Compounds > 2-(4-methoxyphenoxy)propanoic acid
Page last updated: 2024-12-08

2-(4-methoxyphenoxy)propanoic acid

Description

2-(4-methoxyphenoxy)propanoic acid, also known as **mefenamic acid**, is a nonsteroidal anti-inflammatory drug (NSAID) that is used to treat pain and inflammation. It is a derivative of propionic acid and has a methoxy group attached to the phenyl ring.

**Importance in Research:**

**1. Anti-Inflammatory Activity:** Mefenamic acid is a potent inhibitor of cyclooxygenase (COX) enzymes, particularly COX-1 and COX-2. These enzymes are involved in the production of prostaglandins, which are responsible for pain and inflammation. The inhibition of COX enzymes by mefenamic acid contributes to its anti-inflammatory properties.

**2. Analgesic Activity:** Mefenamic acid exhibits analgesic activity, meaning it can relieve pain. Its mechanism of action involves the inhibition of prostaglandin synthesis, which is a key mediator of pain perception.

**3. Antipyretic Activity:** Mefenamic acid can also reduce fever. It achieves this by acting on the hypothalamus, the area of the brain that regulates body temperature.

**4. Other Potential Applications:**

* **Cancer Research:** Mefenamic acid has shown some promising results in preclinical studies as a potential anti-cancer agent. It has been found to inhibit the growth and spread of certain types of cancer cells.
* **Neurological Disorders:** Research is ongoing to explore the potential of mefenamic acid in treating neurological conditions like Alzheimer's disease and Parkinson's disease.

**Research Focus:**

* **Pharmacokinetic and Pharmacodynamic Studies:** Researchers are investigating the absorption, distribution, metabolism, and elimination of mefenamic acid to understand its pharmacokinetic profile.
* **Mechanism of Action:** Further research is being conducted to elucidate the detailed mechanisms of action of mefenamic acid, including its interactions with COX enzymes and other cellular targets.
* **Safety and Efficacy:** Researchers are evaluating the safety and efficacy of mefenamic acid in different patient populations and for various therapeutic indications.
* **Drug Development:** New drug formulations and delivery systems are being explored to improve the effectiveness and minimize side effects of mefenamic acid.

**Conclusion:**

2-(4-methoxyphenoxy)propanoic acid (mefenamic acid) is an important research compound due to its anti-inflammatory, analgesic, and antipyretic properties. Ongoing research is focused on understanding its mechanism of action, exploring potential new applications, and developing safer and more effective formulations.

2-(4-methoxyphenoxy)propanoic acid: a sweetness inhibitor; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID151199
CHEMBL ID573448
CHEBI ID173971
SCHEMBL ID352607
MeSH IDM0241422

Synonyms (49)

Synonym
EN300-35118
BB 0221123
(s)-2-(4-methoxyphenoxy)propanoic acid
CHEBI:173971
nsc-352144
nsc352144
13794-15-5
IDI1_016126
2-(4-methoxyphenoxy)propanoic acid
AN-329/12912216
(+/-)-2-(p-methoxyphenoxy)propionic acid, >=98%
MAYBRIDGE3_004739
STK397551
HMS1444H09
AKOS000101751
(2r)-2-(4-methoxyphenoxy)propanoic acid
lactisol
CHEMBL573448
F3034-0090
BBL002689
CCG-963
2-(4-methoxy-phenoxy)-propionic acid
sodium 2-(4-methoxyphenoxy)propionate
AR3818
SCHEMBL352607
AKOS016050454
mfcd01310545
2-(4-methoxyphenoxy)propionic acid
4276-73-7
unii-k573uz6o8u
DS-1909
2-(p-methoxyphenoxy)propionic acid
lactisole, (+/-)-
propanoic acid, 2-(4-methoxyphenoxy)-
lactisole [mi]
hpmp
K573UZ6O8U ,
Z57825367
2-(4-methoxyphenoxy)propanoicacid
J-007079
Q3215901
(+/-)-2-(p-methoxyphenoxy)propionic acid
2-(4-methoxyphenoxyl)propionic acid
DTXSID00864442
AMY10590
2-(4-methoxy-phenoxy)-propionic acid;(2-(4-methoxyphenoxy)propionic acid
A847043
CS-0074820
SY081492
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
carboxylic acidA carbon oxoacid acid carrying at least one -C(=O)OH group and having the structure RC(=O)OH, where R is any any monovalent functional group. Carboxylic acids are the most common type of organic acid.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[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]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID439612Antagonist activity at human T1R2/T1R3 receptor expressed in HEK293E cells assessed as inhibition of sucralose-induced intracellular calcium mobilization2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Phenoxy herbicides and fibrates potently inhibit the human chemosensory receptor subunit T1R3.
AID439611Antagonist activity at mouse T1R2/T1R3 receptor expressed in HEK293E cells assessed as inhibition of sucralose-induced intracellular calcium mobilization2009Journal of medicinal chemistry, Nov-12, Volume: 52, Issue:21
Phenoxy herbicides and fibrates potently inhibit the human chemosensory receptor subunit T1R3.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (37.50)18.2507
2000's2 (25.00)29.6817
2010's2 (25.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.15

