Synonym
Leptophos; Abar; Fosvel
IUPAC/Chemical Name
Phosphonothioic acid, phenyl-, O-(4-bromo-2,5-dichlorophenyl) O-methyl ester
InChi Key
CVRALZAYCYJELZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10BrCl2O2PS/c1-17-19(20,9-5-3-2-4-6-9)18-13-8-11(15)10(14)7-12(13)16/h2-8H,1H3
SMILES Code
S=P(C1=CC=CC=C1)(OC)OC2=CC(Cl)=C(Br)C=C2Cl
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
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:
Leptophos is an organophosphate insecticide.
In vitro activity:
At a sublethal concentration of 3 microM, both LEP (leptophos) and CB (ester carbaryl) were able to inhibit the outgrowth of axon-like processes from N2a cells after only 4 h of exposure.
Reference: Toxicol In Vitro. 2003 Feb;17(1):115-20. https://pubmed.ncbi.nlm.nih.gov/12537969/
In vivo activity:
Delayed neurotoxicity induced by leptophos, an organophosphorus insecticide, was intensified in hens when phenylmethylsulfonyl fluoride (PMSF) at dose of 30, 60, and 120 mg/kg body weight was administered at different time intervals (24 hr, 3 days, and 5 days) for each dose of PMSF after the hens were exposed to 30 mg/kg (i.v.) of leptophos.
Reference: J Toxicol Sci. 1995 Nov;20(5):609-17. https://pubmed.ncbi.nlm.nih.gov/8720167/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
412.06
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:
1. Sachana M, Flaskos J, Alexaki E, Hargreaves AJ. Inhibition of neurite outgrowth in N2a cells by leptophos and carbaryl: effects on neurofilament heavy chain, GAP-43 and HSP-70. Toxicol In Vitro. 2003 Feb;17(1):115-20. doi: 10.1016/s0887-2333(02)00121-2. PMID: 12537969.
2. Piao FY, Kitabatake M, Xie XK, Yamauchi T. Effects of various post-treatment by phenylmethylsulfonyl fluoride on delayed neurotoxicity induced by leptophos. J Toxicol Sci. 1995 Nov;20(5):609-17. doi: 10.2131/jts.20.5_609. PMID: 8720167.
3. Anthony J. Acetylcholinesterase activity and degenerative changes in various segments of the spinal cord of hens induced by ingestion of subchronic levels of leptophos. J Environ Sci Health B. 1993 Jun;28(3):275-90. doi: 10.1080/03601239309372826. PMID: 7685784.
In vitro protocol:
1. Sachana M, Flaskos J, Alexaki E, Hargreaves AJ. Inhibition of neurite outgrowth in N2a cells by leptophos and carbaryl: effects on neurofilament heavy chain, GAP-43 and HSP-70. Toxicol In Vitro. 2003 Feb;17(1):115-20. doi: 10.1016/s0887-2333(02)00121-2. PMID: 12537969.
In vivo protocol:
1. Piao FY, Kitabatake M, Xie XK, Yamauchi T. Effects of various post-treatment by phenylmethylsulfonyl fluoride on delayed neurotoxicity induced by leptophos. J Toxicol Sci. 1995 Nov;20(5):609-17. doi: 10.2131/jts.20.5_609. PMID: 8720167.
2. Anthony J. Acetylcholinesterase activity and degenerative changes in various segments of the spinal cord of hens induced by ingestion of subchronic levels of leptophos. J Environ Sci Health B. 1993 Jun;28(3):275-90. doi: 10.1080/03601239309372826. PMID: 7685784.
1: Jun D, Musilova L, Pohanka M, Jung YS, Bostik P, Kuca K. Reactivation of human acetylcholinesterase and butyrylcholinesterase inhibited by leptophos-oxon with different oxime reactivators in vitro. Int J Mol Sci. 2010 Aug 3;11(8):2856-63. doi: 10.3390/ijms11082856. PubMed PMID: 21152278; PubMed Central PMCID: PMC2996742.
2: Yamauchi T, Konno N, Kinebuchi H. Delayed neurotoxicity resulting from administration of leptophos to the comb of domestic fowl. Tohoku J Exp Med. 1982 Oct;138(2):199-208. PubMed PMID: 6184852.
3: Riskallah MR, Esaac EG. Metabolism and excretion of leptophos and its phenol in S and R larvae of the Egyptian cotton leafworm. Arch Environ Contam Toxicol. 1982;11(2):253-7. PubMed PMID: 6178375.
