Mebendazol Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Mebendazole is a broad-spectrum anthelmintic that is active against both larval and adult stages of nematodes selectively binding the β-subunit of tubulin, thereby inhibiting intestinal microtubule synthesis in the parasite (IC
50 = 0.19 μM for
Giardia in vitro). As a tubulin-binding agent, mebendazole also possesses antitumor properties, inducing apoptosis of various human carcinomas both
in vitro and
in vivo, thus preventing their growth and migration. Furthermore, mebendazole has been used to inhibit hedgehog signaling in cancer cells
via suppression of the formation of the primary cilium, a microtubule-based organelle that functions as a signaling hub for hedgehog pathway activation. Additionally, mebendazole has been shown to stabilize the transcriptional activator HIF-1α and its downstream targets, abrogating oxidative neuronal death in primary neurons.
Chemische Eigenschaften
White Amorphous Powder
Verwenden
Mebendazole Polymorph C is an Anthelmintic (Nematodes).
Indications
Unlike thiabendazole, mebendazole (Vermox) does not
inhibit fumarate reductase.While mebendazole binds to
both mammalian and nematode tubulin, it exhibits a
differential affinity for the latter, possibly explaining the
selective action of the drug. The selective binding to
nematode tubulin may inhibit glucose absorption, leading
to glycogen consumption and ATP depletion.
Definition
ChEBI: A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.
Allgemeine Beschreibung
White to slightly yellow powder. Pleasant taste. Practically water insoluble.
Air & Water Reaktionen
Insoluble in water.
Reaktivität anzeigen
Mebendazole is a carbamate ester-amine. Amines behave as chemical bases. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Brandgefahr
Flash point data for Mebendazole are not available; however, Mebendazole is probably combustible.
Pharmazeutische Anwendungen
A benzimidazole carbamic acid methyl ester available for oral
administration. It is insoluble in water and stable at room
temperature.
Mechanism of action
Mebendazole is given orally; it is poorly soluble, and
very little is absorbed from the intestinal tract. About 5
to 10%, principally the decarboxylated derivatives, is
recovered in the urine; most of the orally administered
drug is found in the feces within 24 hours.
Pharmakokinetik
Oral absorption is poor. Plasma concentrations achieved after
oral administration of 100 mg every 12 h for three consecutive
days do not exceed 0.03 mg/L. All metabolites are inactive.
Most of the dose, as unchanged drug or a primary metabolite,
is retained in the intestinal tract and passed in the feces, with
the remainder, approximately 2% of the dose, excreted in the
urine.
Clinical Use
Methyl 5-benzoyl-2-benzimidazolecarbamate (Vermox) isa broad-spectrum anthelmintic that is effective against variousnematode infestations, including whipworm, pinworm,roundworm, and hookworm. Mebendazole irreversiblyblocks glucose uptake in susceptible helminths, thereby depletingglycogen stored in the parasite. It apparently does notaffect glucose metabolism in the host. It also inhibits cell divisionin nematodes.
Mebendazole is poorly absorbed by the oral route.Adverse reactions are uncommon and usually consist of abdominaldiscomfort. It is teratogenic in laboratory animalsand, therefore, should not be given during pregnancy.
Nebenwirkungen
Diarrhea and gastrointestinal discomfort may occur, but
adverse reactions are generally mild. Woman of childbearing
age should be informed of a potential risk to the fetus if treated
during pregnancy, particularly during the first trimester.
Sicherheitsprofil
Moderately toxic by
ingestion and intraperitoneal routes. Human
mutation data reported. An experimental
teratogen. Experimental reproductive
effects. When heated to decomposition it
emits toxic fumes of NOx. See also
CARBAMATES.
Mebendazol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
