aminophenazone cyclamate
Small moleculeexperimental
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. — NCATS
Clinical trial activity
7 trials · 7 clinical orgs · 0 marketing orgs
Phase 1
1
Phase 2
5
Phase 3
3
Phase 4
1
Earliest trial started Jan 31, 2019 (NCT03578354)
Timeline
Indications
Approved for
Studied for
- Bronchiectasis · Phase 3
- Carpal Tunnel Syndrome · Phase 2/Phase 3
- Crush Injuries · Phase 3
- Dermatology · Phase 2
- Migraine Disorders · Phase 2
- Nerve Degeneration · Phase 2/Phase 3
- Nerve Fibers · Phase 4
- Peripheral Nerve Injuries · Phase 3
- Prostatic Neoplasms · Phase 4
- Spinal Cord Injuries · Phase 3
- Vestibular Diseases · Phase 2
- Wound Healing · Phase 2
- Wounds and Injuries · Phase 2
Mechanism of action
- Unspecified targetINHIBITOR
inhibitor
- CyclooxygenaseINHIBITOR
Cyclooxygenase inhibitor
- Unspecified targetOTHER
Unknown
Chemistry & pharmacology
Loading structure…
SMILES
CN(C)C1=C(C)N(C)N(C1=O)C2=CC=CC=C2- Mol. weight
- 231.2936 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- NCATS01704YP3MO ↗
- ChEMBLCHEMBL288470 ↗
- ChEMBLCHEMBL2104635 ↗
Also known as
- 1,5-dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone
- 1,5-dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone
- 1-phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone
- 1-phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone
- 1-phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one
- 1-phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one
- 2,3-dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone
- 2,3-dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone
- 3-keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole
- 3-keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole
- 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
- 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
- 4-(dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one
- 4-(dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one
- 4-dimethylamino-1-phenyl-2,3-dimethylpyrazolone
- 4-dimethylamino-1-phenyl-2,3-dimethylpyrazolone
- 4-dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
- 4-dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
- 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone
- 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone
- 4-dimethylaminoantipyrine
- 4-dimethylaminoantipyrine
- 4-(dimethylamino)antipyrine
- 4-(dimethylamino)antipyrine
- 4-dimethylaminophenazone
- 4-dimethylaminophenazone
- amidazophen
- amidazophene
- amidofebrin
- amidofen
- amidophen
- amidophenazone
- amidopyrazoline
- amidopyrin
- amidopyrine
- amidopyrine
- amidopyrine
- aminofenazona
- aminofenazona
- aminofenazone
- aminofenazone
- aminophenazon
- aminophenazon
- aminophenazon
- aminophenazone
- aminophenazone
- aminophenazone
- aminophenazone
- aminophenazone
- aminophenazone
- aminophenazone
- aminophenazone
- aminophenazone cyclamate
- aminophenazone cyclamate
- aminophenazonum
- aminophenazonum
- aminopyrin
- aminopyrine
- aminopyrine
- aminopyrine
- aminopyrine
- aminopyrine
- aminopyrine
- anafebrina
- dimethylaminoantipyrine
- dimethylaminoantipyrine
- dimethylaminoazophene
- dimethylaminoazophene
- dimethylaminoazophene
- dimethylaminophenazon
- dimethylaminophenazon
- dimethylaminophenazone
- dimethylaminophenazone
- (dimethylamino)phenazone
- (dimethylamino)phenazone
- dimethylaminophenyldimethylpyrazolone
- dimethylaminophenyldimethylpyrazolone
- dimethylaminophenyldimethylpyrazone
- dipyrine
- dipyrine
- pyramidon
- pyramidone
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06333171 | Phase 2 | Nov 30, 2024 | University of Arizona |
| NCT06294821 | Phase 2/Phase 3 (Phase 3) | Sep 30, 2024 | University of Arizona |
| NCT06003166 | Phase 3 | Apr 30, 2024 | National Institute of Neurological Disorders and Stroke (NINDS), University of Arizona |
| NCT04026568 | Phase 1/Phase 2 (Phase 2) | Nov 1, 2019 | Pennsylvania State University |
| NCT03899584 | Phase 3 | Jul 31, 2019 | Government of Mexico, Instituto Mexicano del Seguro Social |
| NCT03701581 | Phase 4 | Jul 1, 2019 | Pennsylvania State University, University of Rochester |
| NCT03578354 | Phase 2 | Jan 31, 2019 | Harvard University |
Showing 7 of 7 trials
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Organizations
Research & Development (7)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| University of Arizona | Academic/Hospital | 3 | 3 | 2 | 2024 |
| Pennsylvania State University | Academic/Hospital | 2 | 1 | 2 | 2019 |
| Government of Mexico | Government | 1 | 1 | 1 | 2019 |
| Harvard University | Academic/Hospital | 1 | 1 | 1 | 2019 |
| Instituto Mexicano del Seguro Social | Government | 1 | 0 | 1 | 2019 |
| National Institute of Neurological Disorders and Stroke (NINDS) | Government | 1 | 0 | 1 | 2024 |
| University of Rochester | Academic/Hospital | 1 | 1 | 1 | 2019 |
7 organizations
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