An analog of calcitriol
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22-Oxacalcitriol

Item No. 10794

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-methylene-5Z-[2E-[(3aS)-octahydro-1S-[1S-(3-hydroxy-3-methylbutoxy)ethyl]-7aS-methyl-4H-inden-4-ylidene]ethylidene]-1R,3S-cyclohexanediol
CAS Number
103909-75-7
Synonyms
  • Maxacalcitrol
Molecular Formula
C26H42O4
Formula Weight
418.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Ethanol: 1 mg/ml
λmax
211, 264 nm
SMILES
O[C@@H](C[C@H](O)C/1=C)CC1=C\C=C2[C@@](CC[C@]3([H])[C@H](C)OCCC(C)(C)O)([H])[C@]3(C)CCC\2
InChi Code
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
InChi Key
DTXXSJZBSTYZKE-ZDQKKZTESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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. 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).

    3. 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).

    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. 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).