Leptophos is an organophosphate insecticide that was widely used in agriculture for controlling pests on a variety of crops. It is a highly effective insecticide but has been banned in many countries due to its toxicity to humans and wildlife. Leptophos is synthesized through a multi-step process that involves the reaction of phosphorus oxychloride with 2,4-dichlorophenol followed by a series of reactions with other reagents. It is a potent inhibitor of acetylcholinesterase, an enzyme that plays a critical role in the transmission of nerve impulses. This inhibition leads to a buildup of acetylcholine, a neurotransmitter, in the synapse, causing a wide range of neurological effects. Leptophos is highly toxic to birds, fish, and other aquatic organisms, and can persist in the environment for long periods. Its widespread use and persistence led to its banning in many countries. It has also been linked to various human health effects, including cancer, birth defects, and neurodevelopmental problems. Research on leptophos is ongoing to understand its mechanisms of action, its environmental fate, and its potential for bioremediation. This research is essential for developing strategies to mitigate its environmental impact and protect human health.'
Leptophos: An organothiophosphate insecticide. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
leptophos : A racemate comprising equimolar amounts of (R)- and (S)-leptophos. It is an organothiophosphate insecticide that shows neurotoxic effect in humans. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
O-(4-bromo-2,5-dichlorophenyl) O-methyl phenylphosphonothioate : An organic phosphonate that is phenylphosphonothioic O,O-acid in which the hydroxy groups are substituted by methoxy and 4-bromo-2,5-dichlorophenoxy groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 30709 |
| CHEMBL ID | 2074801 |
| CHEBI ID | 191217 |
| SCHEMBL ID | 116961 |
| MeSH ID | M0016740 |
| Synonym |
|---|
| phosphonothioic acid, phenyl-, o-(4-bromo-2,5-dichlorophenyl) o-methyl ester |
| leptophos |
| nk 711 |
| caswell no. 525b |
| vcs-506 |
| oms 1438 |
| o-methyl-o-(4-bromo-2,5-dichlorophenyl)phenyl thiophosphonate |
| brn 2152663 |
| fosvel |
| k62-105 |
| (r)-phenylphosphonothioic acid o-(4-bromo-2,5-dichlorophenyl) o-methyl ester |
| velsicol vcs 506 |
| phosphonothioic acid, phenyl-, o-(4-bromo-2,5-dichlorophenyl) o-methyl ester, (s)- |
| velsicol 506 |
| abar (velsicol) |
| (s)-phenylphosphonothioic acid o-(4-bromo-2,5-dichlorophenyl) o-methyl ester |
| phosphonothioic acid, phenyl-, o-(4-bromo-2,5-dichlorophenyl) o-methyl ester, (r)- |
| phenylphosphonothioic acid o-(4-bromo-2,5-dichlorophenyl) o-methyl ester |
| o-methyl o-2,5-dichloro-4-bromophenyl phenylthiophosphonate |
| epa pesticide chemical code 525300 |
| o-(4-bromo-2,5-dichlorophenyl) o-methyl phenylphosphonothioate |
| vcs 5-d |
| einecs 244-472-8 |
| (r)-(+)-leptophos |
| (+-)-leptophos |
| mbcp |
| ai3-27378 |
| hsdb 2621 |
| phosvel |
| leptophos [iso] |
| abar |
| o-(2,5-dichloro-4-bromophenyl) o-methyl phenylthiophosphonate |
| oleophosvel |
| (s)-(-)-leptophos |
| leptophos, analytical standard |
| 21609-90-5 |
| CHEBI:191217 |
| 73307-67-2 |
| 73307-66-1 |
| tox21_301903 |
| dtxcid1020279 |
| NCGC00255629-01 |
| cas-21609-90-5 |
| dtxsid3040279 , |
| unii-c45e8fug3z |
| c45e8fug3z , |
| CHEMBL2074801 |
