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P0543

Sigma-Aldrich

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

≥97%

Synonym(s):

Pregnenolone-16α-carbonitrile

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About This Item

Empirical Formula (Hill Notation):
C22H31NO2
CAS Number:
1434-54-4
Molecular Weight:
341.49
MDL number:
MFCD00272045
UNSPSC Code:
51111800
PubChem Substance ID:
24898113
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

sterility

non-sterile

Assay

≥97%

form

powder, crystals or chunks

technique(s)

cell culture | mammalian: suitable

solubility

chloroform: methanol (1:1): 50 mg/mL, clear, colorless to faintly yellow (with heat)

shipped in

ambient

storage temp.

2-8°C

SMILES string

C[C@@]12[C@](C[C@@H](C#N)[C@@H]2C(C)=O)([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC1

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

Application

5-Pregnen-3β-ol-20-one-16α-carbonitrile has been used:
  • in the induction of cytochrome P450
  • as pregnane X receptor (PXR) activator in human liver cell lines.

Biochem/physiol Actions

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

>199.9 °F - closed cup

Flash Point(C)

> 93.3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gene expression profiling of drug metabolism and toxicology markers using a low-density DNA microarray
de Longueville F, et al.
Biochemical Pharmacology, 64(1), 137-149 (2002)
Afonso C D Bainy et al.
Aquatic toxicology (Amsterdam, Netherlands), 142-143, 447-457 (2013-10-15)
The pregnane X receptor (PXR) (nuclear receptor NR1I2) is a ligand activated transcription factor, mediating responses to diverse xenobiotic and endogenous chemicals. The properties of PXR in fish are not fully understood. Here we report on cloning and characterization of
Nozomu Moriya et al.
Biological & pharmaceutical bulletin, 35(4), 473-480 (2012-04-03)
Infection-associated inflammation can alter the expression levels and functions of cytochrome P450s (CYPs). Cyp gene expression is regulated by the activation of several nuclear receptors, including pregnane X receptor (PXR), constitutive androstane receptor (CAR), and aryl hydrocarbon receptor (AhR). These
Guncha Taneja et al.
Scientific reports, 9(1), 6663-6663 (2019-05-02)
Cytochrome P450 (CYP)3A is the most abundant CYP enzyme in the human liver, and a functional impairment of this enzyme leads to unanticipated adverse reactions and therapeutic failures; these reactions result in the early termination of drug development or the
Yongjie Ma et al.
PloS one, 7(6), e38734-e38734 (2012-06-23)
Pregnane X receptor (PXR) is known to function as a xenobiotic sensor to regulate xenobiotic metabolism through selective transcription of genes responsible for maintaining physiological homeostasis. Here we report that the activation of PXR by pregnenolone 16α-carbonitrile (PCN) in AKR/J
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