フェナゾン
- 関
- antipyrine
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/12/31 21:43:15」(JST)
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Phenazone
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Systematic (IUPAC) name |
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
|
Pharmacokinetic data |
Biological half-life |
12 hours |
Identifiers |
CAS Number |
60-80-0 Y |
ATC code |
N02BB01 S02DA03 |
PubChem |
CID: 2206 |
DrugBank |
DB01435 Y |
ChemSpider |
2121 Y |
UNII |
T3CHA1B51H Y |
KEGG |
D01776 Y |
ChEBI |
CHEBI:31225 Y |
ChEMBL |
CHEMBL277474 Y |
Synonyms |
analgesine, antipyrine |
Chemical data |
Formula |
C11H12N2O |
Molecular mass |
188.2258g/mol |
SMILES
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O=C2\C=C(/N(N2c1ccccc1)C)C
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InChI
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InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 Y
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Key:VEQOALNAAJBPNY-UHFFFAOYSA-N Y
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(verify) |
Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), or analgesine) is an analgesic, a non-steroidal anti-inflammatory drug and an antipyretic. It was first synthesized by Ludwig Knorr in 1887.[1][2]:26-27 Phenazone is synthesized[3] by condensation of phenylhydrazine and ethyl acetoacetate under basic conditions and methylation of the resulting intermediate compound 1-phenyl-3-methylpyrazolone[4] with dimethyl sulfate or methyl iodide. It crystallizes in needles which melt at 156 °C. Potassium permanganate oxidizes it to pyridazine tetracarboxylic acid. Phenazone has an elimination half life of about 12 hours.[5] Indication: Used to relieve pain and fever. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver.[6]
Adverse effects
Possible adverse effects include:[citation needed]
- Allergy to pyrazolones
- Nausea
- Agranulocytosis
- Hepatotoxicity
See also
- Propyphenazone
- A/B Otic Drops, ear drops combined with benzocaine to relieve pain and remove cerumen
References
- ^ Brune, K (1997). "The early history of non-opioid analgesics". Acute Pain 1: 33. doi:10.1016/S1366-0071(97)80033-2.
- ^ Enrique Ravina. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons, 2011 ISBN 9783527326693
- ^ https://books.google.ca/books?id=07g30rxCA0EC&lpg=PA225&ots=KjJPobMfjq&dq=synthesis%20of%20phenazone&pg=PA226#v=onepage&q=synthesis%20of%20phenazone&f=false
- ^ http://www.chemspider.com/Chemical-Structure.63516.html
- ^ http://www.mims.com/USA/drug/info/phenazone/?q=Other%20Ear%20Preparations&type=full
- ^ http://www.medicatione.com/?c=ing&s=antipyrine
Drugs used for diseases of the ear (S02)
|
|
Infection |
- Acetic acid
- Aluminium acetotartrate
- Boric acid
- Chloramphenicol
- Chlorhexidine
- Ciprofloxacin
- Clioquinol
- Gentamicin
- Hydrogen peroxide
- Miconazole
- Neomycin
- Nitrofurazone
- Ofloxacin
- Polymyxin B
- Rifamycin
- Tetracycline
|
|
Corticosteroids |
- Betamethasone
- Dexamethasone
- Fluocinolone acetonide
- Hydrocortisone
- Prednisolone
|
|
Analgesics and anesthetics |
- Lidocaine
- Cocaine
- Phenazone
|
|
Index of the ear
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Congenital
- Other
- Symptoms and signs
- Tests
|
|
Treatment |
|
|
|
English Journal
- Synthesis and characterization of some new complexes of Cu(II), Ni(II) and V(IV) with Schiff base derived from indole-3-carboxaldehyde. Biological activity on prokaryotes and eukaryotes.
- Rosu T, Pahontu E, Ilies DC, Georgescu R, Mocanu M, Leabu M, Shova S, Gulea A.SourceInorganic Chemistry Department, Faculty of Chemistry, University of Bucharest, 23 Dumbrava Rosie Street, 050107 Bucharest, Romania.
