Calcipotriene
Calcipotriene Basic information
- Product Name:
- Calcipotriene
- Synonyms:
-
- 5z,7e,22e,24s)--bet
- 9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol,24-cyclopropyl-,(1-alpha,3
- dovonex
- mc903
- CALCIPOTRIOL,CALCIPOTRIENE
- Calciptriol, MC-903, Daivonex, Dovonex, Psorcutan
- (1S,3S,5Z)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(E,2S)-5-Cyclopropyl-5-hydroxy-pent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol
- Calcipotriene
- CAS:
- 112965-21-6
- MF:
- C27H40O3
- MW:
- 412.6
- EINECS:
- 601-218-4
- Product Categories:
-
- Isotope Labelled Compounds
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 112965-21-6.mol
Calcipotriene Chemical Properties
- Melting point:
- 166-168°C
- Boiling point:
- 582.0±50.0 °C(Predicted)
- Density
- 1.12±0.1 g/cm3(Predicted)
- storage temp.
- Desiccate at -20°C
- solubility
- DMSO: soluble15mg/mL, clear
- pka
- 14.29±0.20(Predicted)
- form
- powder
- InChIKey
- LWQQLNNNIPYSNX-HCHVWAPNSA-N
- CAS DataBase Reference
- 112965-21-6(CAS DataBase Reference)
MSDS
- Language:English Provider:Calcipotriene
Calcipotriene Usage And Synthesis
Description
Calcipotriol is a topical vitaminD3 derivative effective in the treatment of psoriasis vulgaris. The drug acts by binding to vitamin D3 receptors in the skin keratinocytes, producing an elevation in cell differentiation and a reduction in cell proliferation. Although its efficacy is comparable to calcitriol, calcipotriol exhibits at least 100 times less effect on calcium metabolism in rats.
Chemical Properties
White Crystalline Solid
Originator
Leo Denmark (Denmark)
Uses
An antipsoriatic. A vitamin D3 analogue with low calcemic activity
Uses
antipsoriatic;viamin D receptor (VDR) affinity
Uses
A labelled antipsoriatic. A vitamin D3 analogue with low calcemic activity.
Indications
Calcipotriene (Dovonex), a synthetic vitamin D3 derivative, is indicated for the treatment of moderate plaque psoriasis. Its mechanism of action is unknown, although it competes for calcitriol receptors on keratinocytes and normalizes differentiation. It also has a variety of immunomodulatory effects in the skin. Although the drug can cause local irritation, the most serious toxicities are hypercalciuria and hypercalcemia, which are usually reversible.
Manufacturing Process
(1S,3R)-Bis-(t-butyldimethylsilyloxy)-(20S)-formyl-9,10-secopregna(5E,7E,10
(19))triene (Calverley Tetrahedron 43.4609 (1967) and (cyclopropyl)(tri-phenylphoshoranylidene)ketone are stirred in dimethyl sulfoxide under
nitrogen. The reaction mixture is then diluted at room temperature with ethyl
acetate and washed with common salt solution. The organic phase is dried on
sodium sulfate and filtered. After removal of the solvent, the residue is filtered
with toluene through silica gel. Evaporation of the solvent and gradient
chromatography (toluene/hexane (1:1)-toluene) of the residue on silica gel
yield (5E,7E,22E),(1S,3R)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-
9,10-secochola-5,7,10(19),22-tetraene-24-one.
(5E,7E,22E),(1S,3R)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-9,10-
secochola-5,7,10(19),22-tetraene-24-one in tetrahydrofuran and methanol are
mixed with a 0.4 M methanol CeCl3·7H2O solution. Sodium borohydride is
added by portions under nitrogen with ice cooling. The suspension is stirred
with ice cooling and then put into ice/common salt solution. The aqueous
phase is extracted with ethyl acetate, the organic phase is washed neutral
with water and dried on sodium sulfate. Filtration and removal of the solvent
yield oil. By chromatography on silica gel with ethyl acetate/hexane (1:9). The
(5E,7E,22E),(1S,3R,24S)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-
9,10-secochola-5,7,10(19),22-tetraene-24-ol is obtained.
(5E,7E,22E),(1S,3R,24S)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-
9,10-secochola-5,7,10(19),22-tetraene-24-ol is dissolved in toluene and after
addition of anthracene and 1 drop of triethylamine it is radiated at room
temperature with a high pressure mercury vapor lamp (Heraeus TQ 150)
through Pyrex glass. The reaction mixture is concentrated by evaporation and
the residue a mixture of (5Z,7E,22E),(1S,3R,24S)-1,3-bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-
24-ol and anthracene - is directly reacted with tetrabutylammonium fluoride.
(5Z,7E,22E),(1S,3R,24S)-1,3-Bis-(t-butyldimethylsilyloxy)-24-cyclopropyl-
9,10-secochola-5,7,10(19),22-tetraene-24-ol in tetrahydrofuran is kept with a
1 M solution of tetrabutylammonium fluoride in tetrahydrofuran under
nitrogen. For working up, the cooled reaction mixture is poured into cold
sodium bicarbonate solution and then extracted with ethyl acetate. After
drying of the organic phase on sodium sulfate, filtration and evaporation of
the solvent yields a resin-like residue. Chromatography on silica gel with ethyl
acetate/hexane (2:1) yields (5Z,7E,22E),(1S,3R,24S)-24-cyclopropyl-9,10-
secochola-5,7,10(19),22-tetraene-1,3,24-triol.
brand name
Dovonex (Leo);Daivonex.
Therapeutic Function
Antipsoriatic
Biological Activity
Vitamin D 3 analog that displays minimal effects on calcium homeostasis. Regulates cell differentiation and proliferation; exhibits antiproliferative activity against human HL-60, HL60/MX2, MCF-7, T47D, SCC-25 and mouse WEHI-3 cancer cell lines.
Pharmacology
Calcipotriene (Dovonex) enhances the effectiveness of ultraviolet B (UVB) but also increases photosensitivity in UVB-treated patients. Ultraviolet light, 6% salicylic acid, 12% lactic acid, hydrocortisone valerate 0.2% ointment, and tazarotene (Tazorac) gel degrade calcipotriene (Dovonex). Halobetasol ointment and 5% tar gel are compatible with Calcipotriene (Dovonex). A British study found calcipotriene (Dovonex) to be safe and effective in a pediatric population over the age of 3, although it is not approved by the FDA.
Calcipotriene Preparation Products And Raw materials
Raw materials
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Calcipotriene(112965-21-6)Related Product Information
- Carboplatin
- (5Z,7E,22E)-9,10-Seco-26,27-cyclo-1α,3β-dihydroxycholesta-5,7,10(19),22-tetren-24-one
- CALCIPOTRIOL MONOHYDRATE
- (1S,4R,E)-4-((1R,3aS,7aR,E)-4-((Z)-2-((3S,5R)-3,5-bis((tert-butyldiMethylsilyl)oxy)-2-Methylenecyclohexylidene)ethylidene)-7a-Methyloctahydro-1H-inden-1-yl)-1-cyclopropylpent-2-en-1-ol
- Calcipotriene
- Calcipotriene
- Tetrapropylammonium hydroxide
- Allyl glycidyl ether
- Allyl chloride
- Propylthiouracil
- Cocoyl amide propyldimethyl glycine
- CHLOROPHOSPHONAZO III
- Allyl bromide
- N,N-Diisopropylethylamine