Grundinformationen
- Standard-SMILES
COC(=O)Nc1nc2ccc(C(=O)c3ccccc3)cc2[nH]1- InChIKey
OPXLLQIJSORQAM-UHFFFAOYSA-N- Summenformel
- C16H13N3O3
- Durchschnittliche Molmasse
- 295,29 g/mol
- Monoisotopische Masse
- 295,09569129
Namen und Bezeichner
- Bevorzugter Name
- Mebendazole
- IUPAC
- methyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate
- Lokaler Name
- Mebendazol
- Englischer Name
- Mebendazole
- Summenformel
- C16H13N3O3
- Molmasse
- 295.29
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
31431-39-7- PubChem CID
- 4030
- DTXSID
DTXSID4040682- ChEMBL
CHEMBL685- ChEBI
CHEBI:6704- UNII
- 81G6I5V05I
- EC Number
- 104-806-4、250-635-4
- Nikkaji
- J2.773A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,8
- Polarare Oberfläche (TPSA)
- 84,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 423
Physikochemische Eigenschaften
- Schmelzpunkt
- 288.5 °C · 288.5°C
- Siedepunkt
- 436.98 °C · 436.98°C (rough estimate)
- Dichte
- 1.1952 · 1.1952 (rough estimate)
- Brechungsindex
- 1.65 · 1.6500 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- Löslichkeit
- Practically insoluble in water, in alcohol and in methylene chloride.
- Aggregatzustand
- Solid
- pka
- 3.43 · pKa 3.43/9.93(H2O,t =25,I=0.025) (Uncertain)
- Farbe
- White to Pale Beige
- Wasserlöslichkeit
- 35.4 mg/L · 35.4mg/L(25 ºC)
- Merck
- 14 · 14,5768
- BRN
- 759809 · 759809
- Henry's Law Constant
- 1.8 · 1.8×1010 mol/(m3Pa) at 25℃, HSDB (2015)
- BCS Class
- 2 · 2,4
- Major Application
- 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 · 31431-39-7(CAS DataBase Reference)
- EPA chemische Informationen
- Mebendazole (31431-39-7)
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811
- hs_code
- 29339900
- RTECS-Nr.
- EY8600000
- risk_code
- 22
- Toxizität
- LD50 orally: >80 mg/kg in sheep; >40 mg/kg in mice, rats and chickens (Van Gelder)
- hazard_code
- Xn
- safety_code
- 36
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 31431-39-7(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Anwendungen
BeschreibungMebendazole 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.
VerwendenMebendazole Polymorph C is an Anthelmintic (Nematodes).
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A carbamate ester that is methyl 1H-benzimidazol-2-ylcarbamate substituted by a benzoyl group at position 5.
Zugehörige Reaktionen
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Verknüpfte Notizen
Wird geladen…