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Details

Stereochemistry ACHIRAL
Molecular Formula C13H9N3O2S
Molecular Weight 271.294
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMOSCANATE

SMILES

[O-][N+](=O)C1=CC=C(NC2=CC=C(C=C2)N=C=S)C=C1

InChI

InChIKey=DKVNAGXPRSYHLB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C13H9N3O2S
Molecular Weight 271.294
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Amoscanate (4-isothiocyanato-4'-nitrodiphenylamine) is an experimental antiparasitic agent. Amoscanate possesses chemotherapeutic activity against schistosomes, and in higher doses against many other helminths including filariids and Hymenolepis diminuta.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: AMP-phosphodiesterases
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Humans: Two prospective, randomized, double blinded, placebo controlled Phase I studies were designed to evaluate the tolerance and safety of the 5% aqueous suspension of 2-mu particles of amoscanate administered to healthy male volunteers. Three of four men who received 3.5 mg/kg of amoscanate developed mild, reversible hepatotoxicity, which could not be unequivocably attributed to the drug. Amoscanate, at 1 mg/kg, is sufficiently well tolerated and safe to justify evaluation for efficacy in patients with schistosomiasis. https://www.ncbi.nlm.nih.gov/pubmed/3766854
Monkey: The antischistosomal activity of oral doses of amoscanate was determined in infected Cebus apella (capuchin monkeys) and Macaca mulatta (rhesus monkeys). In C. apella infected with Schistosoma japonicum or S. mansoni an initial dose of 10 mg/kg body weight did not alter fecal egg counts, but a subsequent dose of 25 mg/kg markedly reduced both egg counts and worm burdens; in animals infected with S. haematobium, a single dose of 25 mg/kg of amoscanate was similarly effective. Comparable schistosomicidal effects were also produced in S. japonicum- and S. mansoni-infected M. mulatta by single oral doses of 20 and 35 mg/kg, respectively. In non-infected monkeys single oral doses of 75 mg/kg of amoscanate with or without erythromycin (50 mg/kg in C. apella or 75 mg/kg in M. mulatta) did not cause any major organ toxicity as revealed by gross and histopathologic examination, hematology, blood chemistry, electrocardiograms and urinalysis.
Route of Administration: Oral
In Vitro Use Guide
Amoscanate showed in vitro good activity against adults (males and females) and free-living stages of Necator americanus with EC50 value of 7.6 mg/L.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:42:38 GMT 2023
Edited
by admin
on Sat Dec 16 16:42:38 GMT 2023
Record UNII
X0MK46CVRB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMOSCANATE
INN   MART.   MI  
INN  
Official Name English
P-(P-NITROANILINO)PHENYL ISOTHIOCYANATE
Common Name English
AMOSCANATE [MI]
Common Name English
AMOSCANATE [MART.]
Common Name English
amoscanate [INN]
Common Name English
4-ISOTHIOCYANATO-4'-NITRODIPHENYLAMINE
Common Name English
Code System Code Type Description
CHEBI
38944
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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MESH
C012391
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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EPA CompTox
DTXSID90180946
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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INN
4042
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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MERCK INDEX
m1841
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
PRIMARY Merck Index
EVMPD
SUB05477MIG
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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NCI_THESAURUS
C169783
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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CAS
26328-53-0
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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FDA UNII
X0MK46CVRB
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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SMS_ID
100000087429
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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PUBCHEM
33488
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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ChEMBL
CHEMBL93385
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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WIKIPEDIA
AMOSCANATE
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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DRUG CENTRAL
189
Created by admin on Sat Dec 16 16:42:38 GMT 2023 , Edited by admin on Sat Dec 16 16:42:38 GMT 2023
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Related Record Type Details
ACTIVE MOIETY