Calcitriol

Calcitriol
Clinical data
Pronunciation	US: /ˌkælsɪˈtraɪɒl/; ; UK: /kælˈsɪtriɒl/
Trade names	Rocaltrol, Calcijex, Decostriol, others
Other names	1,25-dihydroxycholecalciferol, 1alpha,25-dihydroxyvitamin D3, 1,25-dihydroxyvitamin D3, 1α,25-(OH)2D3, 1,25(OH)2D
AHFS/Drugs.com	Monograph
MedlinePlus	a682335
License data	US DailyMed: Calcitriol;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth, intravenous
ATC code	A11CC04 (WHO) D05AX03 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Protein binding	99.9%
Metabolism	Kidney
Elimination half-life	5–8 hours (adults), 27 hours (children)
Excretion	Faeces (50%), urine (16%)
Identifiers
	IUPAC name (1R,3S)-5-[2-[(1R,3aR,7aS)-1-[(2R)-6-hydroxy-6-methyl-heptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H- inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol;
CAS Number	32222-06-3 ;
PubChem CID	5280453;
IUPHAR/BPS	2779;
DrugBank	DB00136 ;
ChemSpider	4444108 ;
UNII	FXC9231JVH;
KEGG	D00129;
ChEBI	CHEBI:17823 ;
ChEMBL	ChEMBL846 ;
PDB ligand	VDX (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5022722 ;
ECHA InfoCard	100.046.315
Chemical and physical data
Formula	C27H44O3
Molar mass	416.646 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C;
	InChI InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1 ; Key:GMRQFYUYWCNGIN-NKMMMXOESA-N ;
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Calcitriol is the active form of vitamin D, normally made in the kidney. It is also known as 1,25-dihydroxycholecalciferol. It is a hormone which binds to and activates the vitamin D receptor in the nucleus of the cell, which then increases the expression of many genes. Calcitriol increases blood calcium (Ca²⁺) mainly by increasing the uptake of calcium from the intestines.

It can be given as a medication for the treatment of low blood calcium and hyperparathyroidism due to kidney disease, low blood calcium due to hypoparathyroidism, osteoporosis, osteomalacia, and familial hypophosphatemia, and can be taken by mouth or by injection into a vein. Excessive amounts or intake can result in weakness, headache, nausea, constipation, urinary tract infections, and abdominal pain. Serious side effects may include high blood calcium and anaphylaxis. Regular blood tests are recommended after the medication is started and when the dose is changed.

Calcitriol was identified as the active form of vitamin D in 1971 and the drug was approved for medical use in the United States in 1978. It is available as a generic medication. In 2021, it was the 258th most commonly prescribed medication in the United States, with more than 1 million prescriptions. It is on the World Health Organization's List of Essential Medicines.

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