![Tacalcitol [1,24(R)-Dihydroxyvitamin D3]](/upload/0201/CgAH6F3JVJaAXFzMAAAVdQ7SbmE551.png)
| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg | |||
| 25mg | |||
| 50mg | |||
| Other Sizes |
Purity: ≥98%
| Targets |
Vitamin D receptor (VDR). In competitive binding assays using cytosolic extracts of cultured human keratinocytes, the concentration of Tacalcitol required to displace 50% of specific [3H]1,25(OH)2D3 binding was 3×10⁻¹¹ M, compared to 6×10⁻¹¹ M for 1,25(OH)2D3, indicating a slightly higher affinity for the receptor. [6]
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| ln Vitro |
In human nasal polyp fibroblast cultures stimulated with LPS, Tacalcitol at 10⁻⁴ M significantly inhibited IL-6 synthesis (mean 3616.61 pg/ml, p=0.0005) compared to LPS-stimulated control (6120.17 pg/ml), and inhibited IL-8 synthesis (mean 5859.50 pg/ml, p=0.0005) compared to LPS-stimulated control (37786.67 pg/ml). At concentrations of 10⁻⁷, 10⁻⁶, and 10⁻⁵ M, no statistically significant inhibition was observed. In healthy nasal mucosa fibroblasts, Tacalcitol at 10⁻⁴ M also significantly reduced IL-6 (p=0.008) and IL-8 (p=0.001) [3].
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| ln Vivo |
In a 7-year-old Japanese boy with segmental vitiligo on the left eyelid, topical application of Tacalcitol ointment (20 μg/g) once daily to the lesion and surrounding area (including left upper cheek) for 9 months, with sun exposure, resulted in moderate repigmentation at 6 months, but also caused hyperpigmented spots (freckles) on the left cheek to increase in number and intensity, which worsened further by 9 months. Dermoscopy showed irregular borders. The freckling was attributed to Tacalcitol treatment [4].
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| Enzyme Assay |
Competitive binding assay: The cytosolic fraction of cultured human keratinocytes was prepared by homogenization in Tris-HCl buffer (50 mM, pH 7.4) containing 300 mM KCl, 10 mM EDTA, 5 mM dithiothreitol, 10 mM sodium molybdate, and 3 mM phenylmethylsulfonyl fluoride, followed by centrifugation at 105,000×g for 1 h. The supernatant was incubated with 9.8 pg (23.6 fmol, 9200 dpm) of [3H]1,25(OH)2D3 and various concentrations of unlabeled Tacalcitol or 1,25(OH)2D3 for 1 h at 25°C. Specific binding was determined by subtracting non-specific binding from total binding. The amount of [3H]1,25(OH)2D3 specifically bound in the absence of competitor was defined as control binding. The concentration of Tacalcitol required to displace 50% of control binding was 3×10⁻¹¹ M. [6]
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| Cell Assay |
Human nasal polyp fibroblasts (passages 6-9) were cultured in RPMI 1640 medium with 10% fetal bovine serum, penicillin (1000 UI/ml) and streptomycin (10 mg/ml). Cells were seeded at 5000 cells per well in 96-well plates. After 24 hours of incubation, bacterial LPS (E. coli) at 10 ng/ml was added and cultures continued for another 24 hours. Then Tacalcitol at concentrations of 10⁻⁷, 10⁻⁶, 10⁻⁵, and 10⁻⁴ M was added. After 24 hours of treatment, culture supernatants were collected and IL-6 and IL-8 concentrations were measured by ELISA according to the manufacturer's protocols. Absorbance was read at 450 nm. Control groups included cultures stimulated with LPS but not treated with Tacalcitol, and unstimulated cultures without LPS. From the time of LPS stimulation onward, the culture medium did not contain fetal bovine serum [3].
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| Toxicity/Toxicokinetics |
Topical application of Tacalcitol (20 μg/g ointment) once daily for 9 months to the left eyelid and cheek of a 7-year-old boy caused freckling and worsening of existing freckles on the treated area. No inflammation occurred on or around the affected lesion. The effect was attributed to the vitamin D3 analog's ability to influence melanocyte maturation and differentiation and to up-regulate melanogenesis [4].
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| References |
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| Additional Infomation |
Tacalcitol is a hydroxyl-opening sterol, belonging to the calcium alcohol class of compounds, with hydroxyl groups at both the 1S and 24R positions. It is a vitamin D3 analog used to treat adult psoriasis vulgaris, particularly scalp psoriasis. It possesses anti-psoriatic, vitamin D receptor agonist, and antitumor effects. Tacalcitol belongs to the vitamin D3 class of compounds and is a hydroxyl-opening sterol, secondary alcohol, and open-ring cholesterol sterol. Its functions are related to those of calcium alcohol compounds.
Tacalcitol is a vitamin D3 analog used topically for psoriasis and vitiligo. It may promote melanocyte maturation and upregulate melanogenesis. Dermatologists should be aware that topical application of Tacalcitol to the cheeks can cause freckling and worsen existing freckles in predisposed children [4]. In nasal polyp fibroblasts, Tacalcitol shows anti-inflammatory effects by reducing IL-6 and IL-8 at high concentration (10⁻⁴ M) [3]. |
| Molecular Formula |
C27H44O3
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|---|---|
| Molecular Weight |
416.646
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| Exact Mass |
416.329
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| Elemental Analysis |
C, 77.84; H, 10.65; O, 11.52
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| CAS # |
57333-96-7
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| Related CAS # |
Tacalcitol monohydrate;93129-94-3
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| PubChem CID |
5283734
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
565.0±50.0 °C at 760 mmHg
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| Flash Point |
238.4±24.7 °C
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| Vapour Pressure |
0.0±3.5 mmHg at 25°C
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| Index of Refraction |
1.546
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| LogP |
6.12
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
30
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| Complexity |
676
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| Defined Atom Stereocenter Count |
7
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| SMILES |
C=C1[C@H](C[C@@H](C/C1=C/C=C2[C@]3([C@@](C)([C@H](CC3)[C@@H](CC[C@H](C(C)C)O)C)CCC/2)[H])O)O
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| InChi Key |
BJYLYJCXYAMOFT-RSFVBTMBSA-N
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| InChi Code |
InChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25-,26+,27-/m1/s1
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| Chemical Name |
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
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| Synonyms |
PRI2191; TV 02; PRI-2191; TV-02; 1,24(R)-Dihydroxyvitamin D3; 1.alpha.,24R-Dihydroxyvitamin D3; Bonalfa; Curatoderm; PRI 2191; TV02;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO: ≥ 100 mg/mL (~240.0 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (6.60 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 27.5 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: ≥ 2.75 mg/mL (6.60 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 27.5 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. View More
Solubility in Formulation 3: ≥ 2.75 mg/mL (6.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4001 mL | 12.0005 mL | 24.0010 mL | |
| 5 mM | 0.4800 mL | 2.4001 mL | 4.8002 mL | |
| 10 mM | 0.2400 mL | 1.2000 mL | 2.4001 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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