Page last updated: 2024-11-05

phenmedipham

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

phenmedipham: minor descriptor (72-84); on-line search CARBAMATES (72-84); Index Medicus search HERBICIDES, CARBAMATE (75-84), CARBAMATES (72-75) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

phenmedipham : A carbamate ester that is (3-methylphenyl)carbamic acid in which the hydrogen of the hydroxy group has been replaced by a 3-[(methoxycarbonyl)amino]phenyl group. [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]

Cross-References

ID SourceID
PubMed CID24744
CHEMBL ID1079421
CHEBI ID81734
SCHEMBL ID54580
MeSH IDM0262746

Synonyms (104)

Synonym
3-[(methoxycarbonyl)amino]phenyl n-(3-methylphenyl)carbamate
carbamic acid, (3-methylphenyl)-, 3-[(methoxycarbonyl)amino]phenyl ester
carbanilic acid, m-hydroxy-, methyl ester, m-methylcarbanilate (ester)
NCGC00090870-01
13684-63-4
3-((methoxycarbonyl)amino)phenyl n-(3-methylphenyl)carbamate (phenmedipham)
methyl-3-m-tolycarbamoloxyphenyl carbamate
m-hydroxycarbanilic acid methyl ester m-methylcarbanilate
hsdb 1402
synbetan p
3-methoxycarbonylaminophenyl n-3'-methylphenylcarbamate
carbamic acid, (3-methylphenyl)-, 3-((methoxycarbonyl)amino)phenyl ester
3-((methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate
3-(methylphenyl)carbamic acid 3-((methoxycarbonyl)amino)phenyl ester
einecs 237-199-0
fenmedifam
3-methoxycarbonylaminophenyl 3'-methylcarbanilate
phenmediphame [iso-french]
methyl m-hydroxycarbanilate m-methylcarbanilate (ester)
carbanilic acid, m-hydroxy, methyl ester, m-methylcarbanilate (ester)
methyl m-hydroxycarbanilate, m-methylcarbanilate
morton ep 452
phenmediphame
kemifam
epa pesticide chemical code 098701
brn 2395027
phenmedipham [ansi:bsi:iso]
schering 4072
methyl 3-(m-tolylcarbamoyloxy)phenylcarbamate
carbanilic acid, m-hydroxy-, methyl ester, m-methylcarbanilate
sn-38584
schering-38584
caswell no. 648b
betanal
methyl-3-hydroxycarbanilate-3-methylcarbanilate
ccris 6091
spin-aid
s 4075
methyl n-(3-(n-(3-methylphenyl)carbamoyloxy)phenyl)carbamate
3-methoxycarbonyl-n-(3'-methylphenyl)-carbamat [german]
sn 4075
3-(carbomethoxyamino)phenyl 3-methylcarbanilate
methyl 3-(3-methylcarbaniloyloxy)carbanilate
ep-452
phenmedipham (3-methoxycarbonylaminophenyl-n-3'-methylphenyl
3-[(methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate
phenmedipham
[3-(methoxycarbonylamino)phenyl] n-(3-methylphenyl)carbamate
bdbm50311785
CHEMBL1079421 ,
chebi:81734 ,
n-[3-[(3-methylanilino)-oxomethoxy]phenyl]carbamic acid methyl ester
A807149
NCGC00090870-02
C18420
3-methoxycarbonyl-n-(3'-methylphenyl)-carbamat
unii-uje31kxp78
uje31kxp78 ,
tox21_303044
dtxsid1024255 ,
dtxcid304255
cas-13684-63-4
NCGC00257194-01
NCGC00258847-01
tox21_201295
FT-0630409
3-((methoxycarbonyl)amino)phenyl m-tolylcarbamate
AKOS015895890
phenmedipham [hsdb]
methyl-m-hydroxycarbanilate-m-methylcarbanilate
phenmedipham [mi]
phenmedipham [iso]
3-((methoxycarbonyl)amino)phenyl n-(3-methylphenyl)carbamate
SCHEMBL54580
3-methoxycarbonyl-n-(3'-methylphenyl)-carbamate
3-(methoxyformamido)phenyl (3-methylphenyl)carbamate
tripart beta
kemifam fl
synbetan mix (salt/mix)
methyl n-[3-[n-(3-methylphenyl)carbamoyloxy]phenyl]carbamate
betamix (salt/mix)
gusto
betanal e
beetomax
betosip
fender
betanal compact (salt/mix)
sn 38584
ethofumesate-phenmedipham (salt/mix)
protrum k
alegro
methyl m-hydroxycarbanilate m-methylcarbanilate
IDOWTHOLJBTAFI-UHFFFAOYSA-N
beetup
medipham (salt/mix)
DS-2923
phenmedipham, pestanal(r), analytical standard
1773497-41-8
J-006924
3-methoxycarbonylaminophenyl n-3'methylphenylcarbamate
Q2085502
CS-0014127
HY-B2032
phenmedipham-d3

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The current study shows that the effects of NPls on bioavailability and toxicity of other contaminants (e."( The role of nanoplastics on the toxicity of the herbicide phenmedipham, using Danio rerio embryos as model organisms.
Amorim, MJB; Barreto, A; Calisto, V; Maria, VL; Santos, J; Sousa, ÉML, 2022
)
0.97

