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Structure Database (LMSD)

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Common Name

1alpha-hydroxyvitamin D3

Systematic Name

(5Z,7E)-(1S,3R)-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol

Synonyms

1alpha-hydroxycholecalciferol

LM ID

LMST03020231

Formula

C₂₇H₄₄O₂

Exact Mass

Calculate m/z

400.33413

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

1-hydroxy Vitamin D3 is a synthetic prodrug which is converted by cytochrome P450 isoforms to the vitamin D receptor agonist 1,25-dihydroxy vitamin D3 in vivo.^1,2 Such prodrugs are effective in suppressing the synthesis and secretion of parathyroid hormone in secondary hyperparathyroidism, an action which requires the vitamin D receptor.^3,2,4 1-hydroxy Vitamin D3 supports bone growth both in postmenopausal women and in glucocorticoid-induced osteoporosis.^5,6 It also provides renal and cardiovascular protection during chronic kidney disease.^7,8

This information has been provided by Cayman Chemical

References

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

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. Gravellone, L., Rizzo, M.A., Martina, V., et al. Vitamin D receptor activators and clinical outcomes in chronic kidney disease. Int. J. Nephrol. 419524 (2011).

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. 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).

6. Jorgensen, H.S., Winther, S., Povlsen, J.V., et al. Effect of vitamin-D analogue on albuminuria in patients with non-dialysed chronic kidney disease stage 4-5: A retrospective single center study. BMC Nephrol. 13(1), (2012).

7. Nuti, R., Bianchi, G., Brandi, M.L., et al. Superiority of alfacalcidol compared to vitamin D plus calcium in lumbar bone mineral density in postmenopausal osteoporosis. Rheumatol. Int. 26, 445-453 (2006).

8. Pereira, R.M.R., de Carvalho, J.F., Paula, A.P., et al. Guidelines for the prevention and treatment of glucocorticoid-induced osteoporosis. Rev. Bras. Reumatol. 52(4), 580-593 (2012).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthesis and biological activity of 1alpha-hydroxyvitamin D3.,
Steroids, 1974

Pubmed ID: 4813304

String Representations

InChiKey (Click to copy)

OFHCOWSQAMBJIW-AVJTYSNKSA-N

InChi (Click to copy)

InChI=1S/C27H44O2/c1-18(2)8-6-9-19(3)24-13-14-25-21(10-7-15-27(24,25)5)11-12-22-16-23(28)17-26(29)20(22)4/h11-12,18-19,23-26,28-29H,4,6-10,13-17H2,1-3,5H3/b21-11+,22-12-/t19-,23-,24-,25+,26+,27-/m1/s1

SMILES (Click to copy)

[C@@H]1(O)C(=C)/C(=C\C=C2\[C@]3([H])CC[C@@]([H])([C@@]3(C)CCC\2)[C@]([H])(C)CCCC(C)C)/C[C@@H](O)C1