Paricalcitol | CAS#131918-61-1

MedKoo Cat#: 318457 | Name: Paricalcitol

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Description:

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

Paricalcitol, marketed by Abbott Laboratories under the trade name Zemplar, is a drug used for the prevention and treatment of secondary hyperparathyroidism associated with chronic renal failure. It is an analog of 1,25-dihydroxyergocalciferol, the active form of vitamin D2. Paricalcitol binds to the vitamin D receptor and has been shown to reduce parathyroid hormone levels. This agent also increases the expression of PTEN ('Phosphatase and Tensin homolog deleted on chromosome Ten'), a tumor-suppressor gene, in leukemic cells and cyclin-dependent kinase inhibitors.

Chemical Structure

Paricalcitol

CAS#131918-61-1

Theoretical Analysis

MedKoo Cat#: 318457

Name: Paricalcitol

CAS#: 131918-61-1

Chemical Formula: C27H44O3

Exact Mass: 416.3290

Molecular Weight: 416.65

Elemental Analysis: C, 77.83; H, 10.64; O, 11.52

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 450.00	2 Weeks
5mg	USD 1,650.00	2 Weeks

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Related CAS #

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Synonym

Paricalcitol; Zemplar; Compound 49510; 19-Nor-1alpha,25-dihydroxyvitamin D2; Paracalcin; Abbott brand of paricalcitol; paricalcitol; paricalcitol-d6; Zemplar;

IUPAC/Chemical Name

(1R,3R)-5-(2-((1R,3aS,7aR,E)-1-((2R,5S,E)-6-hydroxy-5,6-dimethylhept-3-en-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)cyclohexane-1,3-diol

InChi Key

BPKAHTKRCLCHEA-UBFJEZKGSA-N

InChi Code

InChI=1S/C27H44O3/c1-18(8-9-19(2)26(3,4)30)24-12-13-25-21(7-6-14-27(24,25)5)11-10-20-15-22(28)17-23(29)16-20/h8-11,18-19,22-25,28-30H,6-7,12-17H2,1-5H3/b9-8+,21-11+/t18-,19+,22-,23-,24-,25+,27-/m1/s1

SMILES Code

O[C@@H](C[C@H](O)C/1)CC1=C\C=C2CCC[C@@]3(C)[C@@]/2([H])CC[C@]3([H])[C@H](C)/C=C/[C@H](C)C(C)(O)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, not in water

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Paricalcitol, a vitamin D analogue, is a vitamin D receptor agonist.

In vitro activity:

The present study investigates the differential effect of two vitamin D receptor agonists, calcitriol and paricalcitol, on human aortic smooth muscle cells calcification in vitro. Addition of calcitriol to HP medium (HP + CTR) further increased calcification and also enhanced the expression of osteogenic factors together with a significant elevation of nuclear β-catenin levels and the expression of cyclin D1, axin 2, and VCAN. By contrast, the addition of paricalcitol (HP + PC) not only reduced calcification but also downregulated the expression of BMP2 and other osteoblastic phenotype markers as well as the levels of nuclear β-catenin and the expression of its target genes. Reference: Am J Physiol Renal Physiol. 2012 Oct 15;303(8):F1136-44. https://pubmed.ncbi.nlm.nih.gov/22874762/

In vivo activity:

The fixed aortic constriction caused similar increase in blood pressure, both in untreated and paricalcitol- or losartan-treated mice. Treatment with losartan and paricalcitol reduced fibrosis (paricalcitol 1.6±0.3% and losartan 2.9±0.6%, both p<0.05 vs. TAC). This reduction in fibrosis in paricalcitol treated mice was associated with improved indices of LV contraction and relaxation, e.g. dPdtmax and dPdtmin and lower LV end diastolic pressure, and relaxation constant Tau. Also, treatment with paricalcitol and losartan reduced mRNA expression of ANP, fibronectin, collagen III and TIMP-1. Reference: J Steroid Biochem Mol Biol. 2012 Nov;132(3-5):282-9. https://pubmed.ncbi.nlm.nih.gov/22800987/

	Solvent	mg/mL	mM
Solubility
	DMSO	91.5	219.61
	Ethanol	8.8	21.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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

Formulation protocol:

1. Köksal MM, Şekerler T, Çevik Ö, Şener A. Paricalcitol protects against hydrogen peroxide-induced injury in endothelial cells through suppression of apoptosis. Exp Biol Med (Maywood). 2023 Jan;248(2):186-192. doi: 10.1177/15353702221101615. Epub 2022 Nov 14. PMID: 36373746; PMCID: PMC10041050. 2. Martínez-Moreno JM, Muñoz-Castañeda JR, Herencia C, Oca AM, Estepa JC, Canalejo R, Rodríguez-Ortiz ME, Perez-Martinez P, Aguilera-Tejero E, Canalejo A, Rodríguez M, Almadén Y. In vascular smooth muscle cells paricalcitol prevents phosphate-induced Wnt/β-catenin activation. Am J Physiol Renal Physiol. 2012 Oct 15;303(8):F1136-44. doi: 10.1152/ajprenal.00684.2011. Epub 2012 Aug 8. PMID: 22874762. 3. Halder SK, Sharan C, Al-Hendy O, Al-Hendy A. Paricalcitol, a vitamin d receptor activator, inhibits tumor formation in a murine model of uterine fibroids. Reprod Sci. 2014 Sep;21(9):1108-19. doi: 10.1177/1933719114537721. Epub 2014 Jun 12. PMID: 24925855; PMCID: PMC4212343. 4. Meems LM, Cannon MV, Mahmud H, Voors AA, van Gilst WH, Silljé HH, Ruifrok WP, de Boer RA. The vitamin D receptor activator paricalcitol prevents fibrosis and diastolic dysfunction in a murine model of pressure overload. J Steroid Biochem Mol Biol. 2012 Nov;132(3-5):282-9. doi: 10.1016/j.jsbmb.2012.06.004. Epub 2012 Jul 16. PMID: 22800987.

