Amoscanate
Names
Preferred IUPAC name
4-Isothiocyanato-N -(4-nitrophenyl)aniline
Other names
4-Isothiocyanato-4′-nitrodiphenylamine Nithiocyamine
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
InChI=1S/C13H9N3O2S/c17-16(18)13-7-5-12(6-8-13)15-11-3-1-10(2-4-11)14-9-19/h1-8,15H
Y Key: DKVNAGXPRSYHLB-UHFFFAOYSA-N
Y InChI=1/C13H9N3O2S/c17-16(18)13-7-5-12(6-8-13)15-11-3-1-10(2-4-11)14-9-19/h1-8,15H
O=N(=O)c1ccc(Nc2ccc(cc2)N=C=S)cc1
[O-] [N+](=O)c1ccc(cc1)Nc2ccc(N=C=S)cc2
Properties
C 13 H 9 N 3 O 2 S
Molar mass
271.29 g·mol−1
Melting point
204 to 206 °C (399 to 403 °F; 477 to 479 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Amoscanate (INN ), also known as nithiocyamine , is an experimental anthelmintic agent of the aryl isothiocyanate 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.[citation needed ]
Amoscanate was developed by Ciba .[4] [5]
References
^ Shapiro TA, Were JB, Talalay P, et al. (September 1986). "Clinical evaluation of amoscanate in healthy male volunteers" . Am. J. Trop. Med. Hyg . 35 (5): 945–53. doi :10.4269/ajtmh.1986.35.945 . PMID 3766854 .
^ Doshi JC, Vaidya AB, Sen HG, Mankodi NA, Nair CN, Grewal RS (July 1977). "Clinical trials of a new anthelmintic, 4-isothiocyanato-4'-nitrodiphenylamine (C.9333-Go/CGP 4540), for the cure of hookworm infection" . Am. J. Trop. Med. Hyg . 26 (4): 636–9. doi :10.4269/ajtmh.1977.26.636 . PMID 889004 .
^ Singh DS, Bala-Subramaniam R, Bhatia VN, Kumar V, Chandrasekar S (1981). "Study of the efficacy of compound Go.9333 (Ciba-Geigy) in hookworm infestation". Chemotherapy . 27 (3): 220–3. doi :10.1159/000237981 . PMID 7014129 .
^ Vaidya AB, Sen HG, Mankodi NA, Paul T, Sheth UK (August 1977). "Phase 1 tolerability and searching dose studies with 4-isothiocyanato-4'-nitrodiphenylamine (C.9333-Go/CGP 4540), a new anthelmintic" . Br J Clin Pharmacol . 4 (4): 463–7. doi :10.1111/j.1365-2125.1977.tb00763.x . PMC 1429051 . PMID 901739 .
^ Sharma S (1987). "Helminth diseases" . In Jucker E (ed.). Progress in Drug Research . Vol. 31. Boston: Birkhauser. ISBN 3-7643-1837-6 . Retrieved on September 10, 2008 through Google Book Search .