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Bicalutamide

CAS No.
90357-06-5
Chemical Name:
Bicalutamide
Synonyms
CASODEX;25mg;109734;Cosudex;ZD 176334;ICI-176334;90357-06-5;Bicalutamid;BICALUTAMIDE;Bicaiutamide
CBNumber:
CB7457827
Molecular Formula:
C18H14F4N2O4S
Molecular Weight:
430.37
MDL Number:
MFCD00869971
MOL File:
90357-06-5.mol
MSDS File:
SDS

Bicalutamide Properties

Melting point 191-193°C
Boiling point 650.3±55.0 °C(Predicted)
Density 1.52±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >5mg/mL
pka 11.49±0.29(Predicted)
form powder
color White to Off-White
λmax 270nm(CH3CN)(lit.)
Merck 14,1200
CAS DataBase Reference 90357-06-5(CAS DataBase Reference)
FDA UNII A0Z3NAU9DP
NCI Dictionary of Cancer Terms bicalutamide; Casodex
NCI Drug Dictionary bicalutamide
ATC code L02BB03

Pharmacokinetic data

Protein binding 96%
Excreted unchanged in urine Approx 50%
Biological half-life 6-7 days / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H315-H319-H335-H360
Precautionary statements  P261-P305+P351+P338-P201-P202-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P308+P313-P405-P501
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-24/25
RIDADR  3077
WGK Germany  3
RTECS  TX1413500
HazardClass  9
PackingGroup  III
HS Code  29242995

Bicalutamide price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B9061 Bicalutamide (CDX) ≥98% (HPLC), powder 90357-06-5 10mg $131 2022-05-15 Buy
Sigma-Aldrich BP1115 Bicalutamide British Pharmacopoeia (BP) Reference Standard 90357-06-5 100MG $222 2022-05-15 Buy
Sigma-Aldrich 1071202 Bicalutamide United States Pharmacopeia (USP) Reference Standard 90357-06-5 200mg $400 2022-05-15 Buy
TCI Chemical B3206 Bicalutamide >98.0%(HPLC)(N) 90357-06-5 1g $205 2022-04-27 Buy
TCI Chemical B3206 Bicalutamide >98.0%(HPLC)(N) 90357-06-5 200mg $70 2022-04-27 Buy
Product number Packaging Price Buy
B9061 10mg $131 Buy
BP1115 100MG $222 Buy
1071202 200mg $400 Buy
B3206 1g $205 Buy
B3206 200mg $70 Buy

Bicalutamide Chemical Properties,Uses,Production

Description

Bicalutamide was launched in the United Kingdom, its first worldwide market, for the treatment of advanced prostate cancer in combination with an LHRH analog or surgical castration. A non-steroidal, peripherally selective antiandrogen, bicalutamide inhibits the action of dihydrotestosterone and testosterone at target sites by competitive binding to the cytosolic androgen receptor. It was reportedly well tolerated with no significant cardiovascular and metabolic side effects due to the benefit of lacking any steroid activity. The efficacy of bicalutamide as a monotherapy has been demonstrated clinically. Promising response rates were also reported in treating colorectal, breast, pancreas and non-small cell lung cancers.

Chemical Properties

Off-White Crystalline Solid

Originator

Zeneca (United Kingdom)

History

Bicalutamide was discovered in the 1980s by Tucker et al. at Imperial Chemical Industries (now AstraZeneca). Based on previous works on flutamide, key structural features required for a strong anti-androgenic activity include the presence of an electron-poor aromatic ring, attached to an amide moiety. Electron-withdrawing groups at the para and the meta position of the anilide ring are beneficial for the anti-androgenic activity as compared to monosubstituted derivatives.As far as the meta position is concerned, a chloro or trifluoromethyl substituent is the best choice. Nitro and cyano groups are the best substituents at the para position. Replacement of themethyl group at the tertiary carbinol center by a trifluoromethyl group resulted in compounds with agonistic activity. In contrast to flutamide, the amide moiety of bicalutamide was extended by a sulfur linker with a second aromatic portion. The sulfanyl, sulfinyl, and sulfonyl analogues showed the same activity.The sulfanyl group was found to be oxidized to the active metabolite sulfonyl, thus indicating the sulfonyl derivative as the biologically active entity. An unsubstituted phenylsulfonyl moiety at the eastern part, or corresponding derivatives with small substituents such as fluoro at the para position, seemed to be the best in terms of anti-androgenic activity.

