159354-61-7

Basic information

• Product Name: 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione
• CAS NO: 159354-61-7
• Molecular Weight: 312.409
• Mol File: 159354-61-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 480.1±45.0 °C(Predicted)
• Density: 1.22±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione(159354-61-7)
• EPA Substance Registry System: 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione(159354-61-7)

Safety Data

• Hazardous Substances Data: 159354-61-7(Hazardous Substances Data)

Usage

Description

1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione, also known as 1,2-α-Epoxy Exemestane, is a metabolite of Exemestane (E957000), which is a third-generation steroidal aromatase inhibitor. It is derived from a chemical modification of the androst-4-ene-3,17-dione structure, featuring an epoxy group at the 1α,2α positions and a methylidene group at the 6 position. 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione has been utilized in the medical field for its potential therapeutic properties.

Uses

Used in Pharmaceutical Industry:
1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione is used as a pharmaceutical compound for its role in hormone-dependent breast cancer treatment. It functions by inhibiting the aromatase enzyme, which is responsible for converting androgens to estrogens, thus reducing the estrogen levels in post-menopausal women and helping to slow down the growth of hormone-dependent breast cancer cells.
Additionally, due to its structural similarity to other steroidal compounds, 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione may also be used as a precursor in the synthesis of other steroidal drugs, potentially expanding its applications in the pharmaceutical industry.

Upstream product

• 107868-30-4 exemestane 

Relevant articles and documents

Oxymestane, a cytostatic steroid derivative of exemestane with greater antitumor activity in non-estrogen-dependent cell lines

A new promising steroid derivative of Exemestane (Exe), the drug used for the treatment of estrogen-dependent breast cancer, was synthesized and evaluated against a set of human cancer cell lines. The new compound (Oxymestane-D1, Oxy) was tested comparatively with Exe against colon (C2BBe1, WiDr), liver (HepG2, HuH-7), lung (A549, H1299) and prostate (LNCaP, PC3) human cancer cell lines. Likewise, its effect on human colon normal cells (CCD-841 CoN) and human normal fibroblast cells (HFF-1) was studied. The cytostatic activity of Oxy was also compared with that of the reference cytostatic drugs used in chemotherapy protocols, namely carboplatin, cisplatin, doxorubicin, epirubicin, etoposide, flutamide, 5-fluorouracil, irinotecan, oxaliplatin and sorafenib. In all cell lines tested, Oxy proved to be more powerful cytostatic than Exe. Additionally, the IC50 at 72 h showed a three-fold activity greater than 5-fluorouracil in the WiDr cell line, twice as high as cisplatin for cell line A549 and five times higher than cisplatin for cell line H1299. Also, Oxy surprisingly revealed to induce DNA damage and inhibit the DNA damage response (DDR) proteins ATM, ATR, CHK1 and CHK2. The results obtained allow concluding that Oxy can be a promising anticancer agent to be used in chemotherapy protocols. Furthermore, its ability to inhibit crucial components of DDR can also be useful for the monotherapy or for combination with chemo and/or radiotherapy of cancer.