24,25-Dihydroxycholecalciferol

24,25-Dihydroxycholecalciferol
Identifiers
CAS number 40013-87-4 Y
PubChem 6434253
ChemSpider 4939193 Y
ChEMBL CHEMBL47183 Y
Jmol-3D images Image 1
Properties
Molecular formula C27H44O3
Molar mass 416.63 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

24,25-Dihydroxycholecalciferol, also known as 24,25-dihydroxyvitamin D3 and (24R)-hydroxycalcidiol (abbreviated as 24(R),25-(OH)2D3),[1] is a compound which is closely related to 1,25-dihydroxyvitamin D3, the active form of vitamin D3, but like vitamin D3 itself and 25-hydroxyvitamin D3 is inactive as a hormone both in vitro[2] and in vivo.[3]

Formation and significance

24,25-dihydroxyvitamin D3 is formed from 25-hydroxyvitamin D3 by the action of P450cc24 (25-hydroxyvitamin D3-24-hydroxylase), which appears to be "a multicatalytic enzyme catalyzing most, if not all, of the reactions in the C-24/C-23 pathway of 25-OH-D3 metabolism."[4] It has been proposed that 24,25-dihydroxyvitamin D3 is a metabolite of 25-hydroxyvitamin D3 which is destined for excretion.[4]

It is not known whether the compound might also have some physiologically significant activity. Some evidence of a possible receptor has been obtained.[5]

References

  1. ^ "Nomenclature of Vitamin D. Recommendations 1981. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN)" reproduced at the Queen Mary, University of London website. Retrieved 21 March 2010.
  2. ^ Sørnes S, Bjøro T, Berg JP, Torjesen PA, Haug E (1994). "Calcitriol attenuates the basal and vasoactive intestinal peptide-stimulated cAMP production in prolactin-secreting rat pituitary (GH4C1) cells." Mol. Cell. Endocrinol. 101 (1-2): 183–8. PubMed
  3. ^ Mortensen BM, Gautvik KM, Gordeladze JO (1993). "Bone turnover in rats treated with 1,25-dihydroxyvitamin D3, 25-hydroxyvitamin D3 or 24,25-dihydroxyvitamin D3". Biosci. Rep. 13 (1): 27–39. PubMed
  4. ^ a b Beckman, Matthew J.; Tadikonda, Praveen; Werner, Elizabeth; Prahl, Jean; Yamada, Sachiko; Deluca, Hector F. (1996). "Human 25-Hydroxyvitamin D3-24-Hydroxylase, a Multicatalytic Enzyme". Biochemistry 35 (25): 8465–72. doi:10.1021/bi960658i. PMID 8679605. 
  5. ^ Sömjen D, Sömjen GJ, Weisman Y, Binderman I (April 1982). "Evidence for 24,25-dihydroxycholecalciferol receptors in long bones of newborn rats". Biochem. J. 204 (1): 31–6. PMC 1158312. PMID 6981414. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1158312. 

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