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Substance Name: Dipyrone [USAN:JAN]
RN: 68-89-3
UNII: VSU62Z74ON
InChIKey: DJGAAPFSPWAYTJ-UHFFFAOYSA-M

Note

  • A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE. Because of the risk of serious adverse effects its use is justified only in serious situations where no alternative is available or suitable. (From Martindale, The Extra Pharmacopoeia, 30th ed, p13)

Molecular Formula

  • C13-H17-N3-O4-S.Na

Molecular Weight

  • 333.3424
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Dipyrone
  • Dipyrone [USAN:JAN]
  • Metamizole sodium [INN]

MeSH Heading

  • Dipyrone

Synonyms

  • (Antipyrinylmethylamino)methanesulfonic acid sodium salt
  • 1-Phenyl-2,3-dimethyl-4-methylamino-5-pyrazolon-N-methanesulfonsaeuren natrium
  • 1-Phenyl-2,3-dimethyl-4-methylamino-5-pyrazolon-N-methanesulfonsaeuren natrium [German]
  • 1-Phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethanesulfonate sodium
  • 1-Phenyl-2,3-dimethylpyrazolone-(5)-4-methylaminomethanesulfonic acid sodium
  • 4-Methylamino-1,5-dimethyl-2-phenyl-3-pyrazolone sodium methanesulfonate
  • 4-Sodium methanesulfonate methylamine-antipyrine
  • Alginodia
  • Algocalmin
  • Algopyrine
  • Aminopyrine sodium sulfonate
  • Analgin
  • Analgine
  • Analginum
  • Antipyrine, 4-(methylamino)-, monomethosulfate, sodium salt
  • ARPF
  • Barone
  • Bonpyrin
  • CCRIS 4443
  • Conmel
  • Di-podil
  • Dimethone
  • Diprofarn
  • Dipyrone
  • Dipyrone [BAN]
  • EINECS 200-694-7
  • Farmolisina
  • Fenildimetil-pirazolon-metilaminometansolfonato sodico
  • Fenildimetil-pirazolon-metilaminometansolfonato sodico [Italian]
  • Feverall
  • Fevonil
  • Gifaril
  • Keypyrone
  • Metamizol
  • Metamizol sodico
  • Metamizol sodico [INN-Spanish]
  • Metamizol sodico [Spanish]
  • Metamizole
  • Metamizole sodique
  • Metamizole sodique [French]
  • Metamizole sodique [INN-French]
  • Metamizole sodium
  • Metamizolnatrium
  • Metamizolo
  • Metamizolo sodico
  • Metamizolo sodico [DCIT]
  • Metamizolo [Italian]
  • Metamizolum
  • Metamizolum natricum
  • Metamizolum natricum [INN-Latin]
  • Metamizolum natricum [Latin]
  • Metapyrin
  • Methamizole sodium
  • Methampyrone
  • Methanesulfonic acid, (antipyrinylmethylamino)-, sodium salt
  • Methylaminoantipyrine sodium methanesulfonate
  • Methylaminophenyldimethylpyrazolone methanesulfonate sodium
  • Methylmelubrin
  • Metilon
  • Narone
  • Natrium novaminsulfonicum
  • Neo-melubrine
  • Neomelurbrin
  • Nevralgina
  • Noramidopyrine methanesulfonate sodium
  • Noramidopyrine methanesulfonate sodium salt
  • Noramidopyrinium-methanesulphate natrium
  • Noramidopyrinium-methanesulphate natrium [German]
  • Noraminophenazone
  • Noraminophenazone methanesulfonate sodium salt
  • Noraminophenazone sodium mesylate
  • Noraminopyrine methanesulfonate sodium
  • Novalgetol
  • Novalgin
  • Novamidazophen
  • Novamidazophenum
  • Novaminophenazone
  • Novaminsulfon
  • Novaminsulfone
  • Novaminsulfone sodium
  • Novaminsulfonium
  • Novaminsulfonum
  • Noveltex
  • Optalgin
  • Paralgin
  • Pharmalgine
  • Phenyl dimethyl pyrazolon methyl aminomethane sodium sulfonate
  • Prodolina
  • Pyralgin
  • Pyretin
  • Pyretin (pharmaceutical)
  • Pyrojec
  • Sodium (antipyrinylmethylamino)methanesulfonate
  • Sodium 1-phenyl-2,3-dimethyl-4-methylaminopyrazolon-N-methanesulfonate
  • Sodium 1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylamino methanesulfonate
  • Sodium 4-methylamino-1,5-dimethyl-2-phenyl-3-pyrazolone 4-methanesulfonate
  • Sodium methylaminoantipyrine methanesulfonate
  • Sodium noramidopyrine methanesulfonate
  • Sodium novaminsulfonate
  • Sodium phenyldimethylpyrazolon-methylamino-methane sulfonate
  • Sulpin
  • Sulpyrin
  • Sulpyrine
  • Sulpyrinum
  • UNII-VSU62Z74ON

Systematic Names

  • Dipyrone
  • Methanesulfonic acid, ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino)-, sodium salt
  • Methanesulfonic acid, (antipyrinylmethylamino)-, monosodium salt
  • Sodium ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino)methanesulphonate

Registry Numbers

CAS Registry Number

  • 68-89-3

FDA UNII

  • VSU62Z74ON

Other Registry Number

  • 57904-20-8

System Generated Number

  • 0000068893

Molecular Formulas

Molecular Formula

  • C13-H17-N3-O4-S.Na

Molecular Formula Fragments

  • C13-H17-N3-O4-S
  • COMPONENT
  • Na

Structure Descriptors

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

Smiles

[Na+].CN(CS(=O)(=O)[O-])C1=C(C)N(C)N(C1=O)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo subcutaneous 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
mouse LC50 inhalation 37200mg/m3 (37200mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(10), Pg. 36, 1969.
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 107, Pg. 322, 1956.
mouse LD50 intravenous 2197mg/kg (2197mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
mouse LD50 oral 2891mg/kg (2891mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
mouse LD50 subcutaneous 69mg/kg (69mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 53, 1968.
mouse LD50 unreported 2750mg/kg (2750mg/kg)   Journal of Drug Research. Vol. 4, Pg. 89, 1972.
rabbit LD50 oral 2150mg/kg (2150mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 47, 1979.
rabbit LDLo subcutaneous 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
rat LC inhalation > 900mg/m3 (900mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 47, 1979.
rat LD50 intramuscular 1625mg/kg (1625mg/kg)   Russian Pharmacology and Toxicology Vol. 51, Pg. 183, 1988.
rat LD50 intraperitoneal 2470mg/kg (2470mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Kiso to Rinsho. Clinical Report. Vol. 11, Pg. 478, 1977.
rat LD50 intravenous 2182mg/kg (2182mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 703, 1976.
rat LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
rat LD50 subcutaneous 2117mg/kg (2117mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.