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Aminoglutethimid

Aminoglutethimide Struktur
125-84-8
CAS-Nr.
125-84-8
Bezeichnung:
Aminoglutethimid
Englisch Name:
Aminoglutethimide
Synonyma:
3-(4-AMINOPHENYL)-3-ETHYLPIPERIDINE-2,6-DIONE;Cytadren;AMINOGLUTETHAMIDE;DL-AMINOGLUTETHIMIDE;Elipten;Ba-16038;ORIMETEN;NSC-330915;AKOS NCG1-0032;AMINOGLUTETHIMIDE
CBNumber:
CB5131691
Summenformel:
C13H16N2O2
Molgewicht:
232.28
MOL-Datei:
125-84-8.mol

Aminoglutethimid Eigenschaften

Schmelzpunkt:
152-154 °C(lit.)
Siedepunkt:
374.44°C (rough estimate)
Dichte
1.1099 (rough estimate)
Brechungsindex
1.6450 (estimate)
storage temp. 
2-8°C
L?slichkeit
H2O: 0.2 mg/mL, slightly soluble
pka
11.60±0.40(Predicted)
Aggregatzustand
Solid
Farbe
white
Wasserl?slichkeit
Soluble in water (2 mg/ml at 20°C), methanol (50 mg/ml), ethanol (7 mg/ml at 25°C), DMSO (20 mg/ml at 25°C), and chloroform.
Merck 
14,440
CAS Datenbank
125-84-8(CAS DataBase Reference)
NIST chemische Informationen
Aminoglutethimide(125-84-8)
EPA chemische Informationen
Aminoglutethimide (125-84-8)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi
R-S?tze: 36/37/38
S-S?tze: 26-36
RIDADR  3249
WGK Germany  3
RTECS-Nr. MA4026950
HazardClass  6.1(b)
PackingGroup  III
HS Code  2925190100
Giftige Stoffe Daten 125-84-8(Hazardous Substances Data)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P271 Nur im Freien oder in gut belüfteten R?umen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERüHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckm??ig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.

Aminoglutethimid 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.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Beschreibung

Aminoglutethimide is an aromatase inhibitor (IC50 = 7.5 μM). Aromatase inhibitors, including aminoglutethimide, inhibit estrogen synthesis via aromatase, suppressing estrogen levels in post-menopausal women. Formulations containing aromatase inhibitors have been used to treat estrogen receptor-positive breast cancer in post-menopausal women.

Chemische Eigenschaften

White Solid

Verwenden

Aminoglutethimide is used to decrease the production of sex hormones and suppress the growth of tumors that need sex hormones to grow. It blocks the production of steroids derived from cholesterol and is clinically used in the treatment of Cushing's syndrome and metastatic breast cancer. It is also a drug of abuse by body builders.

Indications

Aminoglutethimide (Cytadren) is a competitive inhibitor of desmolase, the enzyme that catalyzes the conversion of cholesterol to pregnenolone; it also inhibits 11-hydroxylase activity.This drug also reduces estrogen production by inhibiting the aromatase enzyme complex in peripheral (skin, muscle, fat) and steroid target tissues.

Definition

ChEBI: A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.

Weltgesundheitsorganisation (WHO)

Aminoglutethimide, a weak anticonvulsant, was introduced in 1960 for use in the treatment of epilepsy. However, its adrenocortical suppressant activity gave rise to serious adverse effects. The FDA decision in 1966 was taken in respect of a preparation indicated in epilepsy. In 1980 preparations containing aminoglutethimide were reintroduced in the USA exclusively for the treatment of Cushing's disease. In 1986 they were also registered in Saudi Arabia for use in Cushing's syndrome and for the treatment of breast cancer. In some other countries these preparations are additionally approved for carcinoma of the prostate.

Allgemeine Beschreibung

Aminoglutethimide, 3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione, is mainly usedto treat Cushing syndrome, a condition of adrenal steroidexcess, a use in which the P450scc inhibition of thiscompound is exploited rather than its aromatase inhibition.Aminoglutethimide is a weak inhibitor of aromataseand has been used successfully in the treatment of estrogen-dependent breast cancer. Because of the developmentof more selective aromatase inhibitors, the use ofaminoglutethimide for its ability to inhibit aromatase is notsupported.

Mechanism of action

This drug blocks the transformation of cholesterol into pregnenolone, and androgens into estrogens in the adrenal glands, thus completely suppressing the production of all steroid hormones. Aminoglutethimide is used for palliative treatment of prostate carcinomas and post-menopausal breast carcinomas. Synonyms of aminoglutethimide are orimeten, citadren and others.

Clinical Use

Aminoglutethimide is suitable for use in Cushing’s syndrome that results from adrenal carcinoma and in congenital adrenal hyperplasia, in which it protects the patient from excessive secretion of endogenous androgens. The drug is not curative, and relapse occurs when treatment is terminated. Since aminoglutethimide therapy is frequently associated with mineralocorticoid deficiency, mineralocorticoid supplements may be needed. Aminoglutethimide and metyrapone are frequently used in combination at lower doses of both drugs as an adjunct to radiation or surgical therapy.

Nebenwirkungen

Such a medical adrenalectomy is an efficacious treatment for metastatic breast and prostate cancer, since it diminishes the levels of circulating sex hormones. Glucocorticoids are administered concomitantly to suppress enhanced corticotrophin release. Cortisol is preferable to dexamethasone in this situation because aminoglutethimide markedly enhances the hepatic microsomal metabolism of dexamethasone. Hepatic enzyme induction may be responsible for the development of tolerance to the side effects of aminoglutethimide, such as ataxia, lethargy, dizziness, and rashes.

