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C4369

Sigma-Aldrich

Calcipotriol hydrate

≥98% (HPLC), powder, Vitamin D3 analog

Synonyma:

(5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol, Calcipotriene

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About This Item

Empirický vzorec (Hillův zápis):
C27H40O3 · xH2O
Číslo CAS:
112965-21-6
Molekulová hmotnost:
412.60 (anhydrous basis)
MDL number:
MFCD10567086
UNSPSC Code:
12352200
PubChem Substance ID:
329775060
NACRES:
NA.77

product name

Calcipotriol hydrate, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

solubility

DMSO: 15 mg/mL, clear

storage temp.

room temp

SMILES string

O.C[C@H](\C=C\[C@@H](O)C1CC1)C2CCC3\C(CCC[C@]23C)=C\C=C4\C[C@@H](O)C[C@H](O)C4=C

InChI

1S/C27H40O3.H2O/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2;/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3;1H2/b13-6+,19-7+,21-10-;/t17-,22-,23-,24+,25-,26+,27-;/m1./s1

InChI key

XBKHACNRWFKJNC-MANNPBRJSA-N

Biochem/physiol Actions

Calcipotriol, a synthetic derivative of calcitriol or Vitamin D, is used in the treatment of psoriasis and marketed under the trade name Dovonex. It has comparable affinity with calcitriol (Vit. D) for the Vitamin D receptor (VDR), while being less than 1% as active as the calcitriol in regulating calcium metabolism. VDR belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. Binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation-related genes.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2 - Repr. 2 - Skin Sens. 1B - STOT RE 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Osvědčení o analýze (COA)

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Andrés Tirado-Sánchez et al.
Cutis, 90(3), 140-144 (2012-10-26)
Calcipotriene ointment is widely used in the topical treatment of psoriasis, with tacrolimus ointment as an effective alternative in controlling stable plaque psoriasis. The efficacy of the combination of both products on stable plaque psoriasis has not been assessed in
E Sato-Deguchi et al.
The British journal of dermatology, 167(1), 77-84 (2012-03-06)
Psoriasis is a chronic inflammatory skin disease of unknown aetiology, and an active form of vitamin D(3) (1α,25-dihydroxyvitamin D(3)) and its analogues (VD3As) are widely used topical reagents for psoriasis treatment. Besides their well-known calcium homeostasis functions, VD3As have been
J Meephansan et al.
Clinical and experimental dermatology, 37(8), 889-896 (2012-08-29)
Vitamin D3 is a potent regulator of cell growth, differentiation and death, tumour invasion, and angiogenesis. Production of matrix metalloproteinase (MMP)-9 and MMP-13 by tumour cells may promote tumour growth, invasion and metastasis. To investigate whether calcipotriol could suppress the
Steven R Feldman et al.
American journal of clinical dermatology, 13(4), 261-271 (2012-05-17)
Topical calcipotriene is frequently prescribed for the treatment of plaque-type psoriasis. Calcipotriene is currently available in the US as an ointment, a solution, a cream, and in a fixed-dose combination ointment with betamethasone dipropionate. Calcipotriene 0.005% has recently been formulated
Christina Rogalski et al.
International journal of hyperthermia : the official journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group, 28(2), 184-190 (2012-02-18)
The combination of excimer laser and topical treatment has not been studied in clinical trials. This within-patient comparison study evaluates the response rates of plaque-type psoriasis after treatment with topical only (dithranol or calcipotriol), laser only, and combination therapy with
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