A vitamin D receptor agonist
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Inecalcitol

Item No. 37288

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,3R)-5-[(2E)-2-[(1R,3aR,7aR)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethyl-3-hexyn-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol
CAS Number
163217-09-2
Synonyms
  • TX 522
  • 19-nor-14-epi-23-yne-1,25-dihydroxy Vitamin D3
Molecular Formula
C26H40O3
Formula Weight
400.6
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
245, 252, 262 nm
SMILES
O[C@H](C/1)C[C@H](O)CC1=C/C=C2[C@]3([H])[C@]([C@]([C@@H](CC#CC(C)(O)C)C)([H])CC3)(C)CCC/2
InChi Code
InChI=1S/C26H40O3/c1-18(7-5-13-25(2,3)29)23-11-12-24-20(8-6-14-26(23,24)4)10-9-19-15-21(27)17-22(28)16-19/h9-10,18,21-24,27-29H,6-8,11-12,14-17H2,1-4H3/b20-10+/t18-,21-,22-,23-,24-,26-/m1/s1
InChi Key
HHGRMHMXKPQNGF-WNSNRMDMSA-N
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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    25 mg

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    Cayman Chemical
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    Product Description

    Inecalcitol is a derivative of calcitriol (Item No. 71820) and an agonist of the vitamin D receptor (VDR).1 It induces reporter gene expression in VDR-expressing COS-1 cells when used at a concentration of 1 nM. Inecalcitol induces differentiation of HL-60 leukemia and MG-63 osteosarcoma cells (EC50s = 6.2 and 0.18 nM, respectively) and reduces the proliferation of MCF-7 breast cancer cells (EC50 = 4.1 nM).2 It protects primary human keratinocytes against DNA damage induced by UVB irradiation in a concentration-dependent manner.3 Inecalcitol (100 nM) inhibits acetylcholine- or ATP-induced contractions of aortic rings isolated from spontaneously hypertensive rats.4 Unlike calcitriol, inecalcitol (80 µg/kg) does not increase serum calcium levels or decrease tibia calcium levels in mice.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Eelen, G., Verlinden, L., Rochel, N., et al. Superagonistic action of 14-epi-analogs of 1,25-dihydroxyvitamin D explained by vitamin D receptor-coactivator interaction. Mol. Pharmacol. 67(5), 1566-1573 (2005).

    2. Verlinden, L., Verstuyf, A., Van Camp, M., et al. Two novel 14-epi-analogues of 1,25-dihydroxyvitamin D3 inhibit the growth of human breast cancer cells in vitro and in vivo. Cancer Res. 60(10), 2673-2679 (2000).

    3. De Haes, P., Garmyn, M., Verstuyf, A., et al. 1,25-Dihydroxyvitamin D3 and analogues protect primary human keratinocytes against UVB-induced DNA damage. J. Photochem. Photobiol. B 78(2), 141-148 (2005).

    4. Wong, M.S.K., Delansorne, R., Man, R.Y.K., et al. Vitamin D derivatives acutely reduce endothelium-dependent contractions in the aorta of the spontaneously hypertensive rat. Am. J. Physiol. Heart Circ. Physiol. 295(1), H289-H296 (2008).