Methylmethacrylate

(BAN, rINN)
Methylmethacrylate Chemical formula

💊 Chemical information

Metacrilato de metilo; Méthacrylate de méthyle; Methylis methacrylas. Methyl 2-methylacrylate; Methyl 2-methylpropenoate.
Chemical formula: C5H8O2 = 100.1.
CAS — 80-62-6.

💊 Adverse Effects and Precautions

Occupational exposure to methylmethacrylate monomer vapour during preparation of the bone cement may irritate the respiratory tract, eyes, and skin. Cases of occupational asthma have been reported. Contact dermatitis, dizziness, nausea and vomiting may also occur. Methylmethacrylate monomer may be harmful to the liver. Methylmethacrylate monomer acts as a peripheral vasodilator and has caused hypotension and, rarely, cardiac arrest and death when absorbed during the use of polymethylmethacrylate (PMMA) as a bone cement during orthopaedic surgery. Other adverse effects associated with the use of polymethylmethacrylate as a bone cement include thrombophlebitis, pulmonary embolism, haemorrhage, haematoma, short-term irregularities in cardiac conduction, cerebrovascular accident, compression of the spinal cord and/or nerve roots, and new fractures in adjacent non-augmented vertebrae. Recommendations when using PMMA include monitoring with high quality imaging systems to detect leakage, and close monitoring of blood pressure during and immediately after the procedure.

Effects on the nervous system.

Sensory polyneuropathy has been reported in a dental technician after occupational exposure to methylmethacrylate monomer.1
1. Sadoh DR, et al. Occupational exposure to methyl methacrylate monomer induces generalised neuropathy in a dental technician. Br Dent J 1999; 186: 380–1.

💊 Uses and Administration

Methylmethacrylate forms the basis of acrylic bone cements used in orthopaedic surgery. A liquid consisting chiefly of methylmethacrylate monomer with a polymerisation initiator is mixed with a powder consisting of polymethylmethacrylate (PMMA) or a methylmethacrylate ester copolymer. The reaction is exothermic. Barium sulfate or zirconium dioxide may be added as a contrast medium. Polymethylmethacrylate beads containing gentamicin have been implanted for the prophylaxis and treatment of bone infections and some soft-tissue infections. Bone cements containing antibacterials such as gentamicin or erythromycin are also available. Polymethylmethacrylate has also been used as a material for intra-ocular lenses, for denture bases, as a cement for dental prostheses, and in composite resins for dental restoration. A number of polymers based on methacrylic acid are used in pharmaceutical technology mainly as film coating agents and binders. Ph. Eur. 6.2 includes:
Ammonio Methacrylate Copolymer (Type A) (a copolymer of acrylic and methacrylic acid esters)
Ammonio Methacrylate Copolymer (Type B) (a copolymer of
acrylic and methacrylic acid esters)
Basic Butylated Methacrylate Copolymer
Methacrylic Acid-Methyl Methacrylate Copolymer (1:1)
Methacrylic Acid-Ethyl Acrylate Copolymer (1:1)
Methacrylic Acid-Ethyl Acrylate Copolymer (1:1) Dispersion 30 per cent
Methacrylic Acid-Methyl Methacrylate Copolymer (1:2)
Polyacrylate Dispersion 30 per cent (a dispersion of an ethylacrylate-methyl methacrylate copolymer in water) USNF 26 includes:
Methacrylic Acid Copolymer (a copolymer of methacrylic acid and an acrylic or methacrylic ester)
Amino Methacrylate Copolymer
Ammonio Methacrylate Copolymer
Ammonio Methacrylate Copolymer Dispersion
Ethyl Acrylate and Methyl Methacrylate Copolymer

Bone disorders.

Polymethylmethacrylate bone cements may be injected percutaneously into vertebral fractures or lesions to relieve pain and stabilise the damaged vertebra.1-6 The technique has been used in the treatment of metastatic bone lesions and myeloma as well as for vertebral compression fractures due to osteoporosis. Complications5,7-9 are uncommon but may include both local and systemic effects (including pulmonary embolism) due to leakage of the cement and sudden drop in blood pressure, probably due to the monomer.
1. Barr JD, et al. Percutaneous vertebroplasty for pain relief and spinal stabilization. Spine 2000; 25: 923–8
2. Lingar L. Percutaneous polymethacrylate vertebroplasty. Radiol Technol 2004; 76: 109–13
3. Burton AW, et al. Vertebroplasty and kyphoplasty: a comprehensive review. Neurosurg Focus 2005; 18: e1. Available at: http:// www.medscape.com/viewarticle/501670 (accessed 15/02/06
4. Suresh SP, Whitehouse RW. Vertebroplasty and kyphoplasty. J Br Menopause Soc 2005; 11: 28–32
5. Guglielmi G, et al. Percutaneous vertebroplasty: indications, contraindications, technique, and complications. Acta Radiol 2005; 46: 256–68
6. Hochmuth K, et al. Percutaneous vertebroplasty in the therapy of osteoporotic vertebral compression fractures: a critical review. Eur Radiol 2006; 16: 998–1004
7. Laredo JD, Hamze B. Complications of percutaneous vertebroplasty and their prevention. Semin Ultrasound CT MR 2005; 26: 65–80
8. Barragan-Campos HM, et al. Percutaneous vertebroplasty for spinal metastases: complications. Radiology 2006; 238: 354–62
9. Health Canada. Complications associated with the use of bone cements in vertebroplasty and kyphoplasty procedures (issued 30th May, 2007). Available at: http://www.hc-sc.gc.ca/ dhp-mps/ alt_formats/hpfb-dgpsa/pdf/medeff/bone_cement-ciment_ acrylique_nth-aah_2_e.pdf (accessed 30/5/08)

💊 Preparations

Proprietary Preparations

Chile: Palacos E†; Palacos R; Ger.: CMW; flint; Palacos R; Palamed; SmartSet HV; Port.: Septopal; Singapore: Palacos R†; Thai.: Palacos R; UK: Palacos R. Multi-ingredient: Arg.: Septopal†; Austral.: Palacos E with Garamycin; Palacos R with Garamycin; Septopal; Austria: Septopal; Belg.: Palacos LV avec Gentamicine†; Palacos R avec Gentamicine†; Septopal; Braz.: Septopal; Chile: Palacos E con Gentamicina; Palacos R con Gentamicina; Perlas De PMMA con Gentamicina; Cz.: Septopal†; Denm.: Septopal; Fin.: Palacos R cum Gentamicin†; Septopal; Fr.: Palacos LV avec Gentamicine; Palacos R avec Gentamicine; Ger.: CMW mit Gentamicin; Copal; Epiglu; Palamed G; Refobacin-Palacos R; Septopal; SmartSet GHV; Gr.: Palacos R with Gentamycin†; Septopal†; Hong Kong: Septopal; Hung.: Plastubol†; Septopal; India: Septopal; Irl.: Epiglu; Malaysia: Septopal†; Neth.: Septopal; Norw.: Septopal; NZ: Antibiotic Simplex; CMW Gentamicin; Palacos with Garamycin; Vacu-Mix Plus with CMW gentamicin; Philipp.: Septopal; S.Afr.: Palacos R with Garamycin; Septopal; Singapore: Refobacin Bone Cement R; Refobacin-Palacos R†; Septopal†; Swed.: Septopal†; Switz.: Septopal; Thai.: Refobacin-Palacos R; Septopal; UK: Epiglu; Palacos LV with Gentamicin; Palacos R with Gentamicin; Septopal.
Published May 08, 2019.