Uses

adrenocortical suppressant, antineoplastic, steroid biosynthesis inhibitor

Uses

Non-steroidal peripherally active antiandrogen. Used as an antiandrogen, antineoplastic (hormonal)

Uses

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Uses

Bicalutamide (CDX) has been used as an androgen receptor (AR) antagonist in prostate, bladder cancer cell lines and human fetal skeletal muscle cells. It has also been used as a supplement in RPMI 1640 for culturing androgen-independent LNCaP (LNCaP-AI) cell line.

Indications

Bicalutamide was the third nonsteroidal anti-androgen that was used for the treatment of prostate cancer. Flutamide, although effective in the treatment of prostate cancer, is a pure antagonist that also affects the hypothalamus pituitary axis, thus preventing the negative feedback mechanism of androgen. Consequently, the production of LH is increased, which subsequently stimulates the synthesis of testosterone, counteracting the effectiveness of the anti-androgen. Furthermore, the half-life of the active metabolite of flutamide, hydroxyflutamide, is fairly short, and a dosing scheme of 250 mg three times daily is therefore required. The main adverse effects reported for flutamide are gynecomastia, diarrhea, and reversible liver abnormalities. Nilutamide has a longer half-life than flutamide and therefore can be administered once daily. Adverse events reported include problems with light/dark adaptation and interstitial pneumonitis. The goal that ultimately led to the discovery of bicalutamide was the identification of a novel peripherally selective anti-androgen with longer half-life than flutamide and with better tolerability as compared to both, flutamide and nilutamide.

Definition

ChEBI: Bicalutamide is a sulfone that is an oral non-steroidal antiandrogen used in the treatment of prostate cancer and hirsutism.

brand name

Casodex (AstraZeneca).

Therapeutic Function

Antitumor

General Description

Bicalutamide, N-4-cyano-3-(trifluoromethyl)phenyl-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-propanamide (Casodex), is more potent than flutamideand has a much longer half-life (5.9 days vs. 6 hoursfor hydroxyflutamide). Because of the longer half-life, bicalutamideis used for once-a-day (50 mg) treatment of advancedprostate cancer. Bicalutamide is available as aracemic mixture, but both animal and human studies withthe AR show that the R-enantiomer has higher affinity forthe AR than the S-enantiomer.

Biological Activity

Orally active non-steroidal androgen receptor antagonist (IC 50 = 190 nM). Displays peripheral selectivity and does not effect serum levels of LH and testosterone. Exhibits potent anticancer activity in vivo .

Biochem/physiol Actions

Bicalutamide (CDX) is a non-steriodal Androgen Receptor (AR) antagonist and a pure antiandrogen. It acts via balancing histone acetylation/deacetylation and recruitment of coregulators. Bicalutamide (CDX) abolishes androgen-mediated expression. For example, MMP13 upregulation in prostate cancer, PLZF (promyelocytic leukemia zinc finger protein), and GADD45γ (growth arrest and DNA damage inducible, gamma). Bicalutamide (CDX) is inhibited by non-genomic, transcription-independent stimulation of PI3K/AKT phosphorylation by androgens.

