Bicalutamide
[CAS# 90357-06-5]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Gonadotropin
• Name: Bicalutamide
• Synonyms: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methyl-propanamide
• Molecular Formula: C₁₈H₁₄F₄N₂O₄S
• Molecular Weight: 430.37
• CAS Registry Number: 90357-06-5
• EC Number: 618-534-3
• SMILES: CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O

Properties

• Solubility: 86 mg/mL (DMSO), <1 mg/mL (water), 7 mg/mL (ethanol) (Expl.)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 191-193 °C
• Index of Refraction: 1.578, Calc.^*
• Boiling Point: 650.3±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 347.1±31.5 °C, Calc.^*

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H319-H335-H351
• Safety Statements: P203-P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Carcinogenicity	Carc.	2	H351
Reproductive toxicity	Repr.	1B	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Reproductive toxicity	Repr.	1A	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	1B	H360FD
Reproductive toxicity	Repr.	2	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H411
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

Bicalutamide is a synthetic nonsteroidal antiandrogen used primarily in the treatment of prostate cancer. It works by inhibiting the action of androgens, such as testosterone, which promote the growth of prostate cancer cells. Bicalutamide was first developed in the late 1980s by the pharmaceutical company AstraZeneca. Its primary function is to block androgen receptors, preventing testosterone from binding to them and thus inhibiting the growth and proliferation of prostate cancer cells.

Bicalutamide is often used in combination with other treatments for prostate cancer, including surgery, radiation therapy, or other hormonal therapies. One of its common applications is in the treatment of advanced or metastatic prostate cancer, where it can be used in combination with other drugs such as luteinizing hormone-releasing hormone (LHRH) agonists to reduce androgen levels. It is usually administered orally, and its therapeutic effects are achieved by blocking the androgen receptor, thus preventing the stimulation of cancerous growth in prostate cells.

The drug's effectiveness in treating prostate cancer has been well-documented, with several clinical trials supporting its use in combination therapy to delay disease progression and alleviate symptoms. Bicalutamide is also used in cases of prostate cancer recurrence after initial treatment, providing additional therapeutic options for patients with advanced stages of the disease. Its role in cancer therapy highlights the critical need for targeted treatments in oncology, particularly in hormone-dependent cancers such as prostate cancer.

In addition to its application in prostate cancer, bicalutamide has also been investigated for use in the treatment of other hormone-dependent conditions, such as hirsutism in women and as part of gender-affirming treatment in transgender individuals. While its primary use remains in prostate cancer therapy, research continues into its potential broader uses.

The development of bicalutamide is part of a broader trend in cancer therapy, where targeting specific molecular pathways, such as androgen signaling, offers a more precise and less invasive approach than traditional chemotherapy. This focus on targeted therapies has significantly improved the prognosis for patients with prostate cancer, making bicalutamide an important drug in modern oncology.

References

2005. Structural basis for antagonism and resistance of bicalutamide in prostate cancer. Proceedings of the National Academy of Sciences of the United States of America, 102(16).
DOI: 10.1073/pnas.0500381102

2005. Exploratory study of drug plasma levels during bicalutamide 150 mg therapy co-administered with tamoxifen or anastrozole for prophylaxis of gynecomastia and breast pain in men with prostate cancer. Cancer Chemotherapy and Pharmacology, 56(4).
DOI: 10.1007/s00280-005-1016-1

2005. Efficacy and Tolerability of Radiotherapy as Treatment for Bicalutamide-induced Gynaecomastia and Breast Pain in Prostate Cancer. European Urology, 47(5).
DOI: 10.1016/j.eururo.2004.12.003