| Identification | Back Directory | [Name]
CALCIPOTRIOL MONOHYDRATE | [CAS]
147657-22-5 | [Synonyms]
CALCIPOTRIOL MONOHYDRATE
Calcipotriol monohydrate CRS
Calcipotriol (Calcipotriene) Monohydrate
(5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1α,3β,24-triol
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-Cyclohexanediol hydrate
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-Cyclohexanediol monohydrate
1,3-Cyclohexanediol,5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-,hydrate (1:1), (1R,3S,5Z)- | [EINECS(EC#)]
689-035-6 | [Molecular Formula]
C27H40O3.H2O | [MDL Number]
MFCD10567086 | [MOL File]
147657-22-5.mol | [Molecular Weight]
430.625 |
| Chemical Properties | Back Directory | [Appearance]
White or almost white, crystalline powder. | [storage temp. ]
4°C, protect from light, stored under nitrogen,unstable in solution, ready to use. | [solubility ]
Practically insoluble in water, freely soluble in ethanol (96 per cent), slightly soluble in methylene chloride. | [form ]
Powder | [color ]
White to off-white | [Stability:]
Hygroscopic, Light sensitive | [InChIKey]
XBKHACNRWFKJNC-IZXATKCONA-N | [SMILES]
C[C@]12CCC/C(=C\C=C3\C[C@@H](O)C[C@H](O)C\3=C)/[C@]1([H])CC[C@]2([H])[C@H](C)/C=C/[C@H](C1CC1)O.O |&1:1,10,13,17,21,23,27,r| | [Uses]
Vitamin D analogue. |
| Hazard Information | Back Directory | [Chemical Properties]
White or almost white, crystalline powder. | [Definition]
ChEBI: A hydrate that is the monohydrate form of calcipotriol. It is used in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients. | [Description]
Calcipotriol (hydrate) is a low-calcemic vitamin D receptor (VDR) agonist. Calcipotriol (hydrate) is about 200 times less potent in its effects on calcium metabolism than vitamin D (1,25[OH]D3).1 Binding of calcipotriol (hydrate) to the VDR increases AP-1, a transcription factor important for keratinocyte differentiation, and reduces expression of JunB protein, a transcriptional activator in the inflammatory response.2 Calcipotriol (hydrate) also induces expression of thymic stromal lymphopoietin, which triggers T-cell differentiation in keratinocytes.3 | [in vivo]
One out of the 32 animals in each of the groups has died, except for the Diclofenac plus DFMO plus Calcipotriol group, where all animals survived. Survival is equally distributed between the groups. The weight gain is significantly smaller in the groups treated with Diclofenac plus Calcipotriol (p=0.018) and Diclofenac plus DFMO plus Calcipotriol (p=0.002) compare with placebo (linear regression model)[3]. | [References]
[1] KRAGBALLE K. Vitamin D analogues in the treatment of psoriasis[J]. Journal of cellular biochemistry, 1992, 49 1: 46-52. DOI: 10.1002/jcb.240490109
[2] C. JOHANSEN. Activator protein 1 DNA binding activity is decreased in lesional psoriatic skin compared with nonlesional psoriatic skin[J]. British Journal of Dermatology, 2004, 151 3: 600-607. DOI: 10.1111/j.1365-2133.2004.06088.x
[3] MEI LI. Topical vitamin D3 and low-calcemic analogs induce thymic stromal lymphopoietin in mouse keratinocytes and trigger an atopic dermatitis.[J]. ACS Catalysis , 2006: 11736-11741. DOI: 10.1073/pnas.0604575103 |
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