Mebendazol
MEBENDAZOL · vermox · Methyl (5-benzoyl-1H-benzo[d]iMidazol-2-yl)carbaMate · (5-Benzoyl-1H-benzimidazol-2-yl)carbamicacidmethylester · mbdz · Mebex · lomper · r17635
Identifikatoren & physikalische Daten
| CAS No. | 31431-39-7 |
|---|---|
| Summenformel | C16H13N3O3 |
| Durchschnittliche Molmasse | 295,29 g/mol |
| Monoisotopische Masse | 295,09569129 g/mol |
| SMILES | COC(=O)Nc1nc2ccc(C(=O)c3ccccc3)cc2[nH]1 |
| InChIKey | OPXLLQIJSORQAM-UHFFFAOYSA-N |
| PubChem CID | 4030 |
| ChEMBL | CHEMBL685 |
| ChEBI | CHEBI:6704 |
| EC No. | 104-806-4 |
| DTXSID | DTXSID4040682 |
| Lokaler Name | Mebendazol |
Chemische & physikalische Eigenschaften
| XLogP | 2,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 84,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 423 |
| Schmelzpunkt | 288.5°C |
| Siedepunkt | 436.98°C (rough estimate) |
| Dichte | 1.1952 (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Löslichkeit | Practically insoluble in water, in alcohol and in methylene chloride.35.4mg/L(25 ºC) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 3.43/9.93(H2O,t =25,I=0.025) (Uncertain) |
| Farbe | White to Pale Beige |
| Merck | 14,5768 |
| BRN | 759809 |
| Henry-Konstante | 1.8×1010 mol/(m3Pa) at 25℃, HSDB (2015) |
| BCS Class | 2,4 |
| Hauptanwendungen | forensics and toxicologypharmaceutical (small molecule) |
| InChI | 1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21) |
| InChIKey | OPXLLQIJSORQAM-UHFFFAOYSA-N |
| SMILES | COC(=O)Nc1nc2cc(ccc2[nH]1)C(=O)c3ccccc3 |
| CAS Datenbank | 31431-39-7(CAS DataBase Reference) |
| EPA chemische Informationen | Mebendazole (31431-39-7) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| UN-Transportnummer | UN 2811 |
| Zollcode | 29339900 |
| RTECS-Nr. | EY8600000 |
| R-Sätze (R) | 22 |
| Toxizität | LD50 orally: >80 mg/kg in sheep>40 mg/kg in mice, rats and chickens (Van Gelder) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 31431-39-7(Hazardous Substances Data) |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
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 (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.
Verwenden
Mebendazole Polymorph C is an Anthelmintic (Nematodes).