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22-Oxacalcitriol (CAS 103909-75-7) LS-H72

Vitamin D receptor agonist
LS-H72-500 / 500 µg / $205
LS-H72-1000 / 1000 µg / $245
LS-H72-5000 / 5000 µg / $515
USA Shipment Only
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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. 22-Oxacalcitriol is an analog of calcitriol that, like calcitriol, is a receptor-active form of vitamin D3 which effectively blocks PTH synthesis. First reported to avoid hypercalcemia, an undesirable side effect of calcitriol, prolonged treatment with 22-oxalcalcitriol can be calcemic in humans. Analogs of calcitriol, including 22-oxacalcitriol, inhibit human keratinocyte proliferation while inducing differentiation and is beneficial in treating psoriasis. 22-Oxacalcitriol also blocks the proliferation while inducing differentiation and apoptosis of certain tumor cells. H72_ChemicalStructureImage.png
4-methylene-5Z-[2E-[(3aS)-octahydro-1S-[1S-(3-hydroxy-3-methylbutoxy)ethyl]-7aS-methyl-4H-inden-4-ylidene]ethylidene]-1R,3S-cyclohexanediol
Maxacalcitrol
biochemical, chemical, agonist
LS-H72
103909-75-7
C26H42O4
≥95%
A crystalline solid
 
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=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
DTXXSJZBSTYZKE-ZDQKKZTESA-N
Shipped at 4°C, store at -20°C, ≥ 2 years shelf life.
This product is for research use only. Not for administration to humans, or for human or veterinary diagnostic or therapeutic use.
Data Sheet DataSheet    SDS SDS
Related Products: Vitamin D Receptor / VDR related products

Usage Information

22-Oxacalcitriol is supplied as a crystalline solid. A stock solution may be made by dissolving the 22-oxacalcitriol in the solvent of choice. 22-Oxacalcitriol is soluble in ethanol, which should be purged with an inert gas. The solubility of 22-oxacalcitriol in ethanol is approximately 1 mg/ml. It is slightly soluble in acetone, chloroform, and DMSO and insoluble in water.

References:
  1. Brown, A.J., Dusso, A.S., and Slatopolsky, E. Vitamin D analogues for secondary hyperparathyroidism. Nephrol. Dial. Transplant. 17, 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, 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, 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. (2012).

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