Prodrug of vitamin D2
Related Products
Active Metabolite(s)
111741,25-dihydroxy Vitamin D2
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1-hydroxy Vitamin D2

Item No. 12077

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-methylene-5Z-[2E-[(1R,3aS)-octahydro-7aR-methyl-1R-[1R,4,5-trimethyl-2E-hexen-1-yl]-4H-inden-4-ylidene]ethylidene]-1,3S-cyclohexanediol
CAS Number
54573-75-0
Synonyms
  • Doxercalciferol
  • Hectorol
  • 1-Hydroxyergocalciferol
  • TSA 840
Molecular Formula
C28H44O2
Formula Weight
412.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
λmax
211, 265 nm
SMILES
C[C@@]12[C@](CC[C@]2([H])[C@H](C)/C=C/[C@H](C)C(C)C)([H])/C(CCC1)=C/C=C3C[C@@H](O)C[C@H](O)C/3=C
InChi Code
InChI=1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/b10-9+,22-11-,23-12+/t19-,20+,24+,25+,26-,27-,28+/m0/s1
InChi Key
HKXBNHCUPKIYDM-VHKYCACESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $41

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    5 mg

    $157

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    10 mg

    $258

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    Product Description

    1-hydroxy Vitamin D2 is a synthetic prodrug of the active 1,25-dihydroxy vitamin D2 (Item No. 11174), as well as of other active metabolites.1 It is used to suppress the synthesis and secretion of parathyroid hormone in secondary hyperparathyroidism, an action which requires vitamin D receptor.2,3,4 1-hydroxy Vitamin D2 is effective in stimulating bone growth and, in combination therapy with angiotensin receptor blockers, ameliorates albuminuria and glomerulosclerosis associated with diabetic nephropathy.5,6 It also inhibits the growth of certain blastomas and prostate cancer cells.7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Upton, R.A., Knutson, J.C., Bishop, C.W., et al. Pharmacokinetics of doxercalciferol, a new vitamin D analogue that lowers parathyroid hormone. Nephrol. Dial. Transplant 18, 750-758 (2003).

    2. Frazao, J.M., Chesney, R.W., Coburn, J.W., et al. Intermittent oral 1α-hydroxyvitamin D2 is effective and safe for the suppression of secondary hyperparathyroidism in haemodialysis patients. Nephrol. Dial. Transplant 13, 68-72 (1998).

    3. Brown, A.J., Dusso, A.S., and Slatopolsky, E. Vitamin D analogues for secondary hyperparathyroidism. Nephrol. Dial. Transplant. 17(Suppl), 10-19 (2002).

    4. Ritter, C.S., and Brown, A.J. Direct suppression of Pth gene expression by the vitamin D prohormones doxercalciferol and calcidiol requires the vitamin D receptor. J. Mol. Endocrinol. 46(2), 63-66 (2011).

    5. Nguyen-Yamamoto, L., Bolivar, I., Strugnell, S.A., et al. Comparison of active vitamin D compounds and a calcimimetic in mineral homeostasis. J. Am. Soc. Nephrol. 21, 1713-1723 (2010).

    6. Zhang, Y., Deb, D.K., Kong, J., et al. Long-term therapeutic effect of vitamin D analog doxercalciferol on diabetic nephropathy: Strong synergism with AT1 receptor antagonist. Am. J. Physiol. Renal Physiol. 297, F791-F801 (2009).

    7. van Ginkel, P.R., Yang, W., Marcet, M.M., et al. 1α-Hydroxyvitamin D2 inhibits growth of human neuroblastoma. J. Neurooncol. 85, 255-262 (2007).

    8. Attia, S., Eickhoff, J., Wilding, G., et al. Randomized, double-blinded phase II evaluation of docetaxel with or without doxercalciferol in patients with metastatic, androgen-independent prostate cancer. Clin. Cancer Res. 14(8), 2437-2443 (2008).