4: Preissig SH, Abou-Donia MB. The neuropathology of leptophos in the hen: a chronologic study. Environ Res. 1978 Oct;17(2):242-50. PubMed PMID: 318517.
5: El-Sebae AH, Soliman SA, Elamayem MA, Ahmed NS. Neurotoxicity of organophosphorus insecticides Leptophos and EPN. J Environ Sci Health B. 1977;12(4):269-87. PubMed PMID: 72768.
6: Moroi K, Kuga T. Inhibitory effect of leptophos on carboxylesterase (isocarboxazid amidase) in rat liver. Toxicol Lett. 1982 Apr;11(1-2):81-5. PubMed PMID: 6178187.
7: Soliman SA, Curley A, Farmer J, Novak R. In vivo inhibition of chicken brain acetylcholinesterase and neurotoxic esterase in relation to the delayed neurotoxicity of leptophos and cyanofenphos. J Environ Pathol Toxicol Oncol. 1986 Sep-Dec;7(1-2):211-24. PubMed PMID: 2432215.
8: Lee PW, Fukuto TR. Penetration and comparative metabolism of leptophos in susceptible and resistant houseflies. Arch Environ Contam Toxicol. 1976;4(4):443-55. PubMed PMID: 63268.
9: Yamaguchi Y. [Pharmacokinetics of the organophosphorous insecticide leptophos in the hen]. Nihon Eiseigaku Zasshi. 1989 Feb;43(6):1159-68. Japanese. PubMed PMID: 2473232.
10: Piao FY, Kitabatake M, Xie XK, Yamauchi T. Effects of various post-treatment by phenylmethylsulfonyl fluoride on delayed neurotoxicity induced by leptophos. J Toxicol Sci. 1995 Nov;20(5):609-17. PubMed PMID: 8720167.
11: Abou-Donia MB. Pharmacokinetics of a neurotoxic oral dose of leptophos in hens. Arch Toxicol. 1976 Oct 28;36(2):103-10. PubMed PMID: 64240.
12: Aldous CN, Farr CH, Sharma RP. Effects of leptophos on rat brain levels and turnover rates of biogenic amines and their metabolites. Ecotoxicol Environ Saf. 1982 Dec;6(6):570-6. PubMed PMID: 6188603.
13: Piao FY, Xie XK, Kitabatake M, Yamauchi T. Transfer of leptophos in hen eggs and tissues of embryonic rats. J Toxicol Sci. 1997 May;22(2):99-109. PubMed PMID: 9198007.
14: Yamauchi T, Katoh K, Konno N, Fukushima M. Delayed neurotoxicity and toxicokinetics of leptophos in hens given repeatedly by low-dose intravenous injections. J Toxicol Sci. 1989 Feb;14(1):11-21. PubMed PMID: 2472490.
15: Yen JH, Tsai CC, Wang YS. Separation and toxicity of enantiomers of organophosphorus insecticide leptophos. Ecotoxicol Environ Saf. 2003 Jun;55(2):236-42. PubMed PMID: 12742374.
16: Abou-Donia MB, Graham DG. Delayed neurotoxicity of subchronic oral administration of leptophos to hens: recovery during four months after exposure. J Toxicol Environ Health. 1979 Nov;5(6):1133-47. PubMed PMID: 93648.
17: Anthony J. Acetylcholinesterase activity and degenerative changes in various segments of the spinal cord of hens induced by ingestion of subchronic levels of leptophos. J Environ Sci Health B. 1993 Jun;28(3):275-90. PubMed PMID: 7685784.
18: Chambers JE, Chambers HW. Oxidative desulfuration of chlorpyrifos, chlorpyrifos-methyl, and leptophos by rat brain and liver. J Biochem Toxicol. 1989 Fall;4(3):201-3. PubMed PMID: 2481746.
19: Reinders JH, Hansen LG, Metcalf RL. In vitro neurotoxic esterase assay using leptophos oxon analogs as inhibitors. Toxicol Lett. 1983 Jun;17(1-2):107-11. PubMed PMID: 6623496.
20: Hussain MA, Oloffs PC. Neurotoxic effects of leptophos (PhosvelR) in chickens and rats following chronic low-level feeding. J Environ Sci Health B. 1979;14(4):367-82. PubMed PMID: 89138.
