Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H17N3O.C9H7NO4S |
| Molecular Weight | 456.515 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(C=CC2=C1N=CC=C2)S(O)(=O)=O.CN(C)C3=C(C)N(C)N(C3=O)C4=CC=CC=C4
InChI
InChIKey=QKTQVOHDBURFQG-UHFFFAOYSA-N
InChI=1S/C13H17N3O.C9H7NO4S/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11;11-9-7(15(12,13)14)4-3-6-2-1-5-10-8(6)9/h5-9H,1-4H3;1-5,11H,(H,12,13,14)
| Molecular Formula | C9H7NO4S |
| Molecular Weight | 225.221 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C13H17N3O |
| Molecular Weight | 231.2936 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Aminophenazone is a phenyl-pyrazolone derivative with potent analgesic and antipyretic properties. Aminophenazone has been used as salt or complexes, including topically as the salicylate. It was recommended for the treatment of a fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. In 1999 the FDA suspended aminophenazone. The drug caused agranulocytosis. Some of the cases of agranulocytosis were fatal. Another reason for suspending this drug from the market was its ability to react with nitrite-containing food, thus forming carcinogenic nitrosamines. 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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095157 |
3.8 mM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Pyramidon Approved UseAminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. |
|||
| Palliative | Pyramidon Approved UseAminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. |
|||
| Palliative | Pyramidon Approved UseAminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. |
|||
| Palliative | Pyramidon Approved UseAminophenazone recommended taking in case of fever, neuralgia, myositis, acute rheumatism, arthritis, chorea. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.7 μg/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOPHENAZONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
17.4 μg/mL |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOPHENAZONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.3 h |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOPHENAZONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
2.6 h |
600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMINOPHENAZONE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15437290/ |
AMINOPHENAZONE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
220 mg 1 times / day multiple, oral Recommended Dose: 220 mg, 1 times / day Route: oral Route: multiple Dose: 220 mg, 1 times / day Co-administed with:: allobarbitone(30 mg; 1-2 tablets once or twice per day for 18 days) Sources: |
unhealthy, 27 years n = 1 Health Status: unhealthy Condition: pain Age Group: 27 years Sex: F Population Size: 1 Sources: |
Other AEs: Agranulocytosis... |
10 % 1 times / day single, topical Studied dose Dose: 10 %, 1 times / day Route: topical Route: single Dose: 10 %, 1 times / day Sources: |
healthy, 28 years n = 1 Health Status: healthy Age Group: 28 years Sex: F Population Size: 1 Sources: |
Other AEs: Contact urticaria... |
286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
Other AEs: Tiredness, Nausea... Other AEs: Tiredness (13.1%) Sources: Nausea (10.7%) Headache (1.2%) Vomiting (1.2%) Mental confusion (5.9%) Palpitation (1.2%) Faintness (1.2%) Loss of memory (1.2%) Urticaria (1.2%) Vertigo (1.2%) |
220 mg 2 times / day multiple, rectal Recommended Dose: 220 mg, 2 times / day Route: rectal Route: multiple Dose: 220 mg, 2 times / day Co-administed with:: codeine(5 mg; 2 per day) Sources: diallymal(30 mg; 2 per day) |
unhealthy, mean age 6.4 years n = 43 Health Status: unhealthy Condition: pain Age Group: mean age 6.4 years Sex: M+F Population Size: 43 Sources: |
Other AEs: Vomiting... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Agranulocytosis | 220 mg 1 times / day multiple, oral Recommended Dose: 220 mg, 1 times / day Route: oral Route: multiple Dose: 220 mg, 1 times / day Co-administed with:: allobarbitone(30 mg; 1-2 tablets once or twice per day for 18 days) Sources: |
unhealthy, 27 years n = 1 Health Status: unhealthy Condition: pain Age Group: 27 years Sex: F Population Size: 1 Sources: |
|
| Contact urticaria | 10 % 1 times / day single, topical Studied dose Dose: 10 %, 1 times / day Route: topical Route: single Dose: 10 %, 1 times / day Sources: |
healthy, 28 years n = 1 Health Status: healthy Age Group: 28 years Sex: F Population Size: 1 Sources: |
|
| Faintness | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Headache | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Loss of memory | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Palpitation | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Urticaria | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Vertigo | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Vomiting | 1.2% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Nausea | 10.7% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Tiredness | 13.1% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Mental confusion | 5.9% | 286 mg 2 times / day multiple, oral Studied dose Dose: 286 mg, 2 times / day Route: oral Route: multiple Dose: 286 mg, 2 times / day Co-administed with:: barbital(114 mg; 2 per day during 2.5 days) Sources: aethylmorphin hydrochlorid(20 mg; 2 per day during 2.5 days) |
