| Identification | More | [Name]
Calcipotriene | [CAS]
112828-00-9 | [Synonyms]
(1r,3s,5z)-5-[(2e)-2-[1-[(e,2r,5r)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
(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
24-CYCLOPROPYL-(1ALPHA,3BETA,5Z,7E,22E,24S)-9,10-SECOCHOLA-5,7,10(19),22-TETRAENE-1,3,24-TRIOL
CALCIPOTRIENE
CALCIPOTRIOL
(1R,3S,5Z)-5-[(2E)-2-[1-[(E,2R,5R)-5-Cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
Calcipotriene | [EINECS(EC#)]
686-849-3 | [Molecular Formula]
C27H40O3 | [MDL Number]
MFCD00866630 | [Molecular Weight]
412.6 | [MOL File]
112828-00-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White or almost white powder | [CAS DataBase Reference]
112828-00-9(CAS DataBase Reference) | [Usage and Efficacy]
Available as a cream, ointment or scalp solution (50mcg/mL), Calcipotriol(112828-00-9) is applied twice daily to plaque psoriasis on the body or scalp, but not the face. Improvement is usually detectable within 2 weeks. Most patients show some improvement, slightly more so than is seen with the use of corticosteroids alone. Tachyphylaxis does not occur, an improvement over glucocorticoid therapy. |
| Hazard Information | Back Directory | [Uses]
Antipsoriatic. | [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. | [Indications]
Calcipotriene (calcipotriol) is a synthetic vitamin D3 derivative that is useful for
the treatment of patients with moderate plaque psoriasis. Its effects are comparable
with those of class II topical steroids, without the associated adverse effects.
Its mechanism of action involves both induction of terminal differentiation of
keratinocytes and inhibition of keratinocyte production. It should be applied to
the face with care, as this region is more susceptible to irritation, burning, and
itching, as seen in approximately 10% of patients. Other adverse effects include
erythema, peeling, xerosis, dermatitis, or worsening psoriasis in 1% to 10% of
patients. Fewer than 1% of patients experience hypercalcemia, atrophy, hyperpigmentation,
or folliculitis. Allergic contact dermatitis to calcipotriene has been
reported.
Most patients demonstrate improvement after 2 weeks; 70% of patients
improve after 8 weeks, with 10% showing complete clearing. It should be avoided
in patients with documented impairment in calcium metabolism, hypercalcemia,
vitamin D toxicity, or history of renal stones.
Calcipotriene may be used as an adjuvant with psoralens plus ultraviolet A
(PUVA) and ultraviolet B (UVB). Pretreatment with or subsequent addition of calcipotriol
to PUVA reduces the cumulative doses of UVA needed to achieve >75%
reduction in severity and distribution of psoriasis. | [Brand name]
Dovonex (Leo). |
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