Tacalcitol
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526201

CAS#: 57333-96-7

Description: Tacalcitol is a D3 derivative, promoting normal bone development, modulating immunological and inflammatory processes, inducing nerve growth factor production in epidermal keratinocytes.


Price and Availability

Size
Price

1mg
USD 275
Size
Price

5mg
USD 1250
Size
Price

Tacalcitol, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526201
Name: Tacalcitol
CAS#: 57333-96-7
Chemical Formula: C27H44O3
Exact Mass: 416.329
Molecular Weight: 416.646
Elemental Analysis: C, 77.84; H, 10.65; O, 11.52


Synonym: Tacalcitol

IUPAC/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

InChi Key: BJYLYJCXYAMOFT-RSFVBTMBSA-N

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

SMILES Code: C=C1[C@@H](O)C[C@H](O)C/C1=C/C=C2[C@H]3[C@]([C@@H]([C@H](C)CC[C@@H](O)C(C)C)CC3)(C)CCC/2


Technical Data

Appearance:
White to off-white 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).

Harmonized System Code:
293490


References

1: Merrigan SL, Kennedy BN. Vitamin D Receptor Agonists Regulate Ocular Developmental Angiogenesis and Modulate Expression of dre-miR-21 and VEGF. Br J Pharmacol. 2017 May 26. doi: 10.1111/bph.13875. [Epub ahead of print] PubMed PMID: 28547797.

2: Li QL, Wu YH, Niu M, Lu XJ, Huang YH, He DH. Protective effects of tacalcitol against oxidative damage in human epidermal melanocytes. Int J Dermatol. 2017 Feb;56(2):232-238. doi: 10.1111/ijd.13407. PubMed PMID: 28074522.

3: Usui K, Okubo Y, Hirano T, Tsuboi R. Vitamin D3 derivatives, alone or in combination with glucocorticoids, suppress streptococcal pyrogenic enterotoxin A-stimulated proliferation of peripheral blood mononuclear cells in patients with psoriasis. J Dermatol. 2017 May;44(5):567-572. doi: 10.1111/1346-8138.13679. Epub 2016 Dec 24. PubMed PMID: 28012189.

4: Li R, Qiao M, Wang X, Zhao X, Sun Q. Effect of narrow band ultraviolet B phototherapy as monotherapy or combination therapy for vitiligo: a meta-analysis. Photodermatol Photoimmunol Photomed. 2017 Jan;33(1):22-31. doi: 10.1111/phpp.12277. Epub 2016 Nov 23. Review. PubMed PMID: 27696531.

5: Sahu P, Jain VK, Aggarwal K, Kaur S, Dayal S. Tacalcitol: a useful adjunct to narrow-band ultraviolet-B phototherapy in vitiligo. Photodermatol Photoimmunol Photomed. 2016 Sep;32(5-6):262-268. doi: 10.1111/phpp.12265. Epub 2016 Sep 12. PubMed PMID: 27552149.

6: Hosomi A, Hirabe M, Tokuda T, Nakamura H, Amano T, Okamoto T. Calcium effects and systemic exposure of vitamin D3 analogues after topical treatment of active vitamin D3-containing ointments in rats. Eur J Pharmacol. 2016 Oct 5;788:98-103. doi: 10.1016/j.ejphar.2016.06.028. Epub 2016 Jun 16. PubMed PMID: 27321871.

7: Aggarwal P, Aggarwal K, Jain VK. Tacalcitol: A useful adjunct to narrow band ultraviolet B phototherapy in psoriasis. J Dermatolog Treat. 2016 Nov;27(6):546-551. Epub 2016 Apr 7. PubMed PMID: 27052200.

8: Almokhtar M, Wikvall K, Ubhayasekera SJ, Bergquist J, Norlin M. Motor neuron-like NSC-34 cells as a new model for the study of vitamin D metabolism in the brain. J Steroid Biochem Mol Biol. 2016 Apr;158:178-88. doi: 10.1016/j.jsbmb.2015.12.010. Epub 2015 Dec 15. PubMed PMID: 26704532.

9: Kotlarz A, Przybyszewska M, Swoboda P, Miłoszewska J, Grygorowicz MA, Kutner A, Markowicz S. Differential interference of vitamin D analogs PRI-1906, PRI-2191, and PRI-2205 with the renewal of human colon cancer cells refractory to treatment with 5-fluorouracil. Tumour Biol. 2016 Apr;37(4):4699-709. doi: 10.1007/s13277-015-4311-4. Epub 2015 Oct 28. PubMed PMID: 26511971.

