Teniposid

Bezeichnung:Teniposid

CAS-Nr29767-20-2

Englisch Name:Teniposide

CBNumberCB0455475

SummenformelC32H32O13S

Molgewicht656.65

MOL-Datei29767-20-2.mol

Synonyma

Teniposid

Teniposid physikalisch-chemischer Eigenschaften

Schmelzpunkt	244-247°C
Siedepunkt	650.86°C (rough estimate)
alpha	D20 -107° (9:1 chloroform/methanol)
Dichte	1.2568 (rough estimate)
Brechungsindex	1.5530 (estimate)
storage temp.	-20°C
Löslichkeit	DMSO: soluble10mg/mL, clear
pka	10.13(at 25℃)
Aggregatzustand	powder
Farbe	white to beige
Optische Aktivität	[α]/D -100 to -115°, c = 1 in chloroform/methanol (9:1)
maximale Wellenlänge (λmax)	283nm(MeOH)(lit.)
Merck	14,9145
Stabilität	Hygroscopic
CAS Datenbank	29767-20-2(CAS DataBase Reference)
IARC	2A (Vol. 76) 2000

Sicherheit

Kennzeichnung gefährlicher	Xi,T
R-Sätze:	36/37/38-45
S-Sätze:	26-36-45-53
RIDADR	UN 2811 6.1 / PGIII
WGK Germany	3
RTECS-Nr.	KC0180000
HS Code	29349990
Giftige Stoffe Daten	29767-20-2(Hazardous Substances Data)
Toxizität	LD50 intraperitoneal in mouse: 29570ug/kg

Gefahreninformationscode (GHS)

Teniposide 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.
Chemische Eigenschaften
White Solid
Originator
Vehem,Sandoz,France,1976
Verwenden
A semi-synthetic derivative of Podophyllotoxin. Antineoplastic.
Verwenden
A labelled semi-synthetic derivative of Podophyllotoxin. Antineoplastic.
Verwenden
Teniposide is a podophyllotoxin derivative that causes dose-dependent single- and double-stranded breaks in DNA by inhibiting topoisomerase II. Its cytostatic effects are related to its ability to stabilize the DNA-topoisomerase II complex during DNA replication, inducing DNA damage and cellular apoptosis. Teniposide has been widely used in the treatment of various cancers including, small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia.
Definition
ChEBI: A furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding.
Indications
Teniposide (VM-26, Vumon) is closely related to etoposide in structure, mechanisms of action and resistance, and adverse effects. It is more lipophilic and approximately threefold more potent than etoposide. Its major uses have been in pediatric cancers, particularly in acute lymphoblastic leukemias.
Manufacturing Process
10 ml of pure thiophene-2-aldehyde and 0.25 g of anhydrous zinc chloride are American Home Products Corporation; British Patent 1,022,642; March 16, 1966
American Home Products Corporation; British Patent 1,022,645; March 16, 1966
Bell, S.C.; British Patent 1,057,492; February 1, 1967; assigned to American Home Products Corporation
Trademarks
Vumon (Bristol-Myers Squibb).
Therapeutic Function
Antineoplastic
Allgemeine Beschreibung
Teniposide is available in 50-mg ampules with Cremophor ELfor IV administration in the treatment of acute lymphoblasticleukemia (ALL). The agent is more potent as an inhibitor oftopoisomerase II. The pharmacokinetics of teniposide issimilar to that of etoposide; however, the more lipophilic teniposideis more highly protein bound (99%) and less isexcreted unchanged in the urine (10%–20%). There is alsogreater overall metabolism of teniposide; however, CYP3A4-mediated conversion to the active catechol is slower comparedwith etoposide. Elimination occurs primarily in the urine witha terminal elimination half-life of 5 hours.
Biochem/physiol Actions
Teniposide (VM-26) is a Topoisomerase II inhibitor with antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA, inducing breaks in double stranded DNA and preventing repair.
Clinical Use
Teniposide is used in combination with other agents for the treatment of refractory childhood acute lymphoblastic leukemia.
Sicherheitsprofil
Poison by intraperitoneal and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion and intravenous route: anorexia, nausea or vomiting, leukopenia, agranulocytosis and aplastic anemia of the blood, bone marrow changes, and hair changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx.
Synthese
Teniposide, [5R-(5|á,5a|?,8a|á,9|?)]-9-[4,6-O-(2-thienylmethylene)-|?-D-glucopyranosyl)oxy]- 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3,4: 6,7]-naphtho[2,3-d]-1,3-dioxol-6(5aH)-one (30.4.9), is basically synthesized by an analogous scheme from 4-benzyloxy-4-desmethylepipodophyllotoxin (30.4.6), which is esterified by 2,3,4,6- tetra-O-acetyl-|?-D-glucose in the presence of boron trifluoride etherate, giving a glycoside 30.4.7. The acetyl and benzyloxycarbonyl protecting groups in this molecule are removed by succesive use of zinc acetate and sodium methoxide, and then by subsequent hydrogen reduction, which forms the diol 30.4.8. The resulting diol is then transformed into the corresponding acetal 2-formylthiophene, which is the desired teniposide (30.4.9) .
Lager
Store at -20°C

Teniposide Upstream-Materialien And Downstream Produkte

Teniposid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

29767-20-2, Teniposide Verwandte Suche:

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