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
Identifiers
CAS Number	19356-17-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17933 ;
ChEMBL	ChEMBL1222 ;
ChemSpider	4446820 ;
DrugBank	DB00146 ;
ECHA InfoCard	100.039.067
IUPHAR/BPS	6921;
KEGG	C01561;
MeSH	Calcifediol
PubChem CID	5283731;
UNII	T0WXW8F54E ;
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 Key: JWUBBDSIWDLEOM-DTOXIADCSA-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;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

^ ^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.
^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
^ ^a ^b "Vitamin D". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 11 February 2021. Retrieved 14 March 2022.
^ ^a ^b ^c ^d "Office of Dietary Supplements - Vitamin D". ods.od.nih.gov. 9 October 2020. Retrieved 31 October 2020.
^ ^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.
^ 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.
^ "Rayaldee (calcifediol) FDA Approval History - Drugs.com". Retrieved 4 March 2021.

[nomen-d-1] "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.

[lpi-3] "Vitamin D". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 11 February 2021. Retrieved 14 March 2022.

[NIH-ODS-2020-4] "Office of Dietary Supplements - Vitamin D". ods.od.nih.gov. 9 October 2020. Retrieved 31 October 2020.

[Bikle2014-5] 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.

[pmid29713796-6] 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.

[RayaldeeFDA-7] "Rayaldee (calcifediol) FDA Approval History - Drugs.com". Retrieved 4 March 2021.

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