Page last updated: 2024-12-05

methylmethacrylate

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

Description

Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component. [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 CID6658
CHEMBL ID49996
CHEBI ID34840
SCHEMBL ID1849
MeSH IDM0029998

Synonyms (132)

Synonym
methyl methacrylate (mma)
BIDD:ER0634
9065-11-6
methyl-methacrylat
methacrylic acid, methyl ester
pegalan
metil metacrilato
metakrylan metylu
diakon
methyl .alpha.-methylacrylate
nsc-4769
methacrylic acid methyl ester
methylmethacrylaat
2-methylacrylic acid, methyl ester
nsc4769
methyl 2-methylpropenoate
methyl 2-methyl-2-propenoate
methyl methacrylate
methacrylate de methyle
methyl methylacrylate
methyl methacrylate monomer, inhibited
80-62-6
nci-c50680
wln: 1uy1&vo1
'monocite' methacrylate monomer
methacrylsaeuremethyl ester
2-propenoic acid, 2-methyl-, methyl ester
methyl 2-methylacrylate
inchi=1/c5h8o2/c1-4(2)5(6)7-3/h1h2,2-3h
propenoic acid,2-methyl,methylester (methacrylate methylester)
NCGC00091089-01
metaplex
methylmethacrylaat [dutch]
2-(methoxycarbonyl)-1-propene
einecs 201-297-1
cranioplast
hsdb 195
2-methylacrylic acid methyl ester
acrylic acid, 2-methyl-, methyl ester
2-methyl-2-propenoic acid methyl ester
brn 0605459
methacrylsaeuremethyl ester [german]
kallocryl a
methyl methacrylate monomer
teb 3k
methyl alpha-methylacrylate
metakrylan metylu [polish]
metil metacrilato [italian]
methacrylate de methyle [french]
simplex p
un1247
acryester m
methylester kyseliny methakrylove [czech]
rcra waste number u162
ai3-24946
rcra waste no. u162
nsc 4769
methylmethacrylate
ccris 1364
methyl-methacrylat [german]
methyl methacrylate, contains <=30 ppm mehq as inhibitor, 99%
methyl methacrylate, 99%, stabilized
eudragit
9011-14-7
plexiglass
2-methyl-acrylic acid methyl ester
CHEMBL49996
methyl 2-methylprop-2-enoate
M0087
CHEBI:34840 ,
AKOS000120216
A839957
NCGC00091089-02
ec 201-297-1
4-02-00-01519 (beilstein handbook reference)
methyl methacrylate monomer, inhibited [un1247] [flammable liquid]
monocite methacrylate monomer
methylester kyseliny methakrylove
196oc77688 ,
unii-196oc77688
C19504
cas-80-62-6
NCGC00257921-01
tox21_200367
dtxcid80844
dtxsid2020844 ,
STL283952
methyl methactrylate
methyl 2-methyl-2-propenoate [fhfi]
methyl methacrylate [iarc]
methyl methacrylate [vandf]
methylmethacrylate [mart.]
methyl methacrylate [inci]
methyl methacrylate [hsdb]
methylmethacrylate [who-dd]
methacrylic acid methyl ester [mi]
EPITOPE ID:131321
methyl meth-d3-acrylate
SCHEMBL1849
143476-91-9
methoxymethacrolein
51391-19-6
ch2=c(ch3)cooch3
na 1247 (salt/mix)
methyl 2-methylacrylate #
methyl-.alpha.-methacrylate
un 1247 (salt/mix)
methyl ester of 2-methyl-2-propenoic acid
55063-97-3
J-522614
F0001-2087
mfcd00008587
methyl methacrylate, saj first grade, >=99.0%
methyl methacrylate, (stabilized with 6-tert-butyl-2,4-xylenol)
methyl methacrylate (mma), 99.5%(gc), contains 30ppm mehq as stabilizer
methyl methacrylate, cp,98.0%
methyl methacrylate (mma), ar, 99.0%, contains 30ppm mehq as stabilizer
methyl methacrylate (stabilized with 6-tert-butyl-2,4-xylenol)
methyl methacrylate, european pharmacopoeia (ep) reference standard
methyl methacrylate, 99.5%
methacrylic acid-methyl ester
methacrylic acid-methyl ester 100 microg/ml in cyclohexane
Q382897
114512-63-9
methyl methacrylate 1000 microg/ml in methanol
mma (stabilized)
methacrylic acid methyl ester (stabilized
methyl methacrylate, stabilized
J69 ,
97555-82-3
EN300-19210
acrylic resins (pmma)

