API 17-AAG 99% Black-purple powder High QUality and Fast Delivery CAS 75747-14-7

17-AAG More Info

17-AAG is a semi-synthetic ansamycin antibiotic and a derivative of the natural product geldanamycin, assigned the CAS Registry Number 75747-14-7. Its molecular structure is characterized by a complex benzoquinone ansamycin core, modified with an allylamino group at the 17-position. This specific chemical alteration reduces the hepatotoxicity associated with the parent compound while retaining its potent biological activity. It functions as a highly specific inhibitor targeting a key molecular chaperone in cancer cells.

The primary mechanism of action for 17-AAG involves the potent and selective inhibition of heat shock protein 90, a critical molecular chaperone required for the stability, activation, and proper folding of numerous client proteins. By binding to the N-terminal ATP-binding pocket of Hsp90, it disrupts the chaperone's ATPase activity. This leads to the ubiquitin-proteasome degradation of Hsp90 client proteins, which include many oncogenic signaling proteins crucial for cancer cell survival, proliferation, and metastasis, such as HER2, Akt, mutant p53, and various hormone receptors.

This compound was developed and extensively investigated as a chemotherapeutic agent for the treatment of various cancers. Its clinical application focused on tumors dependent on specific Hsp90 client proteins, including HER2-positive breast cancer, castration-resistant prostate cancer, and certain leukemias. By simultaneously depleting multiple oncogenic drivers, it represented a promising strategy to overcome drug resistance. It entered numerous Phase I and II clinical trials to evaluate its efficacy and safety profile in these malignancies.

17-AAG was formulated for intravenous infusion due to its poor oral bioavailability. It required a specific lipid-based formulation to improve solubility for clinical administration. The drug's pharmacokinetics and metabolism were complex, and dosing schedules varied across clinical trials. A significant challenge was its extensive metabolism by hepatic enzymes, which contributed to variable exposure and the emergence of resistant forms in some patients.

Despite its promising mechanism, the clinical development of 17-AAG was hampered by significant challenges. Its safety profile included dose-limiting toxicities such as hepatotoxicity (though reduced from geldanamycin), gastrointestinal disturbances, and fatigue. Furthermore, its pharmaceutical properties, including formulation difficulties, metabolic instability, and variable pharmacokinetics, presented substantial hurdles. These limitations ultimately led to the discontinuation of its development in favor of next-generation, more bioavailable and less toxic Hsp90 inhibitors, though it remains a seminal compound in the field of targeted cancer therapy.

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