Metamizole sodium

Chemical properties

solid

The Uses of Metamizole sodium

A non-steroidal anti-inflammatory drug that, when coadministered with morphine, potentiates its antinociceptive action and delays the development of tolerance. Dipyrone is a relatively selective inhibitor of cyclooxygenase-3 (COX-3), with lower activity against COX-1 and no activity against COX-2. Blocks PGE2-induced hyperalgesia in several models.

The Uses of Metamizole sodium

Dipyrone is a non-steroidal anti-inflammatory drug that, when coadministered with morphine, potentiates its antinociceptive action and delays the development of tolerance. Dipyrone is a relatively sel ective inhibitor of cyclooxygenase-3 (COX-3), with lower activity against COX-1 and no activity against COX-2. Dipyrone blocks PGE2-induced hyperalgesia in several models.

The Uses of Metamizole sodium

Methamizole sodium has expressed analgesic and fever-reducing properties and poorly expressed anti-inflammatory action, and is very convenient in cases where high concentrations of drug need to be quickly reached. Methamizole sodium is used for relieving pain of various origins (renal and biliary colic, neuralgia, myalgia, trauma, burns, headaches, and toothaches). Use of this drug may cause allergic reactions, and long-term use may cause granulocytopenia.

What are the applications of Application

Dipyrone is a non-steroidal antiinflammatory drug

Definition

ChEBI: An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic.

brand name

Diprofarn (Farmitalia, Societa Farmaceutici Italia, Italy); Novaldin (Sterling Winthrop);Abalgine;Acabel compositum;Acefalgin;Acrobal;Acrogesico;Adolkin;Algia-nil;Alginodia compose;Algisedal;Algobuscopan;Algopriv;Algopyriv;Alkozin;Amiglan;Aminocid;Amitralil;Ampi tumisan;Anadex;Analcedor;Analject;Anarinyl;Anchrina;Anespas cpto;Angiter;Ankaljin;An-t;Apasmo;Arantil;Arquidon;Artritex;Ascorbalgine;Ascortin;Aseptobron;Atecilina;Atn-020/2;Avafortan;Ayoral;Bayer 1387;Bebealjin;Bebigut;Belatropin;Belflex/2;Beneurin;Bexopirona;Biogamma2;Biotangin;Bipasmin compuesto;Bort;Bristacilia;Britercina;Bromalgin;Bromalgon;Broncofenil;Broncolysin;Bucarboxal;Buscapina comp.;Buscapina compuesto;Buscapina compuestum;Buscol compositum;Buscopan composto;Buscopan compostum;Buscopina compostum;Butalgine;Butylpan;Calgayan-c;Calmetron;Camizol;Causalon;Cessantyl;Chini-med;Cintaverin compuesto;Clizim;Clofexan;Codalgin;Codasal injetavel;Colgenol;Comaril 5000;Corilin pediatric;Cortempirol;Cortitracin;Cronopen balsamico;Deltricin;Devalgin;Dexa butarin;Di-bal-rone;Dimethedon;Dinopirina;Dioxadol;Dipirona;Diprofarm;Dipyrivo;Dispalgine;Divarin;Divarmin;Do-ba-rone;Dolatets;Dolazon;Dolemicin;Dolispasmo;Dolo adamon;Dolo baralgine;Dolo buscopan;Dolo nerv;Dolo neurobion forte;Dolo pangavit;Dolo raptalgin;Dolo spasuret;Dolojudolor;Dolo-neurobion;Dolopirina;Doloscopin;Dopiral;Dorflex merrell;Dorlisin;Doron;Dorscopena;D-pron;Dumalgin;Duralnordin;Dya-tran;Edgartet;Eespanal;Enzipan combinado;Espasfher;Espasmir;Espasmo-cibalgina;Espasmoqual;Espasmotex;Espasmoviral;Espyre;Farbinol;Flogolisin;G.r. ulix compuesto;Genservet;Gentil;Geralgine;Glutisal;Greplicina belsa;H 116;H 117;H 118;Hagalgin;Hasain;Indextron;Influbene;Kb-502;Kefren;Kesan;Killgrip;Kipyrone;Kitax alpha;Kitax n;Konitan;Labymetacincpo;Lactmicina;Lagalgine;Lamprcsnum;Lapalgine;Larq 731;Lasain;Lavaciclina;Levapa;Levismon;Lisalgil;Magdor;Magnalsa;Magnemidon;Mapir;Mecoten;Megal;Melpen;Menalgine;Mialgan;Minalgine;Minoval;Miocitalgan;Nadalgine;Naftalgin;Naltrium;Napasone;Nartate;Natralgin;Natric;Neo-melubrim;Neo-melubrina;Neo-melubrine;Neo-oxipen;Neosal-n;Neosoldina;Neuro-fortamin;Nisidina;Nlo conicilina balsamica;Nobelgin;Nolotil composirum;Notermin;Novacid;Novalcina;Novalgetol;Novalgin quinine;Novalgina;Novalgine;Nova-lyseen;Novamidazofen;Novamidazophen;Novamideazophene;Novaminophenazone;Novaminsulfon ratiopharm;Novaminsulfone sodium;Novaminsulfonium;Novaminsulfonum;Novaminsulton;Novazolon dexametasona;Noveltex;Novemida;Novemina;Novil;Oftlamin;Orphalginen;Ortopirona;Oxiquiunazine;Pabron gold;Panalvon;Patalgin;Pentrodin;Phanalgin;Pharmalgine;Porbiot;Pplan 2500;Probaphen;Prodol;Prydonnal;Pydirone;Pyralgine;Pyrilgin;Pyriligin;Pyrisan;Quarelin;Reflex rectal;Relexal compuesto;Repriman;Resquim;Rheuma-spalt;Ridol;Rumalisine;Rupalgin;Santeprednisan a;Sebon;Sedabel;Sedarel;Sedarene;Sedazepane;Selpiran;Sertalanalgesico;Severen;Sinalgex;Sintaverin;Sinvirol;Spasdolsom;Spaslar;Spasmalgon;Spasmium-comp.;Spasmizol;Spasmodor;Spasmopyralgin;Spasmothil;Sufonovin;Sulfonovin;Supadol;Supergine;Surpyrine;Tanper;Tapal;Tega-pyrone;Tempil;Tepal;Termonil;Tetrabal-hosbon;Tetraspasmil;Tiadexol;Tiartan;Toloxin andromaco;Trenteron;Triartan;Trinalgen.

