Fenbendazol
Febendazole · fenbendazol · Fenbedazole · 5-(phenylthio)-2-benzimidazolecarbamic acid methyl ester · Methyl (6-(phenylthio)-1H-benzo[d]iMidazol-2-yl)carbaMate · [5-(Phenylthio)-1H-benzimidazol-2-yl]carbonic acid, Methyl ester · hoe881 · Axilur
Identifikatoren & physikalische Daten
| CAS No. | 43210-67-9 |
|---|---|
| Summenformel | C15H13N3O2S |
| Durchschnittliche Molmasse | 299,3 g/mol |
| Monoisotopische Masse | 299,07284766 g/mol |
| SMILES | COC(=O)Nc1nc2ccc(Sc3ccccc3)cc2[nH]1 |
| InChIKey | HDDSHPAODJUKPD-UHFFFAOYSA-N |
| PubChem CID | 3334 |
| ChEMBL | CHEMBL37161 |
| ChEBI | CHEBI:77092 |
| EC No. | 256-145-7 |
| DTXSID | DTXSID0040672 |
| Lokaler Name | Fenbendazol |
Chemische & physikalische Eigenschaften
| XLogP | 3,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 92,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 363 |
| Arzneimittel | Drug |
| Löslichkeit | 0.9 [ug/mL] (The mean of the results at pH 7.4)Insoluble in waterDMSO:16.67(Max Conc. mg/mL)55.69(Max Conc. mM)DMF:10.0(Max Conc. mg/mL)33.41(Max Conc. mM) |
| Animal Drugs | EMA approved medicines: Veterinary medicineFDA approved animal drugs -> Active ingredientPharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Schmelzpunkt | 233 °C233°C |
| Physical Description | Solid |
| Collision Cross Section | 174.9 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID0040672]170.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]186.5 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]169.8 Ų [M+H]+ [CCS Type: TW |
| Dichte | 1.2767 (rough estimate) |
| Brechungsindex | 1.6740 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 10.80±0.10(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Light yellow |
| Merck | 14,3960 |
| BRN | 759077 |
| InChI | InChI=1S/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19) |
| InChIKey | HDDSHPAODJUKPD-UHFFFAOYSA-N |
| SMILES | C(OC)(=O)NC1NC2=CC(SC3=CC=CC=C3)=CC=C2N=1 |
| CAS Datenbank | 43210-67-9(CAS DataBase Reference) |
| EPA chemische Informationen | Carbamic acid, N-[6-(phenylthio)-1H-benzimidazol-2-yl]-, methyl ester (43210-67-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.3% (2 of 157) of reports.WarningH361 (66.2%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]P203, P260, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 157 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Fenbendazole: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Carbamic acid, [5-(phenylthio)-1H-benzimidazol-2-yl]-, methyl ester: Environment tier I assessment |
| Hazard Classes and Categories | Repr. 2 (66.2%) |
| Hepatotoxicity | The side effects of fenbendazole therapy in humans have not been well described, but other benzimidazoles are associated with transient and asymptomatic elevations in serum aminotransferase levels in up to 50% of patients treated for more than a few weeks. These abnormalities rapidly improve with stopping therapy. Fenbendazole taken by patients without prescription for its purported antineoplastic activity has been associated with several instances of clinically apparent liver injury. The onset of injury has been within a few days to as long as a year after starting therapy or more rapidly with multiple courses of treatment. The pattern of serum enzyme elevations is typically hepatocellular or mixed. Allergic features (rash, fever, eosinophilia) may be present but are not prominent. Most cases have been mild to moderate in severity, and recovery is rapid once the drug is stopped. However, some cases have been severe and potentially life-threatening. Rapid recurrence with rechallenge has been reported with other benzimidazoles but with similar severity. |
| Toxizitätsübersicht | Fenbendazole has a high safety margin and low toxicity in animals. A study of fenbendazole administered to cattle found that it was well-tolerated, even when administered at six times the prescribed dose and three times the recommended duration. The lethal dose (LD50) in rodents is greater than 10 g/kg, which is 1,000 times the therapeutic level. Lifetime studies in rats indicated no maternal or reproductive toxicity and no carcinogenesis.Fenbendazole (FBZ) is used to treat or prevent pinworm outbreaks in laboratory rodents. At therapeutic levels, FBZ does not alter the total content of cytochromes P450 but does induce certain hepatic cytochrome P450 isoforms known for bioactivating a number of procarcinogens. Lifetime studies in rats have shown that FBZ is not a carcinogen but that it may behave as a tumor promoter when given after certain initiators. FBZ treatment-associated myelosuppression has not been reported to occur in rodents. |
| Wassergefährdungsklasse (WGK) | 2 |
| Zollcode | 29339900 |
| RTECS-Nr. | DD6520500 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | dog,LD50,oral,> 500mg/kg (500mg/kg),Pesticide Science. Vol. 8, Pg. 550, 1977. |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36-24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Aquatic Acute 1Aquatic Chronic 1Repr. 2STOT RE 2 |
Anwendungen & Verwendung
Beschreibung
Fenbendazole is a benzimidazole anthelmintic. It is active against Giardia in vitro (IC50 = 0.3 μM). Fenbendazole (20 mg/kg) prevents infiltration of parasites into the brain in a rabbit model of E. cuniculi infection. Fenbendazole also activates HIF-1α and prevents oxidative stress-induced death in primary neurons in vitro.
Verwenden
Fenbendazole is a benzimidazole anthelmintic that is metabolised in mammals to a series of other benzimidazoles including oxfendazole. It is used for the control of gastrointestinal roundworms, lung worms, Nematodes and tape worms. It is the only benzimidazole approved for use in organic livestock production.
Verwenden
Fenbendazole is a medication used to treat parasites, mainly in dogs. However, studies have found that in a group of mice treated with a combination of fenbendazole and vitamins, tumor growth inhibition was unexpected It may be because it interferes with the uptake of glucose by cancer cells, which is essential for tumor growth and proliferation. It prevents cancer cells from obtaining the glucose needed to grow and divide to inhibit the growth of cancer cells. Studies have found that fenbendazole can kill cancer cells and promote tumor regression in patients with metastatic large B-cell lymphoma, and also plays a role in other metastatic malignant tumors such as bladder cancer and renal cell carcinoma. It is currently being treated in combination with other anti-cancer drugs to study its anti-cancer potential[1-3].