Crufomate, also known as 4-(dibromomethylsulfinyl)phenyl N-methylcarbamate, is a synthetic organophosphate insecticide and anthelmintic. It acts as a cholinesterase inhibitor, disrupting the transmission of nerve impulses in insects and parasites. Crufomate was originally developed as a veterinary medicine to control internal and external parasites in livestock, particularly cattle, sheep, and swine. However, due to its toxicity to birds and concerns about environmental contamination, its use has been restricted or banned in many countries. Research on crufomate focuses on understanding its mechanism of action, its environmental fate, and potential risks to human and animal health. Studies have investigated its effects on various organisms, including the development of resistance in insects and parasites, the potential for bioaccumulation in the environment, and the impact on human health through exposure.'
crufomate: was MH 1976-92 (see under INSECTICIDES, ORGANOPHOSPHATE 1976-90); use ORGANOPHOSPHORUS COMPOUNDS to search CRUFOMATE 1976-92; an insecticide used extensively for the control of cattle grubs, cattle lice, and hornflies [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 9300 |
| CHEMBL ID | 1880767 |
| CHEBI ID | 82111 |
| SCHEMBL ID | 121165 |
| MeSH ID | M0198155 |
| Synonym |
|---|
| phosphoramidic acid, methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester |
| phenol, ester with methyl methylphosphoramidate |
| rulene |
| 4-tert-butyl-2-chlorophenyl o-methyl methylphosphoroamidate |
| o-methyl o-2-chloro-4-tert-butylphenyl n-methylamidophosphate |
| dowco 132 |
| ruelene drench |
| phosphoramidic acid, 4-tert-butyl-2-chlorophenyl methyl ester |
| 299-86-5 |
| n,o-dimethyl-o-(4-tert-butyl-2-chlorophenyl)phosphoramidate |
| 4-tert. butyl 2-chlorophenyl methylphosphoramidate de methyle |
| phosphoramidic acid methyl-,1-dimethylethyl)phenyl methyl ester |
| crufomate |
| crufomat |
| amidophos |
| ruelene |
| o-(4-tert butyl-2-chloor-fenyl)-o-methyl-fosforzuur-n-methyl-amide |
| wln: 1x1 & 1 & r cg dopo & o1 & m1 |
| o-(4-tert-butyl-2-chlor-phenyl)-o-methyl-phosphorsaeure-n-methylamid |
| o-(4-terz.-butil-2-cloro-fenil)-o-metil-fosforammide |
| methylphosphoramidic acid, 4-tert-butyl-2-chlorophenyl methyl ester |
| cruformate |
| ent 25,602-x |
| phosphoramidic acid, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester |
| 4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate |
| amidofos |
| montrel |
| nsc-253463 |
| nsc253463 |
| D03610 |
| crufomate (usan/inn) |
| crufomatum [inn-latin] |
| o-(4-terz.-butil-2-cloro-fenil)-o-metil-fosforammide [italian] |
| crufomate [usan:inn:ban] |
| o-(4-tert-butyl-2-chlor-phenyl)-o-methyl-phosphorsaeure-n-methylamid [german] |
| epa pesticide chemical code 012101 |
| nsc 253463 |
| methylphosphoramidic acid 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester |
| phenol, 4-t-butyl-2-chloro-, ester with methyl methylphosphoramidate |
| o-(4-tert-butyl-2-chlorophenyl) o-methyl n-methylamido phosphate |
| 4-tert. butyl 2-chlorophenyl methylphosphoramidate de methyle [french] |
| crufomate a |
| phosphoramidic acid methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester |
| methylphosphoramidic acid, 4-t-butyl-2-chlorophenyl methyl ester |
| phosphoramidic acid, 4-tert-butyl-2-chlorophenylphosphoramidate |
| 4-t-butyl-2-chlorophenylmethyl methyl phosphoramidate |
| 2-chloro-4-(1,1-dimethylethyl)phenyl methyl methylphosphoramidate |
| hsdb 1547 |
| ruelene 25e |
| m-1261 , |
| crufomate [ansi] |
| o-methyl-o-(4-tert-butyl-2-chlorophenyl)methylphosphoramidate |
| einecs 206-083-1 |
| brn 2133258 |
| 4-t-butyl-2-chlorophenyl methyl methylphosphoramidate |
| caswell no. 263a |
