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D0196

Sigma-Aldrich

Doxercalciferol

≥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
MDL number:
MFCD00871065
UNSPSC Code:
12352200
PubChem Substance ID:
329798592
NACRES:
NA.77

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 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. 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.

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Description
Pricing

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 1 Oral

Storage Class Code

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

Certificates of Analysis (COA)

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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
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
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
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
Neil Kumar et al.
American journal of nephrology, 29(2), 71-78 (2008-08-12)
National Kidney Foundation's Kidney Disease Outcome Quality Initiative (KDOQI) guidelines offer an outline for providing standardized care for best outcomes in chronic kidney disease (CKD). It is unknown whether real-world treatment practices follow these guidelines. The Hectorol Registry Outcome in
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