BICALUTAMIDE, (R)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H14F4N2O4S
Molecular Weight	430.373
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@](O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC2=CC=C(C#N)C(=C2)C(F)(F)F

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	430.373
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020498s025lbl.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11931851	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stage D2 metastatic carcinoma of the prostate 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/020498s025lbl.pdf	Primary		Approved 8583	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 1995

C_max

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

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.8 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020498s028lbl.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: GONADORELIN	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
4% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020498s028lbl.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: GONADORELIN	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: https://pubmed.ncbi.nlm.nih.gov/16771791/	unhealthy, 72.1 years (range: 56-84 years) Health Status: unhealthy Age Group: 72.1 years (range: 56-84 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/16771791/	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: https://pubmed.ncbi.nlm.nih.gov/16771791/
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: https://pubmed.ncbi.nlm.nih.gov/9471040/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9471040/	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: https://pubmed.ncbi.nlm.nih.gov/9471040/
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020498s028lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020498s028lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020498s028lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 UGT1A9 148 P-gp 1741	UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A5 56 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B10 131 UGT2B15 236 UGT2B17 237 UGT2B28 65	CYP 74

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022310lbl.pdf#page=9; https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 18.0	major [IC50 7 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022310lbl.pdf#page=9; https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 18.0	minor [IC50 123 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022310lbl.pdf#page=9; https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 18.0	minor [IC50 44 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022310lbl.pdf#page=9; https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 18.0	minor [IC50 49 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/022310lbl.pdf#page=9; https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 18.0	minor [IC50 58 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25124867/	yes [Inhibition 40 uM]
UGT1A9 155	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	yes [Ki 11.9 uM]
CYP 150	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15509184/ Page: 2.0	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 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
UGT1A1 479	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	low
UGT1A3 470	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	low
UGT1A9 423	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	major
UGT1A8 323	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	minor
UGT2B7 456	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	minor
UGT1A10 331	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT1A4 399	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT1A5 56	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT1A6 343	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT1A7 249	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT2B10 131	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT2B15 236	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT2B17 237	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT2B28 65	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no
UGT2B4 278	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3815647/	no

