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Calcifediol information


Calcifediol
Skeletal formula of calcifediol
Ball-and-stick model of the calcifediol molecule
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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17933 ☒N
ChEMBL
  • ChEMBL1222 checkY
ChemSpider
  • 4446820 ☒N
DrugBank
  • DB00146 checkY
ECHA InfoCard 100.039.067 Edit this at Wikidata
IUPHAR/BPS
  • 6921
KEGG
  • C01561
MeSH Calcifediol
PubChem CID
  • 5283731
UNII
  • T0WXW8F54E checkY
CompTox Dashboard (EPA)
  • DTXSID0022721 Edit this at Wikidata
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 checkY☒N ?)
Infobox references

Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3),[1] is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase.[3][4][5] Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D.[3][4][5]

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]

  1. ^ a b "IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. Recommendations 1981". European Journal of Biochemistry. 124 (2): 223–7. May 1982. doi:10.1111/j.1432-1033.1982.tb06581.x. PMID 7094913.
  2. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
  3. ^ a b "Vitamin D". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 11 February 2021. Retrieved 14 March 2022.
  4. ^ a b c d "Office of Dietary Supplements - Vitamin D". ods.od.nih.gov. 9 October 2020. Retrieved 31 October 2020.
  5. ^ a b c d Bikle DD (March 2014). "Vitamin D metabolism, mechanism of action, and clinical applications". Chemistry & Biology. 21 (3): 319–29. doi:10.1016/j.chembiol.2013.12.016. PMC 3968073. PMID 24529992.
  6. ^ Quesada-Gomez JM, Bouillon R (August 2018). "Is calcifediol better than cholecalciferol for vitamin D supplementation?". Osteoporosis International (review). 29 (8): 1697–1711. doi:10.1007/s00198-018-4520-y. PMID 29713796. S2CID 14005489.
  7. ^ "Rayaldee (calcifediol) FDA Approval History - Drugs.com". Retrieved 4 March 2021.

and 26 Related for: Calcifediol information

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Calcifediol

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Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the...

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Vitamin D

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in multiple locations. Cholecalciferol is converted in the liver to calcifediol (25-hydroxycholecalciferol); ergocalciferol is converted to 25-hydroxyergocalciferol...

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Cholecalciferol

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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...

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Calcitriol

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enzyme which catalyzes the hydroxylation of 25-hydroxycholecalciferol (calcifediol) in the 1-alpha position. The activity of this enzyme is stimulated by...

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Vitamin D toxicity

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of vitamin D raises plasma calcifediol concentrations which exceed the binding capacity of the DBP, and free calcifediol enters the cell Intake of vitamin...

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Calcium metabolism

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from cholecalciferol to calcifediol in the liver. Under the influence of parathyroid hormone, the kidneys convert calcifediol into the active hormone...

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Hypercalcaemia

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and excessive calcitriol intake. Elevated calcifediol is suggestive of vitamin D or excessive calcifediol intake. The normal range is 2.1–2.6 mmol/L...

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Vitamin D deficiency

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osteoporosis in adults and rickets in children. The serum concentration of calcifediol, also called 25-hydroxyvitamin D (abbreviated 25(OH)D), is typically...

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Bone resorption

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of vitamin D does not linearly correlate to increased serum levels of calcifediol, the precursor to calcitriol. Calcitonin is a hormone secreted by the...

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Androgen

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Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

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ATC code A11

Last Update:

A11CC03 Alfacalcidol A11CC04 Calcitriol A11CC05 Colecalciferol A11CC06 Calcifediol A11CC20 Combinations A11CC55 Colecalciferol, combinations A11DA01 Thiamine...

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Dihydrotestosterone

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Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

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Cortisol

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Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

Word Count : 8516

Secondary hyperparathyroidism

Last Update:

which are either calcium-based and non-calcium based. Extended Release Calcifediol was recently approved by the FDA as a treatment for secondary hyperparathyroidism...

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Vitamin D analogues

Last Update:

Agonists: 7-Dehydrocholesterol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin D3) Dihydrotachysterol...

Word Count : 282

Progesterone

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

Word Count : 11590

Estrogen

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

Word Count : 7781

Corticosteroid

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

Word Count : 4133

Steroid

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

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Glucocorticoid

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

Word Count : 5521

Ergocalciferol

Last Update:

Agonists: 7-Dehydrocholesterol 25-Hydroxyergocalciferol Alfacalcidol Calcifediol Calciferol Calcipotriol Calcitriol Cholecalciferol (vitamin D3) Dihydrotachysterol...

Word Count : 1969

ATC code H05

Last Update:

H05BX02 Paricalcitol H05BX03 Doxercalciferol H05BX04 Etelcalcetide H05BX05 Calcifediol H05BX06 Evocalcet "ATC (Anatomical Therapeutic Chemical Classification...

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Mineralocorticoid

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

Word Count : 723

Cortisone

Last Update:

Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

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Testosterone

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Androsterone Estratetraenol Others Vitamin D: 7-Dehydrocholesterol Calcidiol/Calcifediol Calcitriol Cholecalciferol Others: 7α-Hydroxycholesterol 11α-Hydroxyprogesterone...

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TRPV1

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metabolome such as myrcene activate TRPV1. The vitamin D metabolites calcifediol (25-hydroxy vitamin D or 25OHD) and calcitriol (1,25-hydroxy vitamin...

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