CAS 1434-54-4

Pregnenolone 16α-carbonitrile

Description:

Pregnenolone 16α-carbonitrile is a synthetic derivative of pregnenolone, a steroid hormone precursor. It is characterized by the presence of a cyano group (-CN) at the 16α position of the steroid nucleus, which modifies its biological activity. This compound is primarily studied for its role as a selective modulator of steroid hormone receptors, particularly in the context of neurosteroid research. Pregnenolone 16α-carbonitrile exhibits potential neuroprotective effects and may influence various physiological processes, including mood regulation and cognitive function. Its chemical structure contributes to its lipophilicity, allowing it to cross biological membranes effectively. The compound is often utilized in pharmacological studies to explore its effects on the central nervous system and its potential therapeutic applications in conditions such as anxiety and depression. As with many steroid derivatives, its safety profile and pharmacokinetics are important considerations in research and potential clinical use.

Formula: C₂₂H₃₁NO₂

InChI: 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: InChIKey=VSBHRRMYCDQLJF-ZDNYCOCVSA-N

SMILES: C[C@@]12[C@]([C@]3([C@](CC1)([C@]4(C)C(=CC3)C[C@@H](O)CC4)[H])[H])(C[C@@H](C#N)[C@@H]2C(C)=O)[H]

Synonyms:

• (3Beta,16Alpha)-3-Hydroxy-20-Oxopregn-5-Ene-16-Carbonitrile
• (3β,16α)-3-Hydroxy-20-oxopregn-5-ene-16-carbonitrile
• 16α-Cyanopregnenolone
• 3beta-Hydroxy-20-oxo-5-pregnene-16alpha-carbonitrile
• 3β-Hydroxy-20-oxo-5-pregnen-16α-carbonitrile
• 3β-Hydroxy-20-oxopregn-5-ene-16α-carbonitrile
• Ccris 9224
• Pregn-5-ene-16-carbonitrile, 3-hydroxy-20-oxo-, (3beta,16alpha)-
• Pregn-5-ene-16-carbonitrile, 3-hydroxy-20-oxo-, (3β,16α)-
• Pregn-5-ene-16α-carbonitrile, 3β-hydroxy-20-oxo-
• Pregn-5-ene-3β-ol-20-oxo-16α-carbonitrile
• Pregnenolone 16alpha-carbonitrile
• Pregnenolone 16α-carbonitrile
• Pregnenolone carbonitrile
• Sc 4674

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

CAS: 1434-54-4

Formula: C₂₂H₃₁NO₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 341.4870

Ref: IN-DA007YVI

Pregnenolone Carbonitrile

CAS: 1434-54-4

Pregnenolone Carbonitrile

Purity: ≥98%

Molecular weight: 341.49g/mol

Ref: 54-BUP21658

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

CAS: 1434-54-4

Formula: C₂₂H₃₁NO₂

Molecular weight: 341.49

Ref: 7W-GK4863

Pregnenolone Carbonitrile

CAS: 1434-54-4

Pregnenolone Carbonitrile (5-Pregnen-3β-ol-20-one-16α-carbonitrile) is an activator of rodent-PXR and induces the expression of CYP3A.

Formula: C₂₂H₃₁NO₂

Purity: 99.69%

Color and Shape: Solid

Molecular weight: 341.49

Ref: TM-T21818

Pregnenolone Carbonitrile

Controlled Product

CAS: 1434-54-4

Applications Pregnenolone Carbonitrile is a glucocorticoid receptor antagonist that induces the expression of the CYP3A family of steroid hydroxylases and modulates sterol and bile acid biosynthesis in vivo. Pregnenolone Carbonitrile is an an activator of rat pregnane X receptor (PXR).
References Kliewer, S.A., et. al.: Cell, 92, 73 (1998); Savas, U., et. al.: Drug Metab. Dispos., 28, 529 (2000)

Formula: C₂₂H₃₁NO₂

Color and Shape: Neat

Molecular weight: 341.49

Ref: TR-P712240

Pregnenolone-16alpha-carbonitrile

Controlled Product

CAS: 1434-54-4

Pregnenolone-16alpha-carbonitrile is a synthetic pregnane steroid that is a metabolite of progesterone. It has been shown to be active against liver cells, and has been used as an inhibitor for detoxification enzymes. The reaction mechanism of pregnenolone-16alpha-carbonitrile can be described as follows: the carbonitrile group binds to the active site of cytochrome P450, while the 16α-hydroxyl group binds to the heme moiety in the enzyme. This binding inhibits p450 activity, leading to changes in enzyme activities and energy metabolism. Pregnenolone-16alpha-carbonitrile also has a strong affinity for DNA binding domains, which may lead to transcriptional regulation.

Formula: C₂₂H₃₁NO₂

Purity: Min. 95%

Molecular weight: 341.49 g/mol

Ref: 3D-FP168503