154229-26-2

Basic information

• Product Name: (5α)-17-(3-Pyridinyl)androst-16-en-3-one
• Synonyms: (5α)-17-(3-Pyridinyl)androst-16-en-3-one;Abiraterone Related Compound 9 (5-alpha-17-(3-Pyridyl)-16-androstene-3-one)
• CAS NO: 154229-26-2
• Molecular Formula: C24H31NO
• Molecular Weight: 349.50904
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 154229-26-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 486.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.094±0.06 g/cm3(Predicted)
• PKA: 5.32±0.12(Predicted)
• CAS DataBase Reference: (5α)-17-(3-Pyridinyl)androst-16-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5α)-17-(3-Pyridinyl)androst-16-en-3-one(154229-26-2)
• EPA Substance Registry System: (5α)-17-(3-Pyridinyl)androst-16-en-3-one(154229-26-2)

Safety Data

• Hazardous Substances Data: 154229-26-2(Hazardous Substances Data)

Usage

Uses

(5α)-17-(3-Pyridinyl)androst-16-en-3-one is a related compound of Abiraterone (A108490). (5α)-17-(3-Pyridinyl)androst-16-en-3-one is a 17-(3-pyridyl)-substituted steroid useful in cancer treatment such as prostatic cancer and breast cancer.

Upstream product

• 89878-14-8 3-Diethylboranylpyridine 
• 53-41-8 cis-androsterone 
• 1940176-03-3 17-(3-pyridyl)-5β-androsta-16-ene-3α-ol 
• 1482-78-6 3α-(acetyloxy)-5β-androstan-17-one 
• 53-42-9 Etiocholanolone 
• 1692-25-7 3-pyridylboronic acid 
• 1382475-29-7 C₂₄H₃₃NO 
• 32138-70-8 C₁₉H₂₉IO 
• 1382475-26-4 C₁₉H₃₂N₂O 
• 20120-08-5 3β-hydroxyandrostan-17-one 
• 219843-75-1 (3β,5α)-17-(3'-pyridinyl)androst-16-en-3-ol 
• 219843-76-2 3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene 
• 91934-55-3 3β-acetoxy-5α-androsta-16-ene-17-yl trifluoromethanesulfonate 
• 1239-31-2 3β-acetoxy-5α-androstan-17-one 

Downstream Products

• 154229-25-1 17-(3-pyridyl)-5α-androsta-16-ene-3α-ol 

Relevant articles and documents

ALTERING STEROID METABOLISM FOR TREATMENT OF STEROID-DEPENDENT DISEASE

A method of treating steroid-dependent disease such as prostate cancer in a subject is described that includes administering a therapeutically effective amount a CYP17A inhibitor and an effective amount of a 5- -reductase inhibitor to the subject.

CYP11B, CYP17, AND/OR CYP21 INHIBITORS

Provided herein are inhibitors of CYP11B, CYP17, and/or CYP21 enzymes of Formula (Z), (IX), (X), (XI), (XII), (XIII), (XIV), (XV), (XVI), or (XVII). Also described herein are pharmaceutical compositions that include at least one compound described herein and the use of a compound or pharmaceutical composition described herein to treat androgen-dependent diseases, disorders and conditions. Formula (Z)

Novel Steroidal Inhibitors of Human Cytochrome P45017α (17α-Hydroxylase-C17,20-lyase): Potential Agents for the Treatment of Prostatic Cancer

Steroidal compounds having a 17-(3-pyridyl) substituent together with a 16,17-double bond have been synthesized, using a palladium-catalyzed cross-coupling reaction of a 17-enol triflate with diethyl(3-pyridyl)borane, which are potent inhibitors of human testicular 17α-hydroxylase-C17,20-lyase.The requirement for these structural features is stringent: compounds having 2-pyridyl (9), 4-pyridyl (10), or 2-pyridylmethyl (11) substituents instead of the 3-pyridyl substituent were either poor inhibitors or noninhibitory.Reduction of the 16,17-double bond to give 17β-pyridyl derivatives diminished potency with 3-pyridyl substitution (327; IC50 for lyase, 2.923 nM) but increased it with a 4-pyridyl substituent present (1028; IC50 1 μM53 nM).In contrast, a variety of substitution patterns in rings A-C of the steroid skeleton afforded inhibitors having potencies similar to those most closely related structurally to the natural substrates pregnenolone and progesterone, respectively 17-(3-pyridyl)androsta-5,16-dien-3β-ol (3, Kiapp 1 nM; IC50 for lyase, 2.9 nM) and 17-(3-pyridyl)androsta-4,16-dien-3-one (15; IC50 for lyase, 2.1 nM).Thus compounds having variously aromatic ring A (18), saturated rings A/B (21,22), and oxygenated ring C (26) exhibited IC50 values for lyase (1.8-3.0 nM) falling within a 2-fold range.The most potent compounds are candidates for development as drugs for the treatment of hormone-dependent prostatic carcinoma.