WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H315361
CAS#: 54573-75-0
Description: Doxercalciferol, also known as 1-hydroxy Vitamin D2, is a synthetic analog of vitamin D with potential antineoplastic activity. In the liver, doxercalciferol is converted to its biologically active vitamin D metabolites, which control the intestinal absorption of dietary calcium, the tubular reabsorption of calcium by the kidney and, in conjunction with parathyroid hormone (PTH), the mobilization of calcium from the skeleton. Through interaction with specific receptor proteins in target tissues, these vitamin D metabolites act directly on osteoblasts to stimulate skeletal growth, and on the parathyroid glands to suppress PTH synthesis and secretion.
Hodoodo Cat#: H315361
Name: Doxercalciferol
CAS#: 54573-75-0
Chemical Formula: C28H44O2
Exact Mass: 412.33
Molecular Weight: 412.650
Elemental Analysis: C, 81.50; H, 10.75; O, 7.75
Synonym: Doxercalciferol. 1-hydroxy Vitamin D2; Hectorol; 1-Hydroxyergocalciferol; TSA 840.
IUPAC/Chemical Name: (1S,3R,Z)-5-((E)-2-((1S,3aR,7aS)-1-((2S,5S,E)-5,6-dimethylhept-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol.
InChi Key: HKXBNHCUPKIYDM-UHICYICISA-N
InChi Code: InChI=1S/C28H44O2/c1-18(2)19(3)9-10-20(4)25-13-14-26-22(8-7-15-28(25,26)6)11-12-23-16-24(29)17-27(30)21(23)5/h9-12,18-20,24-27,29-30H,5,7-8,13-17H2,1-4,6H3/b10-9+,22-11+,23-12-/t19-,20+,24+,25+,26-,27-,28+/m1/s1
SMILES Code: O[C@@H]1C[C@@H](O)C(/C(C1)=C\C=C2[C@@]3([H])CC[C@@H]([C@H](/C=C/[C@@H](C)C(C)C)C)[C@]3(C)CCC\2)=C
Appearance: White to yellow/brown solid powder.
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO.
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Doxercalciferol is a Vitamin D2 analog, acts as an activator of Vitamin D receptor, and prevents renal disease. |
| In vitro activity: | To further investigate the effects of paricalcitol and doxercalciferol on PTH mRNA expression, primary culture of pig parathyroid cells were treated with different concentrations of paricalcitol or the major active metabolite of doxercalciferol (1α, 25-(OH)2D2, active doxercalciferol). The results from real-time RT-PCR analysis showed that, in a similar manner of paricalcitol, active doxercalciferol suppressed PTH mRNA effectively in a dose-dependent manner achieving a 75% inhibition at 100 nM. Active doxercalciferol did not have a significant effect on VDR mRNA expression. Reference: Int J Endocrinol. 2010;2010:621687. https://pubmed.ncbi.nlm.nih.gov/20204178/ |
| In vivo activity: | WT and Tg mice were subjected to to streptozotocin (STZ) treatment to induce diabetes. At this point the mice were treated with vehicle (V) (60:40 propylene glycol/H2O) or a low dose of vitamin D analog doxercalciferol (Dox) (30 ng/kg, injected intraperitoneally three times per week) for 16 weeks. Vehicle-treated WT mice developed robust progressive albuminuria during the 16 weeks, and the low dose Dox treatment had little effects on the development of albuminuria in WT mice. In contrast, baseline vehicle-treated Tg mice exhibited significantly reduced albuminuria compared with WT+V mice, and the low dose Dox almost completely blocked albuminuria in Tg mice without altering the blood glucose levels and body weight. Reference: J Am Soc Nephrol. 2012 Dec;23(12):1977-86. https://pubmed.ncbi.nlm.nih.gov/23123403/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 66.5 | 161.15 |
The following data is based on the product molecular weight 412.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Duggal J, Harrison JS, Studzinski GP, Wang X. Involvement of microRNA181a in differentiation and cell cycle arrest induced by a plant-derived antioxidant carnosic acid and vitamin D analog doxercalciferol in human leukemia cells. Microrna. 2012;1(1):26-33. doi: 10.2174/2211536611201010026. PMID: 25048087. 2. Wu-Wong JR, Nakane M, Gagne GD, Brooks KA, Noonan WT. Comparison of the pharmacological effects of paricalcitol and doxercalciferol on the factors involved in mineral homeostasis. Int J Endocrinol. 2010;2010:621687. doi: 10.1155/2010/621687. Epub 2010 Mar 2. PMID: 20204178; PMCID: PMC2831199. 3. Li J, Li N, Yan S, Liu M, Sun B, Lu Y, Shao Y. Doxercalciferol Alleviates Bone Deteriorations and Cartilage Degeneration in Aging Mice. Exp Clin Endocrinol Diabetes. 2020 Aug;128(8):540-547. doi: 10.1055/a-0754-1956. Epub 2018 Oct 31. PMID: 30380573. 4. Wang Y, Deb DK, Zhang Z, Sun T, Liu W, Yoon D, Kong J, Chen Y, Chang A, Li YC. Vitamin D receptor signaling in podocytes protects against diabetic nephropathy. J Am Soc Nephrol. 2012 Dec;23(12):1977-86. doi: 10.1681/ASN.2012040383. Epub 2012 Nov 2. PMID: 23123403; PMCID: PMC3507366. |
