関: phenazone

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/03/16 15:08:25」(JST)

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Phenazone (INN and BAN; also known as phenazon, antipyrine (USAN), or analgesine) is an analgesic, a nonsteroidal anti-inflammatory drug (NSAID) 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

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

External links

Chisholm, Hugh, ed. (1911). "Antipyrine". Encyclopædia Britannica. 2 (11th ed.). Cambridge University Press. p. 134.

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1. 小児における急性中耳炎：治療 acute otitis media in children treatment
2. 外耳炎：病因、臨床的特徴、および診断 external otitis pathogenesis clinical features and diagnosis
3. 患者情報：小児における耳感染症（中耳炎）（詳細） ear infections otitis media in children beyond the basics

English Journal

Placental Transfer of Maraviroc in an Ex Vivo Human Cotyledon Perfusion Model and Influence of ABC Transporter Expression.

Vinot C, Gavard L, Tréluyer JM, Manceau S, Courbon E, Scherrmann JM, Declèves X, Duro D, Peytavin G, Mandelbrot L, Giraud C.SourceEA 3620, Université Paris Descartes, Paris, France.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2013 Mar;57(3):1415-20. doi: 10.1128/AAC.01821-12. Epub 2013 Jan 7.
Nowadays, antiretroviral therapy is recommended during pregnancy to prevent mother-to-child transmission of HIV. However, for many antiretroviral drugs, including maraviroc, a CCR5 antagonist, very little data exist regarding placental transfer. Besides, various factors may modulate this transfer, i
PMID 23295922

Antipyrine based arsenate selective fluorescent probe for living cell imaging.

Lohar S, Sahana A, Banerjee A, Banik A, Mukhopadhyay SK, Sanmartín Matalobos J, Das D.SourceDepartment of Chemistry, The University of Burdwan , Burdwan, West Bengal, India.
Analytical chemistry.Anal Chem.2013 Feb 5;85(3):1778-83. doi: 10.1021/ac3031338. Epub 2013 Jan 18.
Condensation of salicylaldehyde and 4-aminoantipyrine has yielded a new fluorescent probe (APSAL) capable of detecting intracellular arsenate at the micromolar level for the first time. The structure of the probe has been established by different spectroscopic techniques and confirmed from X-ray cry
PMID 23298301

Application of hybrid approach based on empirical and physiological concept for predicting pharmacokinetics in humans--usefulness of exponent on prospective evaluation of predictability.

Sayama H, Komura H, Kogayu M.SourceJAPAN TOBACCO INC., Central Pharmaceutical Research Institute, 1-1, Murasaki-cho, Takatsuki, Osaka, 569-1125, Japan. hiroshi.komura@jt.com.
Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2013 Feb;41(2):498-507. doi: 10.1124/dmd.112.048819. Epub 2012 Dec 3.
We developed a hybrid method for predicting plasma concentration-time curves in humans by integrating species differences in in vitro intrinsic clearance (CL(int)) into the Dedrick approach based on the allometry concept. With prediction of clearance (CL) by allometric scaling, taking in vitro CL(in
PMID 23209193

Japanese Journal

Azoles and bis-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents

Kheder Nabila Abdelshafy,Riyadh Sayed Mohamed,Asiry Ahlam Maade
Chemical and Pharmaceutical Bulletin 61(5), 504-510, 2013
… The synthetic utility of bis-hydrazonoyl halide 7 was explored to prepare novel bis-azole 13 with antipyrine moiety. … On the other hand, [1,3,4]thiadiazol-2(3H)-ylidene 17 and thiazol-2(3H)-ylidene 21 derivatives, with antipyrine moiety, were prepared from the reaction of 3-mercapto-3-(phenylamino)acrylamide derivative 10 with N-phenyl benzenecarbohydrazonoyl chloride (14) and 3-(2-bromoacetyl)-2H-chromen-2-one (18), respectively. …
NAID 130003360768

A FACILE AND CONVENIENT SYNTHESIS OF NOVEL PYRIDINE DERIVATIVES INCORPORATING ANTIPYRINE MOIETY AND INVESTIGATION OF THEIR ANTIMICROBIAL ACTIVITIES

Kheder Nabila A.,Riyadh Sayed M.,Asiry Ahlam M.
Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 85(9), 2259-2268, 2012-09-01
NAID 40019393021

Solid-Phase Extraction of Antipyrine Dye for Spectrophotometric Determination of Phenolic Compounds in Water

Morita Emi,Nakamura Eiko
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 27(5), 489-492, 2011-05-10
NAID 10028288620

Related Pictures

★リンクテーブル★

リンク元	「アンチピリン」「phenazone」
拡張検索	「dichloralantipyrine」「antipyrine caffeine citrate」「isopropylantipyrine」

「アンチピリン」

Phenazone
Clinical data
Synonyms	analgesine, antipyrine
ATC code	N02BB01 (WHO) S02DA03 (WHO);
Pharmacokinetic data
Biological half-life	12 hours
Identifiers
	IUPAC name 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one;
CAS Number	60-80-0 ;
PubChem CID	2206;
DrugBank	DB01435 ;
ChemSpider	2121 ;
UNII	T3CHA1B51H;
KEGG	D01776 ;
ChEBI	CHEBI:31225 ;
ChEMBL	CHEMBL277474 ;
ECHA InfoCard	100.000.442
Chemical and physical data
Formula	C11H12N2O
Molar mass	188.2258g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C1C=C(C)N(C)N1c2ccccc2 ;
	InChI InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3 ; Key:VEQOALNAAJBPNY-UHFFFAOYSA-N ;
(verify)

　　[★]

英: antipyrine
ラ: antipyrinum
同: フェナゾン phenazone

「phenazone」

　　[★]

フェナゾン

関: antipyrine

「dichloralantipyrine」

　　[★]

ジクロルアンチピリン

関: dichloralphenazone

「antipyrine caffeine citrate」

　　[★] クエン酸カフェインアンチピリン

「isopropylantipyrine」

　　[★]

イソプロピルアンチピリン

[1] Brune, K (1997). "The early history of non-opioid analgesics". Acute Pain. 1: 33. doi:10.1016/S1366-0071(97)80033-2.

[Ravina-2] Enrique Ravina. The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons, 2011 ISBN 9783527326693

[3] ttps://books.google.ca/books?id=07g30rxCA0EC&lpg=PA225&ots=KjJPobMfjq&dq=synthesis%20of%20phenazone&pg=PA226#v=onepage&q=synthesis%20of%20phenazone&f=false

[4] ttp://www.chemspider.com/Chemical-Structure.63516.html

[5] ttp://www.mims.com/USA/drug/info/phenazone/?q=Other%20Ear%20Preparations&type=full

[6] ttp://www.medicatione.com/?c=ing&s=antipyrine

v t e Drugs used for diseases of the ear (S02)
Infection	Acetic acid Aluminium acetotartrate Aluminium triacetate (Burow's solution) 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

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antipyrine