154229-26-2

Usage

Uses

Used in Pharmaceutical Industry:
(5α)-17-(3-Pyridinyl)androst-16-en-3-one is used as a pharmaceutical compound for the treatment of various types of cancer. Its application is primarily due to its structural similarity to Abiraterone, which is a known drug for the treatment of prostate cancer. The compound's unique 3-pyridyl substitution may offer additional therapeutic benefits or advantages in targeting specific cancer types.
Used in Cancer Treatment:
(5α)-17-(3-Pyridinyl)androst-16-en-3-one is used as an anticancer agent, particularly in the treatment of prostatic cancer and breast cancer. The compound's ability to target and disrupt specific cellular pathways involved in cancer cell growth and proliferation makes it a promising candidate for the development of novel cancer therapies. Its use in cancer treatment is supported by its relatedness to Abiraterone, which has demonstrated efficacy in the treatment of prostate cancer.

Upstream product

• 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 
• 481-29-8 Epiandrosterone 
• 53-41-8 cis-androsterone 

Downstream Products

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

Relevant academic research and scientific papers

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.

A-ring modified steroidal azoles retaining similar potent and slowly reversible CYP17A1 inhibition as abiraterone

Abiraterone acetate is a potent inhibitor of human cytochrome P450c17 (CYP17A1, 17α-hydroxylase/17,20-lyase) and is clinically used in combination with prednisone for the treatment of castration-resistant prostate cancer. Although many studies have documented the potency of abiraterone (Abi) in a variety of in vitro and in vivo systems for several species, the exact potency of Abi for human CYP17A1 enzyme has not yet been determined, and the structural requirements for high-potency steroidal azole inhibitors are not established. We synthesized 4 Abi analogs differing in the A-B ring substitution patterns: 3α-hydroxy-Δ4-Abi (13), 3-keto- Δ4-Abi (11), 3-keto-5α-Abi (6), and 3α-hydroxy- 5α-Abi (5). We measured the spectral binding constants (Ks) using purified and modified human CYP17A1 along with the determination constants (Ki) applying a native human CYP17A1 enzyme in yeast microsomes for these compounds as well as for ketoconazole. For Abi, 3-keto- Δ4-Abi, 3-keto-5α-Abi, and 3α-hydroxy-5α-Abi, the type 2 spectral changes gave the best fit for a quadratic equation, since in these experiments Ks values were 0.1-2.6 nM, much lower than that for ketoconazole and 3α-hydroxy-Δ4-Abi (Ks values were 140 and 1660 nM, respectively). Inhibition experiments showed mixed inhibition patterns with Ki values of 7-80 nM. Abi dissociation from the CYP17A1-Abi complex was incomplete and slow; the t1/2 for dissociation was 1.8 h, with 55% of complex remaining after 5 h. We conclude that Abi and the 3 related steroidal azoles (3-keto-Δ4-Abi, 3-keto-5α-Abi, and 3α-hydroxy-5α-Abi), which also mimic natural substrates, are extraordinarily potent inhibitors of human CYP17A1, whereas the 3α-hydroxy-Δ4-Abi is moderately potent and comparable to ketoconazole.

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)

17-substituted steroids useful in cancer treatment

Compounds of the general formula (1) STR1 wherein X represents the residue of the A, B and C rings of a steroid, R represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, R 14 represents a hydrogen atom and R 15 represents a hydrogen atom or an alkyl or alkoxy group of 1-4 carbon atoms, or a hydroxy or alkylcarbonyloxy group of 2 to 5 carbon atoms or R 14 and R 15 together represent a double bond, and R 16 represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, in the form of the free bases or phannaceutically acceptable acid addition salts, are useful for treatment of androgen-dependent disorders, especially prostatic cancer, and also oestrogen-dependent disorders such as breast cancer.

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.