Metamizole information

Metamizole
Clinical data
Trade names	Novalgin, Algocalmin, Analgin, others
Other names	Dipyrone (BAN UK, USAN US, Sulpyrine (JAN JP)
AHFS/Drugs.com	International Drug Names
Pregnancy; category	None assigned; no evidence of teratogenicity in animal studies, but use in the third trimester may cause adverse effects in the newborn or ductus arteriosus (a heart defect) due to its weak NSAID activity.;
Routes of; administration	Oral, IM, IV, rectal
ATC code	N02BB02 (WHO) ;
Legal status
Legal status	AU: Withdrawn; BR: OTC (Over the counter); CA: Veterinary only; DE: § 48 AMG/§ 1 MPAV (Prescription only); NZ: Prescription only; UK: Withdrawn; US: Veterinary only (horses); EU: Legally available;
Pharmacokinetic data
Bioavailability	100% (active metabolites)
Protein binding	48–58% (active metabolites)
Metabolism	Liver
Elimination half-life	14 minutes (parent compound; parenteral); metabolites: 2–4 h
Duration of action	4–6 h
Excretion	Urine (96%, IV; 85%, oral), faeces (4%, IV).
Identifiers
	IUPAC name [(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino] methanesulfonic acid;
CAS Number	50567-35-6 ; 68-89-3 (sodium salt);
PubChem CID	3111; 522325;
DrugBank	DB04817 ;
ChemSpider	3000 ;
UNII	934T64RMNJ;
KEGG	D08188 ;
ChEBI	CHEBI:62088 ;
ChEMBL	ChEMBL461522 ;
CompTox Dashboard (EPA)	DTXSID8020543 ;
ECHA InfoCard	100.000.631
Chemical and physical data
Formula	C13H17N3O4S
Molar mass	311.36 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccccc1N2N(C)C(C)=C(C2=O)N(C)CS(=O)(=O)O;
	InChI InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20) ; Key:LVWZTYCIRDMTEY-UHFFFAOYSA-N ;
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Metamizole or dipyrone is a painkiller, spasm reliever, and fever reliever drug. It is most commonly given by mouth or by intravenous infusion.^[13]^[11]^[14] It belongs to the ampyrone sulfonate family of medicines and was patented in 1922. Metamizole is marketed under various trade names.^[2]^[3] It was first used medically in Germany under the brand name "Novalgin",^[15] and then became widely known in Slavic nations and India under the name "Analgin".^[16]^[17]

Metamizole is available over-the-counter in many countries, but from in the 1970s it was banned in some countries due to studies linking it to severe adverse effects, including agranulocytosis.^[18] Other studies find that it is a safer drug than other painkillers.^[19]^[20] Metamizole is popular in many countries where it is available.^[21]

