Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H14F4N2O4S |
Molecular Weight | 430.373 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F
InChI
InChIKey=LKJPYSCBVHEWIU-UHFFFAOYSA-N
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
Molecular Formula | C18H14F4N2O4S |
Molecular Weight | 430.373 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Bicalutamide (brand name Casodex) is an oral non-steroidal anti-androgen for prostate cancer. It is indicated for use in combination therapy with a luteinizing hormone-releasing hormone (LHRH) analog for the treatment of Stage D2 metastatic carcinoma of the prostate. Bicalutamide competitively inhibits the action of androgens by binding to cytosol androgen receptors in the target tissue. Prostatic carcinoma is known to be androgen sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen. When CASODEX is combined with luteinizing hormone releasing hormone (LHRH) analog therapy, the suppression of serum testosterone induced by the LHRH analog is not affected. Bicalutamide is well-absorbed following oral administration, although the absolute bioavailability is unknown. Bicalutamide undergoes stereospecific metabolism. The S (inactive) isomer is metabolized primarily by glucuronidation. The R (active) isomer also undergoes glucuronidation but is predominantly oxidized to an inactive metabolite followed by glucuronidation. Both the parent and metabolite glucuronides are eliminated in the urine and feces. The S-enantiomer is rapidly cleared relative to the R-enantiomer, with the R-enantiomer accounting for about 99% of total steady-state plasma levels.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8560673
Curator's Comment: The peripheral selectivity of bicalutamide has been shown to be due to poor penetration across the blood-brain barrier: tissue distribution studies with [3H]bicalutamide show that although it is concentrated in the organs of metabolism and secretion as well as in the prostate, the pituitary glands, and the seminal vesicles, levels in the hypothalamus and the central nervous system (CNS) are much lower than in blood.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11931851 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CASODEX Approved UseBicalutamide 50 mg daily is indicated for use in combination therapy with a luteinizing hormone-releasing hormone (LHRH) analog for the treatment of Stage D2 metastatic carcinoma of the prostate. Bicalutamide 150 mg daily is not approved for use alone or with other treatments [see Clinical Studies (14.2) Launch Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
810.7 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22331758 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BICALUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
202.5 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22331758 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BICALUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.8 day |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: GONADORELIN |
BICALUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
146.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22331758 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
BICALUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4% |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: GONADORELIN |
BICALUTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Other AEs: Gynaecomastia, Breast pain... Other AEs: Gynaecomastia (45.2%) Sources: Breast pain (57.1%) Hot flushes (16.7%) Constipation (31%) Dry skin (2.4%) Insomnia (9.5%) Rash (11.9%) Back pain (14.3%) Asthenia (19%) Diarrhoea (19%) Urinary tract infection (16.7%) Arthralgia (11.9%) Pharyngitis (14.3%) Pain (23.8%) |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Other AEs: Back pain, Constipation... Other AEs: Back pain (6.9%) Sources: Constipation (10.3%) Libido decreased (50%) Impotence (57%) Dyspepsia (6.9%) Dysuria (6.9%) Haematuria (6.9%) Pain (17.2%) Pelvic pain (6.9%) Somnolence (6.9%) Urinary incontinence (6.9%) Urinary urgency (6.9%) Weight gain (10.3%) Gynaecomastia (79%) Breast tenderness (79%) Hot flushes (41%) |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Other AEs: General body pain, Back pain... Other AEs: General body pain (35%) Sources: Back pain (25%) Asthenia (22%) Pelvic pain (21%) Infection (18%) Abdominal pain (11%) Chest pain (8%) Headache (7%) Flu syndrome (7%) Hot flashes (53%) Hypertension (8%) Constipation (22%) Nausea (15%) Diarrhea (12%) Liver function test increased (7%) Dyspepsia (7%) Flatulence (6%) Anorexia (6%) Vomiting (6%) Anemia (11%) Peripheral edema (13%) Weight loss (7%) Hyperglycemia (6%) Alkaline phosphatase increased (5%) Weight gain (5%) Bone pain (9%) Myasthenia (7%) Arthritis (5%) Fracture pathological (4%) Dizziness (10%) Paresthesia (8%) Insomnia (7%) Anxiety (5%) Depression (4%) Dyspnea (13%) Cough increased (8%) Pharyngitis (8%) Bronchitis (6%) Pneumonia (4%) Rhinitis (4%) Rash (9%) Sweating (6%) Nocturia (12%) Hematuria (12%) Urinary tract infection (9%) Gynecomastia (9%) Impotence (7%) Breast pain (6%) Urinary frequency (6%) Urinary retention (5%) Urination impaired (5%) Urinary incontinence (4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Arthralgia | 11.9% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Rash | 11.9% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Back pain | 14.3% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Pharyngitis | 14.3% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Hot flushes | 16.7% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Urinary tract infection | 16.7% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Asthenia | 19% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Diarrhoea | 19% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Dry skin | 2.4% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Pain | 23.8% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Constipation | 31% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Gynaecomastia | 45.2% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Breast pain | 57.1% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Insomnia | 9.5% | 600 mg 1 times / day multiple, oral Highest studied dose Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: |
Constipation | 10.3% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Weight gain | 10.3% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Pain | 17.2% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Hot flushes | 41% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Libido decreased | 50% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Impotence | 57% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Back pain | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Dyspepsia | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Dysuria | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Haematuria | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Pelvic pain | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Somnolence | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Urinary incontinence | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Urinary urgency | 6.9% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Breast tenderness | 79% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Gynaecomastia | 79% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, adult |
