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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16NO6P
Molecular Weight 349.2751
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAFTALOFOS

SMILES

CCOP(=O)(OCC)ON1C(=O)C2=CC=CC3=C2C(=CC=C3)C1=O

InChI

InChIKey=QNSIFYWAPWSAIJ-UHFFFAOYSA-N
InChI=1S/C16H16NO6P/c1-3-21-24(20,22-4-2)23-17-15(18)12-9-5-7-11-8-6-10-13(14(11)12)16(17)19/h5-10H,3-4H2,1-2H3

HIDE SMILES / InChI

Description

The organophosphate compound Naftalofos is an anthelmintic drug. In Australia it is approved for veterinary use. Naftalofos has been used for many years to control nematodes of livestock. Naftalofos boluses are used against nematodes of cattle. Naphthalophos (36.6 to 51.2 mg/kg) was also 93% efficient against the multiple resistant strains of Trichostrongylus colubriformis in sheep. Naphthalophos showed efficacy against Haemonchus contortus (> 99 %),Trichostrongylus axei (99.3 %), Teladorsagia circumcincta (97.8 %), Trichostrongylus colubriformis (99.2 %), Cooperia punctata/curticei/pectinata (90.4 %), Nematodirus spathiger (89.2 %) and Oesophagostomum venulosum/columbianum (93.7 %). Naphthalophos represents an effective therapeutic alternative for incorporation into worm control programmes.

Approval Year

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Principles for the use of macrocyclic lactones to minimise selection for resistance.
2001 Nov
Characterization of moxidectin resistant Trichostrongylus colubriformis and Haemonchus contortus.
2005 Mar 10
A novel high throughput assay for anthelmintic drug screening and resistance diagnosis by real-time monitoring of parasite motility.
2010 Nov 16
Patents

Patents

20020035217
34
EP2084519A2
3
JP2008509189A
188

Sample Use Guides

In Vivo Use Guide
Naftalofos boluses administered to cattle at the dose level of 50 mg of active ingredient per kilogram of body weight reduced fecal egg counts by 83.5%.
Route of Administration: Intravenous
In Vitro Use Guide
Naftalofos inhibited H. contortus larvae with IC50 value of 0.96 uM.
Name Type Language
NAFTALOFOS
INN   MART.   MI   USAN  
INN   USAN  
Official Name English
BAY 9002
Code English
N-Hydroxynaphthalimide diethyl phosphate
Common Name English
naftalofos [INN]
Common Name English
E 9002
Code English
NAFTALOFOS [MART.]
Common Name English
ENT-25567
Code English
NAFTALOFOS [MI]
Common Name English
S-940
Code English
E-9002
Code English
BAY-9002
Code English
1H-BENZ(DE)ISOQUINOLINE-1,3(2H)-DIONE, 2-((DIETHOXYPHOSPHINYL)OXY)-
Systematic Name English
NAFTALOFOS [USAN]
Common Name English
DIETHYL NAPHTHALIMIDOOXYPHOSPHONATE
Common Name English
NSC-229795
Code English
2-((DIETHOXYPHOSPHINYL)OXY)-1H-BENZ(DE)ISOQUINOLINE-1,3(2H)-DIONE
Systematic Name English
MARETIN
Brand Name English
Classification Tree Code System Code
WHO-VATC QP52AB06
Created by admin on Sat Dec 16 16:04:17 GMT 2023 , Edited by admin on Sat Dec 16 16:04:17 GMT 2023
EPA PESTICIDE CODE 204100
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
NCI_THESAURUS C250
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2105556
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
EVMPD
SUB09128MIG
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
NCI_THESAURUS
C90727
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
FDA UNII
H5IT2P8H5I
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
SMS_ID
100000084456
Created by admin on Sat Dec 16 16:04:17 GMT 2023 , Edited by admin on Sat Dec 16 16:04:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID2042193
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
MERCK INDEX
m7708
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY Merck Index
INN
1805
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
CHEBI
51962
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
PUBCHEM
15148
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
ALANWOOD
naftalofos
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
216-078-6
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
CAS
1491-41-4
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
NSC
229795
Created by admin on Sat Dec 16 16:04:16 GMT 2023 , Edited by admin on Sat Dec 16 16:04:16 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of NAFTALOFOS
NIH
NCATS
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