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MedKoo Cat#: 326744 | Name: Ercalcitriol
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Description:

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

Ercalcitriol, also known as RO-17-6218 or 1,25-dihydroxyvitamin D2, is the active circulating metabolite of vitamin D2 formed by 25-hydroxylase in the liver and 25-hydroxyvitamin D-hydroxylase in the kidney. By binding to the vitamin D receptor (VDR), 1,25-dihydroxy Vitamin D2 activates VDR to interact with the retinoid X receptor (RXR), forming the VDR/RXR/cofactor complex, which regulates gene transcription.

Chemical Structure

Ercalcitriol
Ercalcitriol
CAS#60133-18-8

Theoretical Analysis

MedKoo Cat#: 326744

Name: Ercalcitriol

CAS#: 60133-18-8

Chemical Formula: C28H44O3

Exact Mass: 428.3290

Molecular Weight: 428.66

Elemental Analysis: C, 78.46; H, 10.35; O, 11.20

Price and Availability

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1mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
RO-17-6218; RO 17-6218; RO17-6218; Ercalcitriol; 1,25-Dihydroxycalciferol; 1,25-Dihydroxyergocalciferol; 1,25-Dihydroxyvitamin D2.
IUPAC/Chemical Name
(1R,3S,Z)-5-(2-((1R,3aS,7aR,E)-1-((2R,E)-6-hydroxy-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexane-1,3-diol
InChi Key
ZGLHBRQAEXKACO-MIZYFVJYSA-N
InChi Code
InChI=1S/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19?,23-,24-,25+,26+,28-/m1/s1
SMILES Code
O[C@H]1C[C@H](O)C(/C(C1)=C\C=C2[C@]3([H])CC[C@H]([C@H](C)/C=C/C(C)C(C)(O)C)[C@@]3(C)CCC\2)=C
Appearance
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

Preparing Stock Solutions

The following data is based on the product molecular weight 428.66 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.

