An agonist of the vitamin D3 receptor and active metabolite of vitamin D3
Related Products
Labeled Version(s)
22179Calcitriol-d6
Parent Compound(s)
900068325-hydroxy Vitamin D3 11792Vitamin D3
Pro-drug Form(s)
120821-hydroxy Vitamin D3
Technical Support & Resources

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Calcitriol

Item No. 71820

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3S,5Z)-4-methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
CAS Number
32222-06-3
Synonyms
  • 1,25-dihydroxy Cholecalciferol
  • 1α,25-dihydroxy Cholecalciferol
  • 1,25-dihydroxy Vitamin D3
  • 1α,25-dihydroxy Vitamin D3
Molecular Formula
C27H44O3
Formula Weight
416.6
Purity
≥97%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 50 mg/mlEthanol: 1 mg/mlMethanol: 50 mg/ml
λmax
214, 265 nm
SMILES
O[C@@H](C[C@H](O)C/1=C)CC1=C\C=C2[C@@](CC[C@@]3([C@H](C)CCCC(C)(O)C)[H])([H])[C@]3(C)CCC\2
InChi Code
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
InChi Key
GMRQFYUYWCNGIN-NKMMMXOESA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    Product Description

    Calcitriol is a vitamin D3 receptor agonist and active metabolite of vitamin D3 (Item No. 11792).1,2 It is formed via a multi-step process, in which vitamin D3 undergoes hydroxylation to 25-hydroxy vitamin D3 (Item No. 9000683) in the liver, followed by further hydroxylation at the 1α-position in the kidney. Calcitriol binds to the vitamin D3 receptor (Kd = 16 pM) and induces differentiation of U937 acute monocytic leukemia cells (EC50 = 2,000 pM).3 It induces cell cycle arrest at the S phase and apoptosis in primary adenomatous and hyperplastic human parathyroid cells when used at a concentration of 10 nM.4 Calcitriol (0.65 nmol/animal) increases bone calcium mobilization in chicks on a low calcium diet.2 It stimulates calcium absorption in the intestines in a chick model of rickets induced by a vitamin D3-deficient diet when administered at a dose of 25 µg/animal.1 Formulations containing calcitriol have been used in the treatment of hypocalcemia.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lawson, D.E., Fraser, D.R., Kodicek, E., et al. Identification of 1,25-dihydroxycholecalciferol, a new kidney hormone controlling calcium metabolism. Nature 230(5291), 228-230 (1971).

    2. Haussler, M.R., Zerwekh, J.E., Hesse, R.H., et al. Biological activity of 1α-hydroxycholecalciferol, a synthetic analog of the hormonal form of vitamin D3. Proc. Natl. Acad. Sci. USA 70(8), 2248-2252 (1973).

    3. Binderup, L., Latini, S., Binderup, E., et al. 20-epi-vitamin D3 analogues: A novel class of potent regulators of cell growth and immune responses. Biochem. Pharmacol. 42(8), 1569-1575 (1991).

    4. Canalejo, A., Almadén, Y., Torregrosa, V., et al. The in vitro effect of calcitriol on parathyroid cell proliferation and apoptosis. J. Am. Soc. Nephrol. 11(10), 1865-1872 (2000).

    Product Citations

    Ibabao, C.N., Bunaciu, R.P., Schaefer, D.M.W., et al. The AhR agonist VAF347 augments retinoic acid-induced differentiation in leukemia cells. FEBS Open Bio. 5, 308-318 (2015).

    Morelli, S., Salerno, S., Holopainen, J., et al. Osteogenic and osteoclastogenic differentiation of co-cultured cells in polylactic acid-nanohydroxyapatite fiber scaffolds. J. Biotechnol. 204, 53-62 (2015).