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Tamoxifen

Tamoxifen Struktur
10540-29-1
CAS-Nr.
10540-29-1
Bezeichnung:
Tamoxifen
Englisch Name:
Tamoxifen
Synonyma:
Novaldex;TAMOXIFEN BASE;Mammaton;amoxifen;z-tamoxifen;Genox;C07108;Tamoxen;ici47699;IC|47699
CBNumber:
CB9438781
Summenformel:
C26H29NO
Molgewicht:
371.51
MOL-Datei:
10540-29-1.mol

Tamoxifen Eigenschaften

Schmelzpunkt:
97-98 °C(lit.)
Siedepunkt:
501.18°C (rough estimate)
Dichte
1.0630 (rough estimate)
Dampfdruck
0Pa at 25℃
Brechungsindex
1.6000 (estimate)
storage temp. 
2-8°C
L?slichkeit
H2O: insoluble <0.1% at 20°C
pka
pKa 8.71(H2O t = 25 I = 0.025) (Uncertain)
Aggregatzustand
Solid
Farbe
Crystals from pet ether
Wasserl?slichkeit
Insoluble in water. Soluble in methanol, ethanol, propanol or propylene glycol.Soluble in dimethyl sulfoxide, dichloromethane and ethanol. Insoluble in water.
Merck 
13,9137
Stabilit?t:
Light Sensitive
InChI
1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
InChIKey
NKANXQFJJICGDU-QPLCGJKRSA-N
SMILES
CC\C(c1ccccc1)=C(/c2ccccc2)c3ccc(OCCN(C)C)cc3
LogP
6.3 at 20℃
CAS Datenbank
10540-29-1(CAS DataBase Reference)
IARC
1 (Vol. 66, 100A) 2012
EPA chemische Informationen
Tamoxifen (10540-29-1)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher T,Xi
R-S?tze: 45-60-61-64-36/37/38
S-S?tze: 53-45-36-26
WGK Germany  3
RTECS-Nr. KR5919600
HS Code  29221990
Speicherklasse 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard Classifications Aquatic Acute 1
Aquatic Chronic 1
Carc. 1A
Repr. 1B
Giftige Stoffe Daten 10540-29-1(Hazardous Substances Data)
Toxizit?t LD50 orl-rat: 4100 mg/kg DRFUD4 9,186,84
Bildanzeige (GHS) Health Hazard (GHS08)Environment (GHS09)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H350 Kann Krebs verursachen. Karzinogenit?t Kategorie 1A Achtung
H360 Kann die Fruchtbarkeit beeintr?chtigen oder das Kind im Mutterleib sch?digen. Fertility (Fruchtbarkeit) Kategorie 1 Achtung
H410 Sehr giftig für Wasserorganismen mit langfristiger Wirkung. Langfristig (chronisch) gew?ssergef?hrdend Kategorie 1 Warnung P273, P391, P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P273 Freisetzung in die Umwelt vermeiden.
P308+P313 BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.

Tamoxifen Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R45:Kann Krebs erzeugen.
R60:Kann die Fortpflanzungsf?higkeit beeintr?chtigen.
R61:Kann das Kind im Mutterleib sch?digen.
R64:Kann S?uglinge über die Muttermilch sch?digen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Beschreibung

In 1966, ICI Pharmaceuticals (now AstraZeneca) first synthesized tamoxifen in the hope of developing a morning-after contraceptive pill. The UK patent for this compound was in place in 1962, whereas the US patent was repeatedly denied until the 1980s. Tamoxifen was approved for a fertility treatment but it was not proven as useful in regulating human contraception. Even though there was a link between estrogen and breast cancer, developing a cancer treatment was not a priority at the time. In 1971, the first clinical study showed a convincing effect of tamoxifen in treating advanced breast cancer. From 1971 to 1977, this drug was neither clinically nor financially remarkable. In 1980s, however, publications first showed that tamoxifen, in addition to chemotherapy, improved survival for patients with early stage breast cancer. In 1998, the meta-analysis by the Oxford-based Early Breast Cancer Trialists’ Collaborative Group showed that tamoxifen did indeed save lives in early breast cancer. In 2001, tamoxifen sales were over $1.024 billion. Since the expiration of the patent in 2002, it is now widely available as a generic drug. By 2004, tamoxifen was the best selling hormonal drug for the treatment of breast cancer.