Stoffwechselwegen

Following administration of a single oral dose of 14C- aminoglutethimide to rats, guinea pigs, rabbits, and man, more than 89% of the dose is excreted in urine and feces within 72h, and dogs eliminate only 51% in this time. Extensive metabolism occurs in all species, with N-acetylaminoglutethimide being the major metabolite except for dogs and man. In the latter two species, the unchanged drug is the main product excreted. As shown in the pathways, it appears that aminoglutethimide is metabolized by several pathways in man and, of the ten metabolites, only two are present in any quantity, namely N-acetylaminoglutethimide and N-hydroxyaminoglutethimide, the latter increasing during the course of treatment.

Aminoglutethimid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Aminoglutethimid Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 171)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21634 55
career henan chemical co
+86-0371-86658258 +8613203830695
sales@coreychem.com China 29880 58
Shenzhen Nexconn Pharmatechs Ltd
+86-755-89396905 +86-15013857715
admin@nexconn.com China 10311 58
Hubei xin bonus chemical co. LTD
86-13657291602
linda@hubeijusheng.com CHINA 22963 58
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 419 58
Chongqing Chemdad Co., Ltd
+86-023-6139-8061 +86-86-13650506873
sales@chemdad.com China 39894 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427
sales@conier.com China 49374 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000
marketing@targetmol.com United States 32161 58
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418671 +8618949823763
sales@tnjchem.com China 34563 58
HANGZHOU CLAP TECHNOLOGY CO.,LTD
86-571-88216897,88216896 13588875226
sales@hzclap.com CHINA 6312 58

125-84-8(Aminoglutethimid)Verwandte Suche:


  • TIMTEC-BB SBB000711
  • 2-(4-aminophenyl)-2-ethylglutarimide
  • DL-Aminoglutethimide 99 %
  • (+/-)-P-AMINOGLUTETHIMIDE INHIBITS CYTOC HROME P
  • Aminoglutethimide(Ag)
  • 2-(p-aminophenyl)-2-ethyl-glutarimid
  • 2-(p-Aminophenyl)-2-ethylglutarimide
  • 2-(p-Aminophenyl)-2-ethylglutarimide2,6-piperidinedione, 3-(4-aminophenyl)-3-ethyl-
  • 2,6-Piperidinedione, 3-(4-aminophenyl)-3-ethyl-
  • 3-(4-aminophenyl)-3-ethyl-6-piperidinedione
  • 3-Ethyl-3-(p-aminophenyl)-2,6-dioxopiperidine
  • alpha-(p-Aminophenyl)-alpha-ethylglutarimide
  • Ba-16038
  • Elipten
  • Glutarimide, 2-(p-aminophenyl)-2-ethyl-
  • NSC-330915
  • 3-(4-AMINOPHENYL)-3-ETHYL-2,6-PIPERIDINEDIONE (DL-AMINOGLUTETHIMIDE)
  • (S)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione
  • 3-(4-aminophenyl)-3-ethyl-piperidine-2,6-quinone
  • 3-(4-azanylphenyl)-3-ethyl-piperidine-2,6-dione
  • DL-Aminoglutethimide,3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione
  • Aminoglutethimide (200 mg)
  • (RS)-2-(4-AMino-phenyl)-2-ethyl-glutariMide, (RS)-3-(4-AMino-phenyl)-3-ethyl-2,6-dioxo-piperidine
  • 3-(4-AMINOPHENYL)-3-ETHYL-2,6-PIPERIDINEDIONE
  • AKOS NCG1-0032
  • AMINOGLUTETHIMIDE
  • 3-[P-AMINOPHENYL]-3-ETHYLPIPER-IDINE-2,6-DIONE
  • (RS)-2-ETHYL-2-(4-AMINO-PHENYL)-GLUTARIMIDE
  • (RS)-3-(4-AMINO-PHENYL)-3-ETHYL-PIPERIDINE-2,6-DIONE
  • (RS)-3-ETHYL-3-(4-AMINO-PHENYL)-2,6-DIOXO-PIPERIDINE
  • (+/-)-P-AMINOGLUTETHIMIDE
  • ORIMETEN
  • DL-3-(4-AMINOPHENYL)-3-ETHYL-2,6-PIPERIDINEDIONE
  • Aminoglutethimide CRS
  • Aminoglutethimide USP/EP/BP
  • Aminoglutethimide (BA-16038)
  • Aminoglutethimide 98% (HPLC)
  • Aminoglutethimide (1025205)
  • Cytadren
  • AMINOGLUTETHAMIDE
  • 3-(4-AMINOPHENYL)-3-ETHYLPIPERIDINE-2,6-DIONE
  • DL-AMINOGLUTETHIMIDE
  • Venlafaxine Impurity 32
  • 125-84-8
  • 125-84-4
  • C13H16N2O2
  • Cell Biology
  • Cell Signaling and Neuroscience
  • BioChemical
  • Cytokines, Growth Factors and Hormones
  • Hormones
  • Steroid Hormones
  • Other Steroid Products
  • CYTADREN
  • Antitumors for Research and Experimental Use
  • Biochemistry
  • Inhibitors
  • Intermediates & Fine Chemicals
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