Phenazone

Phenazone
Clinical data

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
Synonyms	analgesine, antipyrine
CAS Number	60-80-0^Y
PubChem (CID)	2206
DrugBank	DB01435^Y
ChemSpider	2121^Y
UNII	T3CHA1B51H^Y
KEGG	D01776^Y
ChEBI	CHEBI:31225^Y
ChEMBL	CHEMBL277474^Y
ECHA InfoCard	100.000.442
Chemical and physical data
Formula	C₁₁H₁₂N₂O
Molar mass	188.2258g/mol
3D model (Jmol)	Interactive image
SMILES O=C2\C=C(/N(N2c1ccccc1)C)C
InChI InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3^Y Key:VEQOALNAAJBPNY-UHFFFAOYSA-N^Y
(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:

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

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# (+paracetamol, +aspirin) Morphine^# (+naltrexone) Opium Laudanum Paregoric

Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Thebacon

Synthetic	Alphaprodine Anileridine Butorphanol Dextromoramide Dextropropoxyphene Dezocine Fentanyl (+fluanisone) Ketobemidone Levorphanol Meptazinol Methadone Nalbuphine Pentazocine Pethidine Phenadoxone Phenazocine Piminodine Piritramide Propiram Tapentadol Tilidine Tramadol

Paracetamol-type

Acetanilide^‡
Bucetin^‡
Butacetin^‡
Paracetamol (acetaminophen)^#
Parapropamol^‡
Phenacetin^‡
Propacetamol^‡

NSAIDs

Propionates	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicams	Meloxicam Piroxicam

Acetates	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Etoricoxib Lumiracoxib Parecoxib Rofecoxib ^‡ Valdecoxib ^‡

Fenamates	Meclofenamic acid Mefenamic acid

Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Wintergreen (methyl salicylate)

Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone

Others	Glafenine

Cannabinoids

Ion channel
modulators

Calcium blockers	Gabapentin Gabapentin enacarbil Pregabalin Ziconotide

Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline^#) Na_v1.7/1.8-selective: DSP-2230^§ Funapide^§ PF-05089771^§ Raxatrigine^§

Potassium openers	Flupirtine

Myorelaxants

Others

Camphor
Capsaicin
Clonidine
Ketamine
Menthol
Methoxyflurane
Nefopam
Proglumide
Tricyclic antidepressants (e.g., amitriptyline^#)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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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Phenazone

Adverse effects

See also

References