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^Y
KEGG	D00556^Y
ChEBI	CHEBI:160246^Y
ChEMBL	CHEMBL288470^Y
Chemical and physical data
Formula	C₁₃H₁₇N₃O
Molar mass	231.29358
3D model (Jmol)	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	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

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