Ampyrone WikiZero

Ampyrone
Names

Preferred IUPAC name 4-Amino-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one^[1]
Other names solvapyrin A, aminoazophene, aminoantipyrene, aminoantipyrine, metapyrazone
Identifiers
CAS Number	83-07-8^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:59026^Y
ChEMBL	ChEMBL1165011^Y
ChemSpider	2066^Y
ECHA InfoCard	100.001.321
PubChem CID	2151
UNII	0M0B7474RA^Y
CompTox Dashboard (EPA)	DTXSID8048860
InChI InChI=1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3^Y Key: RLFWWDJHLFCNIJ-UHFFFAOYSA-N^Y InChI=1/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3 Key: RLFWWDJHLFCNIJ-UHFFFAOYAT
SMILES O=C2\C(=C(/N(N2c1ccccc1)C)C)N
Properties
Chemical formula	C₁₁H₁₃N₃O_1^[2]
Molar mass	203.24 g/mol
Density	1.207g/cm³
Melting point	106 to 110 °C (223 to 230 °F; 379 to 383 K)
Boiling point	309 °C (588 °F; 582 K) @760mmHg
Hazards
Flash point	140.7 °C (285.3 °F; 413.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties.^[2] While the parent drug, aminopyrine, has been discouraged due to the risk of agranulocytosis,^[3]^[4] ampyrone itself has significantly lower toxicity.^[5] It is used as a reagent for biochemical reactions producing peroxides or phenols.^[2] Ampyrone stimulates liver microsomes and is also used to measure extracellular water.^[2]

References

[edit]

^ PubChem (25 March 2005). "4-Aminoantipyrine". PubChem. Retrieved 2022-05-09.
^ ^a ^b ^c ^d "4-Aminoantipyrine". pubchem.ncbi.nlm.nih.gov. 25 March 2005. Retrieved 2022-05-09.
^ Bailey, D. N. (1983). "The unusual occurrence of 4-aminoantipyrine (4-aminophenazone) in human biological fluids". Journal of Analytical Toxicology. 7 (2): 76–78. doi:10.1093/jat/7.2.76. ISSN 0146-4760. PMID 6855207.
^ PubChem. "Aminopyrine". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-08-26.
^ PubChem. "4-Aminoantipyrine". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-08-26.

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen ^‡ Fenoprofen Flurbiprofen Ibuprofen^# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac ^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib ^‡ Parecoxib Rofecoxib ^‡ Valdecoxib ^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Cannabinoids

Ion channel
modulators

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin 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^§
Potassium openers	Flupirtine^‡

Myorelaxants

Others

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

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