Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H42O4 |
Molecular Weight | 418.6093 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)C[C@H](O)C3=C)[C@H](C)OCCC(C)(C)O
InChI
InChIKey=DTXXSJZBSTYZKE-ZDQKKZTESA-N
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12617040 | https://www.chugai-pharm.co.jp/english/news/detail/20081128000000.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/12617040 | https://www.chugai-pharm.co.jp/english/news/detail/20081128000000.html
Maxacalcitol (OXAROL®) is a derivative of vitamin D and is used to treat the secondary hyperparathyroidism of hemodialysis (HD) patients as an injection and psoriasis as an ointment. Secondary hyperparathyroidism is one of the complications in HD patients with hyperplasia of parathyroid glands and elevated serum parathyroid hormone (PTH) levels. Maxacalcitol (OXAROL®) suppresses synthesis and secretion of parathyroid hormone, and decreases a concentration of parathyroid hormone in blood. It also inhibits proliferation and induces differentiation of epidermal keratinocytes. Maxacalcitol (OXAROL®) used in patients with keratosis including psoriasis vulgaris, remarkably improving the symptoms.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1977 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12617040 |
37.9 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | OXAROL Approved UseIt is usually used to treat secondary hyperparathyroidism of the patient on dialysis. |
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Palliative | OXAROL Approved UseTreatment drug for keratosis including psoriasis vulgaris. |
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Palliative | OXAROL Approved UseTreatment of palmoplantar pustulosis. |
PubMed
Title | Date | PubMed |
---|---|---|
Actions of vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3. | 1995 Jan |
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Clinical effects of maxacalcitol on secondary hyperparathyroidism of uremic patients. | 2001 Oct |
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Topical treatment with 22-oxacalcitriol (OCT), a new vitamin D analogue, caused severe hypercalcemia with exacerbation of chronic renal failure in a psoriatic patient with diabetic nephropathy; a case report and analysis of the potential for hypercalcemia. | 2003 Dec |
|
Hypercalcemia caused by vitamin D3 analogs in psoriasis treatment. | 2007 Dec |
Sample Use Guides
Inject Oxarol® at a venous side of dialysis circuit just before the completion of dialysis three times a week.
Appropriate amount of Oxarol® product (ointment, lotion) should be applied to the affected area twice daily.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9099905
To investigate the activation of the vitamin D receptor (VDR) by 20S,24R(OH)2D3 and 20S,24S(OH)2D3 together with their 1a-OH derivatives, two cell lines (HaCaT and Caco-2) were transduced by a lentiviral VDRE luciferase reporter vector. 1,25-(OH)2D3 and 22-oxa-1,25(OH)2D3 (maxacalcitol) were used as positive controls. Both 1,25-(OH)2D3 and maxacalcitol showed the expected strong activations of VDRE in both cell lines, with the EC50 values showing that maxacalcitol (HaCaT EC50=37.9 ± 1.2 nM, Caco-2 EC50=40.8 ± 1.7 nM) is more potent than 1,25(OH)2D3 (HaCaT EC50=321.5 ± 14.2 nM, Caco-2 EC50=515.2 ± 22.4 nM).
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NCI_THESAURUS |
C39713
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103909-75-7
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CHEMBL333950
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100000081726
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C051883
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KK-114
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C143087
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m7098
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ACTIVE MOIETY