Febantel Chemical Properties

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)

pka

7.60±0.46(Predicted)

color 

White to Off-White

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 Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

RTECS 

FB3955000

HS Code 

2930902000

Febantel Usage And Synthesis

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

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 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].

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].

References

[1] Thomas, H. “Ovacidal activity of febantel.” New Zealand veterinary journal 27 12 (1979): 273–5.

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