Dizziness | 10% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Abdominal pain | 11% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Anemia | 11% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Diarrhea | 12% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Hematuria | 12% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Nocturia | 12% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Dyspnea | 13% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Peripheral edema | 13% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Nausea | 15% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Infection | 18% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Pelvic pain | 21% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Asthenia | 22% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Constipation | 22% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Back pain | 25% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
General body pain | 35% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Depression | 4% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Fracture pathological | 4% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Pneumonia | 4% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Rhinitis | 4% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Urinary incontinence | 4% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Alkaline phosphatase increased | 5% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Anxiety | 5% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Arthritis | 5% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Urinary retention | 5% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Urination impaired | 5% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Weight gain | 5% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Hot flashes | 53% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Anorexia | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Breast pain | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Bronchitis | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Flatulence | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Hyperglycemia | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Sweating | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Urinary frequency | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Vomiting | 6% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Dyspepsia | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Flu syndrome | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Headache | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Impotence | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Insomnia | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Liver function test increased | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Myasthenia | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Weight loss | 7% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Chest pain | 8% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Cough increased | 8% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Hypertension | 8% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Paresthesia | 8% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Pharyngitis | 8% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Bone pain | 9% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Gynecomastia | 9% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Rash | 9% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Urinary tract infection | 9% | 50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major [IC50 7 uM] | ||||
minor [IC50 123 uM] | ||||
minor [IC50 44 uM] | ||||
minor [IC50 49 uM] | ||||
minor [IC50 58 uM] | ||||
yes [Inhibition 40 uM] | ||||
yes [Ki 11.9 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 2.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 2.0 |
likely | unlikely (co-administration study) Comment: this isoenzyme is also responsible for the metabolism of (R)-bicalutamide; (S)-Bicalutamide is metabolised in vitro by CYP3A4 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 2.0 |
||
low | ||||
low | ||||
major | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no |
PubMed
Title | Date | PubMed |
---|---|---|
Involvement of proteasome in the dynamic assembly of the androgen receptor transcription complex. | 2002 Dec 13 |
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Bicalutamide functions as an androgen receptor antagonist by assembly of a transcriptionally inactive receptor. | 2002 Jul 19 |
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A glucocorticoid-responsive mutant androgen receptor exhibits unique ligand specificity: therapeutic implications for androgen-independent prostate cancer. | 2002 May |
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UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay. | 2003 Jul |
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Regulation of matrix metalloproteinase 13 expression by androgen in prostate cancer. | 2004 Jun |
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Coregulator recruitment and histone modifications in transcriptional regulation by the androgen receptor. | 2004 Nov |
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Evaluation of tamoxifen and anastrozole in the prevention of gynecomastia and breast pain induced by bicalutamide monotherapy of prostate cancer. | 2005 Feb 1 |
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Possible role of adaptive mutation in resistance to antiandrogen in prostate cancer cells. | 2005 Nov 1 |
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Differentially expressed genes in the prostate cancer cell line LNCaP after exposure to androgen and anti-androgen. | 2006 Apr 15 |
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Influence of bicalutamide with or without tamoxifen or anastrozole on insulin-like growth factor 1 and binding proteins in prostate cancer patients. | 2006 Apr-Jun |
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Distinct regulation by steroids of messenger RNAs for FSHR and CYP19A1 in bovine granulosa cells. | 2006 Aug |
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Conditional expression of PTEN alters the androgen responsiveness of prostate cancer cells. | 2006 Jul 1 |
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GREB1 is a novel androgen-regulated gene required for prostate cancer growth. | 2006 Jun 1 |
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Marked sexual dimorphism of lacrimal gland peroxidase in hamster: repression by androgens and estrogens. | 2006 Mar 24 |
