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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H14F4N2O4S
Molecular Weight 430.3751
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BICALUTAMIDE, (R)-

SMILES

C[C@](CS(=O)(=O)c1ccc(cc1)F)(C(=Nc2ccc(C#N)c(c2)C(F)(F)F)O)O

InChI

InChIKey=LKJPYSCBVHEWIU-KRWDZBQOSA-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)/t17-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H14F4N2O4S
Molecular Weight 430.3751
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CASODEX

Approved Use

Bicalutamide 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 Date

8.1276482E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
810.7 μg/L
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

AUC

ValueDoseCo-administeredAnalytePopulation
202.5 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
Sources:
Other AEs: Gynaecomastia, Breast pain...
Other AEs:
Gynaecomastia (45.2%)
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%)
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
Other AEs: Back pain, Constipation...
Other AEs:
Back pain (6.9%)
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%)
Sources:
50 mg 1 times / day multiple, oral
Recommended
Dose: 50 mg, 1 times / day
Route: oral
Route: multiple
Dose: 50 mg, 1 times / day
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
Sources:
Other AEs: General body pain, Back pain...
Other AEs:
General body pain (35%)
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%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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)
n = 42
Health Status: unhealthy
Condition: prostate cancer
Age Group: 72.1 years (range: 56-84 years)
Sex: M
Population Size: 42
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
n = 29
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 29
Sources:
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
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
Co-administed with::
LHRH analog
Sources:
unhealthy, adult
n = 401
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 401
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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
Page: 2.0
low
low
major
minor
minor
no
no
no
no
no
no
no
no
no
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol.
2004 Aug
The androgen receptor co-activator CBP is up-regulated following androgen withdrawal and is highly expressed in advanced prostate cancer.
2004 Oct
Changes in androgen receptor nongenotropic signaling correlate with transition of LNCaP cells to androgen independence.
2004 Oct 1
Androgen receptor regulates Cdc6 in synchronized LNCaP cells progressing from G1 to S phase.
2005 Aug
The ErbB3-binding protein Ebp1 suppresses androgen receptor-mediated gene transcription and tumorigenesis of prostate cancer cells.
2005 Jul 12
Casodex treatment induces hypoxia-related gene expression in the LNCaP prostate cancer progression model.
2005 Mar 24
Direct agonist/antagonist functions of dehydroepiandrosterone.
2005 Nov
The expression of transcription factor activating transcription factor 3 in the human prostate and its regulation by androgen in prostate cancer.
2006 Apr
Differentially expressed genes in the prostate cancer cell line LNCaP after exposure to androgen and anti-androgen.
2006 Apr 15
Dihydrotestosterone decreases tumor necrosis factor-alpha and lipopolysaccharide-induced inflammatory response in human endothelial cells.
2006 Feb
(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3- yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist.
2006 Jan 26
Conditional expression of PTEN alters the androgen responsiveness of prostate cancer cells.
2006 Jul 1
GREB1 is a novel androgen-regulated gene required for prostate cancer growth.
2006 Jun 1
Marked sexual dimorphism of lacrimal gland peroxidase in hamster: repression by androgens and estrogens.
2006 Mar 24
Dual androgen-response elements mediate androgen regulation of MMP-2 expression in prostate cancer cells.
2007 Jan
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.
2007 Jul 17
Ligand-specific dynamics of the androgen receptor at its response element in living cells.
2007 Mar
Gefitinib and bicalutamide show synergistic effects in primary cultures of prostate cancer derived from androgen-dependent naive patients.
2007 Nov
Oriental herbs as a source of novel anti-androgen and prostate cancer chemopreventive agents.
2007 Sep
Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors.
2007 Sep 1
PC-1/PrLZ contributes to malignant progression in prostate cancer.
2007 Sep 15
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
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
Regulation of androgen receptor transcriptional activity by rapamycin in prostate cancer cell proliferation and survival.
2008 Nov 27
Prohibitin and the SWI/SNF ATPase subunit BRG1 are required for effective androgen antagonist-mediated transcriptional repression of androgen receptor-regulated genes.
2008 Sep
Genome-wide impact of androgen receptor trapped clone-27 loss on androgen-regulated transcription in prostate cancer cells.
2009 Apr 1
Interleukin-6 increases prostate cancer cells resistance to bicalutamide via TIF2.
2009 Mar
Inhibition of androgen receptor transcriptional activity as a novel mechanism of action of arsenic.
2009 Mar
Interleukin-6 stimulation of growth of prostate cancer in vitro and in vivo through activation of the androgen receptor.
2009 Mar
Development of a second-generation antiandrogen for treatment of advanced prostate cancer.
2009 May 8
Is prophylactic breast radiotherapy necessary in all patients with prostate cancer and gynecomastia and/or breast pain?
2010 Aug
Androgen-regulated expression of arginase 1, arginase 2 and interleukin-8 in human prostate cancer.
2010 Aug 11
REDD1 is a major target of testosterone action in preventing dexamethasone-induced muscle loss.
2010 Mar
Resveratrol regulates the PTEN/AKT pathway through androgen receptor-dependent and -independent mechanisms in prostate cancer cell lines.
2010 Nov 15
Androgen receptor-mTOR crosstalk is regulated by testosterone availability: implication for prostate cancer cell survival.
2010 Oct
Testosterone, not 5α-dihydrotestosterone, stimulates LRH-1 leading to FSH-independent expression of Cyp19 and P450scc in granulosa cells.
2011 Apr
Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies.
2011 Jan 13
Identification of human triple-negative breast cancer subtypes and preclinical models for selection of targeted therapies.
2011 Jul
Unexpected binding orientation of bulky-B-ring anti-androgens and implications for future drug targets.
2011 Jun 9
Discovery of aryloxy tetramethylcyclobutanes as novel androgen receptor antagonists.
2011 Nov 10
Biological properties of androgen receptor pure antagonist for treatment of castration-resistant prostate cancer: optimization from lead compound to CH5137291.
2011 Sep
Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening.
2011 Sep 22
Red ginseng and 20(S)-Rg3 control testosterone-induced prostate hyperplasia by deregulating androgen receptor signaling.
2012 Jul
Androgen signaling promotes translation of TMEFF2 in prostate cancer cells via phosphorylation of the α subunit of the translation initiation factor 2.
2013
Endocrine disruptors fludioxonil and fenhexamid stimulate miR-21 expression in breast cancer cells.
2013 Jan
Dehydroepiandrosterone post-transcriptionally modifies CYP1A2 induction involving androgen receptor.
2013 May 25
Bisphenol A affects androgen receptor function via multiple mechanisms.
2013 May 25
Targeting cell cycle and hormone receptor pathways in cancer.
2013 Nov 28
Therapeutic targeting of BET bromodomain proteins in castration-resistant prostate cancer.
2014 Jun 12
Patents

