Synonym
Maretin; Naftalofosum; Naphthalophos; Rametin; Rawetin; Naftalofos
IUPAC/Chemical Name
1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl diethyl phosphate
InChi Key
QNSIFYWAPWSAIJ-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C1N(OP(OCC)(OCC)=O)C(C2=CC=CC3=CC=CC1=C23)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Naftalofos is an insecticide and an anthelmintic.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
349.28
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
TBD
1: Kotze AC, Ruffell AP, Ingham AB. Phenobarbital induction and chemical synergism demonstrate the role of UDP-glucuronosyltransferases in detoxification of naphthalophos by Haemonchus contortus larvae. Antimicrob Agents Chemother. 2014 Dec;58(12):7475-83. doi: 10.1128/AAC.03333-14. Epub 2014 Oct 6. PubMed PMID: 25288079; PubMed Central PMCID: PMC4249576.
2: Fiel C, Guzmán M, Steffan P, Rodriguez E, Prieto O, Bhushan C. The efficacy of trichlorphon and naphthalophos against multiple anthelmintic-resistant nematodes of naturally infected sheep in Argentina. Parasitol Res. 2011 Aug;109 Suppl 1:S139-48. doi: 10.1007/s00436-011-2410-8. PubMed PMID: 21739383.
3: Kotze AC, Stein PA, Dobson RJ. Investigation of intestinal nematode responses to naphthalophos and pyrantel using a larval development assay. Int J Parasitol. 1999 Jul;29(7):1093-9. PubMed PMID: 10501619.
4: Cooper NA, Rolfe PF, Searson JE, Dawson KL. Naphthalophos combinations with benzimidazoles or levamisole as effective anthelmintics for sheep. Aust Vet J. 1996 Sep;74(3):221-4. PubMed PMID: 8894038.
5: Le Jambre LF, Barger IA. Efficiency of rafoxanide and naphthalophos against inhibited Haemonchus contortus. Aust Vet J. 1979 Jul;55(7):346-7. PubMed PMID: 518438.
6: Varshney TR, Singh YP. A comparative sutdy of anthelmintic effect of naphthalophos and parbendazole against natural infection of gastro-intestinal worms of sheep. Indian Vet J. 1979 Mar;56(3):207-10. PubMed PMID: 582588.
7: Leland SE Jr, Ridley RK, Dick JW, Slonka GF, Zimmerman GL. Anthelmintic activity of trichlorfon, coumaphos, and naphthalophos against the in vitro grown parastic stages of Cooperia punctata. J Parasitol. 1971 Dec;57(6):1190-6. PubMed PMID: 5157153.
8: Mullee MT, Cox DD, Allen AD. Effect of naphthalophos, phenothiazine, and thiabendazole on gastrointestinal nematode egg counts in feedlot cattle. Am J Vet Res. 1970 Jul;31(7):1203-15. PubMed PMID: 5447693.
9: Nelson DL, White RG, Mozier JO, Allen AD. Toxicity of larger-than-recommended doses of naphthalophos to cattle, sheep, and goats. Am J Vet Res. 1970 Jan;31(1):199-201. PubMed PMID: 5461126.
10: Partosoedjono S, Drudge JH, Lyons ET, Knapp FW. Evaluation of naphthalophos against Oestrus ovis and a thiabendazole-tolerant strain of Haemonchus contortus in lambs. Am J Vet Res. 1969 Jan;30(1):81-3. PubMed PMID: 5812440.
11: Train CT, White RG, Hansen MF. Efficacy of coumaphos and naphthalophos against nematodes of lambs. Am J Vet Res. 1968 Dec;29(12):2331-5. PubMed PMID: 5749116.
12: McDougald LR, White RG, Hansen MF. Efficacy of naphthalophos and coumaphos against nematodes of goats. Am J Vet Res. 1968 May;29(5):1077-9. PubMed PMID: 5646005.