Chemische Eigenschaften

White Crystalline Solid

History

Tamoxifen (trade name: Nolvadex) was a famous "accidental discovery." It wasn't originally designed for cancer treatment, but was synthesized in 1962 by Dora Richardson, a chemist at Imperial Chemical Industries (ICI), initially intended as a contraceptive, codenamed ICI 46,474. However, in animal studies, it exhibited anti-estrogenic properties and was repositioned as a fertility drug, but was ultimately abandoned due to poor efficacy. It wasn't until the early 1970s, thanks to efforts by researchers such as V. Craig Jordan, that the compound was re-evaluated for its potential efficacy in estrogen receptor-positive (ER+) breast cancer and identified as a selective estrogen receptor modulator (SERM) capable of blocking the stimulatory effects of estrogen on breast cancer cells. Based on early clinical trial results, tamoxifen was approved by the U.S. FDA on December 31, 1977, for the treatment of advanced breast cancer in postmenopausal women. Subsequently, through large-scale adjuvant therapy trials (such as NSABP B-14), it established its cornerstone status in adjuvant therapy for early breast cancer, completely changing the landscape of breast cancer treatment and becoming one of the most widely used anticancer drugs in the world.

Verwenden

A nonsteroidal estrogen antagonist of interest in the treatment of some forms of breast cancer. Tamoxifen is a Protein Kinase C inhibitor, and induces apoptosis in human malignant glioma cell lines

Indications

Tamoxifen (Nolvadex) is a synthetic antiestrogen used in the treatment of breast cancer. Normally, estrogens act by binding to a cytoplasmic protein receptor, and the resulting hormone–receptor complex is then translocated into the nucleus, where it induces the synthesis of ribosomal RNA (rRNA) and messenger RNA (mRNA) at specific sites on the DNA of the target cell. Tamoxifen also avidly binds to estrogen receptors and competes with endogenous estrogens for these critical sites. The drug–receptor complex has little or no estrogen agonist activity.Tamoxifen directly inhibits growth of human breast cancer cells that contain estrogen receptors but has little effect on cells without such receptors.

Weltgesundheitsorganisation (WHO)

Tamoxifen is an anti-estrogen agent used mainly to treat breast cancer. Tamoxifen is listed in the WHO Model List of Essential Drugs.

Allgemeine Beschreibung

Tamoxifen is a selective estrogen response modifier (SERM), protein kinase C inhibitor and anti-angiogenetic factor. Tamoxifen is a prodrug that is metabolized to active metabolites 4-hydroxytamoxifen (4-OHT) and endoxifen by cytochrome P450 isoforms CYP2D6 and CYP3A4. In breast cancer, the gene repressor activity of tamoxifen against ERBB2 is dependent upon PAX2. Blocks estradiol-stimulated VEGF production in breast tumor cells.

Mechanism of action

Tamoxifen is slowly absorbed, and maximum serum levels are achieved 4 to 7 hours after oral administration. The drug is concentrated in estrogen target tissues, such as the ovaries, uterus, vaginal epithelium, and breasts. Hydroxylation and glucuronidation of the aromatic rings are the major pathways of metabolism; excretion occurs primarily in the feces.

Pharmakokinetik

Circulating levels of the demethylated metabolite at steady state are up to twice the level of the parent drug, because the elimination half-life of N-demethyl tamoxifen is 14 days, compared with 7 days for tamoxifen. Tamoxifen demonstrates only weak estrogenic effects at several sites, including the endometrium and bone, and on the lipid profile. Tamoxifen undergoes rapid N-dem ethylation to its major metabolite, N-dem ethyltamoxifen, by CYP3A4 and via CYP2D6 to its minor metabolite, 4-hydroxytam oxifen. Evidence suggests that 4-hydroxytamoxifen is the active metabolite of tamoxifen, with a higher binding affinity than the parent drug for the ER

Clinical Use

Tamoxifen is a SERM that is used as an antiestrogen in the treatment of estrogen-dependent breas Tcancer following prim ary treatment (c hemotherapy and/or surgery).

Nebenwirkungen

Tamoxifen administration is associated with few toxic side effects, most frequently hot flashes (in 10–20% of patients) and occasionally vaginal dryness or discharge. Mild nausea, exacerbation of bone pain, and hypercalcemia may occur.

Sicherheitsprofil

Confirmed human carcinogen. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by an unspecified route: nausea or vomiting, leukopenia, thrombocytopenia, and skin changes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Carcinogenicity

Tamoxifen is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.