Sample Use Guides

one 50 mg tablet once daily (morning or evening), with or without food
Route of Administration: Oral
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
by admin
on Sat Jun 26 08:54:21 UTC 2021
Edited
by admin
on Sat Jun 26 08:54:21 UTC 2021
Record UNII
Z9DL98I0AF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BICALUTAMIDE, (R)-
Common Name English
(R)-BICALUTAMIDE
Common Name English
PROPANAMIDE, N-(4-CYANO-3-(TRIFLUOROMETHYL)PHENYL)-3-((4-FLUOROPHENYL)SULFONYL)-2-HYDROXY-2-METHYL-, (2R)-
Systematic Name English
(-)-BICALUTAMIDE
Common Name English
BICALUTAMIDE, (-)-
Common Name English
AZD-1907
Code English
(R)-CASODEX
Brand Name English
R-BICALUTAMIDE
Common Name English
Code System Code Type Description
CAS
113299-40-4
Created by admin on Sat Jun 26 08:54:22 UTC 2021 , Edited by admin on Sat Jun 26 08:54:22 UTC 2021
PRIMARY
DRUG BANK
DB02932
Created by admin on Sat Jun 26 08:54:22 UTC 2021 , Edited by admin on Sat Jun 26 08:54:22 UTC 2021
PRIMARY
FDA UNII
Z9DL98I0AF
Created by admin on Sat Jun 26 08:54:22 UTC 2021 , Edited by admin on Sat Jun 26 08:54:22 UTC 2021
PRIMARY
PUBCHEM
56069
Created by admin on Sat Jun 26 08:54:22 UTC 2021 , Edited by admin on Sat Jun 26 08:54:22 UTC 2021
PRIMARY
Related Record Type Details
PARENT->ACTIVE ISOMER