Tacalcitol | CAS#57333-96-7 | Vitamin D3 Derivative

MedKoo Cat#: 526201 | Name: Tacalcitol

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Description:

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

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

Chemical Structure

Tacalcitol

CAS#57333-96-7 (free)

Theoretical Analysis

MedKoo Cat#: 526201

Name: Tacalcitol

CAS#: 57333-96-7 (free)

Chemical Formula: C27H44O3

Exact Mass: 416.3290

Molecular Weight: 416.65

Elemental Analysis: C, 77.84; H, 10.65; O, 11.52

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00
5mg	USD 1,050.00
50mg	USD 6,250.00

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Related CAS #

93129-94-3 (hydrate) 57333-96-7 (free)

Synonym

Tacalcitol; Bonalfa; Curatoderm; PRI 2191; PRI-2191; PRI2191; TV 02; TV-02; TV02;

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

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).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 416.65 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

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Effects of 1α,25-dihydroxyvitamin D3 and tacalcitol on cell signaling and anchorage-independent growth in T98G and U251 glioblastoma cells. Biochem Biophys Rep. 2022 Jul 31;31:101313. doi: 10.1016/j.bbrep.2022.101313. PMID: 35935021; PMCID: PMC9352528. 8: Gleba JJ, Kłopotowska D, Banach J, Mielko KA, Turlej E, Maciejewska M, Kutner A, Wietrzyk J. Micro-RNAs in Response to Active Forms of Vitamin D3 in Human Leukemia and Lymphoma Cells. Int J Mol Sci. 2022 Apr 30;23(9):5019. doi: 10.3390/ijms23095019. PMID: 35563410; PMCID: PMC9104187. 9: Liu X, Yao Z, Wang Y, Chai L, Zhou X. Vitamin D analogs combined with different types of phototherapy in the treatment of vitiligo: A systematic review of randomized trials and within-patient studies. Int Immunopharmacol. 2022 Aug;109:108789. doi: 10.1016/j.intimp.2022.108789. Epub 2022 Apr 22. PMID: 35468365. 10: Turlej E, Goszczyński TM, Drab M, Orzechowska B, Maciejewska M, Banach J, Wietrzyk J. The Impact of Exosomes/Microvesicles Derived from Myeloid Dendritic Cells Cultured in the Presence of Calcitriol and Tacalcitol on Acute B-Cell Precursor Cell Lines with MLL Fusion Gene. J Clin Med. 2022 Apr 15;11(8):2224. doi: 10.3390/jcm11082224. PMID: 35456315; PMCID: PMC9032710. 11: Gleba JJ, Kłopotowska D, Banach J, Turlej E, Mielko KA, Gębura K, Bogunia- Kubik K, Kutner A, Wietrzyk J. Polymorphism of VDR Gene and the Sensitivity of Human Leukemia and Lymphoma Cells to Active Forms of Vitamin D. Cancers (Basel). 2022 Jan 13;14(2):387. doi: 10.3390/cancers14020387. PMID: 35053549; PMCID: PMC8774213. 12: Hanna N, Lam M, Fleming P, Lynde CW. Therapeutic Options for the Treatment of Darier's Disease: A Comprehensive Review of the Literature. J Cutan Med Surg. 2022 May-Jun;26(3):280-290. doi: 10.1177/12034754211058405. Epub 2021 Nov 28. PMID: 34841914; PMCID: PMC9125141. 13: Rizzo A, Tognetti L, Rubegni P, Cinotti E. Acanthosis nigricans monstre successfully treated with topical tacalcitol, metformin, and oral contraceptives. Dermatol Ther. 2020 Jul;33(4):e13660. doi: 10.1111/dth.13660. Epub 2020 Jun 24. PMID: 32447791. 14: Borgia F, Riso G, Catalano F, Coppola M, Giuffrida R, Cannavò SP. Topical tacalcitol as neoadjuvant for photodynamic therapy of acral actinic keratoses: An intra-patient randomized study. Photodiagnosis Photodyn Ther. 2020 Sep;31:101803. doi: 10.1016/j.pdpdt.2020.101803. Epub 2020 May 8. PMID: 32389738. 15: Pawlik A, Anisiewicz A, Filip-Psurska B, Klopotowska D, Maciejewska M, Mazur A, Wietrzyk J. Divergent Effect of Tacalcitol (PRI-2191) on Th17 Cells in 4T1 Tumor Bearing Young and Old Ovariectomized Mice. Aging Dis. 2020 Mar 9;11(2):241-253. doi: 10.14336/AD.2019.0618. PMID: 32257539; PMCID: PMC7069462. 16: Klopotowska D, Matuszyk J. VDR Agonists Increase Sensitivity of MCF-7 and BT-474 Breast Cancer Cells to 5 FU. 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PMID: 30503385. 20: Cinotti E, Provvidenziale L, Miracco C, Rubegni P. Treatment of nevoid hyperkeratosis of the areola and nipple with topical tacalcitol: A case report. Dermatol Ther. 2018 Jul;31(4):e12602. doi: 10.1111/dth.12602. Epub 2018 Apr 6. PMID: 29624812.