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Structure Database (LMSD)

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Common Name

paricalcitol

Systematic Name

(1R,3R,7E)-17β-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-9,10-secoestra-5,7-diene-1,3-diol

Synonyms

19-Nor-1alpha,25-dihydroxyvitamin D2
Paricalcitol

LM ID

LMST04030163

Formula

C₂₇H₄₄O₃

Exact Mass

Calculate m/z

416.329045

Sum Composition

ST 27:2;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Paricalcitol is a synthetic 1,25-dihydroxy vitamin D2 analog. As vitamin D deficiency, associated with chronic kidney disease, leads to an increase in parathyroid hormone (secondary hyperparathyroidism), paricalcitol is used in renal patients to block parathyroid hormone overproduction.^1,2,3 Vitamin D deficiency is also a risk factor in cancer, cardiovascular disease, hypertension, and diabetes, and paricalcitol may have applications in those contexts as well.⁴

This information has been provided by Cayman Chemical

References

1. Walf, M., and Thadhani, R. Vitamin D in patients with renal failure: A summary of observational mortality studies and steps moving forward. J. Steroid Biochem. Mol. Biol. 103(3-5), 487-490 (2007).

2. Duplancic, D., Cesarik, M., Poljak, N.K., et al. The influence of selective vitamin D receptor activator paricalcitol on cardiovascular system and cardiorenal protection. Clin. Interv. Aging 8, 149-156 (2013).

3. Donate-Correa, J., Domínguez-Pimentel, V., Muros-de-Fuentes, M., et al. Beneficial effects of selective vitamin D receptor activation by paricalcitol in chronic kidney disease. Curr. Drug Targets 15(7), 703-709 (2014).

4. Brown, A.J., Finch, J., Takahashi, F., et al. Calcemic activity of 19-nor-1,25(OH)2D2 decreases with duration of treatment. J. Am. Soc. Nephrol. 11(11), 2088-2094 (2000).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

A new analog of calcitriol, 19-nor-1,25-(OH)2D2, suppresses parathyroid hormone secretion in uremic rats in the absence of hypercalcemia.,
Am J Kidney Dis, 1995

Pubmed ID: 7485144

String Representations

InChiKey (Click to copy)

BPKAHTKRCLCHEA-UBFJEZKGSA-N

InChi (Click to copy)

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 (Click to copy)

C1CC/C(=C\C=C2\C[C@H](C[C@H](O)C\2)O)/[C@]2([H])CC[C@]([H])([C@@H](/C=C/[C@H](C)C(O)(C)C)C)[C@]21C