10: Wang LF, Tai CF, Chien CY, Chiang FY, Chen JY. Vitamin D decreases the secretion of matrix metalloproteinase-2 and matrix metalloproteinase-9 in fibroblasts derived from Taiwanese patients with chronic rhinosinusitis with nasal polyposis. Kaohsiung J Med Sci. 2015 May;31(5):235-40. doi: 10.1016/j.kjms.2015.02.001. Epub 2015 Mar 6. PubMed PMID: 25910558.

11: Wang LF, Chien CY, Tai CF, Chiang FY, Chen JY. Vitamin D decreases the secretion of eotaxin and RANTES in nasal polyp fibroblasts derived from Taiwanese patients with chronic rhinosinusitis with nasal polyps. Kaohsiung J Med Sci. 2015 Feb;31(2):63-9. doi: 10.1016/j.kjms.2014.11.011. Epub 2014 Dec 17. PubMed PMID: 25645983.

12: Fujishima T, Suenaga T, Nozaki T. Synthetic strategy and biological activity of A-ring stereoisomers of 1,25- dihydroxyvitamin D3 and C2-modified analogues. Curr Top Med Chem. 2014;14(21):2446-53. Review. PubMed PMID: 25486939.

13: Salomón DG, Mascaro E, Grioli SM, Ferronato MJ, Vitale CA, Radivoy GE, Curino AC, Facchinetti MM. Phosphonate analogues of 1α, 25 dihydroxyvitamin D3 are promising candidates for antitumoural therapies. Curr Top Med Chem. 2014;14(21):2408-23. Review. PubMed PMID: 25486937.

14: Jabbar-Lopez ZK, Wu KC, Reynolds NJ. Newer agents for psoriasis in adults. BMJ. 2014 Jul 9;349:g4026. doi: 10.1136/bmj.g4026. Review. PubMed PMID: 25008099.

15: Milczarek M, Filip-Psurska B, Swiętnicki W, Kutner A, Wietrzyk J. Vitamin D analogs combined with 5-fluorouracil in human HT-29 colon cancer treatment. Oncol Rep. 2014 Aug;32(2):491-504. doi: 10.3892/or.2014.3247. Epub 2014 Jun 11. PubMed PMID: 24919507; PubMed Central PMCID: PMC4091879.

16: Escribano-Stablé JC, Doménech C, Matarredona J, Pascual JC, Jaen A, Vicente J. Tacalcitol in the treatment of acquired perforating collagenosis. Case Rep Dermatol. 2014 Feb 27;6(1):69-73. doi: 10.1159/000360390. eCollection 2014 Jan. PubMed PMID: 24707254; PubMed Central PMCID: PMC3975195.

17: Kragballe K, van de Kerkhof P. Pooled safety analysis of calcipotriol plus betamethasone dipropionate gel for the treatment of psoriasis on the body and scalp. J Eur Acad Dermatol Venereol. 2014 May;28 Suppl 2:10-21. doi: 10.1111/jdv.12444. PubMed PMID: 24684739.

18: Voisset C, García-Rodríguez N, Birkmire A, Blondel M, Wellinger RE. Using yeast to model calcium-related diseases: example of the Hailey-Hailey disease. Biochim Biophys Acta. 2014 Oct;1843(10):2315-21. doi: 10.1016/j.bbamcr.2014.02.011. Epub 2014 Feb 25. Review. PubMed PMID: 24583118.

19: Neri L, Vena GA, Cassano N. Prescription size and adherence in the management of psoriasis: is the more, the better? G Ital Dermatol Venereol. 2014 Feb;149(1):152-3. PubMed PMID: 24566578.

20: Milczarek M, Chodyński M, Filip-Psurska B, Martowicz A, Krupa M, Krajewski K, Kutner A, Wietrzyk J. Synthesis and Biological Activity of Diastereomeric and Geometric Analogs of Calcipotriol, PRI-2202 and PRI-2205, Against Human HL-60 Leukemia and MCF-7 Breast Cancer Cells. Cancers (Basel). 2013 Oct 31;5(4):1355-78. doi: 10.3390/cancers5041355. PubMed PMID: 24202449; PubMed Central PMCID: PMC3875943.