^ Cite error: The named reference Brune was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference EMA-list was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Pharmaceuticale Press-2009 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference Winthrop Arzneimittel GmbH-2013 was invoked but never defined (see the help page).
^ "Notice of Amendment: Addition of Metamizole (Dipyrone) to the Prescription Drug List (PDL)". Government of Canada. 2022-07-18. Archived from the original on 2022-08-30. Retrieved 2023-08-04.
^ "Recent NZ Gazette Notices Relating to Classification". medsafe.govt.nz. 2020-03-06. Archived from the original on 2023-04-29. Retrieved 2023-08-04.
^ "Minutes of the 63rd meeting of the Medicines Classification Committee - 10 Oct 2019". medsafe.govt.nz. 2019-12-04. Archived from the original on 2023-06-10. Retrieved 2023-08-04.
^ FDA's Center for Veterinary Medicine (November 26, 2019). "Zimeta (dipyrone injection) - Veterinarians". FDA. Archived from the original on 2022-01-17. Retrieved 2023-08-04.
^ Cite error: The named reference EMA2018 was invoked but never defined (see the help page).
^ "Risikoinformationen - Metamizol (Novalgin, Berlosin, Novaminsulfon, etc.): BfArM weist auf richtige Indikationsstellung und Beachtung von Vorsichtsmaßnahmen und Warnhinweisen hin" [Risk information - Metamizol (Novalgin, Berlosin, Novaminsulfon, etc.): BfArM points out the correct indication and compliance with precautionary measures and warnings]. Bundesinstitut für Arzneimittel und Medizinprodukte (Federal Institute for Pharmaceuticals and Medical Products). 2009-05-28. Archived from the original on 2023-05-18. Retrieved 2023-08-04.
^ ^a ^b ^c ^d ^e Jage J, Laufenberg-Feldmann R, Heid F (April 2008). "[Medikamente zur postoperativen Schmerztherapie: Bewährtes und Neues. Teil 1: Nichtopioide]" [Drugs for postoperative analgesia: routine and new aspects. Part 1: non-opioids]. Der Anaesthesist (in German). 57 (4): 382–390. doi:10.1007/s00101-008-1326-x. PMID 18351305. S2CID 32814418.
^ Cite error: The named reference y0 was invoked but never defined (see the help page).
^ "Fachinformation (Zusammenfassung der Merkmale des Arzneimittels) Novaminsulfon injekt 1000 mg Lichtenstein Novaminsulfon injekt 2500 mg Lichtenstein" (PDF). Winthrop Arzneimittel GmbH (in German). Zinteva Pharm GmbH. February 2013. Archived (PDF) from the original on 16 October 2018. Retrieved 19 April 2014.
^ Cite error: The named reference deranaes2004 was invoked but never defined (see the help page).
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 530. ISBN 978-3-527-60749-5.
^ Cite error: The named reference pmid26019521 was invoked but never defined (see the help page).
^ Cite error: The named reference Business Standard India-2014 was invoked but never defined (see the help page).
^ Cite error: The named reference United Nations Department of Economic and Social Affairs-2005 was invoked but never defined (see the help page).
^ Lutz M (November 2019). "Metamizole (Dipyrone) and the Liver: A Review of the Literature". Journal of Clinical Pharmacology. 59 (11): 1433–1442. doi:10.1002/jcph.1512. PMID 31433499. S2CID 201118022.
^ Nikolova I, Tencheva J, Voinikov J, Petkova V, Benbasat N, Danchev N (2014). "Metamizole: A Review Profile of a Well-Known "Forgotten" Drug. Part I: Pharmaceutical and Nonclinical Profile". Biotechnology & Biotechnological Equipment. 26 (6): 3329–3337. doi:10.5504/BBEQ.2012.0089. ISSN 1310-2818. S2CID 56205439.
^ Sznejder H, Amand C, Stewart A, Salazar R, Scala WA (2022). "Real world evidence of the use of metamizole (dipyrone) by the Brazilian population. A retrospective cohort with over 380,000 patients". Einstein. 20. Sociedade Beneficente Israelita Brasileira Hospital Albert Einstein: eAO6353. doi:10.31744/einstein_journal/2022ao6353. PMC 9060643. PMID 35584441.

[Brune-1] Cite error: The named reference Brune was invoked but never defined (see the help page).

[EMA-list-2] Cite error: The named reference EMA-list was invoked but never defined (see the help page).

[Pharmaceuticale_Press-2009-3] Cite error: The named reference Pharmaceuticale Press-2009 was invoked but never defined (see the help page).

[Winthrop_Arzneimittel_GmbH-2013-4] Cite error: The named reference Winthrop Arzneimittel GmbH-2013 was invoked but never defined (see the help page).

[Government_of_Canada-2022-5] "Notice of Amendment: Addition of Metamizole (Dipyrone) to the Prescription Drug List (PDL)". Government of Canada. 2022-07-18. Archived from the original on 2022-08-30. Retrieved 2023-08-04.

[NZ-prescription-6] "Recent NZ Gazette Notices Relating to Classification". medsafe.govt.nz. 2020-03-06. Archived from the original on 2023-04-29. Retrieved 2023-08-04.

[medsafe.govt.nz-2019-7] "Minutes of the 63rd meeting of the Medicines Classification Committee - 10 Oct 2019". medsafe.govt.nz. 2019-12-04. Archived from the original on 2023-06-10. Retrieved 2023-08-04.

[FDA2019horse-8] FDA's Center for Veterinary Medicine (November 26, 2019). "Zimeta (dipyrone injection) - Veterinarians". FDA. Archived from the original on 2022-01-17. Retrieved 2023-08-04.

[EMA2018-9] Cite error: The named reference EMA2018 was invoked but never defined (see the help page).

[Bundesinstitut_für_Arzneimittel_und_Medizinprodukte_(Federal_Institute_for_Pharmaceuticals_and_Medical_Products)-2009-10] "Risikoinformationen - Metamizol (Novalgin, Berlosin, Novaminsulfon, etc.): BfArM weist auf richtige Indikationsstellung und Beachtung von Vorsichtsmaßnahmen und Warnhinweisen hin" [Risk information - Metamizol (Novalgin, Berlosin, Novaminsulfon, etc.): BfArM points out the correct indication and compliance with precautionary measures and warnings]. Bundesinstitut für Arzneimittel und Medizinprodukte (Federal Institute for Pharmaceuticals and Medical Products). 2009-05-28. Archived from the original on 2023-05-18. Retrieved 2023-08-04.