In vitro protocol:

In vivo protocol:

1. Halder SK, Sharan C, Al-Hendy O, Al-Hendy A. Paricalcitol, a vitamin d receptor activator, inhibits tumor formation in a murine model of uterine fibroids. Reprod Sci. 2014 Sep;21(9):1108-19. doi: 10.1177/1933719114537721. Epub 2014 Jun 12. PMID: 24925855; PMCID: PMC4212343. 2. Meems LM, Cannon MV, Mahmud H, Voors AA, van Gilst WH, Silljé HH, Ruifrok WP, de Boer RA. The vitamin D receptor activator paricalcitol prevents fibrosis and diastolic dysfunction in a murine model of pressure overload. J Steroid Biochem Mol Biol. 2012 Nov;132(3-5):282-9. doi: 10.1016/j.jsbmb.2012.06.004. Epub 2012 Jul 16. PMID: 22800987.

1: Bulut G, Basbugan Y, Ari E, Erten R, Bektas H, Alp HH, Bayram I. Paricalcitol may improve oxidative DNA damage on experimental amikacin-induced nephrotoxicity model. Ren Fail. 2016 Mar 16:1-8. [Epub ahead of print] PubMed PMID: 26983906. 2: Lee AS, Jung YJ, Thanh TN, Lee S, Kim W, Kang KP, Park SK. Paricalcitol attenuates lipopolysaccharide-induced myocardial inflammation by regulating the NF-κB signaling pathway. Int J Mol Med. 2016 Mar 4. doi: 10.3892/ijmm.2016.2516. [Epub ahead of print] PubMed PMID: 26954764; PubMed Central PMCID: PMC4790655. 3: Cai P, Tang X, Qin W, Ji L, Li Z. Comparison between paricalcitol and active non-selective vitamin D receptor activator for secondary hyperparathyroidism in chronic kidney disease: a systematic review and meta-analysis of randomized controlled trials. Int Urol Nephrol. 2016 Apr;48(4):571-84. doi: 10.1007/s11255-015-1195-6. Epub 2016 Jan 9. PubMed PMID: 26748501. 4: Riera M, Anguiano L, Clotet S, Roca-Ho H, Rebull M, Pascual J, Soler MJ. Paricalcitol modulates ACE2 shedding and renal ADAM17 in NOD mice beyond proteinuria. Am J Physiol Renal Physiol. 2016 Mar 15;310(6):F534-46. doi: 10.1152/ajprenal.00082.2015. Epub 2015 Dec 23. PubMed PMID: 26697977. 5: Egido J, Martínez-Castelao A, Bover J, Praga M, Torregrosa JV, Fernández-Giráldez E, Solozábal C. The pleiotropic effects of paricalcitol: Beyond bone-mineral metabolism. Nefrologia. 2016 Jan-Feb;36(1):10-18. doi: 10.1016/j.nefro.2015.11.003. Epub 2015 Dec 23. English, Spanish. PubMed PMID: 26705959. 6: Afsar B, Agca E, Turk S. Comparison of erythropoietin resistance in hemodialysis patients using calcitriol, cinacalcet, or paricalcitol. J Clin Pharmacol. 2015 Nov;55(11):1280-5. doi: 10.1002/jcph.556. Epub 2015 Jul 14. PubMed PMID: 26032009. 7: Ekart R, Bevc S, Hojs R, Hojs N. Proteinuria and albuminuria during and after paricalcitol treatment in chronic kidney disease patients. J Clin Pharmacol. 2015 Oct 14. doi: 10.1002/jcph.660. [Epub ahead of print] PubMed PMID: 26465921. 8: Husain K, Suarez E, Isidro A, Hernandez W, Ferder L. Effect of paricalcitol and enalapril on renal inflammation/oxidative stress in atherosclerosis. World J Biol Chem. 2015 Aug 26;6(3):240-8. doi: 10.4331/wjbc.v6.i3.240. PubMed PMID: 26322179; PubMed Central PMCID: PMC4549765. 9: Dáňová K, Klapetková A, Kayserová J, Šedivá A, Špíšek R, Jelínková LP. NF-κB, p38 MAPK, ERK1/2, mTOR, STAT3 and increased glycolysis regulate stability of paricalcitol/dexamethasone-generated tolerogenic dendritic cells in the inflammatory environment. Oncotarget. 2015 Jun 10;6(16):14123-38. PubMed PMID: 26053099; PubMed Central PMCID: PMC4546455. 10: Ritter CS, Zhang S, Delmez J, Finch JL, Slatopolsky E. Differential expression and regulation of Klotho by paricalcitol in the kidney, parathyroid, and aorta of uremic rats. Kidney Int. 2015 Jun;87(6):1141-52. doi: 10.1038/ki.2015.22. Epub 2015 Feb 18. PubMed PMID: 25692955; PubMed Central PMCID: PMC4449811. 