Mechanism of action

Bicalutamide is a racemate and its antiandrogenic activity resides almost exclusively in the (R)-enantiomer, which has an approximately fourfold higher affinity for the prostate AR than hydroxyflutamide does. The (S)-enantiomer has no antiandrogenic activity. (R)-Bicalutamide is slowly absorbed, but absorption is unaffected by food. It has a long plasma elimination half-life of 1 week and accumulates approximately 10 times in plasma during daily administration. (S)-Bicalutamide is much more rapidly absorbed and cleared from plasma. At steady state, the plasma levels of (R)-bicalutamide are 100 times higher than those of (S)-bicalutamide. Although mild to moderate hepatic impairment does not affect pharmacokinetics, evidence suggests slower elimination of (R)-bicalutamide in subjects with severe hepatic impairment.

Pharmacology

Bicalutamide is a competitive AR antagonist, which shows in vitro a lower affinity for the AR as compared to the synthetic androgen R1881 as well as the natural DHT. However it displays a fourfold higher affinity as compared to hydroxyflutamide as assessed by a binding assay. Bicalutamide inhibits the growth of the LNCaP/FGC prostate carcinoma cell line, in which hydroxyflutamide was not effective at all. In vivo anti-androgenic activity of bicalutamide was confirmed by dose-dependent weight reduction of the seminal vesicles and ventrical prostate gland in rats, followed by an antitumor efficacy using Dunning R3327-GH prostate carcinomas in intact and castrated rats.A full overview on all clinical trials including bicalutamide would be out of scope.

Clinical Use

Bicalutamide is a nonsteroidal pure antiandrogen given at a dosage of 150 mg once daily as monotherapy for the treatment of early (localized or locally advanced) nonmetastatic prostate cancer. It also can be used at a lower dosage in combination with a LHRH analogue or surgical castration for the treatment of advanced prostate cancer.

Side effects

Bicalutamide was well tolerated in monotherapy as well as in combination. No dose-related increase in adverse events was reported. Adverse events were partially due to pharmacological effects of an anti-androgen, which include gynecomastia, breast tenderness, and hot flushes. Other non-pharmacological adverse events, with incidence equal or higher than 10% were, for example, constipation, nausea, diarrhea, asthenia, pain, and infection. The frequency of non-pharmacological adverse events was in the same range as reported for comparator in clinical trials. In contrast to flutamide, the incidence of diarrhea and liver abnormalities was much lower for bicalutamide. As compared with castration, monotherapy with bicalutamide allowed patients to maintain libido and have better physical capacity, thus resulting in better quality of life.Based on the results of the clinical trials mentioned above, bicalutamide was first approved in 1995. Bicalutamide is indicated for the use in combination with an LHRH-A analogue for metastatic prostate carcinoma (50mg).

Drug interactions

Potentially hazardous interactions with other drugs
Anticoagulants: possibly enhances anticoagulant effect of coumarins.
Lipid lowering agents: separate lomitapide and bicalutamide administration by 12 hours. See 'Other information'.

Metabolism

Bicalutamide metabolites are excreted almost equally in urine and feces, with little or no unchanged drug excreted in urine. Unmetabolized drug predominates in the plasma. Following oral administration, the racemate displays stereoselective oxidative metabolism of its (R)-enantiomer, with an elimination half-life of approximately 6 days. (R)-Bicalutamide is cleared almost exclusively by CYP3A4-mediated metabolism, but glucuronidation is the predominant metabolic route for (S)-bicalutamide.

Bicalutamide Preparation Products And Raw materials

Global( 490)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Lingding Biological Technology Co., Ltd
+86-19933155420 +86-19933155420 sales1@hbldbiotech.com China 940 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806 sales@capotchem.com China 19995 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 22021 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 fandachem@gmail.com China 9396 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com sales03@shyrchem.com CHINA 739 60
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29960 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293 sales@sdzschem.com CHINA 2940 58
GIHI CHEMICALS CO.,LIMITED
08657186217390 sales@gihichemicals.com CHINA 310 58
Xiamen AmoyChem Co., Ltd
592-6051114 sales@amoychem.com CHINA 6369 58
Hubei xin bonus chemical co. LTD
86-13657291602 linda@hubeijusheng.com CHINA 23034 58

