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Bicalutamide Produkt Beschreibung

Bicalutamide Struktur
90357-06-5
CAS-Nr.
90357-06-5
Englisch Name:
Bicalutamide
Synonyma:
25mg;CASODEX;Cosudex;ZD 176334;ICI-176334;BICALUTAMIDE;Bicaiutamide;Bi Carew aMine;BicalutaMide API;Bicalutamide&Int.
CBNumber:
CB7457827
Summenformel:
C18H14F4N2O4S
Molgewicht:
430.3733728
MOL-Datei:
90357-06-5.mol

Bicalutamide Eigenschaften

Schmelzpunkt:
191-193°C
storage temp. 
Store at RT
Löslichkeit
DMSO: >5mg/mL
Aggregatzustand
powder
maximale Wellenlänge (λmax)
270nm(CH3CN)(lit.)
Merck 
14,1200
CAS Datenbank
90357-06-5(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xi
R-Sätze: 36/37/38
S-Sätze: 26-36-24/25
RIDADR  3077
WGK Germany  3
RTECS-Nr. TX1413500
HazardClass  9
PackingGroup  III
HS Code  29242995
Giftige Stoffe Daten 90357-06-5(Hazardous Substances Data)
Bildanzeige (GHS)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
H360 Kann die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Fertility (Fruchtbarkeit) Kategorie 1 Achtung
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Bicalutamide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Beschreibung

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.

Chemische Eigenschaften

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.

Verwenden

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

Verwenden

adrenocortical suppressant, antineoplastic, steroid biosynthesis inhibitor

Definition

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

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.

Trademarks

Casodex (AstraZeneca).

Allgemeine Beschreibung

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.

Biologische Aktivität

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 .

Pharmakologie

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.

Nebenwirkungen

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).

Bicalutamide Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Bicalutamide Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 369)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19918 60
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 661 60
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30001 58
GIHI CHEMICALS CO.,LIMITED
08657186217390
sales@gihichemicals.com CHINA 308 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23980 58
QUALITY CONTROL CHEMICALS INC.
(323) 306-3136
(626) 453-0409 orders@qcchemical.com United States 8407 58
hdzhl biotechnology co., ltd
86-13032617415
sales@luchibiology.com CHINA 1178 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6372 58

90357-06-5()Verwandte Suche:


  • (+-)--2-hydroxy-2-methyl
  • propanamide,n-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)
  • ICI-176334
  • CASODEX
  • 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 (Subject to patent free)
  • 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
  • (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-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(Casodex)
  • BicalutaMide API
  • 25mg
  • 90357-06-5
  • 90357-06-6
  • C17H14F4N2O4S
  • C18H14N2O4F4S
  • API
  • MODRASTANE
  • Active Pharmaceutical Ingredients
  • Antiandrogen
  • Antineoplastic (Hormonal)
  • anti-neoplastic
  • Aromatics
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Sulfur & Selenium Compounds
  • API's
  • -
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