Altretamin

Bezeichnung:Altretamin

CAS-Nr645-05-6

Englisch Name:Altretamine

CBNumberCB9480937

SummenformelC9H18N6

Molgewicht210.28

MOL-Datei645-05-6.mol

Synonyma

Altretamin

Altretamin physikalisch-chemischer Eigenschaften

Schmelzpunkt	171-175 °C (lit.)
Siedepunkt	339.81°C (rough estimate)
Dichte	1.0441 (rough estimate)
Brechungsindex	1.6100 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	Chloroform (Sparingly), Methanol (Slightly, Heated)
Aggregatzustand	solid
pka	pKa 10.3 (Uncertain)
Farbe	White to Off-White
Wasserlöslichkeit	Insoluble
Merck	13,318
CAS Datenbank	645-05-6(CAS DataBase Reference)
NIST chemische Informationen	Altretamine(645-05-6)
EPA chemische Informationen	Altretamine (645-05-6)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	OS1050000
HS Code	2933690000
Giftige Stoffe Daten	645-05-6(Hazardous Substances Data)
Toxizität	LD50 in rats, guinea pigs (mg/kg): 350, 255 orally (Jasper)

Gefahreninformationscode (GHS)

Altretamine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
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.
Chemische Eigenschaften
White Solid
Originator
Hexastat,Roger Bellon,France,1979
Verwenden
As experimental insect chemosterilant.
Verwenden
antimalarial
Verwenden
An antitumor agent which also acts as a chemosterilant for male houseflies and other insects. Antineoplastic.
Definition
A hexamethyl-2,4,6- triamine derivative of 1,3,5-triazine.
Indications
Although both DNA and RNA synthesis are inhibited in cells exposed to hexamethylmelamine (Hexalen), the molecular mechanisms of these effects are not known.
Manufacturing Process
50 g of hexamethylolmelamine-hexamethyl ether in 950 cc methanol are hydrogenated, at 90°C to 100°C, in the presence of 2 g Raney nickel with 100 atmospheres excess pressure of hydrogen in a steel autoclave holding 2 L until the absorption of hydrogen is terminated. After the catalyst has been filtered off with suction, the methanol is distilled off. As a result, 23.1 g (86% of the theoretical) of crude hexamethylmelamine are formed having a melting point of 158°C to 162°C. After recrystallization from methanol, the pure product is obtained having a melting point of 168°C.
Trademarks
Hexalen (Millot Laboratories, France).
Therapeutic Function
Antitumor
Allgemeine Beschreibung
Colorless crystalline solid. Insoluble in water.
Allgemeine Beschreibung
Altretamine is available in 50-mg capsules for oraladministration as a second-line treatment for ovarian cancer.The mechanism of action has not been firmly established, althoughthe spectrum of activity is similar to that for otheralkylating agents; however, cross-resistance is not seen.Cytotoxicity has been correlated with metabolism to give thecarbinolamines, which may form imines capable of crosslinking,or decompose to give formaldehyde, which may reactwith nucleophiles on DNA or proteins. The agent is well absorbedupon oral administration, well distributed, and highly(90%) plasma protein bound. The agent is extensively metabolizedin the liver by CYP to give demethylated metabolites via the previously mentioned carbinolamines. Elimination occursprimarily in the urine as mostly demethylated metaboliteswith a terminal elimination half-life of 4 to 10 hours.Myleosuppression and nausea/vomiting are dose-limitingtoxicities. Other adverse effects include lethargy, agitation,hallucinations, skin rash, and elevations in transaminase levels,flulike symptoms, abdominal cramps, and diarrhea.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Altretamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Hazard
Toxic.
Mechanism of action
Hexamethylmelamine is readily absorbed after oral administration, with peak plasma levels achieved after 1 hour.The drug is readily metabolized to form a number of demethylated metabolites. Urinary elimination is the primary route of drug excretion.
Clinical Use
Hexamethylmelamine is useful for the treatment of ovarian adenocarcinoma and is frequently combined with cyclophosphamide, cisplatin, and doxorubicin in the treatment of this tumor. It also has some activity against small cell lung cancer.
Nebenwirkungen
Nausea and vomiting are the major toxicities associated with hexamethylmelamine administration. Myelosuppression and a peripheral neuropathy also may occur.
Stoffwechsel
This unique structure is believed to damage tumor cells through the production of the weakly alkylating species formaldehyde, a product of CYP450-mediated N-demethylation. Administered orally, altretamine is extensively metabolized on first pass, producing primarily mono- and didemethylated metabolites. Additional demethylation reactions occur in tumor cells, releasing formaldehyde in situ before the drug is excreted in the urine.

Altretamine Upstream-Materialien And Downstream Produkte

Altretamin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

645-05-6, Altretamine Verwandte Suche:

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