File:Cholecalciferol.svg · Wikimedia Commons · See Wikimedia Commons
cholecalciferol
Sign in to saveAlso known as (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-dimethylhexyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylene-cyclohexan-1-ol, oleovitamin D3, (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol, (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol, (1S,3Z)-3-[(2e)-2-[(1R,3AR,7as)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexan-1-ol, (1S,3Z)-3-{2-[(1R,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol, (5Z,7e)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol, 9,10-secocholesta-5,7,10(19)-trien-3beta-ol
Cholecalciferol, also known as vitamin D3, colecalciferol or calciol, is a skin-made vitamin D that is found in certain foods and used as a dietary supplement. It was first described in 1936, and is on the World Health Organization's List of Essential Medicines. In 2023, it was the 68th most commonly prescribed medication in the United States, with more than 9million prescriptions, and is available as a generic medication.
Key facts
- Drug.INN
- Colecalciferol
- Drug.image
- Cholecalciferol.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Cholecalciferol-vitamin-D3-from-xtal-3D-sticks.png
- Drug.image_class2
- bg-transparent
- Drug.DailyMedID
- Cholecalciferol
- Drug.routes_of_administration
- By mouth, intramuscular
- Drug.ATC_prefix
- A11
- Drug.ATC_suffix
- CC05
- Drug.legal_CA
- Rx-only
- Drug.legal_US
- OTC
- Drug.CAS_number
- 67-97-0
- Drug.PubChem
- 5280795
- Drug.DrugBank
- DB00169
- Drug.ChemSpiderID
- 4444353
- Drug.UNII
- 1C6V77QF41
- Drug.KEGG
- C05443
- Drug.ChEBI
- 28940
via Wikipedia infobox
Chemical data
- Formula
- C27H44O
- Molecular weight
- 384.6 g/mol
- IUPAC name
- (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
- SMILES
- C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
- InChIKey
- QYSXJUFSXHHAJI-YRZJJWOYSA-N
- XLogP
- 7.9
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
32,107 papers- Vitamin D supplementation: cholecalciferol, calcifediol, and calcitriol.European journal of clinical nutrition · 2020
- Cholecalciferol or Calcifediol in the Management of Vitamin D Deficiency.Nutrients · 2020
- Cholecalciferol (D₃) Versus Ergocalciferol (D₂) in Older Adults.The Consultant pharmacist : the journal of the American Society of Consultant Pharmacists · 2017
- [Vitamin D metabolism].Vnitrni lekarstvi · 2012
- Effect of cholecalciferol versus calcifediol on serum 25(OH)D concentrations: a systematic review with meta-analysis.European journal of clinical nutrition · 2025
via PubMed
~13 min read
Encyclopedic overview
13 sectionsContents
- Medical uses
- Vitamin D deficiency
- Other diseases
- Biochemistry
- Structure
- Mechanism of action
- Biosynthesis
- Industrial production
- Stability
- Pesticide
- See also
- References
- External links
Cholecalciferol, also known as vitamin D3, colecalciferol or calciol, is a skin-made vitamin D that is found in certain foods and used as a dietary supplement. It was first described in 1936, and is on the World Health Organization's List of Essential Medicines. In 2023, it was the 68th most commonly prescribed medication in the United States, with more than 9million prescriptions, and is available as a generic medication.
Cholecalciferol is synthesised in the skin following sunlight exposure. It is then converted in the liver to calcifediol (25-hydroxycholecalciferol D), which is further converted in the kidney to calcitriol (1,25-dihydroxycholecalciferol D). One of calcitriol's most important functions is to promote calcium uptake by the intestines. Cholecalciferol is present in food such as fatty fish, beef liver, eggs, and cheese. In some countries, cholecalciferol is also added to products like plants, cow milk, fruit juice, yogurt, and margarine.
Excerpted from Wikipedia’s “cholecalciferol” article, available under the CC BY-SA 4.0 licence.