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Merck

C0225000

Calcitriol

European Pharmacopoeia (EP) Reference Standard

Sinónimos:

1α,25-Dihydroxyvitamin D3, 1α,25-Dihydroxycholecalciferol, Calcitriol

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C27H44O3
Número CAS:
Peso molecular:
416.64
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
7559394
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InChI

1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1

SMILES string

[H][C@@]1(CC[C@@]2([H])C(\CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)CCCC(C)(C)O

InChI key

GMRQFYUYWCNGIN-NKMMMXOESA-N

biological source

sheep wool (grease)

grade

pharmaceutical primary standard

agency

EP

API family

calcitriol

form

solid

manufacturer/tradename

EDQM

technique(s)

gas chromatography (GC): suitable, liquid chromatography (LC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... VDR(7421)

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the authority of the issuing pharmacopoeia. For further information and support please go to the website of the issuing pharmacopoeia.

Calcitriol is a biologically active metabolite of vitamin D, formed via hydroxylation of calcidiol in the kidney.

Application

Calcitriol EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Biologically active form of vitamin D3 in calcium absorption and deposition.
Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - STOT RE 1

Clase de almacenamiento

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

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Optimization of culture conditions for transformation of vitamin D3 to calcitriol by Actinomyces hyovaginalis isolate A11-2
Abbas MA, et al.
Archives of Clinical Microbiology, 2(6) (2011)
Ryoko Okamoto et al.
International journal of cancer, 134(1), 207-217 (2013-06-19)
We have synthesized 39 1,25-dihydroxyvitamin D3 [1,25(OH)2D3] analogs having two side chains attached to carbon-20 (Gemini) with various modifications and compared their anticancer activities. Five structure-function rules emerged to identify analogs with enhanced anticancer activity. One of these active analogs
Joao F de Brito Galvao et al.
Journal of veterinary emergency and critical care (San Antonio, Tex. : 2001), 23(2), 134-162 (2013-04-10)
To review the inter-relationships between calcium, phosphorus, parathyroid hormone (PTH), parent and activated vitamin D metabolites (vitamin D, 25(OH)-vitamin D, 1,25(OH)2 -vitamin D, 24,25(OH)2 -vitamin D), and fibroblast growth factor-23 (FGF-23) during chronic kidney disease (CKD) in dogs and cats.
Edwin C Y Chow et al.
Gastroenterology, 146(4), 1048-1059 (2013-12-25)
Little is known about the effects of the vitamin D receptor (VDR) on hepatic activity of human cholesterol 7α-hydroxylase (CYP7A1) and cholesterol metabolism. We studied these processes in mice in vivo and mouse and human hepatocytes. Farnesoid X receptor (Fxr)(-/-)
Edwin C Y Chow et al.
American journal of physiology. Endocrinology and metabolism, 304(9), E977-E989 (2013-03-14)
The vitamin D receptor (VDR) maintains a balance of plasma calcium and 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3], its natural active ligand, by directly regulating the calcium ion channel (TRPV6) and degradation enzyme (CYP24A1), and indirectly regulating the parathyroid hormone (PTH) for feedback

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