Calcipotriene Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
Calcipotriene also known as 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.
Chemische Eigenschaften
White Crystalline Solid
Verwenden
Calcipotriene is an antipsoriatic that is a vitamin D3 analogue with low calcemic activity. It works by regulating the production and growth of skin cells. In the United States, this drug was first marketed under the trade name Dovonex and is used mainly for the treatment of psoriasis. It is one of the most effective non glucocorticoid topical drugs for the treatment of localized psoriasis.This drug has many off-label applications that are alternative therapies for many dermatologic diseases.
synthetische
A convergent approach for the total synthesis of calcipotriol (brand name: Dovonex), a proven Vitamin D analog used for the treatment of psoriasis, and medicinally relevant synthetic analogs is described.
A Synthesis of calcipotriol via a Key Electroreductive Cross-coupling Approach
Calcipotriol is currently the most successful VitD analog and is prescribed for the treatment of psoriasis, an autoimmune skin disease.
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.
Definition
ChEBI: Calcipotriol is a seco-cholestane that is 26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene carrying additional hydroxy substituents at positions 1, 3 and 24. It is used (as its hydrate) in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients. It has a role as a drug allergen and an antipsoriatic. It is a member of cyclopropanes, a secondary alcohol, a triol, a hydroxy seco-steroid and a seco-cholestane.
Biologische Aktivität
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.
Pharmakologie
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.
Nebenwirkungen
Possible side effects include:
severe burning, stinging, skin rash, or other irritation after applying the medicine;
worsening of your skin condition;
high calcium levels--confusion, tiredness, nausea, vomiting, loss of appetite, constipation, increased thirst or urination, weight loss;
mild skin irritation;
skin rash;
itching.
Calcipotriene Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Liquid sulfur dioxide
tert-Butylchlordimethylsilan
4-METHYLMORPHOLINE-4-OXIDE SOLUTION
Selendioxid
Tetrabutylammoniumfluorid
Anthracen
Cyclopropylmagnesium bromide
N,N-Diethylethanamin
Natriumtetrahydroborat
Certrichlorid
PHOSPHINE OXIDE, [2-[3,5-BIS [[(1,1-DIMETHYLETHYL) DIMETHYLSILY]OXY]-2-METHYLENECYCLOHEXYLIDENE]ETHYL]DIPHENYL-,[3S-(1Z,3A,5B0)]
(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
(5E)-Calcipotriene
Downstream Produkte