Research Excerpts

Overview

Methylmethacrylate (MMA) is a volatile liquid widely used in the manufacture of acrylic polymers. MMA appears to be a stable fixator for osteotomized and fractured bones in young patients.

ExcerptReferenceRelevance
"Methylmethacrylate is a prosthetic material commonly used for the reconstruction of large chest wall defects. "( Staged Repair of an Aortic Pseudoaneurysm Secondary to Delayed Methylmethacrylate Plate Migration.
El Khoury, Z; Golts, EM; Parker, KL; Reid, C; Suliman, AS; Tenenhaus, M; Thistlethwaite, P, 2017
)
2.14
"The methylmethacrylate appears to be a stable fixator for osteotomized and fractured bones in young patients."( The use of methylmethacrylate as an external fixator in children and adolescents.
Demetriades, D; Filiopoulos, K; Hager, J; Nikolaides, N,
)
1
"Methylmethacrylate (MMA) is a volatile liquid widely used in the manufacture of acrylic polymers. "( Increased frequency of sister chromatid exchange in workers exposed to high doses of methylmethacrylate.
Haguenoer, JM; Hildebrand, HF; Marez, T; Shirali, P, 1991
)
1.95

Effects

Methylmethacrylate has been used extensively in the U.S. since 1971 for the fixation of orthopedic prostheses. It is still the most widely used reconstructive material.

ExcerptReferenceRelevance
"Polymethylmethacrylate has been used for cranioplasty since the World War II and is still the most widely used reconstructive material."( Cranioplasty of Hemispherical Defects Using High Impact Methylmethacrylic Plate.
Kumar, NG; Rangarajan, H; Shourie, P, 2015
)
0.9
"Methylmethacrylate has been used as an external fixator on 52 bones in 36 children and adolescents. "( The use of methylmethacrylate as an external fixator in children and adolescents.
Demetriades, D; Filiopoulos, K; Hager, J; Nikolaides, N,
)
1.96
"Methylmethacrylate has been used extensively in the United States since 1971 for the fixation of orthopedic prostheses. "( Cardiovascular collapse associated with the use of methylmethacrylate.
Pinto, PW, 1993
)
1.98
"Methylmethacrylate has excellent biocompatibility and strength and has been used in surgery for over 20 years."( Tobramycin-impregnated methylmethacrylate for mandible reconstruction.
Goode, RL; Reynolds, BN, 1992
)
1.32

