antipyrine
Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. It inhibits cyclooxygenases and shows little anti-inflammatory activity. Like many old and approved substances after almost 100 years of use, antipyrine has been associated with some serious side effects, namely agranulocytosis and shock reactions. — NCATS
Clinical trial activity
2 trials · 9 clinical orgs · 0 marketing orgs
Earliest trial started Nov 1, 2013 (NCT02037893)
Timeline
2010s
- Jan 1, 2013
Earliest Phase 2 Sponsor(trial)
Indications
Approved for
Studied for
Mechanism of action
- Cyclooxygenase-1INHIBITOR
PTGS1 inhibitor
Antipyrine inhibits a brain COX isoform, COX-3. COX-3 is a COX-1 variant that retains intron 1 in its mRNA.
IC50 uM values for Antipyrine inhibition of COX enzymes: COX-1 : >1000 COX-2 : > 1000 COX-3 : 863
Antipyrine inhibits a brain COX isoform, COX-3. COX-3 is a COX-1 variant that retains intron 1 in its mRNA.
Chemistry & pharmacology
SMILES
CN1N(C(=O)C=C1C)C2=CC=CC=C2- Mol. weight
- 188.2258 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- Yes
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaPhenazone ↗
- NCATST3CHA1B51H ↗
- ChEMBLCHEMBL277474 ↗
Also known as
- 1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
- 1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one
- 1-phenyl-4-amino-5-chloropyridazin-6-one
- 2,3-dimethyl-1-phenyl-5-pyrazolone
- 2,3-dimethyl-1-phenyl-5-pyrazolone
- analgesin
- analgesine
- analgesine
- analgesine
- anodynine
- antipyrin
- antipyrin
- antipyrin
- antipyrine
- antipyrine
- antipyrine
- antipyrine
- antipyrine
- antipyrine
- antipyrine
- azophen
- azophene
- chlordiazon
- chloridazon
- dimethyloxychinizin
- dimethyloxyquinazine
- fenazon
- fenazon
- fenazona
- fenazona
- fenazone
- methozin
- oxydimethylquinazine
- pac herbicide
- phenazon
- phenazon
- phenazon
- phenazon
- phenazon
- phenazone
- phenazone
- phenazone
- phenazone
- phenazone
- phenazone
- phenazone
- phenylone
- pyramin
- pyrazon
- pyrazophyl
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT02153541 | Phase 2 | Jul 1, 2014 | Augusta University, Global United Pharmaceutical Corporation |
| NCT02037893 | Phase 2 | Nov 1, 2013 | Carolina Ear, Nose and Throat Clinic, Foothill Family Clinic, Jordan River Family Medcine, Kentucky Pediatric and Adult Research, Pernix, Synexus, Visions Clinical Research |
Organizations
Research & Development (9)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Augusta University | Academic/Hospital | 1 | 0 | 1 | 2014 |
| Carolina Ear, Nose and Throat Clinic | Academic/Hospital | 1 | 0 | 1 | 2013 |
| Foothill Family Clinic | Academic/Hospital | 1 | 0 | 1 | 2013 |
| Global United Pharmaceutical Corporation | For profit | 1 | 1 | 1 | 2014 |
| Jordan River Family Medcine | Academic/Hospital | 1 | 0 | 1 | 2013 |
| Kentucky Pediatric and Adult Research | Academic/Hospital | 1 | 0 | 1 | 2013 |
| Pernix | For profit | 1 | 1 | 1 | 2013 |
| Synexus | For profit | 1 | 0 | 1 | 2013 |
| Visions Clinical Research | For profit | 1 | 0 | 1 | 2013 |