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D0196

Doxercalciferol

Name: Doxercalciferol
Brand: SIGMA

≥98% (HPLC), solubility: >10 mg/mL in DMSO

Synonym(s):

(5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1α,3β-diol, (5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1,3-diol, 1α-Hydroxyergocalciferol, 1α-Hydroxyvitamin D₂, 1α-OHD2, 1-α-Hydroxyvitamin D2, 1-Hydroxyergocalciferol, TSA 840

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About This Item

Empirical Formula (Hill Notation):

C₂₈H₄₄O₂

CAS Number:

54573-75-0

Molecular Weight:

412.65

NACRES:

NA.77

PubChem Substance ID:

329798592

UNSPSC Code:

12352200

MDL number:

MFCD00871065

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

Storage condition:

desiccated

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Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

solubility

DMSO: >10 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/b10-9+,22-11+,23-12-/t19-,20+,24+,25+,26-,27-,28+/m0/s1

InChI key

HKXBNHCUPKIYDM-CGMHZMFXSA-N

Gene Information

human ... VDR(7421)

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Biochem/physiol Actions

Doxercalciferol is a Vitamin D2 analogue, a Vitamin D Receptor Activator (VDRA).

Doxercalciferol is a Vitamin D2 analogue, a Vitamin D Receptor Activator (VDRA). Doxercalciferol acts as a pro-hormone, needing 25-hydroxylation in the liver for bioactivation into 1α, 25-hydroxyvitamin D2. Pivotal studies in adults on dialysis have demonstrated control of secondary hyperparathyroidism that is superior to placebo therapy, without undue suppression of 1st IMA-PTH < 300 pg/mL, or occurrences of hypercalcemia. Doxercalciferol has been shown to be effective in controlling secondary hyperparathyroidism of adult patients with CKD stages 3-4.

Doxercalciferol is a vitamin D₂ analog that acts as a pro-hormone, activated in the liver to 1α,25-dihydroxyvitamin D₂.

Doxercalciferol is a vitamin D₂ analog that acts as a pro-hormone, activated in the liver to 1α,25-dihydroxyvitamin D₂. Despite its relatively low affinity for the vitamin D receptor (VDR) (before activation), it is effective at suppressing expression of the parathyroid hormone (PTH) gene, and appears to act through the VDR.

pictograms

GHS06

signalword

Danger

hcodes

H300

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 1 Oral

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Differential effects of vitamin D receptor activators on aortic calcification and pulse wave velocity in uraemic rats.

William Noonan et al.

Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 23(12), 3824-3830 (2008-07-23)

Vascular calcification is associated with an increase in cardiovascular mortality in stage 5 chronic kidney disease. To determine if vitamin D receptor activators (VDRAs) have differential effects in the pathogenesis of aortic calcification, we assessed the effects of paricalcitol and

Doxercalciferol, a pro-hormone of vitamin D, prevents the development of cardiac hypertrophy in rats.

Jun H Choi et al.

Journal of cardiac failure, 17(12), 1051-1058 (2011-11-30)

Activated vitamin D analog, paricalcitol, has been shown to attenuate the development of cardiac hypertrophy in Dahl salt sensitive (DSS) rats. To determine whether an antihypertrophic effect is class specific, we tested if doxercalciferol (a pro-hormone vitamin D2 analog) could

Therapeutic effects of vitamin D analogs on cardiac hypertrophy in spontaneously hypertensive rats.

Juan Kong et al.

The American journal of pathology, 177(2), 622-631 (2010-07-10)

Vitamin D inhibits renin expression and blocks the compensatory induction of renin associated with the use of renin-angiotensin system inhibitors. Here we test the therapeutic effects of two commonly used vitamin D analogs and their combination with losartan on the

Vitamin D receptor agonist doxercalciferol modulates dietary fat-induced renal disease and renal lipid metabolism.

Xiaoxin X Wang et al.

American journal of physiology. Renal physiology, 300(3), F801-F810 (2011-01-07)

Diet-induced obesity (DIO) and insulin resistance in mice are associated with proteinuria, renal mesangial expansion, accumulation of extracellular matrix proteins, and activation of oxidative stress, proinflammatory cytokines, profibrotic growth factors, and the sterol regulatory element binding proteins, SREBP-1 and SREBP-2

Calcitriol and doxercalciferol are equivalent in controlling bone turnover, suppressing parathyroid hormone, and increasing fibroblast growth factor-23 in secondary hyperparathyroidism.

Katherine Wesseling-Perry et al.

Kidney international, 79(1), 112-119 (2010-09-24)

We compared the effects of calcitriol and doxercalciferol, in combination with either calcium carbonate or sevelamer, on bone, mineral, and fibroblast growth factor-23 (FGF-23) metabolism in patients with secondary hyperparathyroidism. A total of 60 pediatric patients treated with peritoneal dialysis

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Global Trade Item Number

SKU	GTIN
D0196-5MG	04061833024010
D0196-1MG	04061826703113

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