Toxicity

ExcerptReferenceRelevance
" The monomer can release a toxic vapor."( Toxicity of methyl methacrylate monomer in orbital and cranial surgery.
Brinsko, JD; Wesley, RE, 1992
)
0.28
" MMA, tested in the same range of concentration as the MMA found leached from acrylic resin in this study, was found to be toxic in the cell culture."( Release of methyl methacrylate from heat-cured and autopolymerized resins: cytotoxicity testing related to residual monomer.
Charoenworaluk, N; Kedjarune, U; Koontongkaew, S, 1999
)
0.3
" This study aimed to examine possible time-dependent toxic effects of provisional crown and bridge restoration materials, manipulated intraorally or extraorally, on epithelia cells."( Cytotoxicity of provisional crown and bridge restoration materials: an in vitro study.
Dogan, A; Ergün, G; Karaoglu, T; Mutlu-Sagesen, L, 2001
)
0.31
"Precipitated corrosion products were found to be more toxic than ID products."( Assessment of dental material degradation product toxicity using a bioluminescent bacterial assay.
Bundy, KJ; Shettlemore, MG, 2002
)
0.31
" Dental patients are also exposed to MMA leached from some dental appliances and the effects, at least in vitro, appear toxic to cells and may cause local mucosal irritation or even an allergic reaction."( Toxicity of methyl methacrylate in dentistry.
Kedjarune, U; Leggat, PA, 2003
)
0.32
" Experimental and clinical studies have documented that monomers may cause a wide range of adverse health effects."( Assessment of methyl methacrylate vapor toxicity on the rat tracheal epithelium.
Batalha, CF; Bertão, JM; Falcone, CE; Lopes, CC; Nai, GA; Parizi, JL; Rizzo, MF,
)
0.13
"0005), but lipid peroxidation levels for this material showed that it was not safe for dural closure in case it leaked through the dural defect."( Comparative dural closure techniques: a safety study in rats.
Inci, S; Orhan, H; Ozgen, T; Ozisik, PA; Soylemezoglu, F, 2006
)
0.33
" Experimental and clinical studies have documented that monomers may cause a wide range of adverse health effects such as irritation to skin, eyes, and mucous membranes, allergic dermatitis, stomatitis, asthma, neuropathy, disturbances of the central nervous system, liver toxicity, and fertility disturbances."( Toxic effects of methyl methacrylate monomer on male genital tissues. In vitro study in rats.
Aftimos, G; Chababi-Atallah, M; Fakhouri, J; Sarkis, R,
)
0.13
" The main toxic effects of MMA exposure appear to involve the cardiovascular system."( Surgical applications of methyl methacrylate: a review of toxicity.
Kedjarune, U; Leggat, PA; Smith, DR, 2009
)
0.35
"Residual methyl methacrylate (MMA) may leach from the acrylic resin denture bases and have adverse effects on the oral mucosa."( Effect of leaching residual methyl methacrylate concentrations on in vitro cytotoxicity of heat polymerized denture base acrylic resin processed with different polymerization cycles.
Aktaş, E; Bayraktar, G; Bural, C; Deniz, G; Ünlüçerçi, Y, 2011
)
0.37

Pharmacokinetics

ExcerptReferenceRelevance
" This model, developed by simplification of existing physiologically based pharmacokinetic (PBPK) nasal models, has three tissue regions in two flow paths."( Dosimetric adjustment factors for methyl methacrylate derived from a steady-state analysis of a physiologically based clearance-extraction model.
Andersen, ME; Frederick, CB; Kimbell, JS; Sarangapani, R, 1999
)
0.3
"Mathematical models have been developed to describe nasal epithelial tissue dosimetry with two compounds, vinyl acetate (VA) and methyl methacrylate (MMA), that cause toxicity in these tissues These models couple computational fluid dynamics (CFD) calculations that map airflow patterns within the nose with physiologically based pharmacokinetic (PBPK) models that integrate diffusion, metabolism, and tissue interactions of these compounds."( Physiologically based pharmacokinetic (PBPK) models for nasal tissue dosimetry of organic esters: assessing the state-of-knowledge and risk assessment applications with methyl methacrylate and vinyl acetate.
Andersen, ME; Bogdanffy, MS; Frederick, CB; Green, T, 2002
)
0.31

