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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

Related Categories

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ0752
MKCL5756
MKCK4128
MKBZ9946V
MKBX1531V

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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
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
Katie B Paul et al.
Toxicology, 300(1-2), 31-45 (2012-06-05)
This work tests the mode-of-action (MOA) hypothesis that maternal and developmental triclosan (TCS) exposure decreases circulating thyroxine (T4) concentrations via up-regulation of hepatic catabolism and elimination of T4. Time-pregnant Long-Evans rats received TCS po (0-300mg/kg/day) from gestational day (GD) 6
Jian-Ming Liu et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 46(3), 269-273 (2011-06-02)
This study is to investigate the transportation of scutellarin in cell and live models and study on mechanism of absorption and transport of scutellarin in mouse liver. The concentration of scutellarin in plasma and liver from control and pretreated groups
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
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