Page last updated: 2024-11-06

n-acetylaminoantipyrine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

N-acetylaminoantipyrine, also known as aminopyrine, is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is synthesized through a multi-step process starting with the reaction of phenylhydrazine with acetoacetic ester, followed by methylation and acetylation steps. n-acetylaminoantipyrine has been widely used for pain relief and fever reduction. However, its use has been restricted in many countries due to concerns about potential adverse effects, including agranulocytosis (a rare but serious blood disorder). Despite its restricted use, n-acetylaminoantipyrine remains a subject of research due to its potent analgesic and anti-inflammatory effects. Studies continue to explore its potential benefits and risks, as well as its potential for use in combination with other drugs. Research into n-acetylaminoantipyrine aims to better understand its mechanism of action, optimize its therapeutic use, and develop safer alternatives.'

4-acetamidoantipyrine : A member of the class of pyrazoles that is antipyrine substituted by an acetylamino group at position 4. It is a drug metabolite of metamizole. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID65743
CHEMBL ID1831257
CHEBI ID83513
SCHEMBL ID5050992
MeSH IDM0055873

Synonyms (66)

Synonym
acetamide, n-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)-
SDCCGMLS-0064808.P002
SDCCGMLS-0064808.P001
nsc-331807
acetamidoantipyrine
acetamide, n-antipyrinyl-
4-acetoaminoantipyrine
4-acetamidoantipyrine
4-acetylaminophenazone
4-acetaminoantipyrine
acetylaminoantipyrine
n-acetyl-4-aminoantipyrine
antipyrine, 4-acetamido-
83-15-8
nsc331807
4-acetylaminoantipyrine
acetamide, n-(antipyrinyl)-
acetyl-4-aminoantipyrine
acetamide,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)-
OPREA1_507768
OPREA1_016919
inchi=1/c13h15n3o2/c1-9-12(14-10(2)17)13(18)16(15(9)3)11-7-5-4-6-8-11/h4-8h,1-3h3,(h,14,17)
n-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)acetamide
oiagwxkscxpnnz-uhfffaoysa-
AKOS000746331
A840513
n-(1,5-dimethyl-3-oxo-2-phenyl-pyrazol-4-yl)acetamide
chebi:83513 ,
CHEMBL1831257
n-(2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl)acetamide
535h9n144z ,
einecs 201-457-0
unii-535h9n144z
ai3-52432
nsc 331807
n-acetylaminoantipyrine
FT-0631379
n-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)acetamide
F0034-0117
4-(n-acetylamino)antipyrine
OIAGWXKSCXPNNZ-UHFFFAOYSA-N
aminoantipyrine, n-acetyl-
n-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1h-pyrazol-4-yl)acetamide #
DTXSID40232106
n-antipyrinylacetamide
MS-10581
SCHEMBL5050992
J47.302B ,
4-acetamido-2,3-dimethyl-1-phenylpyrazol-5-one
aaa metabolite of metamizole
SR-01000395595-1
sr-01000395595
mfcd00003141
4-acetamidoantipyrine, analytical standard
4-acetamidoantipyrin
4aaa
n-acetyl-4-aminoantipyrin
4-aaa
Q27156901
4-acetamido antipyrine
acetamide,n-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)-
CS-0313868
4-acetylaminoantipyrine 10 microg/ml in acetonitrile
4-acetamidoantipyrine-d3
n-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)acetamide
Z27661913

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Finally, the application of an acute toxicity test (Daphnia magna) showed an increase in toxicity during the photolytic process, a consequence of the formation of toxic photoproducts."( Photodegradation study of three dipyrone metabolites in various water systems: identification and toxicity of their photodegradation products.
Agüera, A; Fernández-Alba, AR; Gómez, MJ; Mezcua, M; Sirtori, C, 2008
)
0.35

Pharmacokinetics

ExcerptReferenceRelevance
" The mean Cmax of 4-MAA increased linearly with dose whereas its AUC was not proportional to dose after administration of 1500 and 3000 mg."( Pharmacokinetics of metamizol metabolites in healthy subjects after a single oral dose of metamizol sodium.
Bacracheva, N; Badian, M; Verho, M; Vlahov, V, 1990
)
0.28

Dosage Studied

ExcerptRelevanceReference
" The trial was open, randomized, and cross-over, with a one-week interval between dosing days."( Pharmacokinetics of metamizol metabolites in healthy subjects after a single oral dose of metamizol sodium.
Bacracheva, N; Badian, M; Verho, M; Vlahov, V, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
marine xenobiotic metaboliteAny metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
drug metabolitenull
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
pyrazoles
acetamidesCompounds with the general formula RNHC(=O)CH3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID619774Antibacterial activity against Escherichia coli RCMB 000103 at 10 mg/ml after 24 hrs by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619770Antibacterial activity against Bacillus subtilis RCMB 000107 at 10 mg/ml after 24 hrs by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619762Antifungal activity against Aspergillus fumigatus RCMB 002003 at 10 mg/ml after 3 to 4 days by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619764Antifungal activity against Geotrichum candidum RCMB 052006 at 10 mg/ml after 3 to 4 days by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619766Antifungal activity against Candida albicans RCMB 052002 at 10 mg/ml after 3 to 4 days by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619768Antibacterial activity against Staphylococcus aureus RCMB 000106 at 10 mg/ml after 24 hrs by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619772Antibacterial activity against Pseudomonas aeruginosa RCMB 000102 at 10 mg/ml after 24 hrs by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
AID619760Antifungal activity against Syncephalastrum racemosum RCMB 052003 at 10 mg/ml after 3 to 4 days by agar well diffusion method2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (38.89)18.7374
1990's4 (22.22)18.2507
2000's4 (22.22)29.6817
2010's3 (16.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.23

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.23 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.23)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (15.79%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (15.79%)4.05%
Observational0 (0.00%)0.25%
Other13 (68.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]