Ampyrone

Ampyrone

IUPAC name 4-Amino- 1,5-dimethyl- 2-phenyl- pyrazol- 3-one
Other names solvapyrin A, aminoazophene, aminoantipyrene, metapyrazone
Identifiers
CAS number	83-07-8^Y
PubChem	2151
ChemSpider	2066^Y
UNII	0M0B7474RA^Y
ChEBI	CHEBI:59026^Y
ChEMBL	CHEMBL1165011^Y
Jmol-3D images	Image 1
SMILES O=C2\C(=C(/N(N2c1ccccc1)C)C)N
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
Properties
Molecular formula	C₁₁H₁₃N₃O
Molar mass	203.24 g mol⁻¹
Density	1.207g/cm³
Melting point	106-110°C
Boiling point	309°C @760mmHg
Hazards
Flash point	140.7°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties. Due to the risk of agranulocytosis its use as a drug is discouraged.^[1] Instead it is used as a reagent for biochemical reactions producing peroxides or phenols. Ampyrone stimulates liver microsomes and is also used to measure extracellular water.

References

^ On-line encyklopedia PWN (in Polish)

Anti-inflammatory products (M01A)

Pyrazolidine/Butylpyrazolidines

Ampyrone • Clofezone • Kebuzone • Metamizole • Mofebutazone • Oxyphenbutazone • Phenazone • Phenylbutazone • Sulfinpyrazone • Feprazone •

Acetic acid derivatives
and related substances

Aceclofenac • Acemetacin • Alclofenac • Bromfenac • Bumadizone • Bufexamac • Diclofenac • Difenpiramide • Etodolac • Fentiazac • Indometacin • Ketorolac • Lonazolac • Oxametacin • Proglumetacin • Sulindac • Tolmetin • Zomepirac • Amfenac

Oxicams

Ampiroxicam • Droxicam • Lornoxicam • Meloxicam • Piroxicam • Tenoxicam

Propionic acid derivatives

Alminoprofen • Benoxaprofen • Dexibuprofen • Dexketoprofen • Fenbufen • Fenoprofen • Flunoxaprofen • Flurbiprofen • Ibuprofen • Ibuproxam • Indoprofen • Ketoprofen • Naproxen • Oxaprozin • Pirprofen • Suprofen • Tiaprofenic acid

Fenamates

Flufenamic acid • Meclofenamic acid • Mefenamic acid • Tolfenamic acid • Niflumic acid • Morniflumate • Azapropazone •

Coxibs

Celecoxib • Etoricoxib • Lumiracoxib • Parecoxib • Rofecoxib • Valdecoxib

Other

Nabumetone • Glucosamine • Benzydamine • Glycosaminoglycan • Magnesium salicylate • Proquazone • Superoxide dismutase/Orgotein • Nimesulide • Diacerein • Tenidap • Oxaceprol • Chondroitin sulfate

M: MUS, DF+DRCT

anat (h/n, u, t/d, a/p, l)/phys/devp/hist

noco(m, s, c)/cong(d)/tumr, sysi/epon, injr

proc, drug (M1A/3)

Non-steroidal anti-inflammatory drug (NSAID) products (primarily M01A and M02A, also N02BA)

Salicylates	Aspirin (acetylsalicylic acid) • Aloxiprin • Benorylate • Diflunisal • Ethenzamide • Magnesium salicylate • Methyl salicylate • Salsalate • Salicin • Salicylamide • Sodium salicylate

Arylalkanoic acids	Diclofenac • Aceclofenac • Acemetacin • Alclofenac • Bromfenac • Etodolac • Indometacin • Indometacin farnesil • Nabumetone • Oxametacin • Proglumetacin • Sulindac • Tolmetin

2-Arylpropionic acids (profens)	Ibuprofen • Alminoprofen • Benoxaprofen • Carprofen • Dexibuprofen • Dexketoprofen • Fenbufen • Fenoprofen • Flunoxaprofen • Flurbiprofen • Ibuproxam • Indoprofen^† • Ketoprofen • Ketorolac • Loxoprofen • Miroprofen • Naproxen • Oxaprozin • Pirprofen • Suprofen • Tarenflurbil • Tiaprofenic acid

