General Information of Drug (ID: DR1037)
Drug Name
Metamizole sodium
Synonyms
Metamizole; Metamizole sodium; Metamizolum natricum; Metapyrin; Methampyrone; Methylmelubrin; Metilon; Alginodia; Algocalmin; Algopyrine; Aminopyrine sodium sulfonate; Analgin; Analgine; Barone; Bonpyrin; Conmel; Di-podil; Dimethone; Diprofarn; Farmolisina; Feverall; Fevonil; Gifaril; Keypyrone; Narone; Neo-melubrine; Neomelurbrin; Nevralgina; Novalgetol; Novalgin; Novamidazophen; Novaminsulfon; Novaminsulfone; Novaminsulfonum; Noveltex; Optalgin; Paralgin; Pharmalgine; Pyralgin; Pyretin; Pyrojec; Sulpin; Sulpyrin; dipyrone; sulpyrine; 68-89-3
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 333.34 Topological Polar Surface Area 92.4
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
522325
PubChem SID
3141602 ; 7978471 ; 8149975 ; 8671880 ; 10321896 ; 11112965 ; 14924439 ; 25672721 ; 26612465 ; 26680273 ; 26748775 ; 26748776 ; 29225232 ; 46509035 ; 48413695 ; 49857349 ; 49991316 ; 53787029 ; 57288770 ; 57406347 ; 79371109 ; 79371110 ; 85091098 ; 88837636 ; 92124570 ; 92125891 ; 92307887 ; 92741959 ; 96024880 ; 99301722 ; 103588113 ; 103914375 ; 109768588 ; 118047367 ; 121363562 ; 124637172 ; 124882743 ; 124882744 ; 125311960 ; 125329714 ; 126408303 ; 126677934 ; 134339964 ; 134971374 ; 137002916 ; 141701141 ; 143432632 ; 143832172 ; 144204310 ; 144207695
ChEBI ID
CHEBI:59033
CAS Number
68-89-3
TTD Drug ID
D06JRD
Formula
C13H16N3NaO4S
Canonical SMILES
CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)CS(=O)(=O)[O-].[Na+]
InChI
1S/C13H17N3O4S.Na/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);/q;+1/p-1
InChIKey
DJGAAPFSPWAYTJ-UHFFFAOYSA-M
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
N-Desmethylaminopyrine DM001564
10618
Hydrolysis - Hydrolysis 1 [3] , [4]
4-amino-antipyrine (AA) DM002650
2151
Oxidation - N-Demethylation 2 [3] , [4]
4-formyl-amino-antipyrine (FAA) DM002649
72666
Oxidation - C-Oxidation 2 [3] , [4]
Arachidonoyl-4-methylaminoantipyrinee (ARA-4-MAA) DM002653 N. A. Unclear 2 [3] , [4]
4-acetyl-amino-antipyrine (AAA) DM002651
65743
Conjugation - Acetylation 3 [3] , [4]
4-amino-antipyrine (AA) DM002650
2151
Oxidation - N-Demethylation 3 [3] , [4]
Arachidonoyl-4-aminoantipyrine (ARA-4-AA) DM002652 N. A. Unclear 3 [3] , [4]
4-acetyl-amino-antipyrine (AAA) DM002651
65743
Conjugation - Acetylation 4 [3] , [4]
Arachidonoyl-4-aminoantipyrine (ARA-4-AA) DM002652 N. A. Unclear 4 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001660 Metamizole sodium N-Desmethylaminopyrine Hydrolysis - Hydrolysis Unclear [3], [4]
MR001654 N-Desmethylaminopyrine 4-formyl-amino-antipyrine (FAA) Oxidation - C-Oxidation Unclear [3], [4]
MR001655 N-Desmethylaminopyrine 4-amino-antipyrine (AA) Oxidation - N-Demethylation CYP2B6 ... [3], [4]
MR001656 N-Desmethylaminopyrine Arachidonoyl-4-methylaminoantipyrinee (ARA-4-MAA) Unclear Unclear [3], [4]
MR001657 4-formyl-amino-antipyrine (FAA) 4-amino-antipyrine (AA) Oxidation - N-Demethylation CYP2B6 ... [3], [4]
MR001658 4-amino-antipyrine (AA) 4-acetyl-amino-antipyrine (AAA) Conjugation - Acetylation Unclear [3], [4]
MR001659 4-amino-antipyrine (AA) Arachidonoyl-4-aminoantipyrine (ARA-4-AA) Unclear Unclear [3], [4]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[2]
References
1 ClinicalTrials.gov (NCT04111315) Efficacy of Metamizole Versus Ibuprofen and a Short Educational Intervention Versus Standard Care in Acute Low Back Pain.
2 N-acetyltransferase 2 polymorphisms and susceptibility to infant leukemia with maternal exposure to dipyrone during pregnancy. Cancer Epidemiol Biomarkers Prev. 2010 Dec;19(12):3037-43.
3 Metamizole (Dipyrone) and the Liver: A Review of the Literature J Clin Pharmacol. 2019 Nov;59(11):1433-1442. doi: 10.1002/jcph.1512.
4 Clinical pharmacokinetics of dipyrone and its metabolites Clin Pharmacokinet. 1995 Mar;28(3):216-34. doi: 10.2165/00003088-199528030-00004.

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