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C4369

Sigma-Aldrich

Calcipotriol hydrate

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

Sinónimos:

(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

Fórmula empírica (notación de Hill):
C27H40O3 · xH2O
Número de CAS:
112965-21-6
Peso molecular:
412.60 (anhydrous basis)
Número MDL:
MFCD10567086
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
329775060
NACRES:
NA.77

Nombre del producto

Calcipotriol hydrate, ≥98% (HPLC)

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

solubilidad

DMSO: 15 mg/mL, clear

temp. de almacenamiento

room temp

cadena SMILES

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

Clave InChI

XBKHACNRWFKJNC-MANNPBRJSA-N

Acciones bioquímicas o fisiológicas

Calcipotriol is a synthetic derivative of calcitriol, or Vitamin D.
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.

Pictogramas

Skull and crossbonesHealth hazard
GHS06,GHS08

Palabra de señalización

Danger

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
0000249127
0000364499
0000364496
0000249127
0000364499

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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
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
Nina Østergaard Knudsen et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 81(3), 532-539 (2012-04-28)
The D-vitamin analogue calcipotriol is commonly used for topical treatment of psoriasis, but skin penetration is required for calcipotriol to reach its pharmacological target: the keratinocytes in the lower epidermis. Liposomes can enhance the delivery of drugs into the skin
Nina Ø Knudsen et al.
International journal of pharmaceutics, 428(1-2), 171-177 (2012-03-15)
Peptide conjugation to the surface of stealth liposomes has been studied for liposomal drug targeting to cells expressing specific receptors to provide a site-specific drug delivery. This study investigated the potential of peptide-conjugated liposomes for targeting cells expressing the human
Zuzana Hegyi et al.
The Journal of investigative dermatology, 132(5), 1416-1424 (2012-03-10)
The antimicrobial peptides (AMP) psoriasin (S100A7) and koebnerisin (S100A15) are differently induced in psoriatic skin. They act synergistically as chemoattractants and "alarmins" to amplify inflammation in psoriasis. Th17 cytokines are key players in psoriasis pathogenesis and vitamin D analogs feature
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