U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H8Cl2N2O6
Molecular Weight 359.118
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITROCLOFENE

SMILES

OC1=C(Cl)C=C(C=C1CC2=C(O)C(=CC(Cl)=C2)[N+]([O-])=O)[N+]([O-])=O

InChI

InChIKey=DIRNVHCNISKNQF-UHFFFAOYSA-N
InChI=1S/C13H8Cl2N2O6/c14-8-2-6(13(19)11(4-8)17(22)23)1-7-3-9(16(20)21)5-10(15)12(7)18/h2-5,18-19H,1H2

HIDE SMILES / InChI

Molecular Formula C13H8Cl2N2O6
Molecular Weight 359.118
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nitroclofene is an anthelminthic drug. Nitroclofene is a selective inhibitor of the fumarate reductase system of the adult liver fluke at a concentration of 4 umol/L. The enzyme plays an important role in the process of energy utilization. Consequently, it possesses good flukicidal activity against both Fasciola hepatica and F. gigantica.

Approval Year

PubMed

PubMed

TitleDatePubMed
Some pharmacokinetic data of the liver-fluke anthelmintic nitroclofene in ruminant and pre-ruminant kids.
1989 Dec
Patents

Sample Use Guides

The pharmacokinetic results suggest that extensive biodegradation of nitroclofene in the forestomach system may account for the reduced oral bioavailability of the drug in ruminants. At an oral dose rate of 10 mg/kg nitroclofene was not effective 16 weeks post-experimental infection (dose: 450 metacercariae), whereas after i.m. injection of 3 mg/kg a 95-100% reduction in EPG (eggs per g faeces) has been recorded in similar infected goats.
Route of Administration: Other
In Vitro Use Guide
Curator's Comment: In vitro plasma protein binding studies showed that more than 99% of the compound was bound to proteins in the plasma of goats, sheep and cattle, even at a relatively high concentration of 480 umol/L.
Nitroclofene is a selective inhibitor of the fumarate reductase system of the adult liver fluke at a concentration of 4 umol/L.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:13:18 GMT 2023
Edited
by admin
on Sat Dec 16 17:13:18 GMT 2023
Record UNII
NT0758136A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITROCLOFENE
INN  
INN  
Official Name English
4,6'-DICHLORO-4',6-DINITRO-2,2'-METHYLENEDIPHENOL
Systematic Name English
nitroclofene [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2106865
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID90192483
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
PUBCHEM
71718
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
EVMPD
SUB09322MIG
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
INN
4589
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
MESH
C062731
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
NCI_THESAURUS
C75224
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
CAS
39224-48-1
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
SMS_ID
100000084140
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
FDA UNII
NT0758136A
Created by admin on Sat Dec 16 17:13:18 GMT 2023 , Edited by admin on Sat Dec 16 17:13:18 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY