Cholecalciferol

Cholecalciferol, also known as vitamin D3 and colecalciferol, is a type of vitamin D that is made by the skin when exposed to sunlight; it is found in some foods and can be taken as a dietary supplement.

Cholecalciferol
INN: Colecalciferol
Clinical data
Pronunciation/ˌkləkælˈsɪfərɒl/
Other namesvitamin D3, calciol, activated 7-dehydrocholesterol
AHFS/Drugs.comProfessional Drug Facts
License data
Routes of
administration
By mouth, intramuscular
ATC code
Legal status
Legal status
  • CA: ℞-only
  • US: OTC
Identifiers
  • (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.612
Chemical and physical data
FormulaC27H44O
Molar mass384.648 g·mol−1
3D model (JSmol)
Melting point83 to 86 °C (181 to 187 °F)
Boiling point496.4 °C (925.5 °F)
Solubility in waterPractically insoluble in water, freely soluble in ethanol, methanol and some other organic solvents. Slightly soluble in vegetable oils.
SMILES
  • O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(C)C)C
  • InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1 N
  • Key:QYSXJUFSXHHAJI-YRZJJWOYSA-N

Cholecalciferol is made in the skin following UVB light exposure. It is converted in the liver to calcifediol (25-hydroxyvitamin D) which is then converted in the kidney to calcitriol (1,25-dihydroxyvitamin D). One of its actions is to increase calcium uptake by the intestines. It is found in food such as some fish, beef liver, eggs, and cheese. Plants, cow milk, fruit juice, yogurt, and margarine also may have cholecalciferol added to them in some countries, including the United States.

Cholecalciferol can be taken as an oral dietary supplement to prevent vitamin D deficiency or as a medication to treat associated diseases, including rickets. It is also used for familial hypophosphatemia, hypoparathyroidism that is causing low blood calcium, and Fanconi syndrome. Vitamin-D supplements may not be effective in people with severe kidney disease. Excessive doses in humans can result in vomiting, constipation, weakness, and confusion. Other risks include kidney stones. Doses greater than 40,000 IU (1,000 μg) per day are generally required before high blood calcium occurs. Normal doses, 800–2000 IU per day, are safe in pregnancy.

Cholecalciferol was first described in 1936. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 65th most commonly prescribed medication in the United States, with more than 10 million prescriptions. Cholecalciferol is available as a generic medication and over the counter.

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