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Anastrozole

Anastrozole Struktur
120511-73-1
CAS-Nr.
120511-73-1
Englisch Name:
Anastrozole
Synonyma:
ARIMIDEX;ANASTRAZOLE;Anastrozol;MDPT;zd;Anatrozole;Arimidex(Anastrozole);ZD-1033;Anastrol;Astrozole
CBNumber:
CB3121715
Summenformel:
C17H19N5
Molgewicht:
293.37
MOL-Datei:
120511-73-1.mol

Anastrozole Eigenschaften

Schmelzpunkt:
81-82°C
Siedepunkt:
469.7±55.0 °C(Predicted)
Dichte
1.08±0.1 g/cm3(Predicted)
storage temp. 
room temp
L?slichkeit
DMSO: soluble40mg/mL
pka
2.62±0.10(Predicted)
Aggregatzustand
solid
Farbe
White to off-white
BCS Class
1 (LogP), 3 (CLogP)
InChI
InChI=1S/C17H19N5/c1-16(2,9-18)14-5-13(8-22-12-20-11-21-22)6-15(7-14)17(3,4)10-19/h5-7,11-12H,8H2,1-4H3
InChIKey
YBBLVLTVTVSKRW-UHFFFAOYSA-N
SMILES
C(#N)C(C1=CC(CN2C=NC=N2)=CC(C(C#N)(C)C)=C1)(C)C
CAS Datenbank
120511-73-1(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi,Xn
R-S?tze: 36/37/38-22-61-60
S-S?tze: 26-37/39
RIDADR  3249
WGK Germany  3
RTECS-Nr. CZ1465000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29339980
Giftige Stoffe Daten 120511-73-1(Hazardous Substances Data)
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P308+P313 BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.

Anastrozole Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

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

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

Chemische Eigenschaften

Crystalline Solid. soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide. The solubility of anastrozole in these solvents is approximately 20, 13, and 14 mg/ml.

Verwenden

Anastrozole is a nonsteroidal inhibitor of aromatase which effectively blocks estrogen synthesis in postmenopausal women and is used as therapy of estrogen receptor positive breast cancer. Anastrozole has been associated with a low rate of serum enzyme elevations during therapy and rare instances of clinically apparent liver injury.

synthetische

synthesis of anastrozole can be realized in four steps based on 3,5-bis(bromomethyl)toluene. Starting with a S N 2 displacement using potassium nitrile and tetrabutylammonium bromide as a phase transfer catalyst to give bis-nitrile compound. Bis-nitrile compound formed undergoes deprotonation with NaH and methylated afterwards with methyl iodide to give bis-dimethyated product.Product undergoes radical substitution reaction following the Wohl-Ziegler reaction using N-bromosuccinamide and benzoyl peroxide as the radical initiator.In the final step, benzylbromide undergoes SN2 displacement with sodium triazole to give anastrozole.
synthesis of anastrozole

Application

Anastrozole (aromatase inhibitor) has been used:
as a positive control in DNA fragmentation (ladder) assay
to investigate its effects along with extra virgin olive oil and its major fatty acid component (omega-9 OA) in estrogen receptor positive mammary adenocarcinoma cells
to study its effects on viability, cell proliferation and apoptosis in Glioblastoma multiforme model in vivo

Definition

ChEBI: Anastrozole is a 1,2,4-triazole compound having a 3,5-bis(2-cyano-2-propyl)benzyl group at the 1-position. It has a role as an antineoplastic agent and an EC 1.14.14.14 (aromatase) inhibitor. It is a member of triazoles and a nitrile.

Allgemeine Beschreibung

Anastrozole(120511-73-1) is a non-steroidal and expensive drug marketed under the trade name Arimidex. It was the first specific aromatase inhibitor approved in theUnited States. It is indicated for first-line treatment of postmenopausalwomen with advanced or metastatic breast cancer,for second-line treatment of postmenopausal patientswith advanced breast cancer who have had disease progressionfollowing tamoxifen therapy, and for adjuvant treatmentof women with early breast cancer. Patients who did not respondto tamoxifen therapy rarely respond to anastrozole.

