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Maxacalcitol (22-Oxacalcitriol) is a novel analog of calcitriol that doesn't cause hypercalcemia. It can successfully prevent PTH synthesis because it is an agonist of the vitamin D3/2 receptor (VDR). Human orally bioavailable epithelial cells are stimulated to produce hCAP-18/LL-37 by maxacalcitol (OCT). Maxacalcitol Has Cardioprotective Properties in People with Diabetes Mellitus. By attracting PPM1A/VDR complex to pSmad3, maxacalcitol improves tubulointerstitial fibrosis in blocked kidneys.
Physicochemical Properties
| Molecular Formula | C26H42O4 |
| Molecular Weight | 418.61 |
| Exact Mass | 418.308 |
| Elemental Analysis | C, 74.60; H, 10.11; O, 15.29 |
| CAS # | 103909-75-7 |
| Related CAS # | 103909-75-7 |
| PubChem CID | 6398761 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 581.4±50.0 °C at 760 mmHg |
| Flash Point | 305.4±30.1 °C |
| Vapour Pressure | 0.0±3.7 mmHg at 25°C |
| Index of Refraction | 1.549 |
| LogP | 4.38 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 30 |
| Complexity | 691 |
| Defined Atom Stereocenter Count | 6 |
| SMILES | C[C@@H]([C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C)OCCC(C)(C)O |
| InChi Key | DTXXSJZBSTYZKE-ZDQKKZTESA-N |
| 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 |
| Chemical Name | (1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aS)-1-[(1S)-1-(3-hydroxy-3-methylbutoxy)ethyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol |
| Synonyms | OCT; Maxacalcitol; Maxacalcitriol; MC 1275; Prezios; 22-Oxacalcitriol; Sch 209579; 22-Oxa-1,25-dihydroxyvitamin D3; alpha,25-Dihydroxy-22-oxavitamin D3 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.(3). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1]. Inhibitory effects of 22-oxa-calcitriol and all-trans retinoic"nacid on the growth of a canine osteosarcoma derived cell-line in vivo"nand its pulmonary metastasis in vivo. Res.Vet.Sci. (2000)68 79. [2]. 22-Oxacalcitriol suppresses secondary hyperparathyroidism"nwithout inducing low bone turnover in dogs with renal failure. Kidney"nInt. (1999)55 821. [3]. Maxacalcitol ameliorates tubulointerstitial fibrosis in"nobstructed kidneys by recruiting PPM1A/VDR complex to pSmad3.Lab Invest."n2012 Aug 27. [4]. Successful Treatment of Bowen's Disease with Topical Maxacalcitol.Acta Derm Venereol. 2012 Jan 26. [5]. Effects of maxacalcitol ointment on skin lesions in patients with psoriasis receiving treatment with adalimumab. J Dermatol. 2016 Nov;43(11):1354-1357. doi: 10.1111/1346-8138.13515. Epub 2016 Jul 23. PubMed PMID: 27450634. |
| Additional Infomation | Maxacalcitol is an organic molecular entity. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~50 mg/mL (~119.4 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.67 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.67 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 1.67 mg/mL (3.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3889 mL | 11.9443 mL | 23.8886 mL | |
| 5 mM | 0.4778 mL | 2.3889 mL | 4.7777 mL | |
| 10 mM | 0.2389 mL | 1.1944 mL | 2.3889 mL |