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Dipyrone

PubChem CID
522325
Structure
Dipyrone_small.png
Dipyrone_3D_Structure.png
Molecular Formula
Synonyms
  • dipyrone
  • Analgin
  • Metamizole sodium
  • 68-89-3
  • Novalgin
Molecular Weight
333.34 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Parent Compound
Dates
  • Create:
    2005-03-27
  • Modify:
    2024-12-14
Description
Metamizole sodium is an organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic. It has a role as a non-narcotic analgesic, an antirheumatic drug, a peripheral nervous system drug, an antipyretic, a prodrug, a cyclooxygenase 3 inhibitor and an anti-inflammatory agent. It contains a metamizole(1-).
A drug that has analgesic, anti-inflammatory, and antipyretic properties. It is the sodium sulfonate of AMINOPYRINE.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dipyrone.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

DJGAAPFSPWAYTJ-UHFFFAOYSA-M
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N(C)CS(=O)(=O)[O-].[Na+]
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C13H16N3NaO4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

68-89-3

2.3.2 Deprecated CAS

57904-20-8

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 PharmGKB ID

2.3.13 RXCUI

2.3.14 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Algopyrin
  • Analgin
  • Biopyrin
  • Dipyrone
  • Dipyronium
  • Metamizol
  • Metamizole
  • Metamizole Sodium
  • Methamizole
  • Methampyrone
  • Narone
  • Noramidopyrine Methanesulfonate
  • Noramidopyrine Methanesulfonate Sodium
  • Normelubrine
  • Novalgetol
  • Novalgin
  • Novamidazophen
  • Novaminsulfone
  • Optalgin
  • Pyralgin
  • Sulpyrin
  • Sulpyrine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
333.34 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
333.07592146 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
333.07592146 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
92.4Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
22
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
552
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Kovats Retention Index

Standard non-polar
1975, 2000

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal
3.3.1.2 Animal Drugs
Active Ingredients (Dipyrone) -> FDA Greenbook
Pharmaceuticals -> UK Veterinary Medicines Directorate List
S104 | UKVETMED | UK Veterinary Medicines Directorate's List | DOI:10.5281/zenodo.7802119

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian A-60
Source of Sample
Winthrop Laboratories, New York, New York
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
Unknown
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

56 99.99

83 26.30

42 21.80

217 18.70

123 15

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 5
View All
MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
HITACHI RMU-6E
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

56 99.99

217 78

123 72

83 65

215 52

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2.2 Other MS

1 of 2
Authors
SASAKI S, TOYOHASHI UNIV. OF TECH.
Instrument
Unknown
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Top 5 Peaks

56 999

83 263

42 218

217 187

123 150

Thumbnail
Thumbnail
License
CC BY-NC-SA
2 of 2
Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
HITACHI RMU-6E
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

56 999

217 780

123 720

83 650

215 520

Thumbnail
Thumbnail
License
CC BY-NC-SA

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Anti-inflammatory Agents, Nonsteroidal

7.2 FDA Green Book

7.3 Drug Labels

Drug and label
Active ingredient and drug

7.4 Clinical Trials

7.4.1 ClinicalTrials.gov

7.4.2 EU Clinical Trials Register

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Antipyretics
Drugs that are used to reduce body temperature in fever. (See all compounds classified as Antipyretics.)
Anti-Inflammatory Agents, Non-Steroidal
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they 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. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

8.2 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N02 - Analgesics

N02B - Other analgesics and antipyretics

N02BB - Pyrazolones

N02BB02 - Metamizole sodium

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 95.8% (91 of 95) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 4.2% (4 of 95) of reports.
Pictogram(s)
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H302 (11.6%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (49.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H334 (49.5%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

H361 (30.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H372 (29.5%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

H411 (29.5%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P318, P319, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 95 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 4 of 95 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 9 notifications provided by 91 of 95 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (11.6%)

Skin Sens. 1 (49.5%)

Resp. Sens. 1 (49.5%)

Repr. 2 (30.5%)

STOT RE 1 (29.5%)

Aquatic Chronic 2 (29.5%)

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Dipyrone: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

10.3 Other Safety Information

Chemical Assessment

IMAP assessments - Methanesulfonic acid, [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]-, sodium salt: Environment tier I assessment

IMAP assessments - Methanesulfonic acid, [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]-, sodium salt: Human health tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

After ingestion by the mother, dipyrone and its metabolites appear in breastmilk in rather large amounts. It is found in the blood and urine of breastfed infants and can cause pharmacological effects in the breastfed infant. One case of cyanotic episodes in a breastfed infant was attributed to dipyrone in breastmilk. The drug and metabolites are eliminated from the breastmilk by 48 hours after a dose.