N-Arylanthranilic acids (fenamic acids)	Mefenamic acid • Flufenamic acid • Meclofenamic acid • Tolfenamic acid

Pyrazolidine derivatives	Phenylbutazone • Ampyrone • Azapropazone • Clofezone • Kebuzone • Metamizole • Mofebutazone • Oxyphenbutazone • Phenazone • Sulfinpyrazone

Oxicams	Piroxicam • Droxicam • Lornoxicam • Meloxicam • Tenoxicam • Ampiroxicam

COX -2 inhibitors	Celecoxib • Deracoxib^‡ • Etoricoxib • Firocoxib^‡ • Lumiracoxib^† • Parecoxib • Rofecoxib^† • Valdecoxib^†

Sulfonanilides	Nimesulide

Topically used products	Bendazac • Diclofenac • Etofenamate • Felbinac • Flurbiprofen • Ibuprofen • Indometacin • Ketoprofen • Naproxen • Piroxicam • Suprofen

COX-inhibiting nitric oxide donators	Naproxcinod

Others	Fluproquazone

Items listed in bold indicate initially developed compounds of specific groups. ^†Withdrawn drugs. ^‡Veterinary use medications.

Analgesics (N02A, N02B)

Opioids
See also: Opioids template

Opium & alkaloids thereof	Codeine^# • Morphine^# • Opium • Laudanum • Paregoric

Semi-synthetic opium derivatives	Acetyldihydrocodeine • Benzylmorphine • Buprenorphine • Desomorphine • Dihydrocodeine • Dihydromorphine • Ethylmorphine • Diamorphine • Hydrocodone • Hydromorphinol • Hydromorphone • Nicocodeine • Nicodicodeine • Nicomorphine • Oxycodone • Oxymorphone

Synthetic opioids	Alphaprodine • Anileridine • Butorphanol • Dextromoramide • Dextropropoxyphene • Dezocine • Fentanyl • Ketobemidone • Levorphanol • Methadone • Meptazinol • Nalbuphine • Pentazocine • Propoxyphene • Propiram • Pethidine • Phenazocine • Piminodine • Piritramide • Tapentadol • Tilidine • Tramadol

Pyrazolones

Ampyrone/Aminophenazone • Metamizole • Phenazone • Propyphenazone

Cannabinoids

Ajulemic acid • AM404 • Cannabidiol • Cannabis • Nabilone • Nabiximols • Tetrahydrocannabinol

Anilides

Paracetamol (acetaminophen)^# • Phenacetin • Propacetamol

Non-steroidal
anti-inflammatories
See also: NSAIDs template

Propionic acid class	Fenoprofen • Flurbiprofen • Ibuprofen^# • Ketoprofen • Naproxen • Oxaprozin

Oxicam class	Meloxicam • Piroxicam

Acetic acid class	Diclofenac • Indometacin • Ketorolac • Nabumetone • Sulindac • Tolmetin

COX-2 inhibitors	Celecoxib • Rofecoxib • Valdecoxib • Parecoxib • Lumiracoxib

Anthranilic acid (fenamate) class	Meclofenamate • Mefenamic acid

Salicylates	Aspirin (Acetylsalicylic acid)^# • Benorylate • Diflunisal • Ethenzamide • Magnesium salicylate • Salicin • Salicylamide • Salsalate • Trisalate • Wintergreen (Methyl salicylate)

Atypical, adjuvant and potentiators,
Metabolic agents and miscellaneous

Amitryptiline • Befiradol • Bicifadine • Carisoprodol • Camphor • Cimetidine • Clonidine • Chlorzoxazone • Cyclobenzaprine • Duloxetine • Esreboxetine • Flupirtine • Gabapentin • Glafenine • Hydroxyzine • Ketamine • Menthol • Mephenoxalone • Methocarbamol • Nefopam • Orphenadrine • Pregabalin • Proglumide • Scopolamine • Tebanicline • Trazodone • Gabapentin enacarbil • Ziconotide

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

M: CNS

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)