| o-(4-tert butyl-2-chloor-fenyl)-o-methyl-fosforzuur-n-methyl-amide [dutch] |
| 4-tert-butyl-2-chlorophenyl n-methyl o-methylphosphoramidate |
| phosphoramidic acid, methyl-, 4-tert-butyl-2-chlorophenyl methyl ester |
| ai3-25602 |
| crufomato [inn-spanish] |
| NCGC00163827-01 |
| ruerene |
| n-[(4-tert-butyl-2-chlorophenoxy)-methoxyphosphoryl]methanamine |
| FT-0665229 |
| NCGC00163827-02 |
| C18972 |
| dtxsid1037515 , |
| tox21_302262 |
| dtxcid9017515 |
| cas-299-86-5 |
| NCGC00255615-01 |
| chebi:82111 , |
| CHEMBL1880767 |
| crufomato |
| crufomatum |
| unii-v82q65924l |
| phosphorsaeure-methyl-(2-chlor-4-tert-butyl-phenyl)-diestermethylamid |
| 4-06-00-03312 (beilstein handbook reference) |
| v82q65924l , |
| AKOS015888331 |
| crufomate [mi] |
| crufomate [usan] |
| crufomate [hsdb] |
| crufomate [inn] |
| (rs)-(4-tert-butyl-2-chlorophenyl methyl methylphosphoramidate) |
| SCHEMBL121165 |
| phenol, 4-tert-butyl-2-chloro-, ester with methyl methylphosphoramidate |
| BOFHKBLZOYVHSI-UHFFFAOYSA-N |
| 4-tert-butyl-2-chlorophenyl methyl methylamidophosphate # |
| sr-01000945046 |
| SR-01000945046-1 |
| crufomate, pestanal(r), analytical standard |
| J-017722 |
| phosphoramidic acid, methyl-, 2-chloro-4-(1,1-dimethylethyl), phenylmethyl ester |
| Q20983235 |
| m 1261 |
| 4-(tert-butyl)-2-chlorophenyl methyl methylphosphoramidate |
| [(4-tert-butyl-2-chlorophenoxy)(methoxy)phosphoryl](methyl)amine |
| Class | Description |
|---|---|
| alkylbenzene | A monocyclic arene that is benzene substituted with one or more alkyl groups. |
| [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) |
|---|---|---|---|---|---|---|---|
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 70.9799 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
| acetylcholinesterase | Homo sapiens (human) | Potency | 60.7754 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347397; AID1347398 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 43.9604 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 31.8596 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 39.5759 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743035; AID743036; AID743063 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 34.0629 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 61.1306 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 27.0320 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 47.9483 | 0.0015 | 30.6073 | 15,848.9004 | AID1224848; AID1224849; AID1259403 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 18.5908 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 43.6412 | 0.0002 | 29.3054 | 16,493.5996 | AID743075 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 43.6412 | 0.0010 | 19.4141 | 70.9645 | AID743191 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 68.5896 | 0.0007 | 23.0674 | 1,258.9301 | AID743085 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 8.6349 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 10.9622 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
| thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 3.1623 | 0.0100 | 39.5371 | 1,122.0200 | AID588547 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 68.5896 | 0.0003 | 23.4451 | 159.6830 | AID743067 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 47.3641 | 0.0006 | 27.2152 | 1,122.0200 | AID651741; AID720636; AID743202; AID743219 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 61.1306 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 8 (80.00) | 18.7374 |
| 1990's | 1 (10.00) | 18.2507 |
| 2000's | 1 (10.00) | 29.6817 |
| 2010's | 0 (0.00) | 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 (21.07) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 10 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||