|
DHT and testosterone, but not DHEA or E2, differentially modulate IGF-I, IGFBP-2, and IGFBP-3 in human prostatic stromal cells. | 2006 May |
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Androgen induction of prostate cancer cell invasion is mediated by ezrin. | 2006 Oct 6 |
|
Nuclear and membrane receptor-mediated signalling pathways modulate polyamine biosynthesis and interconversion. | 2007 Apr |
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Androgen receptor or estrogen receptor-beta blockade alters DHEA-, DHT-, and E(2)-induced proliferation and PSA production in human prostate cancer cells. | 2007 Aug 1 |
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Labeling and identification of LNCaP cell surface proteins: a pilot study. | 2007 Jun 15 |
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Gefitinib and bicalutamide show synergistic effects in primary cultures of prostate cancer derived from androgen-dependent naive patients. | 2007 Nov |
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Oriental herbs as a source of novel anti-androgen and prostate cancer chemopreventive agents. | 2007 Sep |
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Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors. | 2007 Sep 1 |
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Androgen receptor-mediated repression of novel target genes. | 2007 Sep 15 |
|
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism. | 2008 Apr |
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Anaemia following initiation of androgen deprivation therapy for metastatic prostate cancer: a retrospective chart review. | 2008 Dec |
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Effects of dihydrotestosterone on differentiation and proliferation of human mesenchymal stem cells and preadipocytes. | 2008 Dec 16 |
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Hormonal regulation of beta2-adrenergic receptor level in prostate cancer. | 2008 Jul 1 |
|
Chronic azacitidine treatment results in differentiating effects, sensitizes against bicalutamide in androgen-independent prostate cancer cells. | 2008 May 15 |
|
Spectrophotometric estimation of bicalutamide in tablets. | 2008 Nov |
|
A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice. | 2008 Oct 15 |
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Differential mechanisms of bicalutamide-induced apoptosis in prostate cell lines. | 2009 |
|
Interactions of methoxyacetic acid with androgen receptor. | 2009 Jul 15 |
|
Resveratrol regulates the PTEN/AKT pathway through androgen receptor-dependent and -independent mechanisms in prostate cancer cell lines. | 2010 Nov 15 |
|
Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies. | 2011 Jan 13 |
|
Dehydroepiandrosterone post-transcriptionally modifies CYP1A2 induction involving androgen receptor. | 2013 May 25 |
|
Therapeutic targeting of BET bromodomain proteins in castration-resistant prostate cancer. | 2014 Jun 12 |
Sample Use Guides
one 50 mg tablet once daily (morning or evening), with or without food
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19285710
Primary tumor cultures and PCa cell lines were treated with bicalutamide (0.1-10 uM) in the presence of dehydrotestosterone (10(-12) M) for 4 days. After bicalutamide treatment, no significant differences in the concentration that inhibits 50% were found among the different tumor cell lines (P = .081).
Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 19:15:55 GMT 2025
by
admin
on
Mon Mar 31 19:15:55 GMT 2025
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Record UNII |
A0Z3NAU9DP
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QL02BB03
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NDF-RT |
N0000000243
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WHO-ATC |
L02AE51
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NCI_THESAURUS |
C146993
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WHO-ATC |
L02BB03
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NDF-RT |
N0000175560
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LIVERTOX |
NBK547970
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Code System | Code | Type | Description | ||
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A0Z3NAU9DP
Created by
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PRIMARY | |||
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BICALUTAMIDE
Created by
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PRIMARY | |||
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367
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SUB05817MIG
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PRIMARY | |||
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2375
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PRIMARY | |||
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DTXSID2022678
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PRIMARY | |||
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2863
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PRIMARY | |||
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C053541
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PRIMARY | |||
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7021
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PRIMARY | |||
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C1599
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GG-51
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83008
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1071202
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90357-06-5
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CHEMBL409
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759816
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7655
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m2474
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PRIMARY | Merck Index | ||
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100000085878
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A0Z3NAU9DP
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DB01128
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3090
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Related Record | Type | Details | ||
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ACTIVE ISOMER -> PARENT | |||
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INACTIVE ISOMER -> PARENT |
Bicalutamide is a racemate and its antiandrogenic activity resides almost exclusively in the (R)-enantiomer, with little, if any, activity in the (S)-enantiomer.
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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TARGET -> INHIBITOR | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BINDER->LIGAND |
BINDING
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TARGET -> AGONIST |
BINDING
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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