Inecalcitol | CAS#163217-09-2 | cancer growth inhibitor

MedKoo Cat#: 562897 | Name: Inecalcitol

Description:

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

Inecalcitol is an inhibitor of the growth of human breast cancer cells in vitro and in vivo.

Chemical Structure

Inecalcitol

CAS#163217-09-2

Theoretical Analysis

MedKoo Cat#: 562897

Name: Inecalcitol

CAS#: 163217-09-2

Chemical Formula: C26H40O3

Exact Mass: 400.2977

Molecular Weight: 400.60

Elemental Analysis: C, 77.95; H, 10.06; O, 11.98

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Inecalcitol; TX-522; TX 522; TX522;

IUPAC/Chemical Name

(1R,3R)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(2R)-6-Hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol

InChi Key

HHGRMHMXKPQNGF-WNSNRMDMSA-N

InChi Code

InChI=1S/C26H40O3/c1-18(7-5-13-25(2,3)29)23-11-12-24-20(8-6-14-26(23,24)4)10-9-19-15-21(27)17-22(28)16-19/h9-10,18,21-24,27-29H,6-8,11-12,14-17H2,1-4H3/b20-10+/t18-,21-,22-,23-,24-,26-/m1/s1

SMILES Code

O[C@H]1C[C@H](O)C/C(C1)=C\C=C2[C@@H](CC[C@@H]3[C@H](C)CC#CC(C)(O)C)[C@]3(C)CCC\2

Appearance

Solid powder

Purity

>96% (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 400.60 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