- European journal of medicinal chemistry.Eur J Med Chem.2012 Jul;53C:380-9. Epub 2012 Apr 2.
- Six new Cu(II), Ni(II), and VO(II) complexes (1-6) with Schiff base 1-phenyl-2,3-dimethyl-4-(1H-indole-3-carboxaldehyde)-3-pyrazolin-5-one (HL) were synthesized. The Schiff base was prepared through the condensation of 1-phenyl-2,3-dimethyl-4-amino-3-pyrazolin-5-one (antipyrine) with 1H-indole-3-car
- PMID 22516425
- Screening and human health risk assessment of pharmaceuticals and their transformation products in Dutch surface waters and drinking water.
- de Jongh CM, Kooij PJ, de Voogt P, Ter Laak TL.AbstractNumerous studies describe the presence of pharmaceuticals in the water cycle, while their transformation products are usually not included. In the current study 17 common pharmaceuticals and 9 transformation products were monitored in the Dutch waters, including surface waters, pre-treated surface waters, river bank filtrates, two groundwater samples affected by surface water and drinking waters. In these samples, 12 pharmaceuticals and 7 transformation products were present. Concentrations were generally highest in surface waters, intermediate in treated surface waters and river bank filtrates and lowest or not detected in produced drinking water. However, the concentrations of phenazone and its environmental transformation product AMPH were significantly higher in river bank filtrates, which is likely due to historical contamination. Fairly constant ratios were observed between concentrations of transformation products and parent pharmaceuticals. This might enable prediction of concentrations of transformation products from concentrations of parent pharmaceuticals. The toxicological relevance of the observed pharmaceuticals and transformation products was assessed by deriving (i) a substance specific provisional guideline value (pGLV) and (ii) a group pGLV for groups of related compounds were under the assumption of additivity of effects within each group. A substantial margin exists between the maximum summed concentrations of these compounds present in different water types and the derived (group) pGLVs. Based on the results of this limited screening campaign no adverse health effects of the studied compounds are expected in (sources of) drinking water in the Netherlands. The presence of transformation products with similar pharmacological activities and concentration levels as their parents illustrates the relevance of monitoring transformation products, and including these in risk assessment. More thorough monitoring yielding information on statistical uncertainty and variability in time and space, and research on possible synergistic effects of low concentration mixtures of compounds belonging to similar pharmacological classes require attention.
- The Science of the total environment.Sci Total Environ.2012 Jun 15;427-428:70-7. Epub 2012 May 1.
- Numerous studies describe the presence of pharmaceuticals in the water cycle, while their transformation products are usually not included. In the current study 17 common pharmaceuticals and 9 transformation products were monitored in the Dutch waters, including surface waters, pre-treated surface w
- PMID 22551934
Japanese Journal
- Carcinogenicity of analgesics: long-term treatmemt of Sprague-Dawley rats with phenacetin, phenazone, caffeine and paracetamol (acetaminophen)
- Sisterchromatid exhanges and chromosomal aberrations in rats treated with phenacetin, phenazone and caffeine
Related Links
- Phenazone, known in the U.S. as antipyrine, is a pain reliever, and a fever reducer. It is combined in ear drops... ... Before using this medication tell your doctor about all of your medical conditions. Especially tell your doctor if you: ...
- phenazone /phen·a·zone/ (fen´ah-zōn) antipyrine. antipyrine [an″te-, an″ti-pi´rēn] a compound formerly used as an analgesic and antipyretic, now replaced by safer and more effective agents. Its current uses are as a component of ...
Related Pictures
★リンクテーブル★
[★]
- 英
- antipyrine
- ラ
- antipyrinum
- 同
- フェナゾン phenazone
[★]
- 英
- phenazone
- 関
- アンチピリン
[★]
アンチピリン
- 関
- phenazone
[★]
ジクロラルフェナゾン
- 関
- dichloralantipyrine
[★]
アミノフェナゾン
- 関
- aminopyrine