Calcifediol

"Calcidiol" redirects here. For the drug marketed as "Calcidol", see Ergocalciferol.

Calcifediol
IUPAC name (6R)-6-[(1R,3aR,4E,7aR)-4-[(2Z)-2-[(5S)-5- Hydroxy-2-methylidene-cyclohexylidene] ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro- 1H-inden-1-yl]-2-methyl-heptan-2-ol
Other names 25-Hydroxyvitamin D3 25-Hydroxycholecalciferol Calcifediol
Identifiers
CAS number	19356-17-3 Y
PubChem	5283731
ChemSpider	4938806 Y
UNII	T0WXW8F54E Y
DrugBank	DB00146
MeSH	Calcifediol
ChEMBL	CHEMBL1222 N
Jmol-3D images	Image 1
SMILES O[C@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3(C2CC[C@@H]3[C@H](C)CCCC(O)(C)C)C
InChI InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23-,24-,25?,27-/m1/s1 Y Key: JWUBBDSIWDLEOM-BNQRRPJDSA-N Y InChI=1/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23-,24-,25?,27-/m1/s1 Key: JWUBBDSIWDLEOM-BNQRRPJDBR
Properties
Molecular formula	C27H44O2
Molar mass	400.64 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Calcifediol (INN), also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D (abbreviated 25(OH)D),^[1] is a prehormone that is produced in the liver by hydroxylation of vitamin D₃ (cholecalciferol) by the enzyme cholecalciferol 25-hydroxylase. Calcifediol is then converted in the kidneys (by the enzyme 25(OH)D-1α-hydroxylase) into calcitriol (1,25-(OH)₂D₃), a secosteroid hormone that is the active form of vitamin D. It can also be converted into 24-hydroxycalcidiol in the kidneys via 24-hydroxylation.^[2][3]

Blood test

In medicine, a 25-hydroxy vitamin D (calcidiol) blood test is used to determine how much vitamin D is in the body.^[4] The blood concentration of calcidiol is considered the best indicator of vitamin D status.^[5] It is the most sensitive measure,^[6] though experts have called for improved standardization and reproducibility across different laboratories.^[5] According to MedlinePlus, the normal range of calcidiol is 30.0 to 74.0 ng/mL.^[4] The normal range varies widely depending on several factors, including age and geographic location. A broad reference range of 20–150 nmol/L (8-60 ng/ml) has also been suggested,^[7] while other studies have defined levels below 80 nmol/L (32 ng/ml) as indicative of vitamin D deficiency.^[8]

Clinical significance

Increasing calcidiol levels are associated with increasing fractional absorption of calcium from the gut up to levels of 80 nmol/L (32 ng/mL).^{[citation needed]} Urinary calcium excretion balances intestinal calcium absorption and does not increase with calcidiol levels up to ~400 nmol/L (160 ng/mL).^[9]

A study by Cedric F. Garland and Frank C. Garland of the University of California, San Diego analyzed the blood from 25,000 volunteers from Washington County, Maryland, finding that those with the highest levels of calcifediol had a risk of colon cancer that was one-fifth of typical rates.^[10]

See also

• Hypervitaminosis D
• Hypovitaminosis D
• Vitamin D
  • Health effects

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. ^ Bender, David A.; Mayes, Peter A (2006). "Micronutrients: Vitamins & Minerals". In Victor W. Rodwell; Murray, Robert F.; Harper, Harold W.; Granner, Darryl K.; Mayes, Peter A.. Harper's Illustrated Biochemistry. New York: Lange/McGraw-Hill. pp. 492–3. ISBN 0-07-146197-3. http://books.google.com.br/books?id=QrJCZ1v5T6AC.  Retrieved December 10, 2008 through Google Book Search.
3. ^ Institute of Medicine (1997). "Vitamin D". Dietary Reference Intakes for Calcium, Phosphorus, Magnesium, Vitamin D, and Fluoride. Washington, D.C: National Academy Press. pp. 254. ISBN 0-309-06403-1. http://www.nap.edu/openbook.php?record_id=5776&page=250. 
4. ^ ^{a b} ""25-hydroxy vitamin D test: Medline Plus". Retrieved 21 March 2010.
5. ^ ^{a b} Heaney, Robert P (Dec 2004). "Functional indices of vitamin D status and ramifications of vitamin D deficiency". American Journal of Clinical Nutrition 80 (6): 1706S–9S. PMID 15585791. http://www.ajcn.org/cgi/content/full/80/6/1706S. 
6. ^ Institute of Medicine (1997), p. 259
7. ^ Bender, David A. (2003). "Vitamin D". Nutritional biochemistry of the vitamins. Cambridge: Cambridge University Press. ISBN 0-521-80388-8. http://books.google.com.br/books?id=pxEJNs0IUo4C.  Retrieved December 10, 2008 through Google Book Search.
8. ^ Hollis BW (February 2005). "Circulating 25-hydroxyvitamin D levels indicative of vitamin D sufficiency: implications for establishing a new effective dietary intake recommendation for vitamin D". J Nutr 135 (2): 317–22. PMID 15671234. http://jn.nutrition.org/cgi/pmidlookup?view=long&pmid=15671234. 
9. ^ Kimball et al. (2004). "Safety of vitamin D3 in adults with multiple sclerosis". J Clin Endocrinol Metab 86 (3): 645–51. PMID 17823429. 
10. ^ Maugh II, Thomas H. "Frank C. Garland dies at 60; epidemiologist helped show importance of vitamin D: Garland and his brother Cedric were the first to demonstrate that vitamin D deficiencies play a role in cancer and other diseases.", Los Angeles Times, August 31, 2010. Accessed September 4, 2010.

External links

• A11CC06