| Identification | More | [Name]
Febantel | [CAS]
58306-30-2 | [Synonyms]
[[2-[(Methoxyacetyl)amino]-4-(phenylthio)phenyl]-carbonimidoyl]biscarbamicaciddimethylester
bayvh5757
carbamicacid,((2-((methoxyacetyl)amino)-4-(phenylthio)phenyl)carbonimidoyl)bi
Carbamicacid,[[2-[(methoxyacetyl)amino]-4-(phenylthio)phenyl]carbonimidoyl]bis-,dimethylester
n-(2-(2,3-bis-(methoxycarbonyl)-guanidino)-5-(phenylthio)-phenyl)-2-methoxya
rintal
FEBANTEL PESTANAL
2-Acetamido-5-nitrothiazole VETRANAL
DIMETHYL[[2-[(METHOXYACETYL)AMINO]-4-(PHENYLTHIO)PHENYL]CARBONIMIDOYL]BISCARBAMATE(FEBANTEL)
Febantel
N-{2-[2,3-Bis-(methoxycarbonyl)-guanido]-5-(phenylthio)-phenyl}-2-methoxyacetamide
[N-[2-[(Methoxyacetyl)amino]-4-(phenylthio)phenyl]carbonimidoyl]biscarbamic acid dimethyl ester
Bay h-5757
N,N'-[[2-[(2-Methoxyacetyl)amino]-4-(phenylthio)phenyl]imidocarbonyl]bis(carbamic acid methyl) ester | [EINECS(EC#)]
261-205-0 | [Molecular Formula]
C20H22N4O6S | [MDL Number]
MFCD01738527 | [Molecular Weight]
446.48 | [MOL File]
58306-30-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Solid | [Melting point ]
129-130°C | [Boiling point ]
215°C (rough estimate) | [density ]
1.2962 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Sparingly) | [form ]
neat | [pka]
7.60±0.46(Predicted) | [color ]
White to Off-White | [Usage]
Used as an anthelmintic | [Merck ]
14,3944 | [InChI]
InChI=1S/C20H22N4O6S/c1-28-12-17(25)21-16-11-14(31-13-7-5-4-6-8-13)9-10-15(16)22-18(23-19(26)29-2)24-20(27)30-3/h4-11H,12H2,1-3H3,(H,21,25)(H2,22,23,24,26,27) | [InChIKey]
HMCCXLBXIJMERM-UHFFFAOYSA-N | [SMILES]
N(C1C=C(SC2C=CC=CC=2)C=CC=1/N=C(\NC(=O)OC)/NC(=O)OC)C(=O)COC | [CAS DataBase Reference]
58306-30-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [WGK Germany ]
3 | [RTECS ]
FB3955000 | [HS Code ]
2930902000 |
| Hazard Information | Back Directory | [Description]
Febantel [N-2-( [2,3-bis-(methoxycarbonyl)-guanidine] 5- phenylthio)-phenyl) -2-methoxyacetamide] is a new anthelmintic that is highly active against various species of nematodes and cestodes in rodents, sheep, cattle, and horses. In 1978, febantel was introduced to South Africa under the trade name of Rintal? as a sheep drench, and to New Zealand as a sheep and cattle drench, and the USA and Australia as a paste for horse[1].
| [Chemical Properties]
Febantel is White to Off-White Solid
| [Originator]
Rintal, Bayer,W. Germany,1979 | [Uses]
Febantel is used as an anthelmintic
| [Definition]
ChEBI: Febantel is an aryl sulfide. | [Manufacturing Process]
2-Amino-5-phenylthiornethoxyacetanilide in methanol solution is heated with
N,N'-bis-methoxycarbonyl-isothiourea-S-methyl ether with the addition of a
catalytic amount of p-toluenesulfonic acid for three hours with stirring under
reflux. The mixture is then filtered hot and after cooling the febantel product
crystallizes out. It is filtered off, rinsed with ether and dried under high
vacuum to give the final product, melting at 129°C to 130°C. | [Brand name]
Combotel (Bayer AnimalHealth); Negabot Plus Paste (Bayer Animal Health);
Oratel (Bayer Animal Health); Rintal (Bayer Animal
Health). | [Therapeutic Function]
Anthelmintic | [in vivo]
In vitro assays showed a negative correlation between febantel concentrations and the survival of G. Kobayashi. However, increasing the febantel concentration to 2.0 mg/L did not result in the complete death of all worms. Oral administration of febantel demonstrated limited anthelmintic activity, with only 49 % efficacy at 200 mg/kg body weight daily over five days. Acute toxicity assays revealed that the 48-h LC50 value of febantel was 5.47 mg/L, 182.23 times higher than the 48-h EC50 value, indicating that febantel has a favorable safety profile. However, febantel exposure potentially interfered with hepatic metabolism and oxidative status, as indicated by variations in SOD, GST, and P450 gene expression[1]. | [in vivo]
In vivo assays indicated that febantel exhibited potent anthelmintic activity against G. kobayashii with an EC50 value of 0.03 mg/L and 100 % anthelmintic efficacy at 0.1 mg/L after 48 h of exposure. Moreover, in vivo trials also revealed a notable post-treatment effect of febantel, where infected goldfish transferred to drug-free water after short 6-h exposure could still result in full eradication of the worms, indicating febantel might induce persistent perturbations in parasite physiology[1].
| [storage]
Store at -20°C | [References]
[1] Thomas, H. “Ovacidal activity of febantel.” New Zealand veterinary journal 27 12 (1979): 273–5.
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