Compound-Compound Interactions

ExcerptReferenceRelevance
" The authors conclude that this surgical approach is safe and feasible for the radical resection of vertebral metastasis when combined with reconstruction and stabilization."( Single-stage posterior vertebrectomy and replacement combined with posterior instrumentation for spinal metastasis.
Akeyson, EW; McCutcheon, IE, 1996
)
0.29
" Most importantly, we developed a procedure to specifically stain the mineralized matrix green in combination with a red staining of the NCPs."( Immunolocalization and quantification of noncollagenous bone matrix proteins in methylmethacrylate-embedded adult human bone in combination with histomorphometry.
Birkenhäger-Frenkel, DH; Bosman, FT; Derkx, P; Houtsmuller, AB; Nigg, AL; Pols, HA; van Leeuwen, JP, 1998
)
0.53
" The objective of this experimental study was to determine the wear of tibial polyethylene inserts combined with metallic and ceramic femoral components under third-body wear conditions initiated by bone cement particles."( Third-body abrasive wear of tibial polyethylene inserts combined with metallic and ceramic femoral components in a knee simulator study.
Bader, R; Bergschmidt, P; Lange, R; Mittelmeier, W; Zietz, C, 2013
)
0.39
" Tibial polyethylene inserts were combined with the identical femoral component design, but made of two different materials (cobalt-chromium and ceramic)."( Third-body abrasive wear of tibial polyethylene inserts combined with metallic and ceramic femoral components in a knee simulator study.
Bader, R; Bergschmidt, P; Lange, R; Mittelmeier, W; Zietz, C, 2013
)
0.39
"The average gravimetrical wear of the tibial polyethylene inserts in combination with 
cobalt-chromium and ceramic femoral components under third-body wear conditions amounted to 31."( Third-body abrasive wear of tibial polyethylene inserts combined with metallic and ceramic femoral components in a knee simulator study.
Bader, R; Bergschmidt, P; Lange, R; Mittelmeier, W; Zietz, C, 2013
)
0.39
"The wear simulator test demonstrates that wear of polyethylene inserts under third-body wear conditions, in combination with ceramic femoral components, was significantly lower than with metallic femoral components."( Third-body abrasive wear of tibial polyethylene inserts combined with metallic and ceramic femoral components in a knee simulator study.
Bader, R; Bergschmidt, P; Lange, R; Mittelmeier, W; Zietz, C, 2013
)
0.39

