3-methyl-1-phenyl-5-pyrazolone

Structural formula
General
Non-proprietary name	Edaravon
other names	3-methyl-1-phenyl-2-pyrazolin-5-one
Molecular formula	C 10 H 10 N 2 O
Brief description	white to yellowish odorless solid
External identifiers / databases
CAS number 89-25-8 EC number 201-891-0 ECHA InfoCard 100.001.719 PubChem 4021 DrugBank DB12243 Wikidata Q335099
properties
Molar mass	174.20 g mol −1
Physical state	firmly
density	1.12 g cm −3
Melting point	127.5-129.5 ° C
boiling point	191 ° C
solubility	sparingly soluble in water (3.3 g l −1 at 23 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-317-411 P: 261-273-280-302 + 352-333 + 313-501
Toxicological data	1920 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-Methyl-1-phenyl-5-pyrazolone is a chemical compound from the group of lactams . The substance ( international non-proprietary name : Edaravon ) is approved in America and Japan for the treatment of amyotrophic lateral sclerosis .

Extraction and presentation

3-Methyl-1-phenyl-5-pyrazolone can be obtained by reacting phenylhydrazine with ethyl acetoacetate in a solvent in the presence of a suitable catalyst.

properties

3-Methyl-1-phenyl-5-pyrazolone is a flammable, hardly ignitable, crystalline white to yellowish odorless solid that is sparingly soluble in water. Its aqueous solution is acidic.

use

Chemical analysis

3-Methyl-1-phenyl-5-pyrazolone is used as a reagent for the detection of reducing carbohydrates.

medicine

Edaravon is approved as a drug for the treatment of ALS in Japan, China, the USA and Switzerland . For this purpose, it is infused intravenously. Edaravon has been studied in randomized, placebo-controlled studies in 137 Japanese ALS patients over six months. The progression of the disease is not stopped, but it is slowed down. A few years earlier, Edaravon had already hit the market in Japan as a neuroprotective agent for stroke patients. The approval application to the European Medicines Agency (EMA) was withdrawn by the pharmaceutical company Mitsubishi Tanabe Pharma Corporation (MTPC) after the authority had recommended that the approval application be rejected due to the duration of the studies submitted and the authorities claim that there was insufficient evidence of extended survival.

The mechanism of action is unknown.

Trade names : Radicava (USA), Radicut (J)

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on 3-methyl-1-phenyl-5-pyrazolone in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
2. ↑ Google Patents: Patent CN102180834A - Preparation method for edaravone , accessed December 29, 2016.
3. ↑ Data sheet 3-Methyl-1-phenyl-2-pyrazolin-5-one, 98 +% from AlfaAesar, accessed on December 29, 2016 ( PDF )(JavaScript required) .
4. ↑ Charité, Outpatient Clinic for ALS and Other Motor Neuron Diseases: New ALS drug approved in Japan , accessed on December 29, 2016.
5. ↑ Office of the Commissioner: Press Announcements - FDA approves drug to treat ALS. Retrieved May 9, 2017 . 
6. ↑ Paul A. Lapchak: A Critical Assessment of Acute Ischemic Stroke Edaravone Efficacy Trials: is Edaravone an Effective Neuroprotective Therapy? In: Expert opinion on pharmacotherapy . tape 11 , no. 10 , December 29, 2016, p. 1753–1763 , doi : 10.1517 / 14656566.2010.493558 , PMC 2891515 (free full text).
7. ↑ Charité, outpatient clinic for ALS and other motor neuron diseases: The Japanese pharmaceutical company Mitsubishi Tanabe Pharma Corporation (MTPC) has withdrawn the application for approval of the drug Edaravone (Radicava) from the European Medicines Agency (EMA). Retrieved March 15, 2020.
8. ↑ European Medicines Agency: Withdrawal of the marketing authorization application for Radicava (edaravone) , May 29, 2019 ( PDF ).