World Health Organization (WHO)

Metamizole sodium, a pyrazolone derivative with analgesic, antipyretic and antinflammatory activity, was introduced in 1921 and has since been widely available in over-the-counter products. By the early 1970s its use had been associated, as with some other pyrazolones, with serious and sometimes fatal adverse reactions, notably cases of blood dyscrasias including agranulocytosis, which led to its withdrawal by some regulatory authorities. Although preparations of metamirole sodium are prohibited in certain countries, they remain widely available in others and, in some cases, in over-the-counter products.

Safety Profile

Poison by subcutaneous route. Moderately toxic by several other routes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. Questionable carcinogen with experimental neoplastigenic data. See also SULFONATES. When heated to decomposition it emits very toxic fumes of NOx,, Na2O, and SOx,.

Synthesis

Methamizole sodium, 1-phenyl-2,3-dimethyl-4-methylaminopyrazolone-5-N-sodium methansulfonate (3.2.16), is synthesized in a multi-stage synthesis from acetoacetic ester and phenylhydrazine. Their reaction leads to the formation of 1-phenyl- 3-methylpyrazolone-5 (3.2.9). Methylation of this product with methyl iodide gives 1-phenyl- 2,3-dimethylpyrazolone-5 (3.2.10). This compound is used independently in medicine as a fever-reducing and anti-inflammatory analgesic under the name antipyrin. It undergoes nitrozation by sodium nitrite in an acidic medium, forming 1-phenyl-2,3-dimethyl-4- nitrozopyrazolone-5 (3.2.11). Reduction of the nitrous derivative (3.2.11) by different reducing agents leads to the formation of 1-phenyl-2,3-dimethyl-4-aminopyrazolone-5 (3.2.12). This product is reacted with benzaldehyde, forming an easily separable crystalline 1-phenyl- 2,3-dimethyl-4-benzylidenaminopyrazolone-5 (3.2.13), which is methylated at the imine atom of nitrogen by dimethylsulfate, giving a quaternary salt (3.2.14). Hydrolysis of the resulting salt gives 1-phenyl-2,3-dimethyl-4-methylaminopyrazolone-5 (3.2.15). Treating the product with a water solution of a mixture of sodium bisulfite and formaldehyde leads to the formation of 1-phenyl-2,3-dimethyl-4-methylaminopyrazolone-5-N-sodium methanesulfonate (3.2.16), the desired sodium methamizole [72¨C75].