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P0543 Sigma

5-Pregnen-3β-ol-20-one-16α-carbonitrile

≥97%

Synonym: Pregnenolone-16α-carbonitrile

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Description

Biochem/physiol Actions

Pregnenolone-16α-carbonitrile (PCN) is a glucocorticoid receptor antagonist and a PXR (pregnane X receptor) activator.

Packaging

100, 250 mg in poly bottle

50 mg in glass bottle

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Safety & Documentation

Safety Information

WGK Germany 
3
RTECS 
TU4536500
Flash Point(F) 
>199.4 °F
Flash Point(C) 
>93 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Human pregnane X receptor agonism by Ginkgo biloba extract: assessment of the role of individual ginkgolides. Lau AJ, Yang G, Rajaraman G, et al. J. Pharmacol. Exp. Ther. 335(3), 771-80, (2010)

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PXR prevents cholesterol gallstone disease by regulating biosynthesis and transport of bile salts. He J, Nishida S, Xu M, et al. Gastroenterology 140(7), 2095-106, (2011)

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Assessment of cytochrome P450 fluorometric substrates with rainbow trout and killifish exposed to dexamethasone, pregnenolone-16alpha-carbonitrile, rifampicin, and beta-naphthoflavone. Smith EM, Wilson JY. Aquat. Toxicol. 97, 324-333, (2010)

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Pregnane X receptor as a therapeutic target to inhibit androgen activity. Zhang B, Cheng Q, Ou Z, et al. Endocrinology 151(12), 5721-9, (2010)

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PXR agonism decreases plasma HDL levels in ApoE3-Leiden.CETP mice. de Haan W, de Vries-van der Weij J, Mol IM, et al. Biochim. Biophys. Acta 1791(3), 191-7, (2009)

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Gestational and pregnane X receptor-mediated regulation of placental ATP-binding cassette drug transporters in mice. Gahir SS and Piquette-Miller M Drug Metab. Dispos. 39(3), 465-71, (2011)

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The steroid and xenobiotic receptor negatively regulates B-1 cell development in the fetal liver. Casey SC and Blumberg B Mol. Endocrinol. 26(6), 916-25, (2012)

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[Effect of pravastatin on transportation of scutellarin in mouse liver and its mechanism]. Liu JM and Xiong YQ Yao Xue Xue Bao 46(3), 269-73, (2011)

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Decreased apoptosis during CAR-mediated hepatoprotection against lithocholic acid-induced liver injury in mice. Beilke LD, Aleksunes LM, Olson ER, et al. Toxicol. Lett. 188(1), 38-44, (2009)

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Development of humanized steroid and xenobiotic receptor mouse by homologous knock-in of the human steroid and xenobiotic receptor ligand binding domain sequence. Igarashi K, Kitajima S, Aisaki K, et al. J. Toxicol. Sci. 37(2), 373-80, (2012)

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Regulation of tissue-specific carboxylesterase expression by pregnane x receptor and constitutive androstane receptor. Xu C, Wang X, and Staudinger JL Drug Metab. Dispos. 37(7), 1539-47, (2009)

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Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Argikar UA, Senekeo-Effenberger K, Larson EE, et al. Xenobiotica 39(11), 826-35, (2009)

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The cytochrome P450 2AA gene cluster in zebrafish (Danio rerio): expression of CYP2AA1 and CYP2AA2 and response to phenobarbital-type inducers. Kubota A, Bainy AC, Woodin BR, et al. Toxicol. Appl. Pharmacol. 272(1), 172-9, (2013)

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Cholesterol 25-hydroxylation activity of CYP3A. Honda A, Miyazaki T, Ikegami T, et al. J. Lipid Res. 52(8), 1509-16, (2011)

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Metabolomics reveals a novel vitamin E metabolite and attenuated vitamin E metabolism upon PXR activation. Cho JY, Kang DW, Ma X, et al. J. Lipid Res. 50(5), 924-37, (2009)

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Pregnane X receptor agonists impair postprandial glucose tolerance. Rysä J, Buler M, Savolainen MJ, et al. Clin. Pharmacol. Ther. 93(6), 556-63, (2013)

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Possible protective role of pregnenolone-16 alpha-carbonitrile in lithocholic acid-induced hepatotoxicity through enhanced hepatic lipogenesis. Miyata M, Nomoto M, Sotodate F, et al. Eur. J. Pharmacol. 636(1-3), 145-54, (2010)

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Role of UDP-glucuronosyltransferase (UGT) 2B2 in metabolism of triiodothyronine: effect of microsomal enzyme inducers in Sprague Dawley and UGT2B2-deficient Fischer 344 rats. Richardson TA and Klaassen CD Toxicol. Sci. 116(2), 413-21, (2010)

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Disruption of thyroid hormone homeostasis in Ugt1a-deficient Gunn rats by microsomal enzyme inducers is not due to enhanced thyroxine glucuronidation. Richardson TA and Klaassen CD Toxicol. Appl. Pharmacol. 248(1), 38-44, (2010)

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Activation of pregnane X receptor inhibits experimental dermal fibrosis. Beyer C, Skapenko A, Distler A, et al. Ann. Rheum. Dis. 72(4), 621-5, (2013)

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The nuclear receptors constitutive active/androstane receptor and pregnane x receptor activate the Cyp2c55 gene in mouse liver. Konno Y, Kamino H, Moore R, et al. Drug Metab. Dispos. 38(7), 1177-82, (2010)

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Effect of lipopolysaccharide on the xenobiotic-induced expression and activity of hepatic cytochrome P450 in mice. Moriya N, Kataoka H, Fujino H, et al. Biol. Pharm. Bull. 35(4), 473-80, (2012)

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Organic anion transporting polypeptide 2-mediated uptake of paclitaxel and 2'-ethylcarbonate-linked paclitaxel in freshly isolated rat hepatocytes. Tanino T, Nawa A, Nakao M, et al. J. Pharm. Pharmacol. 61(8), 1029-35, (2009)

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Activation of pregnane X receptor by pregnenolone 16 α-carbonitrile prevents high-fat diet-induced obesity in AKR/J mice. Ma Y and Liu D PLoS ONE 7(6), e38734, (2012)

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A PXR-mediated negative feedback loop attenuates the expression of CYP3A in response to the PXR agonist pregnenalone-16α-carbonitrile. Bailey I, Gibson GG, Plant K, et al. PLoS ONE 6(2), e16703, (2011)

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Effects of pregnenolone-16alpha-carbonitrile on vitamin E status and protein levels of antioxidant enzymes in male rats fed a vitamin E-supplemented diet. Shaw HM and Chen WH Redox Rep. 14(2), 61-8, (2009)

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