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0243	http://www.3bsc.com/index/pro_info.php?id=19599
AA Blocks	AA00H0UA	https://www.aablocks.com/goods/Goods/detail?id=AA00H0UA
Aaron Chemicals	AR00H1M2	http://www.aaronchem.com/90357-06-5
abcr GmbH	AB282481	http://www.abcr.com/shop/en/AB282481
AbMole Bioscience	M1960	http://www.abmole.com/products/bicalutamide.html
Achemo Scientific Limited	AC-13010	http://www.achemo.com/product_view.asp?ID=2900
Achemtek	0104-018953	http://www.achemtek.com/90357-06-5
Acros Organics	AC461000010	https://www.fishersci.com/shop/products/bicalutamide-97-acros-organics/AC461000010
Adooq BioScience	Bicalutamide - Casodex	http://www.adooq.com/bicalutamide-casodex.html
AHH Chemical co.,ltd	API-1229	http://www.ahhchemical.com/product/API-1229.html
AHH Chemical co.,ltd	MT-01087	http://www.ahhchemical.com/product/MT-01087.html
AK Scientific, Inc. (AKSCI)	J10442	http://www.aksci.com/item_detail.php?cat=J10442
Alfa Chemistry	90357-06-5	https://www.alfa-chemistry.com/bicalutamide-cas-90357-06-5-item-294076.htm
Alfa Chemistry	AP90357065-A	https://reagents.alfa-chemistry.com/product/bicalutamide-cdx-cas-90357-06-5-18339.html
Alfa Chemistry	AP90357065-B	https://reagents.alfa-chemistry.com/product/bicalutamide-cas-90357-06-5-18340.html
Alfa Chemistry	AP90357065-C	https://reagents.alfa-chemistry.com/product/bicalutamide-cas-90357-06-5-18341.html
Alsachim	1265	http://www.alsachim.com/product-C1621-glo.bal-view.html
Ambeed	A176397	https://www.ambeed.com/products/90357-06-5.html
Ambinter	Amb10231002	http://www.ambinter.com/reference/10231002
Angel Pharmatech	AG201149	http://www.angelpharmatech.com/113299-40-4.html
Angel Pharmatech	AG301719	http://www.angelpharmatech.com/90357-06-5.html
Angene	AGN-PC-00TUFT	http://www.angenechemical.com/productshow/AGN-PC-00TUFT.html
ApexBio Technology	A5065	http://www.apexbt.com/bicalutamide.html
Ark Pharm	AK544272	http://www.arkpharminc.com/products/90357-06-5.html
AstaTech, Inc.	21414	http://www.astatechinc.com/CPSResult.php?CRNO=430
Aurora Fine Chemicals LLC	A17.901.727	http://online.aurorafinechemicals.com/info?ID=A17.901.727
AvaChem Scientific	2621	http://www.avachem.com/productSearch.asp?2621
Axon MedChem	3313	https://www.axonmedchem.com/product/3313
BioChemPartner	BCP02110	http://www.biochempartner.com/90357-06-5-BCP02110
BioCrick	BCC2481	http://www.biocrick.com/Bicalutamide-BCC2481.html
BLD Pharm	BD16821	http://www.bldpharm.com/products/90357-06-5.html
BOC Sciences	1185035-71-5	https://www.bocsci.com/bicalutamide-d4-cas-1185035-71-5-item-467499.html
BOC Sciences	1217826-87-3	https://www.bocsci.com/r-bicalutamide-d4-cas-1217826-87-3-item-467500.html
Boerchem	BC204097	http://www.boerchem.com/?product_34304.html
Capot Chemical	18237	http://www.capotchem.com/en/18237.htm
Capot Chemical	PubChem18237	http://www.capotchem.com/en/18237.htm
Chem Scene	CS-1296	http://www.chemscene.com/90357-06-5.html
ChemMol	30101941	http://www.chemmol.com/chemmol/30101941.html
ChemMol	44001697	http://www.chemmol.com/chemmol/44001697.html
ChemMol	49401258	http://www.chemmol.com/chemmol/49401258.html
ChemMol	97900772	http://www.chemmol.com/chemmol/97900772.html
ChemMol	99183973	http://www.chemmol.com/chemmol/99183973.html
Chemspace	CSSB00015190076	https://chem-space.com/CSSB00015190076
Clearsynth	CS-EG-00189	https://www.clearsynth.com/en/CSEG00189.html
