LIPID MAPS

Common Name

1alpha,25-dihydroxy-22-oxavitamin D3

Systematic Name

(5Z,7E)-(1S,3R)-22-oxa-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol

Synonyms

1alpha,25-dihydroxy-22-oxacholecalciferol

LM ID

LMST03020060

Formula

C₂₆H₄₂O₄

Exact Mass

Calculate m/z

418.30831

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Category

Main Class

Sub Class

Sterol Lipids [ST]

Secosteroids [ST03]

Vitamin D3 and derivatives [ST0302]

Agonists of the vitamin D receptor are used to suppress parathyroid hormone (PTH) synthesis and secretion in the treatment of hyperparathyroidism associated with renal failure.¹ 22-Oxacalcitriol is an analog of calcitriol that, like calcitriol, is a receptor-active form of vitamin D3 which effectively blocks PTH synthesis.^2,3 First reported to avoid hypercalcemia, an undesirable side effect of calcitriol, prolonged treatment with 22-oxalcalcitriol can be calcemic in humans.^2,3 Analogs of calcitriol, including 22-oxacalcitriol, inhibit human keratinocyte proliferation while inducing differentiation and is beneficial in treating psoriasis.^4,5 22-Oxacalcitriol also blocks the proliferation while inducing differentiation and apoptosis of certain tumor cells.⁶

This information has been provided by Cayman Chemical

References

1. Brown, A.J., Ritter, C.R., Finch, J.L., et al. The noncalcemic analogue of vitamin D, 22-oxacalcitriol, suppresses parathyroid hormone synthesis and secretion. J. Clin. Invest. 84(3), 728-732 (1989).

2. Akizawa, T., Suzuki, M., Akiba, T., et al. Long-term effect of 1,25-dihydroxy-22-oxavitamin D3 on secondary hyperparathyroidism in haemodialysis patients. One-year administration study. Nephrol. Dial. Transplant. 17(Suppl), 28-36 (2002).

3. Seubwai, W., Wongkham, C., Puapairoj, A., et al. 22-Oxa-1,25-dihydroxyvitamin D3 efficiently inhibits tumor growth in inoculated mice and primary histoculture of cholangiocarcinoma. Cancer 116(23), 5535-5543 (2010).

4. Takahashi, H., Ibe, M., Kinouchi, M., et al. Similarly potent action of 1,25-dihydroxyvitamin D3 and its analogues, tacalcitol, calcipotriol, and maxacalcitol on normal human keratinocyte proliferation and differentiation. J. Dermatol. Sci. 31(1), 21-28 (2003).

5. Okubo, Y., Natsume, S., Usui, K., et al. Combination therapy using maxacalcitol and corticosteroid lotions preliminary to monotherapy with maxacalcitol lotion for scalp psoriasis. J. Dermatolog. Treat. 25(1), 34-37 (2012).

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

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic studies of vitamin D analogues. XI. Synthesis and differentiation-inducing activity of 1 alpha,25-dihydroxy-22-oxavitamin D3 analogues.,
Chem Pharm Bull (Tokyo), 1992

Pubmed ID: 1327561

InChiKey (Click to copy)

DTXXSJZBSTYZKE-ZDQKKZTESA-N

InChi (Click to copy)

InChI=1S/C26H42O4/c1-17-20(15-21(27)16-24(17)28)9-8-19-7-6-12-26(5)22(10-11-23(19)26)18(2)30-14-13-25(3,4)29/h8-9,18,21-24,27-29H,1,6-7,10-16H2,2-5H3/b19-8+,20-9-/t18-,21+,22+,23-,24-,26+/m0/s1

SMILES (Click to copy)

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

CHEBI ID

31801

LIPIDBANK ID

VVD0062

PubChem CID

6398761

Cayman ID

10794

PDB ID

MCZ