View Lastest Price from Bicalutamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-06-21 Bicalutamide
90357-06-5
US $2.00-12.00 / kg 1kg 0.99 20tons Hebei Ruiyao Biotechnology Co. Ltd
2022-03-11 Bicalutamide
90357-06-5
US $1.00 / kg 1kg 99% 2000tons/year Wuhan Dujiang Industrial Co., Ltd.
2022-02-25 Bicalutamide
90357-06-5
US $1.00 / g 10g 99.5% 1000kg Guangzhou Biocar Biotechnology Co.,Ltd.
  • Bicalutamide
    90357-06-5
  • US $2.00-12.00 / kg
  • 0.99
  • Hebei Ruiyao Biotechnology Co. Ltd
  • Bicalutamide
    90357-06-5
  • US $1.00 / kg
  • 99%
  • Wuhan Dujiang Industrial Co., Ltd.
  • Bicalutamide
    90357-06-5
  • US $1.00 / g
  • 99.5%
  • Guangzhou Biocar Biotechnology Co.,Ltd.
(+-)--2-hydroxy-2-methyl propanamide,n-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl) Bicalutamide (Subject to patent free) ICI-176334 BICALUTAMIDE N-[(4-CYANO-3-TRIFLUOROMETHYL)PHENYL]-3-[(4-FLUOROPHENYL)SULFONYL]-2-HYDROXY-2-METHYLPROPANAMIDE N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-3-[(4-FLUOROPHENYL)SULFONYL]-2-HYDROXY-2-METHYLPROPIONANILIDE Bicalutamide&Int. ICI-176334, Casodex, N-[4-Cyano-3-trifluoromethyl)phenyl]- 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide BicalutaMide iMpurity Bi Carew aMine BicalutaMide SynonyMs N-[4-Cyano-3-(trifluoroMethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-Methyl-propanaMide Bicalutamide for system suitability Bicalutamide, >=99% N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methylpropanami 4-cyano-3-trifluoromethyl-N-(3-p-fluorophenylsulfonyl-2-hydroxy-2-methylpropionyl)aniline (bicalutamide) 4''-CYANO-3-[(4-FLUROPHENYL)SULFONYL]-2-HYDROXY-3-METHYL-3''-(TRIFUROMETHYL)-PROPIONANILIDE (+-)-4'-Cyano-α,α,α-trifluoro-3-[(p-fluorophenyl)sulfonyl]-2-methyl-m-lactotoluidide Cosudex Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl- Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (+-)- Bicaiutamide Bicalutamide(CDX) Bicalutamide (200 mg) BicalutaMide API 25MG/100MG/100G BicalutaMide(Casodex) (2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methylpropanamidenone ZD 176334 4-cyano-3-trifluoromethyl-N-(3-p-fluorophenylsulfonyl-2-hydroxy 109734 Bicalutamide, ≥98% (HPLC), powder Bicalutamide CRS Bicalutamide for system suitability CRS Bicalutamide > Bicalutamid N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropionamide Bicalutamide USP/EP/BP Bicalutamide crude Bicaultamide Bicalutamide--Manufacturer BicalutamideQ: What is Bicalutamide Q: What is the CAS Number of Bicalutamide Q: What is the storage condition of Bicalutamide Q: What are the applications of Bicalutamide Bicalutamide D5Q: What is Bicalutamide D5 Q: What is the CAS Number of Bicalutamide D5 Q: What is the storage condition of Bicalutamide D5 Q: What are the applications of Bicalutamide D5 Bicalutamide (1071202) CASODEX 25mg 90357-06-5 90357-06-5 90357-06-6 C17H14F4N2O4S C18H14N2O4F4S MODRASTANE API Aromatics Intermediates & Fine Chemicals Pharmaceuticals Sulfur & Selenium Compounds API's