CHEBI:62088 - metamizole

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name metamizole
ChEBI ID CHEBI:62088
Definition A pyrazole that is antiipyrine substituted at C-4 by a methyl(sulfomethyl)amino group, the sodium salt of which, metamizole sodium, was widely used as a powerful analgesic and antipyretic, but withdrawn from many markets from the 1970s due to a risk of causing risk of causing agranulocytosis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C13H17N3O4S
Net Charge 0
Average Mass 311.35700
Monoisotopic Mass 311.09398
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)
InChIKey LVWZTYCIRDMTEY-UHFFFAOYSA-N
SMILES CN(CS(O)(=O)=O)c1c(C)n(C)n(-c2ccccc2)c1=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
cyclooxygenase 3 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 3.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing metamizole (CHEBI:62088) has functional parent antipyrine (CHEBI:31225)
metamizole (CHEBI:62088) has role antipyretic (CHEBI:35493)
metamizole (CHEBI:62088) has role antirheumatic drug (CHEBI:35842)
metamizole (CHEBI:62088) has role cyclooxygenase 3 inhibitor (CHEBI:73263)
metamizole (CHEBI:62088) has role non-narcotic analgesic (CHEBI:35481)
metamizole (CHEBI:62088) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
metamizole (CHEBI:62088) has role peripheral nervous system drug (CHEBI:49110)
metamizole (CHEBI:62088) has role prodrug (CHEBI:50266)
metamizole (CHEBI:62088) is a amino sulfonic acid (CHEBI:37793)
metamizole (CHEBI:62088) is a pyrazoles (CHEBI:26410)
metamizole (CHEBI:62088) is conjugate acid of metamizole(1−) (CHEBI:62086)
Incoming metamizole(1−) (CHEBI:62086) is conjugate base of metamizole (CHEBI:62088)
IUPAC Name
[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonic acid
Synonyms Sources
(antipyrinylmethylamino)methanesulfonic acid ChEBI
[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulfonic acid ChEBI
metamizol ChemIDplus
metamizolum ChemIDplus
N-(2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)-N-methylaminomethanesulfonic acid ChEBI
Manual Xrefs Databases
4659 DrugCentral
D08188 KEGG DRUG
LSM-5839 LINCS
View more database links
Registry Numbers Types Sources
327442 Reaxys Registry Number Reaxys
50567-35-6 CAS Registry Number KEGG DRUG
50567-35-6 CAS Registry Number ChemIDplus
Last Modified
22 February 2017