Clearsynth	CS-ER-02475	https://www.clearsynth.com/en/CSER02475.html
Clearsynth	CS-O-01015	https://www.clearsynth.com/en/CSO01015.html
Clearsynth	CS-O-07365	https://www.clearsynth.com/en/CSO07365.html
Combi-Blocks	ST-7244	http://www.combi-blocks.com/cgi-bin/find.cgi?ST-7244
CSNpharm	CSN12437	https://www.csnpharm.com/products/bicalutamide.html
DC Chemicals	DC31087	http://www.dcchemicals.com//product_show-ICI_176334.html
Debye Scientific	DB-041165	http://www.debyesci.com/cas_113299-40-4.html
eNovation Chemicals	D672520	https://www.enovationchem.com/ProductDetails.asp?ProductID=D672520
eNovation Chemicals	D767647	https://www.enovationchem.com/ProductDetails.asp?ProductID=D767647
eNovation Chemicals	Y1049756	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1049756
Excenen	EX-A962	http://www.excenen.com/searchresultlist.php?id=90357-06-5
Finetech	FT-0618286	http://www.finetechnology-ind.com/prod/detail/pub/90357-06-5.html
Finetech	FT-0631069	http://www.finetechnology-ind.com/prod/detail/pub/113299-40-4.html
Finetech	FT-0663100	http://www.finetechnology-ind.com/prod/detail/pub/113299-38-0.html
Glentham Life Sciences	GP8076	http://www.glentham.com/products/product/GP8076/
iChemical	EBD32195	http://www.ichemical.com/products/90357-06-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01271632	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01271632
LGC Standards	LGCFOR0894.00	https://www.lgcstandards.com/US/en/p/LGCFOR0894.00
LGC Standards	MM0894.00-0250	https://www.lgcstandards.com/US/en/p/MM0894.00-0250
Matrix Scientific	146650	https://www.matrixscientific.com/146650.html
MedChem Express	HY-14249	https://www.medchemexpress.com/Bicalutamide.html
OChem	337	http://www.ocheminc.com/index.php?act=psearch&pid=357B065
Parchem	28347	http://www.parchem.com/chemical-supplier-distributor/Bicalutamide-018347.aspx
Parchem	28348	http://www.parchem.com/chemical-supplier-distributor/Bicalutamide-018348.aspx
Selleck Chemicals	S1190	http://www.selleckchem.com/products/Bicalutamide(Casodex).html
Sigma-Aldrich	1071202_USP	https://www.sigmaaldrich.com/catalog/product/usp/1071202?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	B9061_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/b9061?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP1115_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp1115?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1678_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1678?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0001444_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0001444?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S548655	http://www.smolecule.com/products/s548655
Smolecule	S810223	https://www.smolecule.com/products/s810223
Synblock Inc	SB17301	http://www.synblock.com/product/90357-06-5.html
TCI (Tokyo Chemical Industry)	B3206	http://www.tcichemicals.com/eshop/en/us/commodity/B3206/index.html
THE BioTek	bt-288062	https://www.thebiotek.com/product/inhibitors/bt-288062
Tocris	3389	https://www.tocris.com/products/bicalutamide_3389
TripleBond	CB0180	http://www.triplebond-canada.com/prod/1144/
VladaChem	VL281207-1G	https://www.vladachem.com/product.php?products=90357-06-5
Wuhan Atomole Chemicals Co., Ltd.	AT-9158	http://www.atomole.com/en/products-view.asp?id=129046
Yuhao Chemical	LX2477	http://www.chemyuhao.com/90357-06-5.html