Biologische Aktivit?t

Potent and highly selective aromatase (CYP19) inhibitor (IC 50 = 15nM) that has no discernible effect on adrenocorticoid hormone synthesis. Reduces plasma estrogen levels and exhibits antitumor activity in vivo . Orally active.

Mechanism of action

Anastrozole, a benzyltriazole derivative, competes with the natural s ubstrate for binding to the active site of the aromatase. The mechanism of enzyme inhibition resides in the coordination of the triazole ring with the hemeiron atom of the aromatase enzyme complex. This coordination ultimately prevents arom atization of androgens into estrogens and, therefore, deprives the tumor of estrogen. This effect is reversible. In the presence of anastrozole, estradiol levels are reduced to undetectable levels, with no adverse effects on levels of any other horm one, including cortisol and aldosterone. Maximal estrogen suppression is produced by a 1mg dose. Estrogen suppression is maintained for up to 6 days after discontinuing anastrozole.

Pharmakokinetik

Anastrozole is well absorbed orally, with biliary elimination as its primary route (85%) and an elimination half-life of approxim ately 50 hours. Approximately 60% of an oral dose is m etabolized in the liver by N-dealkylation, hydroxylation, and glucuronidation to inactive triazole metabolites.

Clinical Use

Anastrozole is a potent and highly selective, nonsteroidal aromatase inhibitor utilized in the treatment of advanced breast cancer that is horm one-responsive. It is considered to be second-line therapy (after tamoxifen) in the treatment of postm enopaus al breast cancer.

Nebenwirkungen

The most common anastrozole side effects are related to lower estrogen levels in the body. They include hot flashes, nausea and vomiting, and mood changes. Anastrozole could cause your bones to thin, which raises your risk of osteoporosis. It can also cause high cholesterol.

Environmental Fate

Anastrozole is classified as readily biodegradable and is moderately mobile in soils. The measured octanol-water partition coefficient is low, therefore anastrozole is not predicted to bioaccumulate in aquatic organisms.

Einzelnachweise

[1] DUKESM. The preclinical pharmacology of “Arimidex” (anastrozole; ZD1033)–a potent, selective aromatase inhibitor.[J]. Journal of Steroid Biochemistry and Molecular Biology, 1996. DOI:10.1016/0960-0760(96)00064-7.
[2] U B. Anastrozole: a new addition to the armamentarium against advanced breast cancer.[J]. American Journal of Clinical Oncology-Cancer Clinical Trials, 1998. DOI:10.1097/00000421-199804000-00014.
[3] L?NNINGP E   DowsettM  GeislerJ. Pharmacological and clinical profile of anastrozole.[J]. Breast Cancer Research and Treatment, 1998. DOI:10.1023/a:1006000806630.
[4] HOZUMIYASUO. Effects of anastrozole on lipid metabolism compared with tamoxifen in rats.[J]. Breast Cancer Research and Treatment, 2002. DOI:10.1023/a:1020571617274.

Anastrozole Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Anastrozole Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 678)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Wuhan Fortuna Chemical Co., Ltd
+86-027-59207850
info@fortunachem.com China 5986 58
Shenzhen Monkono Technology Co.,Ltd
+86-17063441314
sansbiotech@outlook.com China 677 58
Wuhan Cell Pharmaceutical Co., Ltd
+86-13129979210 +86-13129979210
sales@cellwh.com China 376 58
Doublewin Biological Technology Co., Ltd
+86-19971437628
doublewin-bella@nandrolonesteroid.com China 97 58
qingdao future trading Co., Ltd
+86-13335044410 +86-13335044410
cui56813@163.com China 110 58
Guangdong Tuoyuan Biotechnology Co., LTD
+85267545345
sterodschina@gmail.com China 152 58
Hangzhou Hyper Chemicals Limited
+86-0086-57187702781 +8613675893055
info@hyper-chem.com China 295 58
Shaanxi Xianhe Biotech Co., Ltd
+8617709210191
Jerry@xhobio.com China 484 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578
sales@hbmojin.com China 12795 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177
peter@yan-xi.com China 5858 58

