A rodent PXR agonist
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Pregnenolone Carbonitrile

Item No. 16343

Technical Information
Formal Name
3β-hydroxy-20-oxo-pregn-5-ene-16α-carbonitrile
CAS Number
1434-54-4
Synonyms
  • PCN
  • Pregnenolone 16α-carbonitrile
  • SC-4674
Molecular Formula
C22H31NO2
Formula Weight
Purity
≥97%
Formulation
A crystalline solid
Acetonitrile: 1 mg/mlEthanol: 1 mg/mlMethanol: 1 mg/ml
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])C[C@@H](C#N)[C@@H]4C(C)=O
InChi Code
InChI=1S/C22H31NO2/c1-13(24)20-14(12-23)10-19-17-5-4-15-11-16(25)6-8-21(15,2)18(17)7-9-22(19,20)3/h4,14,16-20,25H,5-11H2,1-3H3/t14-,16-,17+,18-,19-,20-,21-,22-/m0/s1
InChi Key
VSBHRRMYCDQLJF-ZDNYCOCVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Pregnenolone carbonitrile (PCN) is a catatoxic steroid that acts as an agonist of the rodent pregnane X receptor (PXR) at µM concentrations.1,2,3 It has been shown to mediate induction of hepatic cytochrome P450 3A, organic anion transporting peptide-2, and cholesterol 7α-hydroxylase, regulating both xenobiotic and bile acid homeostasis by enhancing hepatic uptake and biliary excretion.2,3,4 Activation of PXR by 50 mg/kg PCN administered to obesity-prone AKR/J mice has been reported to attenuate the development of high-fat diet-induced obesity and insulin resistance.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kliewer, S.A., Moore, J.T., Wade, L., et alAn orphan nuclear receptor activated by pregnanes defines a novel steroid signaling pathway. Cell 92(1), 73-82 (1998).

    2. Staudinger, J., Liu, Y., Madan, A., et alCoordinate regulation of xenobiotic and bile acid homeostasis by pregnane X receptor. Drug Metab. Dispos. 29(11), 1467-1472 (2001).

    3. Lehmann, J.M., McKee, D.D., Watson, M.A., et alThe human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions. J. Clin. Invest. 102(5), 1016-1123 (1998).

    4. Elshourbagy, N.A., Barwick, J.L., and Guzelian, P.S. Induction of cytochrome P-450 by pregnenolone-16α-carbonitrile in primary monolayer cultures of adult rat hepatocytes and in a cell-free translation system. The Journal of Biological Chemisty 256(12), 6060-6068 (1981).

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