Bioavailability

ExcerptReferenceRelevance
" These graft copolymer nanoparticles enhanced the absorption and improved the bioavailability of insulin via the gastrointestinal (GI) tract of normal male Sprague-Dawley (SD) strain rats to a greater extent than that of the phosphate buffer solution (PBS) of insulin."( Chitosan graft copolymer nanoparticles for oral protein drug delivery: preparation and characterization.
Cui, F; Ding, J; Qian, F; Tang, C; Yin, C, 2006
)
0.33
" Results revealed a theophylline absorption rate in the order FD-HSMMA≥Theo-Dur(®)≥OD-CSMMA>Theolair(®)≥FD-CSMMA."( Invivo absorption behaviour of theophylline from starch-methyl methacrylate matrix tablets in beagle dogs.
Colom, H; Fernández-Campos, F; Ferrero, C; Jiménez-Castellanos, MR, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" Control and polymer-exposed atria superfused with oxygen-saturated buffer yielded dose-response curves which were essentially identical with regard to maximal increase and potency of isoproterenol."( Inhibition of isoproterenol positive atrial chronotropic effect by methylmethacrylate polymer and monomer.
Born, CK; Campbell, MJ; Hamrick, ME; Ravis, WR; Willis, DW, 1986
)
0.51
" Preclinical trials in an animal model could permit earlier detection of promising agents and proper dosage schedules."( Experimental osteomyelitis: description of a canine model and the role of depot administration of antibiotics in the prevention and treatment of sepsis.
Fitzgerald, RH, 1983
)
0.27
" Higher conjugate concentrations resulted in steeper dose-response curves."( A sol particle agglutination assay for human chorionic gonadotrophin.
Leuvering, JH; Schuurs, AH; Thal, PJ; Van der Waart, M, 1981
)
0.26
" A spoiler will increase the contribution of scattered medium energy electrons and photons, thereby increasing superficial dosing and maintaining skin sparing due to displacement of the spoiler from the skin."( Use of a lucite beam spoiler for high-energy breast irradiation.
Klein, EE; Michalet-Lorenz, M; Taylor, ME, 1995
)
0.29
"005) of the femoral neck at all dosage levels."( Risedronate treatment does not increase microdamage in the canine femoral neck.
Burr, DB; Eastman, DF; Forwood, MR; Schwardt, JD; Smith, PN; Takano, Y, 1995
)
0.29
" The dosage forms include fibers, film/slabs, and injectable systems, some of which are degradable, while others are not and need to be removed at the termination of the treatment."( Subgingival delivery of therapeutic agents in the treatment of periodontal diseases.
Soskolne, WA, 1997
)
0.3
"The aim of the present study was to develop a multi-unit dosage form containing 5-aminosalicylic acid (5-ASA) for the treatment of ulcerative colitis (UC), optimised on the basis of recent studies indicating that UC patients have higher intestinal pH than was previously thought to be the case."( A new 5-aminosalicylic acid multi-unit dosage form for the therapy of ulcerative colitis.
Beckert, TE; Dressman, JB; Klein, S; Petereit, H; Rudolph, MW, 2001
)
0.31
" Concentrations leading to 50% cell survival (TC50 values) were calculated from fitted dose-response curves."( Responses of L929 mouse fibroblasts, primary and immortalized bovine dental papilla-derived cell lines to dental resin components.
Hiller, KA; Schmalz, G; Schweikl, H; Thonemann, B, 2002
)
0.31
" The initial slopes of the dose-response curves were used to calculate the inflammatory potential, or potency factor (PF), of the samples."( Interleukin-8 secretion from monocytic cell lines for evaluation of the inflammatory potential of organic dust.
Allermann, L; Poulsen, OM, 2002
)
0.31
" The semi-batch ozonation experiments were proceeded under different reaction conditions to study the effects of ozone dosage and UV radiation on the oxidation of MMA."( Oxidation of methyl methacrylate from semiconductor wastewater by O3 and O3/UV processes.
Chang, CH; Chen, YH; Lee, CH; Lee, CW; Ma, HW; Shang, NC; Yu, YH, 2007
)
0.34
" These preliminary results underline that the ingestion of metal ions at high concentrations could affect the drug liberation from gastroresistant dosage forms."( Effects of metal ions on entero-soluble poly(methacrylic acid-methyl methacrylate) coating: a combined analysis by ATR-FTIR spectroscopy and computational approaches.
Cilurzo, F; Gennari, CG; Selmin, F; Vistoli, G, 2010
)
0.36
" On the basis of simulated plasma theophylline levels, a twice daily dosage (every 12h) with the FD-CSMMA tablets should be recommended."( Invivo absorption behaviour of theophylline from starch-methyl methacrylate matrix tablets in beagle dogs.
Colom, H; Fernández-Campos, F; Ferrero, C; Jiménez-Castellanos, MR, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
allergenA chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
polymerisation monomerAny compound used as a monomer for a polymerisation process. The term is generally used in relation to industrial polymerisation processes.
[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 (2)

ClassDescription
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
[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 (1)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency31.62280.011212.4002100.0000AID1030
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID174708Gastric cytoprotective activity in male wistar rat1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structure-cytoprotective activity relationship of simple molecules containing an alpha,beta-unsaturated carbonyl system.
AID1469819Glutathione reactivity of the compound in DMSO and phosphate buffer assessed as second order rate constant for adduct formation2017Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3
Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.
AID1469829Toxicity in Tetrahymena pyriformis assessed as growth inhibition after 48 hrs2017Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3
Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,740)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990378 (21.72)18.7374
1990's553 (31.78)18.2507
2000's414 (23.79)29.6817
2010's325 (18.68)24.3611
2020's70 (4.02)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 80.59

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index80.59 (24.57)
Research Supply Index7.57 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index148.75 (26.88)
Search Engine Supply Index2.05 (0.95)

This Compound (80.59)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials57 (3.03%)5.53%
Reviews68 (3.62%)6.00%
Case Studies230 (12.24%)4.05%
Observational1 (0.05%)0.25%
Other1,523 (81.05%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]