120511-73-1()Verwandte Suche:


  • ICI-D-1033
  • 1-[3,5-DI-(1-METHYL-1-CYANO)-ETHYL]-BENZYL-1,2,4-TRIAZOLE
  • α,α,α’,α'-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-benzenediacetonitrile
  • 2-[3-(2-Cyanopropan-2-yl)-5-(1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropanenitrile
  • α1,α1,α3,α3-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-benzenediacetonitrile
  • Anastrozole(AriMidex)
  • Anastrozole (200 mg)
  • 2-[3-(1-cyano-1-Methylethyl)-5-(1H-1,2,4-triazol-1-ylMethyl)phenyl]-2-Methylpropanenitrile
  • Anastrozole IMpurity B
  • 2"-[5-(1H-1
  • 3-Phenylene]bis(2-methyl-propiononitrile
  • 4-Triazol-1-ylmethyl)-1
  • Anastrolozole
  • alpha,alpha,alpha',alpha'-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-benzenediacetonitrile
  • Anastrozole USP
  • 2,2'-(5-((1H-1,2,4-Triazol-1-yl)Methyl)-1,3-phenylene)bis(2-Methylpropanenitrile)
  • 3-tetraMethyl-5-(1H-1,2,4-triazol-1-ylMethyl)-
  • ANASTROZOLE
  • tetramethyl-5-(1h-1,2,4-triazol-1ylmethyl) 1,3-benzenediacetionitrile
  • ZD-1033
  • ZD-1033, ICI-D-1033, Arimidex
  • 2-[3-(2-Cyano-2-propyl)-5-(1,2,4-triazol-1-ylmethyl)phenyl]-2-methylpropiononitrile
  • 1,3-benzenediacetonitrile, alpha,alpha,alpha',alpha'-tetramethyl- 5-(1h-1,2,4-triazol-1-ylmethyl)-
  • 1,3-benzenediacetonitrile,alpha,alpha,alpha’,alpha’-tetramethyl-5-(1h-1,2,4-t
  • riazol-1-ylmethyl)-
  • a1,a1,a3,a3-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-benzenediacetonitrile
  • Anastrol
  • a,a,a′,a′-Tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-1,3-benzenediacetonitrile
  • Anastrozole, >=98%
  • Letrozole:4,4,-(dinitrilephenyl)methyl 1-yl -1,2,4-triazol
  • Astrozole
  • MDPT mdpt crystal kf-wang(at)kf-chem.com
  • 1,3-Benzenediacetonitrile, α1,α1,α3,α3-tetramethyl-5-(1H-1,2,4-triazol-1-ylmethyl)-
  • Arimidex 120511-73-1
  • Anastrozole CRS
  • Anastrozole USP/EP/BP
  • Nolvadex (Tamoxifen Citrate )
  • Powder Anastrozole
  • AnastrazoleAPI & intermediates
  • Anastrozole (ZD1033)
  • Anastrozole (Arimidex, ANA)-1 gram(21)
  • AnastrozoleQ: What is Anastrozole Q: What is the CAS Number of Anastrozole Q: What is the storage condition of Anastrozole Q: What are the applications of Anastrozole
  • Anastrozole (1034807)
  • ARIMIDEX
  • ANASTRAZOLE
  • zd
  • Anastrozol
  • Anatrozole
  • MDPT
  • Arimidex(Anastrozole)
  • 1H-Pyrrole-2,5-dione,7-methyl-
  • Anastrozole / Arimidex CAS:120511-73-1
  • Anatrazole
  • Anastrozole Mono Bromo
  • CCRIS 9352
  • HSDB 7462
  • 120511-73-1
  • 120511-12-1
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