ContaminantDB: Dipyrone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:26:40 UTC

Update Date

2026-04-03 09:08:03 UTC

Accession Number

CHEM016300

Identification

Common Name

Dipyrone

Class

Small Molecule

Description

Metamizole, formerly marketed as Dimethone tablets and injection, Protemp oral liquid, and other drug products, was associated with potentially fatal agranulocytosis. Approvals of the NDA's for Metamizole drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977 (42 FR 30893)). Withdrawn from the Canadian market in 1963.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Algocalmin	ChEBI
Aminopyrine sodium sulfonate	ChEBI
Analgin	ChEBI
Analgin (sodium salt)	ChEBI
Dipyrone	ChEBI
Meamizol sodico	ChEBI
Metamizole sodique	ChEBI
Metamizolum natricum	ChEBI
Methampyrone	ChEBI
Methylmelubrin	ChEBI
Mexican aspirin	ChEBI
Neomelurbrin	ChEBI
Noraminophenazone methanesulfonate sodium salt	ChEBI
Noraminophenazone sodium mesylate	ChEBI
Novalgin	ChEBI
Sodium (antipyrinylmethylamino)methanesulfonate	ChEBI
Sodium methylaminoantipyrine methanesulfonate	ChEBI
Sodium noramidopyrine methanesulfonate	ChEBI
Sulpyrine	ChEBI
Vetalgin	ChEBI
Metamizole sodium	Kegg
Aminopyrine sodium sulfonic acid	Generator
Aminopyrine sodium sulphonate	Generator
Aminopyrine sodium sulphonic acid	Generator
Noraminophenazone methanesulfonic acid sodium salt	Generator
Noraminophenazone methanesulphonate sodium salt	Generator
Noraminophenazone methanesulphonic acid sodium salt	Generator
Noraminophenazone sodium mesylic acid	Generator
Sodium (antipyrinylmethylamino)methanesulfonic acid	Generator
Sodium (antipyrinylmethylamino)methanesulphonate	Generator
Sodium (antipyrinylmethylamino)methanesulphonic acid	Generator
Sodium methylaminoantipyrine methanesulfonic acid	Generator
Sodium methylaminoantipyrine methanesulphonate	Generator
Sodium methylaminoantipyrine methanesulphonic acid	Generator
Sodium noramidopyrine methanesulfonic acid	Generator
Sodium noramidopyrine methanesulphonate	Generator
Sodium noramidopyrine methanesulphonic acid	Generator
Novalgetol	MeSH
Novamidazophen	MeSH
Biopyrin	MeSH
Methanesulfonate sodium, noramidopyrine	MeSH
Methanesulfonate, noramidopyrine	MeSH
Noramidopyrine methanesulfonate	MeSH
Novaminsulfone	MeSH
Optalgin	MeSH
Pyralgin	MeSH
Dipyronium	MeSH
Methamizole	MeSH
Narone	MeSH
Sulpyrin	MeSH
Algopyrin	MeSH
Metamizol	MeSH
Noramidopyrine methanesulfonate sodium	MeSH
Normelubrine	MeSH

Chemical Formula

C₁₃H₁₆N₃NaO₄S

Average Molecular Mass

333.339 g/mol

Monoisotopic Mass

333.076 g/mol

CAS Registry Number

68-89-3

IUPAC Name

sodium [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonate

Traditional Name

sodium metamizole(1-)

SMILES

[Na+].CN(CS([O-])(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1

InChI Identifier

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

InChI Key

DJGAAPFSPWAYTJ-UHFFFAOYSA-M

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
Dialkylarylamine
Monocyclic benzene moiety
Pyrazolinone
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Alkanesulfonic acid
Vinylogous amide
Heteroaromatic compound
Lactam
Organic alkali metal salt
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic salt
Organosulfur compound
Organic oxygen compound
Organic sodium salt
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic sodium salt (CHEBI:59033 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.8 g/L	ALOGPS
logP	1.07	ALOGPS
logP	-0.82	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-1.2	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.92 m³·mol⁻¹	ChemAxon
Polarizability	31.11 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9210000000-0afef355301fc17c2ab5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-066r-9120000000-b465330a1885c099bc73	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-3950000000-68aa296020d535c13e5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-008a-0589000000-b2e06a3bc03abe2c7ad1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-2390000000-f96215f9805484d3d245	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9700000000-723448621b6d4d8c57ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-3903000000-2a615794737c974d93b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-2893000000-f8d185e5d45c2b2b7599	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l6-9510000000-0f180ea4f7628f16bdbc	Spectrum