Dipyrone is not approved for marketing in the United States by the U.S. Food and Drug Administration nor in Canada and many European countries because of its adverse reactions, including agranulocytosis. However, it is widely used in other countries during labor and breastfeeding. The European Medicines Agency recommends that dipyrone not be used in nursing mothers; however, several drug consultation centers in Israel disagree. One manufacturer recommends to withhold breastfeeding for 48 hours after a dose. Safer alternatives are available for analgesia during breastfeeding.

◉ Effects in Breastfed Infants

A 42-day-old breastfed infant had 2 cyanotic episodes within 30 minutes after his mother took 3 doses of dipyrone 500 mg orally, 18, 7 and 2 hours before the first episode. A third episode occurred 24 hours after admission to the hospital. Dipyrone was detected in the mother's breastmilk 24 hours after the last dose and in the infant's serum and urine. No explanation could be found for the cyanotic episodes other than dipyrone and after suspending maternal dipyrone intake, no further episodes occurred in the infant up to age 3 years. The reaction is rated as possibly caused by dipyrone in breastmilk.

In a blinded study, mothers who were at least 3 days postpartum and requesting analgesia for postpartum uterine pain were given either 1 gram of dipyrone or placebo. The infants of mothers who received dipyrone cried fewer times and for shorter durations in the 14 hours after drug administration than the infants of mothers who received placebo. This effect was more apparent in infants who demand fed than in those who fed on a fixed schedule. Although this study appears to demonstrate a pharmacologic effect in the infants from dipyrone in milk, there is no clear explanation for the change in infant behavior.

A multicenter case-control study in Brazil compared 231 children who developed leukemia before 2 years of age with 411 children with various other nonmalignant diseases. Mothers were interviewed to ascertain their analgesic use during pregnancy and lactation. Nursing mothers who took dipyrone during the three months after delivery had a 2-fold risk of having a child with acute lymphocytic leukemia and a 3.87-fold risk in having rearrangement of the MLL gene in infants under one year of age.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11.1.2 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 FDA Green Book Patents

14.4 Chemical Co-Occurrences in Patents

14.5 Chemical-Disease Co-Occurrences in Patents

14.6 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: ATC

17.5 KEGG: Drug Groups

17.6 WHO ATC Classification System

17.7 ChemIDplus

17.8 ChEMBL Target Tree

17.9 UN GHS Classification

17.10 NORMAN Suspect List Exchange Classification

17.11 EPA DSSTox Classification

17.12 EPA Substance Registry Services Tree

17.13 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Methanesulfonic acid, [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]-, sodium salt
    https://services.industrialchemicals.gov.au/search-assessments/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Sodium [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulphonate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.000.631
    Sodium [(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methanesulphonate (EC: 200-694-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/118030
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  7. ChEBI
  8. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  9. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  10. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  11. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  12. DailyMed
  13. Drugs and Lactation Database (LactMed)
  14. EU Clinical Trials Register
  15. FDA Approved Animal Drug Products (Green Book)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  16. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Metamizole
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  19. MassBank Europe
  20. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  21. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  22. SpectraBase
    (antipyrinylmethylamino)methanesulfonic acid, sodium salt
    https://spectrabase.com/spectrum/6ZgtL5nigu2
  23. Metabolomics Workbench
  24. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  25. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  26. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  27. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  28. Springer Nature
  29. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  30. Wikidata
  31. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Anti-Inflammatory Agents, Non-Steroidal
    https://www.ncbi.nlm.nih.gov/mesh/68000894
  32. PubChem
  33. GHS Classification (UNECE)
  34. EPA Substance Registry Services
  35. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  36. PATENTSCOPE (WIPO)
CONTENTS