BICALUTAMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1995)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L02BB03
UNII: A0Z3NAU9DP

Structure
InChI Key LKJPYSCBVHEWIU-UHFFFAOYSA-N
Smile CC(O)(CS(=O)(=O)c1ccc(F)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H14F4N2O4S
Molecular Weight 430.38
AlogP 2.88
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 107.26
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Androgen Receptor antagonist DailyMed
Primary Target
Androgen receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- - - - 7
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
- 5600-5600 - 7200 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
31-4300 54-44260 - 19-160 16-84
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 29300-79600 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Prostatic Neoplasms 3 D011471 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Gynecomastia 2 D006177 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Puberty, Precocious 2 D011629 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Salivary Gland Neoplasms 2 D012468 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Hot flush 53.0
Reproductive system and breast disorders Menopausal symptoms 53.0
General disorders and administration site conditions Hot flush 49.0
Reproductive system and breast disorders Menopausal symptoms 49.0
General disorders and administration site conditions Pain 27.0
General disorders and administration site conditions Asthenia 22.0
Gastrointestinal disorders Constipation 22.0
Gastrointestinal disorders Constipation 17.0
General disorders and administration site conditions Asthenia 15.0
Musculoskeletal and connective tissue disorders Back pain 15.0
General disorders and administration site conditions Fatigue 15.0
Gastrointestinal disorders Nausea 14.0
Cardiac disorders Oedema peripheral 13.0
Gastrointestinal disorders Pelvic pain 13.0
Renal and urinary disorders Haematuria 12.0
Gastrointestinal disorders Abdominal pain 11.0
Gastrointestinal disorders Gastrointestinal pain 11.0
Gastrointestinal disorders Nausea 11.0
Gastrointestinal disorders Diarrhoea 10.0
Cardiac disorders Dizziness 10.0
Infections and infestations Infection 10.0
Skin and subcutaneous tissue disorders Dermatitis 9.0
Endocrine disorders Gynaecomastia 9.0
Renal and urinary disorders Nocturia 9.0
Skin and subcutaneous tissue disorders Rash 9.0
Gastrointestinal disorders Abdominal pain 8.0
Cardiac disorders Chest pain 8.0
Gastrointestinal disorders Gastrointestinal pain 8.0
Cardiac disorders Oedema peripheral 8.0
Blood and lymphatic system disorders Anaemia 7.0
Cardiac disorders Dizziness 7.0
Gastrointestinal disorders Dyspepsia 7.0
Cardiac disorders Dyspnoea 7.0
Psychiatric disorders Erectile dysfunction 7.0
Gastrointestinal disorders Flatulence 7.0
Renal and urinary disorders Haematuria 7.0
Reproductive system and breast disorders Breast tenderness 6.0
Cardiac disorders Chest pain 6.0
General disorders and administration site conditions Decreased appetite 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
General disorders and administration site conditions Hyperhidrosis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Infections and infestations Urinary tract infection 6.0
Psychiatric disorders Erectile dysfunction 5.0
Gastrointestinal disorders Flatulence 5.0
Endocrine disorders Hyperglycaemia 5.0
Vascular disorders Hypertension 5.0
Nervous system disorders Insomnia 5.0
Investigations Weight increased 5.0
Skin and subcutaneous tissue disorders Alopecia 4.0
Musculoskeletal and connective tissue disorders Bone pain 4.0
Skin and subcutaneous tissue disorders Dry skin 4.0
Nervous system disorders Headache 4.0
General disorders and administration site conditions Influenza like illness 4.0
Investigations Weight decreased 4.0
Skin and subcutaneous tissue disorders Pruritus 3.0
Nervous system disorders Somnolence 3.0
Gastrointestinal disorders Vomiting 3.0
Psychiatric disorders Disturbance in sexual arousal 2.0
Endocrine disorders Hirsutism 2.0
Psychiatric disorders Libido decreased 2.0
Nervous system disorders Urinary incontinence 2.0
Investigations Liver function test abnormal 1.5
General disorders and administration site conditions Hot flush 1.0
Reproductive system and breast disorders Menopausal symptoms 1.0
Gastrointestinal disorders Vomiting 0.7

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
13.55
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
7.39
Nervous system disorders
7.39
Vascular disorders
6.71
Cardiac disorders
6.27
Reproductive system and breast disorders
6.12
Investigations
5.88
Respiratory, thoracic and mediastinal disorders
5.67
Musculoskeletal and connective tissue disorders
5.17
Gastrointestinal disorders
4.45
Metabolism and nutrition disorders
4.02
Psychiatric disorders
3.88
Injury, poisoning and procedural complications
3.72
Skin and subcutaneous tissue disorders
3.64
Endocrine disorders
3.0
Renal and urinary disorders
2.86
Blood and lymphatic system disorders
2.56
Immune system disorders
2.1

Cross References

Resources Reference
CAS NUMBER 90357-06-5
ChEBI 144093
ChEMBL CHEMBL409
DrugBank DB01128
DrugCentral 367
EPA CompTox DTXSID2022678
FDA SRS A0Z3NAU9DP
Human Metabolome Database HMDB0015260
Guide to Pharmacology 2863
PDB 198
PharmGKB PA164746255
PubChem 2375
SureChEMBL SCHEMBL3611
ZINC ZINC00538564
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