Tamoxifen Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Tamoxifen Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 422)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Shandong Huisheng Import & Export Co., Ltd.
+86-13176845580
da@zhongda-biotech.com China 232 58
Hubei KDG Web Science&Technology Co., Ltd
+8618672314556
sales@kdg-tech.com China 933 58
Anhui Zhongda Biotechnology Co., Ltd
+8619956560829
justine@zhongda-biotech.com China 286 58
Anhui Ruihan Technology Co., Ltd
+8617756083858
daisy@anhuiruihan.com China 973 58
Hebei Anlijie Biotechnology Co., Ltd
+8619031013551
ably@aljbio.com China 144 58
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+undefined17712220823
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+8618873369619
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ARCTIC EXPORTS INC
+1-3026880818 +1-3026880818;
ARCTICEXPORTSINC@GMAIL.COM Canada 71 58
Shanghai Getian Industrial Co., LTD
+86-15373193816
mike@ge-tian.com China 269 58
Shaanxi Xianhe Biotech Co., Ltd
+86-17709210191; +8617709210191
Jerry@xhobio.com China 906 58

10540-29-1(Tamoxifen)Verwandte Suche:


  • (Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine
  • 2-[4-[(Z)-1,2-Di(phenyl)but-1-enyl]phenoxy]-N,N-dimethylethanamine
  • 2-[4-[(Z)-1,2-Diphenyl-1-butenyl]phenoxy]-N,N-dimethylethanamine
  • 2-[p-[(Z)-1,2-Diphenyl-1-butenyl]phenyloxy]-N,N-dimethylethanamine
  • N,N-Dimethyl-2-[p-[(Z)-1,2-diphenyl-1-butenyl]phenoxy]ethanamine
  • C07108
  • Tamoxifen,(Z)-1-(p-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene, trans-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine
  • 1-p-β-DiMethylaMinoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • (Z)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-diMethylethanaMine
  • TaMoxiefen
  • EthanaMine,2-[4-[(1Z)-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-diMethyl-
  • (z)-2-(4-(1,2-diphenyl-1-butenyl)phenoxy)phenoxy)-n,n-dimethylethanamine
  • (z)-2-(para-(1,2-diphenyl-1-butenyl)phenoxy)-n,n-dimethylamine
  • 1-para-beta-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • 1-p-beta-dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene
  • Tamoxifen, >=99%
  • Tamoxifen(ICI46,474)
  • (Z)-1-(4-Dimethylaminoethoxyphenyl)-1,2-diphenyl-1-butene
  • TAMOXIFEN
  • TRANS-2-[4-(1,2-DIPHENYL-1-BUTENYL)PHENOXY]-N,N-DIMETHYLETHYLAMINE
  • (Z)-2-[4-(1,2-DIPHENYL-1-BUTENYL)PHENOXY]-N,N-DIMETHYLETHANAMINE
  • [Z]-1-[P-DIMETHYLAMINOETHOXYPHENYL]-1,2-DIPHENYL-1-BUTENE
  • Genox
  • Tamoxen
  • tamoxifen free base
  • Ethanamine, 2-4-(1Z)-1,2-diphenyl-1-butenylphenoxy-N,N-dimethyl-
  • ici47699
  • n-dimethyl-2-(p-(1,2-diphenyl-1-butenyl)phenoxy)-(z)-ethylamin
  • Nolvadex-D
  • tamoxifen(z)
  • tamoxifendrugstandardsolution
  • trans-tamoxifen
  • (Z)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine
  • TAMOXIFEN (ICI 47699)
  • 2-[4-[(1Z)-1,2-Diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethylethanamine
  • Tamoxiphen CAS NO.10540-29-1
  • Tamoxifen citrate for performance test CRS
  • Tamoxifen citrate CRS
  • Steroids Raw Powder Tamoxife
  • Tamoxifen USP/EP/BP
  • Tamoxifen (1.0 mg/mL in Methanol)
  • Tamoxifen Nolvadex
  • Mammaton
  • TAMOXIFEN BASE
  • z-tamoxifen
  • amoxifen
  • 4’-Hydroxy Tamoxifen-d6 (contains up to 10% E isomer)
  • (Z)-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethylamine
  • Tamoxifen in methanol
  • Tamoxifen solution
  • Tamoxifen 20mg
  • Tamoxifen - Bio-X ?
  • IC|47699
  • T5648-1G
  • MeRCK 10540-29-1
  • Novaldex
  • 10540-29-1
  • C26H28NO
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