Dosage Studied

ExcerptRelevanceReference
" The dry matter dose-response relationships and the energy pipeline presentation confirmed the same trend."( Monitoring the efficacy and metabolism of phenylcarbamates in sugar beet and black nightshade by chlorophyll fluorescence parameters.
Abbaspoor, M; Streibig, JC, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
herbicideA substance used to destroy plant pests.
[role 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]

Drug Classes (1)

ClassDescription
carbamate esterAny ester of carbamic acid or its N-substituted derivatives.
[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 Targets (40)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency9.47410.007215.758889.3584AID1224835
pregnane X receptorRattus norvegicus (Norway rat)Potency50.11870.025127.9203501.1870AID651751
RAR-related orphan receptor gammaMus musculus (house mouse)Potency12.04590.006038.004119,952.5996AID1159521; AID1159523
AR proteinHomo sapiens (human)Potency13.32110.000221.22318,912.5098AID1259243; AID1259247; AID588515; AID743035; AID743042; AID743054
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency23.75580.011212.4002100.0000AID1030
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency17.49840.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency3.06380.000417.946075.1148AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency8.01970.003041.611522,387.1992AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency11.82370.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
pregnane X nuclear receptorHomo sapiens (human)Potency19.07420.005428.02631,258.9301AID1346982; AID720659
estrogen nuclear receptor alphaHomo sapiens (human)Potency12.88500.000229.305416,493.5996AID1259244; AID1259248; AID1259383; AID588514; AID743069; AID743075; AID743079; AID743080; AID743091
aryl hydrocarbon receptorHomo sapiens (human)Potency18.80690.000723.06741,258.9301AID651777; AID743085; AID743122
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency13.27280.001723.839378.1014AID743083
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency6.85900.000323.4451159.6830AID743065
histone deacetylase 9 isoform 3Homo sapiens (human)Potency28.40600.037617.082361.1927AID1259364; AID1259388
mitogen-activated protein kinase 1Homo sapiens (human)Potency31.62280.039816.784239.8107AID995
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency36.95350.000627.21521,122.0200AID651741; AID720636; AID743202; AID743219
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency25.11890.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency4.85580.001557.789015,848.9004AID1259244
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency4.85580.001551.739315,848.9004AID1259244
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
GABA theta subunitRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
ATPase family AAA domain-containing protein 5Homo sapiens (human)Potency15.35530.011917.942071.5630AID651632
Ataxin-2Homo sapiens (human)Potency15.35530.011912.222168.7989AID651632
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency25.11891.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Fatty-acid amide hydrolase 1Homo sapiens (human)IC50 (µMol)0.26450.00020.59827.0000AID468444; AID468447
Fatty-acid amide hydrolase 1Rattus norvegicus (Norway rat)IC50 (µMol)0.07700.00051.33138.0000AID468445
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
fatty acid catabolic processFatty-acid amide hydrolase 1Homo sapiens (human)
arachidonic acid metabolic processFatty-acid amide hydrolase 1Homo sapiens (human)
positive regulation of vasoconstrictionFatty-acid amide hydrolase 1Homo sapiens (human)
monoacylglycerol catabolic processFatty-acid amide hydrolase 1Homo sapiens (human)
cell population proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of B cell proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
nuclear DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
signal transduction in response to DNA damageATPase family AAA domain-containing protein 5Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
isotype switchingATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of isotype switching to IgG isotypesATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloadingATPase family AAA domain-containing protein 5Homo sapiens (human)
regulation of mitotic cell cycle phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of cell cycle G2/M phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
protein bindingFatty-acid amide hydrolase 1Homo sapiens (human)
phospholipid bindingFatty-acid amide hydrolase 1Homo sapiens (human)
fatty acid amide hydrolase activityFatty-acid amide hydrolase 1Homo sapiens (human)
identical protein bindingFatty-acid amide hydrolase 1Homo sapiens (human)
acylglycerol lipase activityFatty-acid amide hydrolase 1Homo sapiens (human)
amidase activityFatty-acid amide hydrolase 1Homo sapiens (human)
protein bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP hydrolysis activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloader activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneFatty-acid amide hydrolase 1Homo sapiens (human)
cytoskeletonFatty-acid amide hydrolase 1Homo sapiens (human)
organelle membraneFatty-acid amide hydrolase 1Homo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
Elg1 RFC-like complexATPase family AAA domain-containing protein 5Homo sapiens (human)
nucleusATPase family AAA domain-containing protein 5Homo sapiens (human)
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID468443Inhibition of human FAAH at 1 uM2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468448Inhibition of human FAAH assessed as reduction in AA-AMC substrate Vmax2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468445Inhibition of rat FAAH2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468451Toxicity in rat2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468449Inhibition of human FAAH assessed as increase in AA-AMC substrate KM2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468447Inhibition of human FAAH-mediated hydrolysis of [3H]AEA2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468444Inhibition of human FAAH2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
AID468450Non-competitive inhibition of human FAAH by Lineweaver-Burke analysis2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (31)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (12.90)18.7374
1990's3 (9.68)18.2507
2000's16 (51.61)29.6817
2010's7 (22.58)24.3611
2020's1 (3.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.24

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.

MetricThis Compound (vs All)
Research Demand Index33.24 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index48.33 (26.88)
Search Engine Supply Index2.51 (0.95)

This Compound (33.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (3.03%)4.05%
Observational0 (0.00%)0.25%
Other32 (96.97%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]