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.15 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (12.50%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
glycine
[no description available]		2.0110alpha-amino acid;
amino acid zwitterion;
proteinogenic amino acid;
serine family amino acid		EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor;
fundamental metabolite;
hepatoprotective agent;
micronutrient;
neurotransmitter;
NMDA receptor agonist;
nutraceutical
indoleacetic acid
indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group.		2.0510indole-3-acetic acids;
monocarboxylic acid		auxin;
human metabolite;
mouse metabolite;
plant hormone;
plant metabolite
phenylacetic acid
phenylacetic acid : A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.		2.0510benzenes;
monocarboxylic acid;
phenylacetic acids		allergen;
Aspergillus metabolite;
auxin;
EC 6.4.1.1 (pyruvate carboxylase) inhibitor;
Escherichia coli metabolite;
human metabolite;
plant growth retardant;
plant metabolite;
Saccharomyces cerevisiae metabolite;
toxin
2,4-dichlorophenoxyacetic acid
2,4-Dichlorophenoxyacetic Acid: An herbicide with irritant effects on the eye and the gastrointestinal system.. 2,4-D : A chlorophenoxyacetic acid that is phenoxyacetic acid in which the ring hydrogens at postions 2 and 4 are substituted by chlorines.		2.0510chlorophenoxyacetic acid;
dichlorobenzene		agrochemical;
defoliant;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
environmental contaminant;
phenoxy herbicide;
synthetic auxin
clofibric acid
Clofibric Acid: An antilipemic agent that is the biologically active metabolite of CLOFIBRATE.. clofibric acid : A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.		2.0510aromatic ether;
monocarboxylic acid;
monochlorobenzenes		anticholesteremic drug;
antilipemic drug;
antineoplastic agent;
herbicide;
marine xenobiotic metabolite;
PPARalpha agonist
dicamba
Dicamba: A chlorinated organic herbicide.. dicamba : A methoxybenzoic acid that is O-methylsalicylic acid substituted by chloro groups at positions 3 and 6.		2.0510dichlorobenzene;
methoxybenzoic acid		agrochemical;
environmental contaminant;
herbicide;
synthetic auxin;
xenobiotic
gemfibrozil
[no description available]		2.0510aromatic etherantilipemic drug
indolepropionic acid
indolepropionic acid: structure in third source. 3-(1H-indol-3-yl)propanoic acid : An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.		2.0510indol-3-yl carboxylic acidauxin;
human metabolite;
plant metabolite
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		2.0110alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
serine
Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.		2.0110L-alpha-amino acid;
proteinogenic amino acid;
serine family amino acid;
serine zwitterion;
serine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
1-naphthaleneacetic acid
1-naphthaleneacetic acid: a plant growth regulator; RN given refers to parent cpd. naphthylacetic acid : A monocarboxylic acid that is naphthalene substituted by a carboxymethyl group at any position.. 1-naphthaleneacetic acid : A naphthylacetic acid substituted by a carboxymethyl group at position 1.		2.0510naphthylacetic acidsynthetic auxin
mecoprop
mecoprop: RN given refers to cpd without isomeric designation; structure. 2-(4-chloro-2-methylphenoxy)propanoic acid : A monocarboxylic acid that is lactic acid in which the hydroxyl hydrogen is replaced by a 4-chloro-2-methylphenyl group.. mecoprop : A racemate comprising equimolar amounts of (R)- and (S)-mecoprop.		2.0510aromatic ether;
monocarboxylic acid;
monochlorobenzenes
fenoprop
fenoprop: RN given is for parent cpd; structure		2.0510monocarboxylic acidphenoxy herbicide
dichlorprop
dichlorprop: RN given refers to parent cpd without isomeric designation; structure. 2-(2,4-dichlorophenoxy)propanoic acid : An aromatic ether that is 2-hydroxypropanoic acid in which the hydroxy group at position 2 has been converted to its 2,4-dichlorophenyl ether.. dichlorprop : A racemate comprising equimolar amounts of (R)- and (S)-dichlorprop. It is widely used as a herbicide for killing annual and broad leaf weeds. Only the R-enantiomer has herbicidal activity; the S-enantiomer is inactive.		2.0510aromatic ether;
dichlorobenzene;
monocarboxylic acid
indolebutyric acid
indolebutyric acid: RN given refers to parent cpd. indole-3-butyric acid : A indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1.		2.0510indol-3-yl carboxylic acidauxin;
plant hormone;
plant metabolite
4-chlorophenoxyacetic acid
4-chlorophenoxyacetic acid: RN given refers to parent cpd; structure. (4-chlorophenoxy)acetic acid : A chlorophenoxyacetic acid that is phenoxyacetic acid carrying a chloro substituent at position 4.		2.0510chlorophenoxyacetic acid;
monochlorobenzenes		phenoxy herbicide
bezafibrate
[no description available]		2.0510aromatic ether;
monocarboxylic acid amide;
monocarboxylic acid;
monochlorobenzenes		antilipemic drug;
environmental contaminant;
geroprotector;
xenobiotic
inosinic acid
Inosine Monophosphate: Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.		2.0110inosine phosphate;
purine ribonucleoside 5'-monophosphate		Escherichia coli metabolite;
human metabolite;
mouse metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Plasmodium falciparum Malaria
[description not available]		02.110
Malaria, Falciparum
Malaria caused by PLASMODIUM FALCIPARUM. This is the severest form of malaria and is associated with the highest levels of parasites in the blood. This disease is characterized by irregularly recurring febrile paroxysms that in extreme cases occur with acute cerebral, renal, or gastrointestinal manifestations.		02.110
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310
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