| AKOS015903160 |
| (+/-)-leptophos |
| leptophos [mi] |
| leptophos [hsdb] |
| (rs)-(o-4-bromo-2,5-dichlorophenyl o-methyl phenylphosphonothioate) |
| o-(4-bromo-2,5-dichlorophenyl) o-methyl p-phenylphosphonothioate |
| SCHEMBL116961 |
| vcs 506 |
| CVRALZAYCYJELZ-UHFFFAOYSA-N |
| (.+/-.)-leptophos |
| phosphonothioic acid,p-phenyl-,o-(4-bromo-2,5-dichlorophenyl)o-methyl ester |
| 4-bromo-2,5-dichlorophenyl methyl phenyl(sulfanylidene)phosphonite |
| leptophos, pestanal(r), analytical standard |
| J-014173 |
| o-4-bromo-2,5-dichlorophenyl o-methyl phenylphosphonothioate |
| o-(4-bromo-2,5-dichlorophenyl)-o-methyl phenyl phosphonothioate |
| Q6528275 |
| (4-bromo-2,5-dichlorophenoxy)-methoxy-phenyl-sulfanylidene-lambda5-phosphane |
| WAA60990 |
Leptophos is a potent acetylcholinesterase inhibitor which causes delayed central-peripheral neuropathy.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Leptophos is a potent acetylcholinesterase inhibitor which causes delayed central-peripheral neuropathy. " | ( Effects of leptophos on rat brain levels and turnover rates of biogenic amines and their metabolites. Aldous, CN; Farr, CH; Sharma, RP, 1982) | 2.1 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Treatment with Leptophos for the same period produced slight motor dysfunction and a small but significant reduction in the level of striatal dopamine." | ( Role of striatal dopamine in delayed neurotoxic effects of organophosphorus compounds. Fang, SC; Freed, VH; Kar, PP; Matin, MA, 1976) | 0.6 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " It is believed that the phosphonate ester configuration of EPN and Leptophos has a specific mode of toxic action which is mainly located at the central nervous system." | ( Neurotoxicity of organophosphorus insecticides Leptophos and EPN. Ahmed, NS; El-Sebae, AH; Elamayem, MA; Soliman, SA, 1977) | 0.75 |
| "The oral LD50 of a compound in hens does not reliably predict the neurotoxic dose of that compound." | ( Consideration of dose levels for delayed neurotoxicity testing in hens: the relationship of neurotoxic dosages to acute LD50 values. Hixson, EJ, 1983) | 0.27 |
The organophosphorous insecticide leptophos is known to produce delayed neurotoxicity (DNT) A practical method for the analysis of leptphos in tissue samples has been developed by utilizing high-performance liquid chromatography.
| Excerpt | Reference | Relevance |
|---|---|---|
| "A pharmacokinetic profile of [14C] leptophos was determined in laying hens following a single oral dose of 400 mg/kg (0." | ( Pharmacokinetics of a neurotoxic oral dose of leptophos in hens. Abou-Donia, MB, 1976) | 0.79 |
| "In an attempt to carry out a pharmacokinetic study of the organophosphorous insecticide leptophos, which is known to produce delayed neurotoxicity (DNT), a practical method for the analysis of leptophos in tissue samples has been developed by utilizing high-performance liquid chromatography." | ( [Pharmacokinetics of the organophosphorous insecticide leptophos in the hen]. Yamaguchi, Y, 1989) | 0.75 |
The susceptibility of wild mallard ducklings to the delayed neurotoxic effect of the neurotoxic organophosphorus insecticides cyanofenphos and leptophos was evaluated following a daily dosing regimen. Hens given leptonophos and TOCP demonstrated delayed neuropathy with obvious inhibition of NTE.