[deranaes2008-11] Jage J, Laufenberg-Feldmann R, Heid F (April 2008). "[Medikamente zur postoperativen Schmerztherapie: Bewährtes und Neues. Teil 1: Nichtopioide]" [Drugs for postoperative analgesia: routine and new aspects. Part 1: non-opioids]. Der Anaesthesist (in German). 57 (4): 382–390. doi:10.1007/s00101-008-1326-x. PMID 18351305. S2CID 32814418.

[y0-12] Cite error: The named reference y0 was invoked but never defined (see the help page).

[Winthrop_Arzneimittel_GmbH-2013a-13] "Fachinformation (Zusammenfassung der Merkmale des Arzneimittels) Novaminsulfon injekt 1000 mg Lichtenstein Novaminsulfon injekt 2500 mg Lichtenstein" (PDF). Winthrop Arzneimittel GmbH (in German). Zinteva Pharm GmbH. February 2013. Archived (PDF) from the original on 16 October 2018. Retrieved 19 April 2014.

[deranaes2004-14] Cite error: The named reference deranaes2004 was invoked but never defined (see the help page).

[Fis20064-15] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 530. ISBN 978-3-527-60749-5.

[pmid26019521-16] Cite error: The named reference pmid26019521 was invoked but never defined (see the help page).

[Business_Standard_India-2014-17] Cite error: The named reference Business Standard India-2014 was invoked but never defined (see the help page).

[United_Nations_Department_of_Economic_and_Social_Affairs-2005-18] Cite error: The named reference United Nations Department of Economic and Social Affairs-2005 was invoked but never defined (see the help page).

[pmid31433499-2-19] Lutz M (November 2019). "Metamizole (Dipyrone) and the Liver: A Review of the Literature". Journal of Clinical Pharmacology. 59 (11): 1433–1442. doi:10.1002/jcph.1512. PMID 31433499. S2CID 201118022.

[NikolovaTencheva20144-20] Nikolova I, Tencheva J, Voinikov J, Petkova V, Benbasat N, Danchev N (2014). "Metamizole: A Review Profile of a Well-Known "Forgotten" Drug. Part I: Pharmaceutical and Nonclinical Profile". Biotechnology & Biotechnological Equipment. 26 (6): 3329–3337. doi:10.5504/BBEQ.2012.0089. ISSN 1310-2818. S2CID 56205439.

[pmid35584441-21] Sznejder H, Amand C, Stewart A, Salazar R, Scala WA (2022). "Real world evidence of the use of metamizole (dipyrone) by the Brazilian population. A retrospective cohort with over 380,000 patients". Einstein. 20. Sociedade Beneficente Israelita Brasileira Hospital Albert Einstein: eAO6353. doi:10.31744/einstein_journal/2022ao6353. PMC 9060643. PMID 35584441.

Metamizole information

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Clinical data


Trade names	Novalgin, Algocalmin,^[1] Analgin, others^[2]
Other names	Dipyrone (BAN UK, USAN US, Sulpyrine (JAN JP)
AHFS/Drugs.com	International Drug Names
Pregnancy category	None assigned; no evidence of teratogenicity in animal studies, but use in the third trimester may cause adverse effects in the newborn or ductus arteriosus (a heart defect) due to its weak NSAID activity.^[3]^[4]
Routes of administration	Oral, IM, IV, rectal
ATC code	N02BB02 (WHO)
Legal status
Legal status	AU: Withdrawn BR: OTC (Over the counter) CA: Veterinary only^[5] DE: § 48 AMG/§ 1 MPAV (Prescription only)^[10] NZ: Prescription only^[6]^[7] UK: Withdrawn US: Veterinary only (horses)^[8] EU: Legally available^[9]
Pharmacokinetic data
Bioavailability	100% (active metabolites)^[11]
Protein binding	48–58% (active metabolites)^[11]
Metabolism	Liver^[11]
Elimination half-life	14 minutes (parent compound; parenteral);^[4] metabolites: 2–4 h^[11]
Duration of action	4–6 h^[12]
Excretion	Urine (96%, IV; 85%, oral), faeces (4%, IV).^[4]
Identifiers
IUPAC name [(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino] methanesulfonic acid
CAS Number	50567-35-6^Y 68-89-3 (sodium salt)
PubChem CID	3111 522325
DrugBank	DB04817^Y
ChemSpider	3000^N
UNII	934T64RMNJ
KEGG	D08188^N
ChEBI	CHEBI:62088^Y
ChEMBL	ChEMBL461522^Y
CompTox Dashboard (EPA)	DTXSID8020543
ECHA InfoCard	100.000.631
Chemical and physical data
Formula	C₁₃H₁₇N₃O₄S
Molar mass	311.36 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1ccccc1N2N(C)C(C)=C(C2=O)N(C)CS(=O)(=O)O
InChI InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)^N Key:LVWZTYCIRDMTEY-UHFFFAOYSA-N^N
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