Aminophenazone

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Aminophenazone
INN: aminophenazone
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Clinical data
AHFS/Drugs.comInternational Drug Names
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Pharmacokinetic data
MetabolismN-demethylation[1]
Identifiers
  • 4-Dimethylamino-1,5-dimethyl-2-phenylpyrazol-3-one
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Chemical and physical data
FormulaC13H17N3O
Molar mass231.299 g·mol−1
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  • O=C2\C(=C(/N(N2c1ccccc1)C)C)N(C)C
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Aminophenazone (or aminopyrine, amidopyrine, Pyramidon) is a non-narcotic analgesic substance. It is a pyrazolone and a derivative of phenazone, which also has anti-inflammatory and antipyretic properties. While inexpensive and effective, especially in the treatment of rheumatism, the drug carries a serious risk of severe and sometimes fatal side-effects, including agranulocytosis.[2] While its production and use have been banned in many countries, including France, Thailand, India, Japan and USA, it is still sometimes used in the developing world.[2]

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.[3]

History

Aminophenazone was first synthesized by Friedrich Stolz and Ludwig Knorr in the late nineteenth century, and sold as an anti-fever medicine known as Pyramidon by Hoechst AG from 1897 until its eventual replacement in the late 1970s by the safer propyphenazone molecule.

Symptoms

Symptoms of exposure to this compound include:[4]

  • allergic reactions
  • strong spasmolytic effect on smooth muscle of peripheral blood vessels
  • irritability
  • palsy
  • copious sweating
  • dilated pupils
  • sharp drop then rise in body temperature
  • dysuria
  • dyspnea
  • anxiety
  • rectal tenesmus
  • urinary frequency
  • intermittent fever
  • fatty infiltration of the liver
  • heart muscle degeneration
  • death due to circulatory failure following cardiovascular collapse

Agranulocytosis often occurs. Ingestion may cause central nervous system stimulation, vomiting, convulsions, cyanosis, tinnitus, leukopenia, kidney damage and coma. Ingestion may also lead to nausea, mental disturbances, methemoglobinemia, chocolate-colored blood, dizziness, epigastric pain, difficulty in hearing, thready pulse and liver damage.

Other symptoms reported via ingestion include hemolytic anemia, porphyria and severe gastrointestinal bleeding. Bone marrow depression also occurs. Rare eye effects include acute transient myopia.

Chronic symptoms include:

When heated to decomposition this compound emits toxic fumes of nitrogen oxides.

Metabolism

Amidopyrine is metabolized by demethylation and acetylation. Amidopirina metabolites are 4-aminoantipyrine, metilaminoantipirin, rubazonovaya and metilrubazonovaya acid. These acids have a reddish color. At high amidopirine doses, urine can have a reddish brown coloration, due to the presence in the urine of these acid markers.[5]

Drug Interactions

When aminophenazone is combined with other medications, severe side effects, including fatal ones, may occur. Aminophenazone may reduce the effect of other tablet medications

aminophenazone may interact with a wide range of tablet medications. Among them, the following stand out in the table below.[6]

Drug Side effect
Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Aminophenazone.
Acamprosate The excretion of Acamprosate can be decreased when combined with Aminophenazone.
Acebutolol Aminophenazone may decrease the antihypertensive activities of Acebutolol.
Aceclofenac The risk or severity of adverse effects can be increased when Aminophenazone is combined with Aceclofenac.

Hospital Universitario Ramón y Cajal in Madrid, Spain was built as a center for specialized surgery, a panacea for the ills of the health system in Madrid. Locals hence nicknamed it Script error: No such module "Lang"..[7]

References

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  1. ^ a b Page Module:Citation/CS1/styles.css has no content.Caubet MS, Laplante A, Caillé J, Brazier JL (June 2002). "[13C]aminopyrine and [13C]caffeine breath test: influence of gender, cigarette smoking and oral contraceptives intake". Isotopes in Environmental and Health Studies. 38 (2): 71–7. Bibcode:2002IEHS...38...71C. doi:10.1080/10256010208033314. PMID 12219983. S2CID 22002940.
  2. ^ a b Page Module:Citation/CS1/styles.css has no content."Aminophenazone". go.drugbank.com. Retrieved 1 September 2025.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Aminophenazone — Compound Summary". PubChem. The National Library of Medicine. 26 March 2005. Retrieved 12 June 2008.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Pubchem. "aminophenazone". pubchem.ncbi.nlm.nih.gov. Retrieved 9 November 2017.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Vyzanie. "Amidopirina". soundlike.ru. Archived from the original on 1 February 2022. Retrieved 9 November 2017.
  6. ^ Page Module:Citation/CS1/styles.css has no content."Aminophenazone". go.drugbank.com. Retrieved 2 September 2025.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Bellver C (27 January 1980). "La ubicacion de los hospitales, un ejemplo perfecto de mala planificación sanitaria". El País (in español). De acuerdo con todo ello, el Ramón y Cajal comenzó a ser esperado como la gran panacea que tenía que resolver gran parte de los problemas hospitalarios madrileños. Por ello, alguien pensó que, siguiendo con los términos médicos, el citado centro venía a ser a la sanidad madrileña como el Piramidón -un antipirético muy utilizado para eliminar los síntomas de la enfermedad, aunque no la enfermedad en sí- a cualquier enfermo. De ahí a que el Centro Ramón y Cajal pasara ser conocido por todos como el Piramidón no medió ni un paso.

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