1: Duffy MJ, Murray A, Synnott NC, O'Donovan N, Crown J. Vitamin D analogues: Potential use in cancer treatment. Crit Rev Oncol Hematol. 2017 Apr;112:190-197. doi: 10.1016/j.critrevonc.2017.02.015. Epub 2017 Feb 22. Review. PubMed PMID: 28325259. 2: Murray A, Madden SF, Synnott NC, Klinger R, O'Connor D, O'Donovan N, Gallagher W, Crown J, Duffy MJ. Vitamin D receptor as a target for breast cancer therapy. Endocr Relat Cancer. 2017 Apr;24(4):181-195. doi: 10.1530/ERC-16-0463. Epub 2017 Feb 17. PubMed PMID: 28213567. 3: Suares A, Russo de Boland A, Verstuyf A, Boland R, González-Pardo V. The proapoptotic protein Bim is up regulated by 1α,25-dihydroxyvitamin D3 and its receptor agonist in endothelial cells and transformed by viral GPCR associated to Kaposi sarcoma. Steroids. 2015 Oct;102:85-91. doi: 10.1016/j.steroids.2015.08.005. Epub 2015 Aug 6. PubMed PMID: 26254608. 4: Van Belle TL, Vanherwegen AS, Feyaerts D, De Clercq P, Verstuyf A, Korf H, Gysemans C, Mathieu C. 1,25-Dihydroxyvitamin D3 and its analog TX527 promote a stable regulatory T cell phenotype in T cells from type 1 diabetes patients. PLoS One. 2014 Oct 3;9(10):e109194. doi: 10.1371/journal.pone.0109194. eCollection 2014. PubMed PMID: 25279717; PubMed Central PMCID: PMC4184870. 5: Medioni J, Deplanque G, Ferrero JM, Maurina T, Rodier JM, Raymond E, Allyon J, Maruani G, Houillier P, Mackenzie S, Renaux S, Dufour-Lamartinie JF, Elaidi R, Lerest C, Oudard S. Phase I safety and pharmacodynamic of inecalcitol, a novel VDR agonist with docetaxel in metastatic castration-resistant prostate cancer patients. Clin Cancer Res. 2014 Sep 1;20(17):4471-7. doi: 10.1158/1078-0432.CCR-13-3247. Epub 2014 Jul 10. PubMed PMID: 25013124. 6: Liang C, Li YY. Use of regulators and inhibitors of Pim-1, a serine/threonine kinase, for tumour therapy (review). Mol Med Rep. 2014 Jun;9(6):2051-60. doi: 10.3892/mmr.2014.2139. Epub 2014 Apr 11. Review. PubMed PMID: 24737044. 7: González-Pardo V, Suares A, Verstuyf A, De Clercq P, Boland R, de Boland AR. Cell cycle arrest and apoptosis induced by 1α,25(OH)2D3 and TX 527 in Kaposi sarcoma is VDR dependent. J Steroid Biochem Mol Biol. 2014 Oct;144 Pt A:197-200. doi: 10.1016/j.jsbmb.2013.11.014. Epub 2013 Dec 5. Review. PubMed PMID: 24316429. 8: Ferreira GB, Baeke F, Verstuyf A, De Clercq P, Waelkens E, Mathieu C, Overbergh L. A proteomic approach on the effects of TX527, a 1α,25-dihydroxyvitamin D3 analog, in human T lymphocytes. J Steroid Biochem Mol Biol. 2014 Oct;144 Pt A:96-101. doi: 10.1016/j.jsbmb.2013.10.013. Epub 2013 Oct 28. PubMed PMID: 24176759. 9: González-Pardo V, Verstuyf A, Boland R, Russo de Boland A. Vitamin D analogue TX 527 down-regulates the NF-κB pathway and controls the proliferation of endothelial cells transformed by Kaposi sarcoma herpesvirus. Br J Pharmacol. 2013 Aug;169(7):1635-45. doi: 10.1111/bph.12219. PubMed PMID: 23647513; PubMed Central PMCID: PMC3724118. 10: Ma Y, Yu WD, Hidalgo AA, Luo W, Delansorne R, Johnson CS, Trump DL. Inecalcitol, an analog of 1,25D3, displays enhanced antitumor activity through the induction of apoptosis in a squamous cell carcinoma model system. Cell Cycle. 2013 Mar 1;12(5):743-52. doi: 10.4161/cc.23846. Epub 2013 Feb 6. PubMed PMID: 23388458; PubMed Central PMCID: PMC3610722. 11: Ferreira GB, Overbergh L, Verstuyf A, Mathieu C. 1α,25-Dihydroxyvitamin D3 and its analogs as modulators of human dendritic cells: a comparison dose-titration study. J Steroid Biochem Mol Biol. 2013 Jul;136:160-5. doi: 10.1016/j.jsbmb.2012.10.009. Epub 2012 Oct 23. Review. PubMed PMID: 23098690. 12: Verlinden L, Leyssens C, Beullens I, Marcelis S, Mathieu C, De Clercq P, Verstuyf A. The vitamin D analog TX527 ameliorates disease symptoms in a chemically induced model of inflammatory bowel disease. J Steroid Biochem Mol Biol. 2013 Jul;136:107-11. doi: 10.1016/j.jsbmb.2012.09.017. Epub 2012 Sep 20. PubMed PMID: 23000190. 13: Baeke F, Van Belle TL, Takiishi T, Ding L, Korf H, Laureys J, Gysemans C, Mathieu C. Low doses of anti-CD3, ciclosporin A and the vitamin D analogue, TX527, synergise to delay recurrence of autoimmune diabetes in an islet-transplanted NOD mouse model of diabetes. Diabetologia. 2012 Oct;55(10):2723-2732. doi: 10.1007/s00125-012-2630-1. Epub 2012 Jul 3. PubMed PMID: 22752077. 14: Okamoto R, Delansorne R, Wakimoto N, Doan NB, Akagi T, Shen M, Ho QH, Said JW, Koeffler HP. Inecalcitol, an analog of 1α,25(OH)(2) D(3) , induces growth arrest of androgen-dependent prostate cancer cells. Int J Cancer. 2012 May 15;130(10):2464-73. doi: 10.1002/ijc.26279. Epub 2011 Aug 27. PubMed PMID: 21732345; PubMed Central PMCID: PMC3288172. 15: Baeke F, Korf H, Overbergh L, Verstuyf A, Thorrez L, Van Lommel L, Waer M, Schuit F, Gysemans C, Mathieu C. The vitamin D analog, TX527, promotes a human CD4+CD25highCD127low regulatory T cell profile and induces a migratory signature specific for homing to sites of inflammation. J Immunol. 2011 Jan 1;186(1):132-42. doi: 10.4049/jimmunol.1000695. Epub 2010 Dec 3. PubMed PMID: 21131424. 16: Gonzalez-Pardo V, Martin D, Gutkind JS, Verstuyf A, Bouillon R, de Boland AR, Boland RL. 1 Alpha,25-dihydroxyvitamin D3 and its TX527 analog inhibit the growth of endothelial cells transformed by Kaposi sarcoma-associated herpes virus G protein-coupled receptor in vitro and in vivo. Endocrinology. 2010 Jan;151(1):23-31. doi: 10.1210/en.2009-0650. Epub 2009 Nov 13. PubMed PMID: 19915163. 17: Motrich RD, van Etten E, Depovere J, Riera CM, Rivero VE, Mathieu C. Impact of vitamin D receptor activity on experimental autoimmune prostatitis. J Autoimmun. 2009 Mar;32(2):140-8. doi: 10.1016/j.jaut.2009.02.002. Epub 2009 Mar 9. PubMed PMID: 19269787. 18: Wong MS, Delansorne R, Man RY, Vanhoutte PM. Vitamin D derivatives acutely reduce endothelium-dependent contractions in the aorta of the spontaneously hypertensive rat. Am J Physiol Heart Circ Physiol. 2008 Jul;295(1):H289-96. doi: 10.1152/ajpheart.00116.2008. Epub 2008 May 16. PubMed PMID: 18487433. 19: Stio M, Martinesi M, Bruni S, Treves C, Mathieu C, Verstuyf A, d'Albasio G, Bagnoli S, Bonanomi AG. The Vitamin D analogue TX 527 blocks NF-kappaB activation in peripheral blood mononuclear cells of patients with Crohn's disease. J Steroid Biochem Mol Biol. 2007 Jan;103(1):51-60. Epub 2006 Oct 16. PubMed PMID: 17049230. 20: van Etten E, Decallonne B, Bouillon R, Mathieu C. NOD bone marrow-derived dendritic cells are modulated by analogs of 1,25-dihydroxyvitamin D3. J Steroid Biochem Mol Biol. 2004 May;89-90(1-5):457-9. PubMed PMID: 15225820.