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C0225000

Calcitriol

European Pharmacopoeia (EP) Reference Standard

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Synonym(s):
1α,25-Dihydroxyvitamin D3, 1α,25-Dihydroxycholecalciferol, Calcitriol
Empirical Formula (Hill Notation):
C27H44O3
CAS Number:
32222-06-3
Molecular Weight:
416.64
Beilstein/REAXYS Number:
7559394
MDL number:
MFCD00867079
UNSPSC Code:
41116107
PubChem Substance ID:
329774770
NACRES:
NA.24

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

storage temp.

−20°C

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

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

InChI key

GMRQFYUYWCNGIN-NKMMMXOESA-N

Gene Information

human ... VDR(7421)

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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. 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
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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EB1089 ≥98% (HPLC)

Sigma-Aldrich

SML1727

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Sigma-Aldrich

C4369

Calcipotriol hydrate

1α-Hydroxyvitamin D3 ≥97.0% (HPLC)

Sigma-Aldrich

17946

1α-Hydroxyvitamin D3

1α,25-Dihydroxyvitamin D3-26,26,26,27,27,27-d6 solution 100 μg/mL in ethanol, ≥98 atom % D, ≥95% (CP)

Sigma-Aldrich

809926

1α,25-Dihydroxyvitamin D3-26,26,26,27,27,27-d6 solution

Cholecalciferol ≥98% (HPLC)

Sigma-Aldrich

C9756

Cholecalciferol

1α,25-Dihydroxyvitamin D2 ≥97.0% (sum of vitamin and previtamin, HPLC)

Sigma-Aldrich

17944

1α,25-Dihydroxyvitamin D2

Calcifediol United States Pharmacopeia (USP) Reference Standard

USP

1086108

Calcifediol

25-Hydroxycholecalciferol ≥98% (HPLC)

Sigma-Aldrich

H4014

25-Hydroxycholecalciferol

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)
Moira Cheung et al.
The Journal of clinical endocrinology and metabolism, 98(5), E954-E961 (2013-03-28)
X-linked hypophosphatemic rickets is caused by mutations in PHEX. Even though the disease is characterized by disordered skeletal mineralization, detailed bone densitometric studies are lacking. The aim of the study was to assess volumetric bone mineral density (vBMD) in X-linked
Evelyne Van Etten et al.
Journal of cellular biochemistry, 88(2), 223-226 (2003-01-10)
The active form of vitamin D(3), 1,25(OH)(2)D(3), is known, besides its classical effects on calcium and bone, for its pronounced immunomodulatory effects that are exerted both on the antigen-presenting cell level as well as directly on the T lymphocyte level.
Gabriela Bomfim Ferreira et al.
The Journal of steroid biochemistry and molecular biology, 136, 160-165 (2012-10-27)
The biologically active form of vitamin D, 1α,25-dihydroxyvitamin D3 (1α,25(OH)2D3), presents pronounced immunomodulatory effects, mainly mediated through its actions on different immune cells such as dendritic cells (DC) and T lymphocytes. Because of the high concentrations needed to obtain immune
Beth J Kirby et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 28(9), 1987-2000 (2013-03-19)
Pregnancy invokes a doubling of intestinal calcium absorption whereas lactation programs skeletal resorption to provide calcium to milk. Postweaning bone formation restores the skeleton's bone mineral content (BMC), but the factors that regulate this are not established. We used Pth-null
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