Maxacalcitol

Non-calcemic vitamin D3 analog and VDR ligand. CAS# 103909-75-7

Maxacalcitol

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Chemical structure

Maxacalcitol

3D structure

Chemical Properties of Maxacalcitol

Cas No. 103909-75-7 SDF Download SDF
PubChem ID 6398761 Appearance Powder
Formula C26H42O4 M.Wt 418.62
Type of Compound N/A Storage Desiccate at -20°C
Synonyms 22-Oxacalcitriol
Solubility DMSO : 100 mg/mL (238.89 mM; Need ultrasonic)
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
SMILES CC(C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)OCCC(C)(C)O
Standard InChIKey DTXXSJZBSTYZKE-ZDQKKZTESA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Maxacalcitol

DescriptionMaxacalcitol (22-Oxacalcitriol) is non-calcemic analog of vitamin D3 and VDR ligand of VDR-like receptors.

Maxacalcitol Dilution Calculator

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Maxacalcitol Molarity Calculator

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Preparing Stock Solutions of Maxacalcitol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3888 mL 11.944 mL 23.888 mL 47.776 mL 59.72 mL
5 mM 0.4778 mL 2.3888 mL 4.7776 mL 9.5552 mL 11.944 mL
10 mM 0.2389 mL 1.1944 mL 2.3888 mL 4.7776 mL 5.972 mL
50 mM 0.0478 mL 0.2389 mL 0.4778 mL 0.9555 mL 1.1944 mL
100 mM 0.0239 mL 0.1194 mL 0.2389 mL 0.4778 mL 0.5972 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Maxacalcitol

Maxacalcitol (22-oxacalcitriol (OCT)) is an analog of active vitamin D.
In human vascular smooth muscle cells (VSMCs), vehicle-treated VSMCs exhibited massive mineralization, which was inhibited by maxacalcitol in a concentration-dependent manner. [1] In vitro, maxacalcitol and calcitriol markedly inhibited the proliferation and caused a G1 phase cell cycle arrest. In vivo, maxacalcitol suppressed the growth of BxPC-3 xenografts more significantly than calcitriol, and did not inducing hypercalcemia. Responsive cells had many functional vitamin D receptors. [2]
In diabetic rats aged 20 weeks, maxacalcitol reduced albuminuria and mesangial matrix enlargement, with limited differences were observed in blood pressure and creatinine clearance among the 3 treatment groups which were insulin, maxacalcitol, and vehicle groups. Systemic and intrarenal oxidative stress was reduced by maxacalcitol therapy. Maxacalcitol attenuates the progression of diabetic nephropathy by suppression of oxidative stress and amelioration of the Nrf2-Keap1 pathway in nonobese type 2 diabetes without significant changes in blood pressure and glomerular filtration rate. [3]
References:
1.Aoshima Y, Mizobuchi M, Ogata H et al. Vitamin D receptor activators inhibit vascular smooth muscle cell mineralization induced by phosphate and TNF-α. Nephrol Dial Transplant. 2012 May;27(5):1800-6.
2. Kawa S1, Yoshizawa K, Nikaido T et al. Inhibitory effect of 22-oxa-1,25-dihydroxyvitamin D3, maxacalcitol, on the proliferation of pancreatic cancer cell lines. J Steroid Biochem Mol Biol. 2005 Oct;97(1-2):173-7. Epub 2005 Jul 20.
3. Nakai K, Fujii H, Kono K et al. Vitamin D activates the Nrf2-Keap1 antioxidant pathway and ameliorates nephropathy in diabetic rats. Am J Hypertens. 2014 Apr;27(4):586-95. doi: 10.1093/ajh/hpt160. Epub 2013 Sep 11.

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References on Maxacalcitol

The Influence of Maxacalcitol, Vitamin D3 Analog, on Detrusor Overactivity in Conscious Rats.[Pubmed:27018369]

Urology. 2016 Jul;93:224.e7-224.e15.

OBJECTIVES: To test the hypothesis that Maxacalcitol, vitamin D3 analog, would ameliorate detrusor overactivity (DO) induced by retinyl acetate instillation; to test the outcome of the combined administration of Maxacalcitol and the rho kinase inhibitor - GSK 269962, amlodipine besylate, or oxybutynin chloride in this model. METHODS: The rats were treated with Maxacalcitol for 14 days. Then, cystometric studies were performed during which the animals were administered test compounds. RESULTS: Maxacalcitol in a dose of 30 but not 15 microg/kg/day induced reduction in DO index, non-voiding contractions frequency (FNVC), and amplitude (ANVC), while increasing volume threshold to elicit non-voiding contractions (VTNVC). The 14-day-long administration of Maxacalcitol at a dose of 15 microg/kg/day to animals, followed by GSK 269962 at a single dose of 10 mg/kg, led to a statistically significant reduction of intercontraction interval and bladder compliance, and an increase in DO index, without any effect on ANVC, FNVC, and VTNVC. The assessment of the combined effect of Maxacalcitol (15 microg/kg/day) and amlodipine besylate (0.25 mg/kg) demonstrated an increase in intercontraction interval, bladder compliance and VTNVC, with a decrease in FNVC. No statistically significant changes were found in DO index and ANVC. The combined outcome of administering Maxacalcitol (15 microg/kg/day) and oxybutynin chloride (0.25 mg/kg) did not show any statistically significant value of the measured cystometric parameters. CONCLUSION: The outcomes of Maxacalcitol administration can be the result of 3 mechanisms, that is, the upregulation of L-type Ca(2+) channels, the inhibition of the rho kinase pathway, and a so far unknown central mechanism.

