Aminophenazone

Aminophenazone
Clinical data


AHFS/Drugs.com	International Drug Names
ATC code	N02BB03 (WHO)
Pharmacokinetic data
Metabolism	N-demethylation^[1]
Identifiers
IUPAC name 4-Dimethylamino-1,5-dimethyl-2-phenylpyrazol-3-one
CAS Number	58-15-1^Y
PubChem CID	6009
DrugBank	DB01424^Y
ChemSpider	5787^Y
UNII	01704YP3MO
KEGG	D00556^Y
ChEBI	CHEBI:160246^Y
ChEMBL	CHEMBL288470^Y
ECHA InfoCard	100.000.332
Chemical and physical data
Formula	C₁₃H₁₇N₃O
Molar mass	231.29358
3D model (JSmol)	Interactive image
SMILES O=C2\C(=C(/N(N2c1ccccc1)C)C)N(C)C
InChI InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3^Y Key:RMMXTBMQSGEXHJ-UHFFFAOYSA-N^Y
(verify)

Aminophenazone (or aminopyrine) is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with ¹³C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests.^[1] It is also used in measuring the total body water in the human body system.^[2]

References

1 2 Caubet, M. S.; Laplante, A.; Caillé, J.; Brazier, J. L. (4 Jan 2007). "[13C]Aminopyrine and [13C]Caffeine Breath Test: Influence of Gender, Cigarette Smoking and Oral Contraceptives Intake". Isotopes in Environmental and Health Studies. 38 (2): 71–77. doi:10.1080/10256010208033314.
↑ "Aminophenazone — Compound Summary". PubChem. The National Library of Medicine. 2005-03-26. Retrieved June 12, 2008.

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	Alfentanil Alphaprodine Anileridine Butorphanol Carfentanil Dextromoramide Dextropropoxyphene Dezocine Fentanyl (+fluanisone) Ketobemidone Levorphanol Lofentanil Meptazinol Methadone Nalbuphine NFEPP Pentazocine Pethidine Phenadoxone Phenazocine Piminodine Piritramide Propiram Remifentanil Sufentanil 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 (+paracetamol/caffeine)
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

Analgecine
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

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