PubMed

Title	Date	PubMed
Therapeutic targeting of BET bromodomain proteins in castration-resistant prostate cancer.	2014-06-12	24759320
Targeting cell cycle and hormone receptor pathways in cancer.	2013-11-28	23708653
Dehydroepiandrosterone post-transcriptionally modifies CYP1A2 induction involving androgen receptor.	2013-05-25	23603339
Bisphenol A affects androgen receptor function via multiple mechanisms.	2013-05-25	23562765
Endocrine disruptors fludioxonil and fenhexamid stimulate miR-21 expression in breast cancer cells.	2013-01	23052036
Androgen signaling promotes translation of TMEFF2 in prostate cancer cells via phosphorylation of the α subunit of the translation initiation factor 2.	2013	23405127
Red ginseng and 20(S)-Rg3 control testosterone-induced prostate hyperplasia by deregulating androgen receptor signaling.	2012-07	22101440
Discovery of aryloxy tetramethylcyclobutanes as novel androgen receptor antagonists.	2011-11-10	21936524
Inhibitors of androgen receptor activation function-2 (AF2) site identified through virtual screening.	2011-09-22	21846139
Biological properties of androgen receptor pure antagonist for treatment of castration-resistant prostate cancer: optimization from lead compound to CH5137291.	2011-09	21308717
Identification of human triple-negative breast cancer subtypes and preclinical models for selection of targeted therapies.	2011-07	21633166
Unexpected binding orientation of bulky-B-ring anti-androgens and implications for future drug targets.	2011-06-09	21506597
Testosterone, not 5α-dihydrotestosterone, stimulates LRH-1 leading to FSH-independent expression of Cyp19 and P450scc in granulosa cells.	2011-04	21273442
Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies.	2011-01-13	21128595
Resveratrol regulates the PTEN/AKT pathway through androgen receptor-dependent and -independent mechanisms in prostate cancer cell lines.	2010-11-15	20729295
Androgen receptor-mTOR crosstalk is regulated by testosterone availability: implication for prostate cancer cell survival.	2010-10	21036700
Androgen-regulated expression of arginase 1, arginase 2 and interleukin-8 in human prostate cancer.	2010-08-11	20711410
Is prophylactic breast radiotherapy necessary in all patients with prostate cancer and gynecomastia and/or breast pain?	2010-08	20620411
REDD1 is a major target of testosterone action in preventing dexamethasone-induced muscle loss.	2010-03	20032058
Interactions of methoxyacetic acid with androgen receptor.	2009-07-15	18486176
Development of a second-generation antiandrogen for treatment of advanced prostate cancer.	2009-05-08	19359544
Genome-wide impact of androgen receptor trapped clone-27 loss on androgen-regulated transcription in prostate cancer cells.	2009-04-01	19318562
Interleukin-6 increases prostate cancer cells resistance to bicalutamide via TIF2.	2009-03	19240160
Inhibition of androgen receptor transcriptional activity as a novel mechanism of action of arsenic.	2009-03	19131511
Interleukin-6 stimulation of growth of prostate cancer in vitro and in vivo through activation of the androgen receptor.	2009-03	19011039
Differential mechanisms of bicalutamide-induced apoptosis in prostate cell lines.	2009	18475288
Effects of dihydrotestosterone on differentiation and proliferation of human mesenchymal stem cells and preadipocytes.	2008-12-16	18801408
Anaemia following initiation of androgen deprivation therapy for metastatic prostate cancer: a retrospective chart review.	2008-12	18937151
Regulation of androgen receptor transcriptional activity by rapamycin in prostate cancer cell proliferation and survival.	2008-11-27	18776922
Spectrophotometric estimation of bicalutamide in tablets.	2008-11	21369450
A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice.	2008-10-15	18922931
Prohibitin and the SWI/SNF ATPase subunit BRG1 are required for effective androgen antagonist-mediated transcriptional repression of androgen receptor-regulated genes.	2008-09	18487222
Hormonal regulation of beta2-adrenergic receptor level in prostate cancer.	2008-07-01	18454446
Chronic azacitidine treatment results in differentiating effects, sensitizes against bicalutamide in androgen-independent prostate cancer cells.	2008-05-15	18324645
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Therapeutic potential of CDK inhibitor NU2058 in androgen-independent prostate cancer.	2007-12-06	17599054
Gefitinib and bicalutamide show synergistic effects in primary cultures of prostate cancer derived from androgen-dependent naive patients.	2007-11	17914592
Downregulation of thymosin beta4 expression by androgen in prostate cancer LNCaP cells.	2007-10-06	17916567
PC-1/PrLZ contributes to malignant progression in prostate cancer.	2007-09-15	17875733
Androgen receptor-mediated repression of novel target genes.	2007-09-15	17624924
Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors.	2007-09-01	17804755
Oriental herbs as a source of novel anti-androgen and prostate cancer chemopreventive agents.	2007-09	17723170
Androgen receptor or estrogen receptor-beta blockade alters DHEA-, DHT-, and E(2)-induced proliferation and PSA production in human prostate cancer cells.	2007-08-01	17503469
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.	2007-07-17	17606915
Labeling and identification of LNCaP cell surface proteins: a pilot study.	2007-06-15	17440980
Androgen regulation of aldehyde dehydrogenase 1A3 (ALDH1A3) in the androgen-responsive human prostate cancer cell line LNCaP.	2007-06	17526768
Reactive oxygen species mediate androgen receptor- and serum starvation-elicited downstream signaling of ADAM9 expression in human prostate cancer cells.	2007-05-15	17342749
Nuclear and membrane receptor-mediated signalling pathways modulate polyamine biosynthesis and interconversion.	2007-04	17371283
Ligand-specific dynamics of the androgen receptor at its response element in living cells.	2007-03	17189428
Androgen induces adaptation to oxidative stress in prostate cancer: implications for treatment with radiation therapy.	2007-01	17325745

Patents

Sample Use Guides

In Vivo Use Guide

one 50 mg tablet once daily (morning or evening), with or without food

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 22:49:46 GMT 2025` Edited by `admin` on `Mon Mar 31 22:49:46 GMT 2025`
Record UNII	Z9DL98I0AF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BICALUTAMIDE, (R)-

Common Name

English

(R)-CASODEX

Preferred 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-BICALUTAMIDE

Common Name

English

Code System Code Type Description

CAS

113299-40-4