| In vitro protocol: | 1. Duggal J, Harrison JS, Studzinski GP, Wang X. Involvement of microRNA181a in differentiation and cell cycle arrest induced by a plant-derived antioxidant carnosic acid and vitamin D analog doxercalciferol in human leukemia cells. Microrna. 2012;1(1):26-33. doi: 10.2174/2211536611201010026. PMID: 25048087. 2. Wu-Wong JR, Nakane M, Gagne GD, Brooks KA, Noonan WT. Comparison of the pharmacological effects of paricalcitol and doxercalciferol on the factors involved in mineral homeostasis. Int J Endocrinol. 2010;2010:621687. doi: 10.1155/2010/621687. Epub 2010 Mar 2. PMID: 20204178; PMCID: PMC2831199. |
| In vivo protocol: | 1. Li J, Li N, Yan S, Liu M, Sun B, Lu Y, Shao Y. Doxercalciferol Alleviates Bone Deteriorations and Cartilage Degeneration in Aging Mice. Exp Clin Endocrinol Diabetes. 2020 Aug;128(8):540-547. doi: 10.1055/a-0754-1956. Epub 2018 Oct 31. PMID: 30380573. 2. Wang Y, Deb DK, Zhang Z, Sun T, Liu W, Yoon D, Kong J, Chen Y, Chang A, Li YC. Vitamin D receptor signaling in podocytes protects against diabetic nephropathy. J Am Soc Nephrol. 2012 Dec;23(12):1977-86. doi: 10.1681/ASN.2012040383. Epub 2012 Nov 2. PMID: 23123403; PMCID: PMC3507366. |
1: Wang XX, Jiang T, Shen Y, Santamaria H, Solis N, Arbeeny CM, Levi M. The Vitamin D Receptor Agonist Doxercalciferol Modulates Dietary Fat Induced Renal Disease and Renal Lipid Metabolism. Am J Physiol Renal Physiol. 2011 Jan 5. [Epub ahead of print] PubMed PMID: 21209008.
2: Ritter CS, Brown AJ. Direct Suppression of PTH Gene Expression by the Vitamin D Prohormones Doxercalciferol and Calcidiol Requires the Vitamin D Receptor. J Mol Endocrinol. 2010 Dec 17. [Epub ahead of print] PubMed PMID: 21169421.
3: Ray K. Doxercalciferol is as effective as calcitriol for the treatment of secondary hyperparathyroidism in CKD. Nat Rev Nephrol. 2010 Dec;6(12):692. PubMed PMID: 21155068.
4: Chow EC, Sondervan M, Jin C, Groothuis GM, Pang KS. Comparative effects of doxercalciferol (1α-hydroxyvitamin D(2)) versus calcitriol (1α,25-dihydroxyvitamin D(3)) on the expression of transporters and enzymes in the rat in vivo. J Pharm Sci. 2010 Oct 21. [Epub ahead of print] PubMed PMID: 20967888.
5: Wesseling-Perry K, Pereira RC, Sahney S, Gales B, Wang HJ, Elashoff R, Jüppner H, Salusky IB. Calcitriol and doxercalciferol are equivalent in controlling bone turnover, suppressing parathyroid hormone, and increasing fibroblast growth factor-23 in secondary hyperparathyroidism. Kidney Int. 2011 Jan;79(1):112-9. Epub 2010 Sep 22. PubMed PMID: 20861820.
6: Wu-Wong JR, Nakane M, Gagne GD, Brooks KA, Noonan WT. Comparison of the pharmacological effects of paricalcitol and doxercalciferol on the factors involved in mineral homeostasis. Int J Endocrinol. 2010;2010:621687. Epub 2010 Mar 2. PubMed PMID: 20204178; PubMed Central PMCID: PMC2831199.
7: Moe SM, Saifullah A, LaClair RE, Usman SA, Yu Z. A randomized trial of cholecalciferol versus doxercalciferol for lowering parathyroid hormone in chronic kidney disease. Clin J Am Soc Nephrol. 2010 Feb;5(2):299-306. Epub 2010 Jan 7. PubMed PMID: 20056760; PubMed Central PMCID: PMC2827596.
8: Kubodera N. A new look at the most successful prodrugs for active vitamin D (D hormone): alfacalcidol and doxercalciferol. Molecules. 2009 Sep 29;14(10):3869-80. Review. PubMed PMID: 19924035.
9: Zhang Y, Deb DK, Kong J, Ning G, Wang Y, Li G, Chen Y, Zhang Z, Strugnell S, Sabbagh Y, Arbeeny C, Li YC. Long-term therapeutic effect of vitamin D analog doxercalciferol on diabetic nephropathy: strong synergism with AT1 receptor antagonist. Am J Physiol Renal Physiol. 2009 Sep;297(3):F791-801. Epub 2009 Jun 17. PubMed PMID: 19535571; PubMed Central PMCID: PMC2739712.
10: Fadem SZ, Al-Saghir F, Zollner G, Swan S. Converting hemodialysis patients from intravenous paricalcitol to intravenous doxercalciferol - a dose equivalency and titration study. Clin Nephrol. 2008 Oct;70(4):319-24. PubMed PMID: 18826857.