Vitamin D3 analog maxacalcitol (OCT) induces hCAP-18/LL-37 production in human oral epithelial cells.[Pubmed:27356607]

Biomed Res. 2016;37(3):199-205.

Maxacalcitol (22-oxacalcitriol: OCT) is a synthetic vitamin D3 analog with a limited calcemic effect. In this study, we investigated whether OCT increases the production of LL-37/CAP-18, a human cathelicidin antimicrobial peptide, in human gingival/oral epithelial cells. A human gingival epithelial cell line (Ca9-22) and human oral epithelial cell lines (HSC-2, HSC-3, and HSC-4) exhibited the enhanced expression of LL-37 mRNA upon stimulation with OCT as well as active metabolites of vitamins D3 and D2. Among the human epithelial cell lines, Ca9-22 exhibited the strongest response to these vitamin D-related compounds. OCT induced the higher production of CAP-18 (ng/mL order) until 6 days time-dependently in Ca9-22 cells in culture. The periodontal pathogen Porphyromonas gingivalis was killed by treatment with the LL-37 peptide. These findings suggest that OCT induces the production of hCAP-18/LL-37 in a manner similar to that induced by the active metabolite of vitamin D3.

Effects of maxacalcitol ointment on skin lesions in patients with psoriasis receiving treatment with adalimumab.[Pubmed:27450634]

J Dermatol. 2016 Nov;43(11):1354-1357.

Adalimumab is a biologic that is very effective for treatment of psoriasis. However, recalcitrant or recurrent lesions sometimes occur during treatment. Maxacalcitol is an active vitamin D3 ointment that is effective in treatment of psoriasis. Topical therapy may be beneficial in treatment of recalcitrant or recurrent lesions during treatment with systemic therapy, but there is little evidence on this topic. We investigated the effect of Maxacalcitol on skin lesions during treatment with adalimumab in patients with psoriasis. Twelve patients with psoriasis were randomly assigned to two groups after informed consent - treatment with adalimumab only (n = 6), and treatment with adalimumab and Maxacalcitol (n = 6) - and they were evaluated every 4 weeks for 44 weeks. Exacerbation was defined as an increase of the Psoriasis Area and Severity Index (PASI) score. The interval between adalimumab treatments was elongated to 3-4 weeks from 2 weeks according to the individual patient's condition. The PASI score was evaluated every 4 weeks, and the frequency of exacerbations was counted. The overall improvement in PASI score was not statistically different between the two groups, but the frequency of exacerbations was significantly less in the Maxacalcitol combination group compared with the adalimumab monotherapy group (Mann-Whitney U-test, P < 0.05). The better control of skin lesions in patients who elongated the interval of adalimumab administration was achieved in the Maxacalcitol combination group compared with the adalimumab monotherapy group. Topical Maxacalcitol treatment is effective and useful in controlling skin lesions in patients with psoriasis when used in combination with adalimumab.

Hypercalcemia in a Dog with Chronic Ingestion of Maxacalcitol Ointment.[Pubmed:27259026]

J Am Anim Hosp Assoc. 2016 Jul-Aug;52(4):256-8.

A miniature dachshund male with severe azotemia of unknown cause was referred. Serum biochemistry revealed severe azotemia and hypercalcemia, but serum intact parathormone and parathormone-related protein were normal. Although the owner reported that the dog had never ingested any drugs or supplements, it was revealed that the owner's son used antipsoriatic ointment, Maxacalcitol, which contained an active vitamin D3 analogue, daily and the dog often ate the son's dander and licked his skin, especially after he applied the Maxacalcitol ointment. After the dog was insulated from the Maxacalcitol ointment and the son as much as possible, the hypercalcemia and azotemia improved gradually and had mostly resolved at 3 mo. The dog has been generally free of clinical signs without any treatment for over 2 yr.

Description

Maxacalcitol (22-Oxacalcitriol) is non-calcemic vitamin D3 analog and ligand of VDR-like receptors.

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