Amoscanate

Title: Amoscanate
CAS Registry Number: 26328-53-0
CAS Name: 4-Isothiocyanato-N-(4-nitrophenyl)benzeneamine
Additional Names: isothiocyanic acid p-(p-nitroanilino)phenyl ester; 4-isothiocyanato-4¢-nitrodiphenylamine; nithiocyamine
Manufacturers' Codes: C-9333-Go; CGP-4540
Molecular Formula: C13H9N3O2S
Molecular Weight: 271.29
Percent Composition: C 57.55%, H 3.34%, N 15.49%, O 11.80%, S 11.82%
Literature References: Analog of nitroscanate, q.v. Prepn: K. Antos et al., DE 1932690 (1970 to Cesk. Akad. Ved), C.A. 72, 100265 (1970); S. Rajappa et al., J. Chem. Soc. Perkin Trans. 1 1979, 2001; N. Viswanathan, R. C. Desai, Indian J. Chem. 20B, 308 (1981). Anthelmintic activity: H. P. Striebel, Experientia 32, 457 (1976); K. R. Middleton et al., ibid. 35, 243 (1979); H. G. Sen, B. N. Deb, Am. J. Trop. Med. Hyg. 30, 992 (1981). HPLC determn in human plasma: W. M. Kofi-Tsekpo, C. W. Karekezi, Drugs Exp. Clin. Res. 14, 31 (1988). Clinical pharmacology: A. B. Vaidya et al., Br. J. Clin. Pharmacol. 4, 463 (1977). Mutagenicity study: B. S. Reddy et al., Antimicrob. Agents Chemother. 22, 707 (1982). Brief review: J. I. Bruce, Int. J. Parasitol. 17, 131-140 (1987).
Properties: Crystals from acetone, mp 196-198°.
Melting point: mp 196-198°
Therap-Cat: Anthelmintic (Schistosoma).
Keywords: Anthelmintic (Nematodes); Anthelmintic (Schistosoma).
Amosulalol Amotriphene Amoxapine Amoxicillin AMPA

Amoscanate
Skeletal formula
Space-filling model
Identifiers
CAS number 26328-53-0 YesY
PubChem 33488
ChemSpider 30904 YesY
ChEBI CHEBI:38944 YesY
ChEMBL CHEMBL93385 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C13H9N3O2S
Molar mass 271.29 g mol−1
Melting point 204–206 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Amoscanate (INN), also known as nithiocyamine, is an experimental anthelmintic agent of the arylisothiocyanate class which was found to be highly effective in animals against the four major species of schistosomes which infect humans,[1] and is also highly active against hookworm infection.[2][3] However, significant liver toxicity was seen in lab animals at higher doses. The ether analogue of amoscanate, nitroscanate, is used in veterinary medicine as an anthelmintic.

Amoscanate was developed by Ciba.[4][5]