11: Trillini M, Cortinovis M, Ruggenenti P, Reyes Loaeza J, Courville K, Ferrer-Siles C, Prandini S, Gaspari F, Cannata A, Villa A, Perna A, Gotti E, Caruso MR, Martinetti D, Remuzzi G, Perico N. Paricalcitol for secondary hyperparathyroidism in renal transplantation. J Am Soc Nephrol. 2015 May;26(5):1205-14. doi: 10.1681/ASN.2013111185. Epub 2014 Sep 5. PubMed PMID: 25194004; PubMed Central PMCID: PMC4413751. 12: Akizawa T, Akiba T, Hirakata H, Kinugasa E, Tominaga Y, Fukagawa M, Yokoyama K, Zhang W, Linde PG, Suzuki M. Comparison of paricalcitol with maxacalcitol injection in Japanese hemodialysis patients with secondary hyperparathyroidism. Ther Apher Dial. 2015 Jun;19(3):225-34. doi: 10.1111/1744-9987.12242. Epub 2014 Nov 3. PubMed PMID: 25363733. 13: Nuijten M, Roggeri DP, Roggeri A, Novelli P, Marshall TS. Health economic evaluation of paricalcitol(®) versus cinacalcet + calcitriol (oral) in Italy. [corrected]. Clin Drug Investig. 2015 Apr;35(4):229-38. doi: 10.1007/s40261-014-0264-4. Erratum in: Clin Drug Investig. 2015 May;35(5):341. PubMed PMID: 25724153. 14: Thethi TK, Bajwa MA, Ghanim H, Jo C, Weir M, Goldfine AB, Umpierrez G, Desouza C, Dandona P, Fang-Hollingsworth Y, Raghavan V, Fonseca VA. Effect of paricalcitol on endothelial function and inflammation in type 2 diabetes and chronic kidney disease. J Diabetes Complications. 2015 Apr;29(3):433-7. doi: 10.1016/j.jdiacomp.2015.01.004. Epub 2015 Jan 13. PubMed PMID: 25633573; PubMed Central PMCID: PMC4392813. 15: Pisani A, Sabbatini M, Duro G, Colomba P, Riccio E. Antiproteinuric effect of add-on paricalcitol in Fabry disease patients: a prospective observational study. Nephrol Dial Transplant. 2015 Apr;30(4):661-6. doi: 10.1093/ndt/gfu273. Epub 2014 Aug 20. PubMed PMID: 25143556. 16: Nuijten M, Roggeri DP, Roggeri A, Novelli P, Marshall TS. Erratum to: Health Economic Evaluation of Paricalcitol(®) Versus Cinacalcet + Calcitriol (Oral) in Italy. Clin Drug Investig. 2015 May;35(5):341. doi: 10.1007/s40261-015-0284-8. PubMed PMID: 25808395. 17: Hotha KK, Mullangi R, Lakshmanarao Krishnarao R, Roychowdhury S. Sensitive method for the determination of paricalcitol by liquid chromatography and mass spectrometry and its application to a clinical pharmacokinetic study. Biomed Chromatogr. 2015 Mar;29(3):452-8. doi: 10.1002/bmc.3296. Epub 2014 Aug 6. PubMed PMID: 25098404. 18: Martinez-Fernandez I, Saracho R. Effects of paricalcitol on urinary calcium in patients with chronic kidney disease stages 2 - 4. Clin Nephrol. 2015 Apr;83(4):201-7. doi: 10.5414/CN108306. PubMed PMID: 25707454. 19: Diez ER, Altamirano LB, García IM, Mazzei L, Prado NJ, Fornes MW, Carrión FD, Zumino AZ, Ferder L, Manucha W. Heart remodeling and ischemia-reperfusion arrhythmias linked to myocardial vitamin d receptors deficiency in obstructive nephropathy are reversed by paricalcitol. J Cardiovasc Pharmacol Ther. 2015 Mar;20(2):211-20. doi: 10.1177/1074248414538704. Epub 2014 Jun 12. PubMed PMID: 24924917. 20: Stavenuiter AW, Farhat K, Vila Cuenca M, Schilte MN, Keuning ED, Paauw NJ, ter Wee PM, Beelen RH, Vervloet MG. Protective Effects of Paricalcitol on Peritoneal Remodeling during Peritoneal Dialysis. Biomed Res Int. 2015;2015:468574. doi: 10.1155/2015/468574. Epub 2015 Oct 29. PubMed PMID: 26605330; PubMed Central PMCID: PMC4641933.