Calcifediol

Calcifediol

Names
Preferred IUPAC name (1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(2R)-6-Hydroxy-6-methylheptan-2-yl]-7a-methyloctahydro-4H-inden-4-ylidene}ethylidene]-4-methylidenecyclohexan-1-ol
Other names 25-Hydroxyvitamin D3 25-Hydroxycholecalciferol Calcidiol[1]
Identifiers
CAS Number	19356-17-3 Y
3D model ( JSmol )	Interactive image
ChEBI	CHEBI:17933 N
ChEMBL	ChEMBL1222 Y
ChemSpider	4446820 N
DrugBank	DB00146 Y
ECHA InfoCard	100.039.067
IUPHAR/BPS	6921
KEGG	C01561
MeSH	Calcifediol
PubChem CID	5283731
UNII	T0WXW8F54E Y
CompTox Dashboard (EPA)	DTXSID0022721
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 N Key: JWUBBDSIWDLEOM-DTOXIADCSA-N N 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-DTOXIADCBI
SMILES O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(O)(C)C)C
Properties
Chemical formula	C27H44O2
Molar mass	400.64 g/mol
Pharmacology
ATC code	H05BX05 (WHO)
Legal status	CA: ℞-only[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D₃ (abbreviated 25(OH)D₃),

Calcifediol is strongly bound in blood by the vitamin D-binding protein.^[5] Measurement of serum calcifediol is the usual test performed to determine a person's vitamin D status, to show vitamin D deficiency or sufficiency.^[4][5] Calcifediol is available as an oral medication in some countries to supplement vitamin D status.^[4][6][7]

Biology

Calcifediol is the precursor for calcitriol, the active form of vitamin D.

In medical practice, a blood test for 25-hydroxy-vitamin D, 25(OH)D, is used to determine an individual's vitamin D status.^[11] The name 25(OH)D refers to any combination of calcifediol (25-hydroxy-cholecalciferol), derived from vitamin D₃, and ercalcidiol (25-hydroxy-ergocalciferol),^[1] derived from vitamin D₂. The first of these (also known as 25-hydroxy vitamin D3) is made by the body, or is sourced from certain animal foods or cholecalciferol supplements. The second (25-hydroxy vitamin D2) is from certain vegetable foods or ergocalciferol supplements.^[11] Clinical tests for 25(OH)D often measure the total level of both of these two compounds together, generally without differentiating.^[12]

This measurement is considered the best indicator of overall vitamin D status.^[11][13][14] US labs generally report 25(OH)D levels as ng/mL. Other countries use nmol/L. Multiply ng/mL by 2.5 to convert to nmol/L.^[4]

This test can be used to diagnose vitamin D deficiency, and is performed in people with high risk for vitamin D deficiency, when the results of the test can be used to support beginning replacement therapy with vitamin D supplements.^[4][15] Patients with osteoporosis, chronic kidney disease, malabsorption, obesity, and some other infections may be at greater risk for being vitamin D-deficient and so are more likely to have this test.^[15] Although vitamin D deficiency is common in some populations including those living at higher latitudes or with limited sun exposure, the 25(OH)D test is not usually requested for the entire population.^[15] Physicians may advise low risk patients to take over-the-counter vitamin D supplements in place of having screening.^[15]

It is the most sensitive measure, though experts have called for improved standardization and reproducibility across different laboratories.^[4][13] According to MedlinePlus, the recommended range of 25(OH)D is 20 to 40 ng/mL (50 to 100 nmol/L) though they recognize many experts recommend 30 to 50 ng/mL (75 to 125 nmol/L).^[11] The normal range varies widely depending on several factors, including age and geographic location. A broad reference range of 20 to 150 nmol/L (8-60 ng/mL) has also been suggested,^[16] while other studies have defined levels below 80 nmol/L (32 ng/mL) as indicative of vitamin D deficiency.^[17]

Increasing calcifediol levels up to levels of 80 nmol/L (32 ng/mL) are associated with increasing the fraction of calcium that is absorbed from the gut.^[13] Urinary calcium excretion balances intestinal calcium absorption and does not increase with calcifediol levels up to ~400 nmol/L (160 ng/mL).^[18]

Supplementation

Calcifediol supplements have been used in some studies to improve vitamin D status.

In 2016, the FDA approved a formulation of calcifediol (Rayaldee) 60 microgram daily as a prescription medication to treat secondary hyperparathyroidism in patients with chronic kidney disease.^[7]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|alt=Vitamin D Synthesis Pathway (view / edit)]]

Vitamin D Synthesis Pathway (view / edit)

1. ^ The interactive pathway map can be edited at WikiPathways: "VitaminDSynthesis_WP1531".

History

Research in the laboratory of

Studies are ongoing comparing the effects of calcifediol with other forms of vitamin D including cholecalciferol in prevention and treatment of osteoporosis.^[3][20]

References