Enzalutamide

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Cat Number

API915087331

CAS Number

915087-33-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

915087-33-1

EINECS

805-022-1

Storage

Store at 2-8℃

Synonyms

MDV-3100; 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide; XTANDI; Enzalutamida; 93T0T9GKNU

Molecular Formula

C21H16F4N4O2S

Molecular Weight

464.4

Smiles

CC1(C(=O)N(C(=S)N1C2=CC(=C(C=C2)C(=O)NC)F)C3=CC(=C(C=C3)C#N)C(F)(F)F)C

Appearance

White to off-white powder

Relative Density

1.49

General Description

Enzalutamide is a second-generation, oral androgen receptor signaling inhibitor approved for the treatment of advanced prostate cancer. It is a small-molecule antagonist that binds directly to the androgen receptor with high affinity. Unlike first-generation antiandrogens such as bicalutamide, enzalutamide lacks agonist activity and remains effective in settings of androgen receptor overexpression and mutation.

Mechanism of Action

Enzalutamide competitively inhibits binding of androgens to the androgen receptor, preventing nuclear translocation of the receptor and its association with DNA. It also interferes with coactivator recruitment and impairs androgen receptor-mediated gene transcription. The drug has been shown to reduce tumor cell proliferation and induce apoptosis in castration-resistant prostate cancer. Importantly, it does not promote the nuclear translocation of the androgen receptor, overcoming a key resistance mechanism seen with first-generation antiandrogens.

Application

It is indicated for the treatment of patients with castration-resistant prostate cancer across multiple disease states, including non-metastatic and metastatic disease. It is also approved in combination with androgen deprivation therapy for metastatic castration-sensitive prostate cancer. Common adverse effects include fatigue, hypertension, and hot flashes. A unique but serious risk is posterior reversible encephalopathy syndrome, requiring prompt recognition and management.

In this phase III trial (PROSPER), 1401 men with nonmetastatic castration‑resistant prostate cancer and a rapid PSA doubling time (≤10 months) were randomized to enzalutamide 160 mg/day or placebo. Median metastasis‑free survival was 36.6 months with enzalutamide versus 14.7 months with placebo (hazard ratio for metastasis or death 0.29; P<0.001). Enzalutamide also prolonged time to first subsequent antineoplastic therapy (39.6 vs. 17.7 months) and time to PSA progression (37.2 vs. 3.9 months). Grade ≥3 adverse events occurred in 31% vs. 23%. The authors conclude that enzalutamide reduces the risk of metastasis or death by 71% in this high‑risk population, with a manageable safety profile.

Fig. 1 Kaplan–Meier Estimate of Metastasis-free Survival. (Hussain M, et al., 2018)

References

Hussain M, et al. Enzalutamide in Men with Nonmetastatic, Castration-Resistant Prostate Cancer. N Engl J Med. 2018; 378(26):2465-2474.

Does Enzalutamide require protection from light during storage?

Yes, it is photosensitive. Prolonged exposure to light can cause photodegradation. Store in light-resistant containers, ideally in the original packaging, away from UV sources.

What is the recommended storage temperature for Enzalutamide?

Store at 2-8°C (refrigerated) for long-term stability. It is thermally stable, but avoid temperatures above 30°C to prevent potential polymorphic changes or degradation.

Is Enzalutamide hygroscopic, and how does this affect stability?

It exhibits low hygroscopicity. However, under high humidity (>70% RH), it may absorb moisture, leading to caking. Storage with desiccant is recommended.

How is the impurity N-methyl enzalutamide controlled during storage?

This process-related impurity is monitored using a validated HPLC method, ensuring it remains below ICH qualification thresholds throughout the product's shelf life.