Mebendazole

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H302：삼키면 유해함

Mebendazole MSDS

• 5-Benzoyl-2-benzimidazolylcarbamic acid methyl ester

Mebendazole 화학적 특성, 용도, 생산

• 개요

  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 (IC₅₀ = 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.

• 화학적 성질

  White Amorphous Powder

• 용도

  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.

• 정의

  ChEBI: A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.

• 일반 설명

  White to slightly yellow powder. Pleasant taste. Practically water insoluble.

• 공기와 물의 반응

  Insoluble in water.

• 반응 프로필

  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.

• 화재위험

  Flash point data for Mebendazole are not available; however, Mebendazole is probably combustible.

• Pharmaceutical Applications

  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.

• Pharmacokinetics

  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.

• 부작용

  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.

• Safety Profile

  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.

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