWLKWWNNJHPT-UHFFFAOYSA-N | [SMILES]
Oc1cccc2Cc3cccc(O)c3C(=O)c12 | [CAS DataBase Reference]
1143-38-0(CAS DataBase Reference) | [IARC]
3 (Vol. 13; Sup 7) 1987 | [EPA Substance Registry System]
Dithranol (1143-38-0) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi,T | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R45:May cause cancer. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
3
| [RTECS ]
CB8927000
| [HS Code ]
29144000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
ANTHRALIN(1143-38-0) reacts as a weak acid. Soluble in aqueous bases. May react with strong oxidizing agents. May be sensitive to light and moisture . | [Air & Water Reactions]
Unstable in air when in alkaline solution. Insoluble in water. | [Fire Hazard]
Flash point data are not available for this chemical; however, ANTHRALIN is probably combustible. | [Description]
Anthralin is an anthrone inhibitor of keratinocyte proliferation and a modulator of differentiation.1 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.2 Anthralin (0.25 μM) decreases the expression of β-defensin-2 (Item No. 24577) 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.1 It also inhibits leukotriene B4 (LTB4; Item No. 20110) production, stimulated by the calcium ionophore A23187 (Item No. 11016), from human neutrophils (IC50 = 7 μM).3 Topical anthralin (0.1%) induces hair regrowth in a Dundee experimental bald rat (DEBR) model of alopecia areata.4 | [Chemical Properties]
Yellow Crystalline Solid | [Uses]
Antipsoriatic | [Uses]
Dithranol, a potential anti-psoriasis medication, may be used to study its safety, efficacy, metabolism and pharmacological profile. Dithranol may be used to study is physicochemical properties, as a reference compound and to develop effective drug delivery vehicles. Dithranol may be used as a matrix for matrix assisted laser desorption/ionization imaging on a Fourier transform ion cyclotron resonance mass spectrometer. | [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. | [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. | [Brand name]
Anthra-Derm (Dermik); DrithoCreme
(Dermik); Drithoscalp (Dermik); Lasan (Stiefel). | [Hazard]
Very irritating. Do not use on scalp or near eyes. | [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] SCHR?DER 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 |
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