Recalculate based on batch purity %
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: Fang H, Yu S, Cheng Q, Cheng X, Han J, Qin X, Xia L, Jiang X, Qiu L. Determination of 1,25-dihydroxyvitamin D2 and 1,25-dihydroxyvitamin D3 in human serum using liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Aug 1;1027:19-26. doi: 10.1016/j.jchromb.2016.04.034. Epub 2016 May 12. PubMed PMID: 27240300. 2: Mahlow J, Bunch DR, Wang S. Quantification of 1,25-Dihydroxyvitamin D2 and D3 in Serum Using Liquid Chromatography-Tandem Mass Spectrometry. Methods Mol Biol. 2016;1378:291-300. doi: 10.1007/978-1-4939-3182-8_31. PubMed PMID: 26602141. 3: Hedman CJ, Wiebe DA, Dey S, Plath J, Kemnitz JW, Ziegler TE. Development of a sensitive LC/MS/MS method for vitamin D metabolites: 1,25 Dihydroxyvitamin D2&3 measurement using a novel derivatization agent. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 15;953-954:62-7. doi: 10.1016/j.jchromb.2014.01.045. Epub 2014 Feb 4. PubMed PMID: 24576767; PubMed Central PMCID: PMC4050665. 4: Lawrence JA, Akman SA, Melin SA, Case LD, Schwartz GG. Oral paricalcitol (19-nor-1,25-dihydroxyvitamin D2) in women receiving chemotherapy for metastatic breast cancer: a feasibility trial. Cancer Biol Ther. 2013 Jun;14(6):476-80. doi: 10.4161/cbt.24350. PubMed PMID: 23760489; PubMed Central PMCID: PMC3813563. 5: Biancuzzo RM, Clarke N, Reitz RE, Travison TG, Holick MF. Serum concentrations of 1,25-dihydroxyvitamin D2 and 1,25-dihydroxyvitamin D3 in response to vitamin D2 and vitamin D3 supplementation. J Clin Endocrinol Metab. 2013 Mar;98(3):973-9. doi: 10.1210/jc.2012-2114. Epub 2013 Feb 5. PubMed PMID: 23386645; PubMed Central PMCID: PMC3590486. 6: Sudsakorn S, Phatarphekar A, O'Shea T, Liu H. Determination of 1,25-dihydroxyvitamin D2 in rat serum using liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Jan 15;879(2):139-45. doi: 10.1016/j.jchromb.2010.11.025. Epub 2010 Dec 1. PubMed PMID: 21168373. 7: Sochorová K, Budinský V, Rozková D, Tobiasová Z, Dusilová-Sulková S, Spísek R, Bartůnková J. Paricalcitol (19-nor-1,25-dihydroxyvitamin D2) and calcitriol (1,25-dihydroxyvitamin D3) exert potent immunomodulatory effects on dendritic cells and inhibit induction of antigen-specific T cells. Clin Immunol. 2009 Oct;133(1):69-77. doi: 10.1016/j.clim.2009.06.011. Epub 2009 Aug 5. PubMed PMID: 19660988. 8: Zierold C, Mings JA, Deluca HF. 19nor-1,25-dihydroxyvitamin D2 specifically induces CYP3A9 in rat intestine more strongly than 1,25-dihydroxyvitamin D3 in vivo and in vitro. Mol Pharmacol. 2006 May;69(5):1740-7. Epub 2006 Feb 16. PubMed PMID: 16484501. 9: Kumagai T, O'Kelly J, Said JW, Koeffler HP. Vitamin D2 analog 19-nor-1,25-dihydroxyvitamin D2: antitumor activity against leukemia, myeloma, and colon cancer cells. J Natl Cancer Inst. 2003 Jun 18;95(12):896-905. PubMed PMID: 12813173. 10: Horst RL, Omdahl JA, Reddy S. Rat cytochrome P450C24 (CYP24) does not metabolize 1,25-dihydroxyvitamin D2 to calcitroic acid. J Cell Biochem. 2003 Feb 1;88(2):282-5. PubMed PMID: 12520527. 11: Llach F, Keshav G, Goldblat MV, Lindberg JS, Sadler R, Delmez J, Arruda J, Lau A, Slatopolsky E. Suppression of parathyroid hormone secretion in hemodialysis patients by a novel vitamin D analogue: 19-nor-1,25-dihydroxyvitamin D2. Am J Kidney Dis. 1998 Oct;32(2 Suppl 2):S48-54. PubMed PMID: 9808143. 12: Sato K, Emoto N, Toraya S, Tsushima T, Demura H, Tsuji N, Inaba S, Takeuchi A, Kobayashi T. Progressively increased serum 1,25-dihydroxyvitamin D2 concentration in a hypoparathyroid patient with protracted hypercalcemia due to vitamin D2 intoxication. Endocr J. 1994 Aug;41(4):329-37. PubMed PMID: 8528347. 13: Reinhardt TA, Ramberg CF, Horst RL. Comparison of receptor binding, biological activity, and in vivo tracer kinetics for 1,25-dihydroxyvitamin D3, 1,25-dihydroxyvitamin D2, and its 24 epimer. Arch Biochem Biophys. 1989 Aug 15;273(1):64-71. PubMed PMID: 2547343. 14: DeLuca HF, Sicinski RR, Tanaka Y, Stern PH, Smith CM. Biological activity of 1,25-dihydroxyvitamin D2 and 24-epi-1,25-dihydroxyvitamin D2. Am J Physiol. 1988 Apr;254(4 Pt 1):E402-6. PubMed PMID: 2833108. 15: Reddy GS, Tserng KY. Isolation and identification of 1,24,25-trihydroxyvitamin D2, 1,24,25,28-tetrahydroxyvitamin D2, and 1,24,25,26-tetrahydroxyvitamin D2: new metabolites of 1,25-dihydroxyvitamin D2 produced in rat kidney. Biochemistry. 1986 Sep 9;25(18):5328-36. PubMed PMID: 3490274. 16: Jones G, Baxter LA, DeLuca HF, Schnoes HK. Biological activity of 1,25-dihydroxyvitamin D2 in the chick. Biochemistry. 1976 Feb 10;15(3):713-6. PubMed PMID: 1252421. 17: Jones G, Schnoes HK, DeLuca HF. Isolation and identification of 1,25-dihydroxyvitamin D2. Biochemistry. 1975 Mar 25;14(6):1250-6. PubMed PMID: 1078978.