| Excerpt | Relevance | Reference |
|---|---|---|
| "The susceptibility of wild mallard ducklings to the delayed neurotoxic effect of the neurotoxic organophosphorus insecticides cyanofenphos and leptophos was evaluated following a daily dosing regimen." | ( Delayed neurotoxicity in the wild mallard duckling caused by the organophosphorus insecticides cyanofenphos and leptophos. Ahmed, NS; el-Bakary, AS; el-Gendy, KS; el-Sebae, AH; Soliman, SA, 1986) | 0.68 |
| " Surviving ducks of this group completely recovered from the cholinergic effect 2 or 3 d after finishing the dosing regimen." | ( Delayed neuropathy in adult Peking ducks induced by some organophosphorus esters. Farmer, JD; Soliman, SA, 1984) | 0.27 |
| " Rats were administered multiple doses of leptophos until motor deficits were observed in rotorod performance in the highest dosage group." | ( Effects of leptophos on rat brain levels and turnover rates of biogenic amines and their metabolites. Aldous, CN; Farr, CH; Sharma, RP, 1982) | 0.92 |
| " The oral LD50 in rats does not predict either the oral LD50 in hens or the neurotoxic dose in hens, so there is no justification for using the rat value to predict the neurotoxic dosage in hens." | ( Consideration of dose levels for delayed neurotoxicity testing in hens: the relationship of neurotoxic dosages to acute LD50 values. Hixson, EJ, 1983) | 0.27 |
| " On the other hand, none of the EPN-treated sheep showed clinical signs of neurotoxicity during the course of the experiment at the dosage tested." | ( Six-month daily treatment of sheep with neurotoxic organophosphorus compounds. Curley, A; Durham, WF; Farmer, JD; Soliman, SA; Svendsgaard, D, 1983) | 0.27 |
| " Hens given leptophos and TOCP demonstrated delayed neuropathy with obvious inhibition of NTE, but the times of onset and the degrees of peak inhibition of NTE activity were different: 6-24 hours after dosing and 73-82% of normal activity for leptophos, and 24-48 hours and 45-80% for TOCP, respectively." | ( Delayed neuropathy and inhibition of soluble neuropathy target esterase following the administration of organophosphorus compounds to hens. Piao, FY; Tian, Y; Xie, XK; Yamauchi, T, 1998) | 0.68 |
| Class | Description |
|---|---|
| dichlorobenzene | Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions. |
| bromobenzenes | A member of the class of benzenes that is benzene substituted by at least one bromo group. |
| organic phosphonate | |
| phosphonic ester | A phosphonic acid derivative in which one or both OH groups have been esterified. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| acetylcholinesterase | Homo sapiens (human) | Potency | 57.8695 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347397; AID1347398; AID1347399 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 54.7229 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| AR protein | Homo sapiens (human) | Potency | 26.8269 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743035; AID743036 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 30.6379 | 0.0006 | 57.9133 | 22,387.1992 | AID1259378 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 17.0657 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 44.2183 | 0.0004 | 17.9460 | 75.1148 | AID1346784; AID1346795 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 24.5412 | 0.0002 | 14.3764 | 60.0339 | AID720692 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 63.1503 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 13.3201 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 61.8914 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 24.5412 | 0.3758 | 27.4851 | 61.6524 | AID743217 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 24.3365 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 48.9662 | 0.0002 | 29.3054 | 16,493.5996 | AID743069 |
| peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 61.6448 | 0.0010 | 24.5048 | 61.6448 | AID743215 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 43.9307 | 0.0010 | 19.4141 | 70.9645 | AID743140; AID743191 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 43.6412 | 0.0237 | 23.2282 | 63.5986 | AID743241 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 19.5219 | 0.0007 | 23.0674 | 1,258.9301 | AID743085; AID743122 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 10.8245 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 62.3263 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 54.4827 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID680510 | TP_TRANSPORTER: inhibition of Doxorubicin efflux (Doxorubicin: 50 uM, Leptophoos: 250 uM) in MDR1-expressing B16/F10 cells | 1996 | Toxicology and applied pharmacology, Nov, Volume: 141, Issue:1 | Interaction of structurally diverse pesticides with the human MDR1 gene product P-glycoprotein. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 68 (86.08) | 18.7374 |
| 1990's | 6 (7.59) | 18.2507 |
| 2000's | 3 (3.80) | 29.6817 |
| 2010's | 2 (2.53) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (21.14) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (3.37%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 86 (96.63%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||