unhealthy, mean age 24.3 years n = 84 Health Status: unhealthy Condition: pain Age Group: mean age 24.3 years Sex: M+F Population Size: 84 Sources: |
| Vomiting | 5.5% | 220 mg 2 times / day multiple, rectal Recommended Dose: 220 mg, 2 times / day Route: rectal Route: multiple Dose: 220 mg, 2 times / day Co-administed with:: codeine(5 mg; 2 per day) Sources: diallymal(30 mg; 2 per day) |
unhealthy, mean age 6.4 years n = 43 Health Status: unhealthy Condition: pain Age Group: mean age 6.4 years Sex: M+F Population Size: 43 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Bilateral renal cortical necrosis following pyrazolone treatment]. | 1967 Jun 9 |
|
| Short-term study of the effect of phenacetin, phenazone and amidopyrine on the rat kidney. | 1968 Jan |
|
| Tumor induction in rats by feeding aminopyrine or oxytetracycline with nitrite. | 1975 Aug 15 |
|
| Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms. | 1977 Mar 12 |
|
| Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates. | 1979 May |
|
| Toxic etiology of aplastic anemia. The Cooperative Study Group for Aplastic and Refractory Anemias. | 1984 Oct-Dec |
|
| Effects of nonvolatile agents on oxygen demand and energy status in isolated hepatocytes. | 1988 Oct |
|
| Mechanism of peroxidative activation of the bladder carcinogen 2-amino-4-(5-nitro-2-furyl)-thiazole (ANFT): comparison with benzidine. | 1990 Nov |
|
| [Amidazophen. Yes or no?]. | 1995 Sep 24 |
|
| Role of caffeine in combined analgesic drugs from the point of view of experimental pharmacology. | 1997 Aug |
|
| Breath tests: concepts, applications and limitations. | 1997 Aug |
|
| Toxic epidermal necrolysis in a patient with severe aplastic anemia treated with cyclosporin A and G-CSF. | 2001 |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
| Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Potent effects of a 3,4-dichloromaleimide derivative. | 2002 |
|
| Identification and significance of phenazone drugs and their metabolites in ground- and drinking water. | 2002 Nov |
|
| Determination of polar drug residues in sewage and surface water applying liquid chromatography-tandem mass spectrometry. | 2004 Nov 15 |
|
| Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention. | 2005 Dec |
|
| Oxidation of pharmaceuticals during water treatment with chlorine dioxide. | 2005 Sep |
|
| [Detection of phenol by means of 4-aminophenazone according to Emerson]. | 2006 Sep |
|
| Ethnoveterinary medicines used for ruminants in British Columbia, Canada. | 2007 Feb 26 |
|
| Investigation of the behavior and metabolism of pharmaceutical residues during purification of contaminated ground water used for drinking water supply. | 2007 Nov |
|
| Efficient use of the iron ortho-nitrophenylporphyrin chloride to mimic biological oxidations of dimethylaminoantipyrine. | 2007 Oct |
|
| Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury. | 2008 |
|
| A study of the teratogenic and fetotoxic effects of large doses of barbital, hexobarbital and butobarbital used for suicide attempts by pregnant women. | 2008 Feb-Mar |
|
| Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters. | 2008 Jan |
|
| Scavenging activity of aminoantipyrines against hydroxyl radical. | 2010 Jun |
|
| Synthesis and anti-bacterial activities of some novel Schiff bases derived from aminophenazone. | 2010 Oct 8 |
|
| The study of aminophenazone radical cation and its interaction with some antioxidants. | 2010 Oct-Dec |
|
| Development of a cell-based assay system considering drug metabolism and immune- and inflammatory-related factors for the risk assessment of drug-induced liver injury. | 2014 Jul 3 |
| Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 16:34:39 UTC 2023
by
admin
on
Sat Dec 16 16:34:39 UTC 2023
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| Record UNII |
9FJ50DJA4M
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| Record Status |
Validated (UNII)
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| Record Version |
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9FJ50DJA4M
Created by
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10027070
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3520-48-7
Created by
admin on Sat Dec 16 16:34:39 UTC 2023 , Edited by admin on Sat Dec 16 16:34:39 UTC 2023
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NON-SPECIFIC STOICHIOMETRY |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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