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5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one structure

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
  • CAS：89-25-8
  • MW:174.1992
  • MF：C10H10N2O
Edaravone was marketed in Japan for improving neurologic recoveryfollowing acute brain infarction. Currently, several agents classified as neuroprotectantsand acting by diverse mechanisms (inhibition of glutamate release, blockade of calciumchannels, lazaroids) have been marketed for treating the outcomes of brain damage due totrauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radicalscavenging activity to be introduced for this pathology. This previously described molecule(in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can besimply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevoneis a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edemain the brain following ischemia by blocking the arachidonic acid cascade triggeringperoxidative neurodegeneration. Interestingly, this agent has been shown to quench activeoxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective duringreperfusion following ischemic injury. As an additional indication, phase III trials started with edaravone for increasing the chance of recovery after subarachnoid hemorrhage. View more+
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1. Names and Identifiers
1.1 Name
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
1.2 Synonyms
1-pheny-3-methyl-5-pyrazolone (PMP); 1-PHENYL-3-METHYL-2-PYRAZOLIN-5-ONE; 1-PHENYL-3-METHYL-5- PYRAZOLONE; 1-PHENYL-3-METHYL-5-OXO-2-PYRAZOLINE; 1-PHENYL-3-METHYL-5-PYRAZALONE; 1-PHENYL-3-METHYL-5-PYRAZOLE; 1-PHENYL-3-METHYL-5-PYRAZOLONE; 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-on; 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one; 2-Pyrazolin-5-one, 3-methyl-1-phenyl-; 3H-Pyrazol-3-one,2,4-dihydro-5-methyl-; 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one; 3-methyl-1-phenyl-2-pyrazolin-5-on; 3-METHYL-1-PHENYL-2-PYRAZOLIN-5ONE; 3-Methyl-1-phenyl-2-pyrazolin-5-one; 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE (EDARAVONE); 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE FOR SYNTHESIS; 3-Methyl-1-phenyl-2-pyrazoline-5-one; 3-METHYL-1-PHENYL-2-PYRAZOLINE-5-ONE / EDARAVONE; 3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one; 3-methyl-1-phenyl-5-pyrazolon; 3-Methyl-1-phenyl-5-pyrazolone; 5-METHYL-2-PHENYL-1,2-DIHYDROPYRAZOL-3-ONE EDARAVONE; 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one; c.i. developer 1; Edaravone (MCI-186); EINECS 201-891-0; MFCD00003138; MONOPYRAZOLONE; TIMTEC-BB SBB003801;
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1.3 CAS No.
89-25-8
1.4 CID
4021
1.5 EINECS
201-891-0
1.6 Molecular Formula
C10H10N2O
1.7 Inchi
InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
1.8 InChkey
QELUYTUMUWHWMC-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1=NN(C(=O)C1)C2=CC=CC=C2
1.10 Isomers Smiles
CC1=NN(C(=O)C1)C2=CC=CC=C2
2. Properties
2.1 Solubility
3.30g/l
2.2 Appearance
1-phenyl-3-methyl-5-pyrazolone appears as white to off-white powder or crystals. (NTP, 1992)
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
Off white to light yellow powder
2.5 Color/Form
MONOCLINIC PRISMS FROM WATER|WHITE POWDER OR CRYSTALS
2.6 PH
4.0-4.4 (H2O, 20℃)(saturated aqueous solution)
2.7 pKa
2.73±0.50(Predicted)
2.8 Water Solubility
H2O: 3 g/L (20 oC)
2.9 Spectral Properties
MAX ABSORPTION (ALCOHOL): 280 NM SHOULDER (LOG E= 3.6) INDEX OF REFRACTION: 1.637; MAX ABSORPTION (ALCOHOL): 245 NM (LOG E= 1.1)
IR: 15451 (Sadtler Research Laboratories IR Grating Collection)
UV: 985 (Sadtler Research Laboratories Spectral Collection)
MASS: 136 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
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2.10 Stability
Stable under normal temperatures and pressures.
2.11 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively.
3.2 Description

Edaravone is a strong novel free radical scavenger, and inhibits MMP-9-related brain hemorrhage in rats treated with tissue plasminogen activator.


1-phenyl-3-methyl-5-pyrazolone appears as white to off-white powder or crystals. (NTP, 1992)|DryPowder


1-phenyl-3-methyl-5-pyrazolone appears as white to off-white powder or crystals. (NTP, 1992)|Edaravone is a pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively. It has a role as a radical scavenger and an antioxidant.|Edaravone is a free radical scavenger approved in May, 2017 for the treatment of amyotrophic lateral scleorosis (ALS). Clinical studies showed that the treatment attenuated deterioration of the disease when compared to placebo. It has been previously investigated for the treatment of ischemic stroke, reperfusion Injury, and myocardial Infarction as it possesses antioxidant and anti-apoptotic properties. Being a low molecular weight molecule with good water and lipid-soluble properies, it is therapeutically advantageous in crossing the blood-brain barrier to mediate nootropic and neuroprotective effects. Oral formulation of edaravone is currently under development.|Edaravone is a free radical scavenger and neuroprotective agent used for therapy of amyotrophic lateral sclerosis. Edaravone is associated with a low rate of serum aminotransferase elevations during therapy but has not been linked to instances of clinically apparent, acute liver injury.|An antipyrine derivative that functions as a free radical scavenger and neuroprotective agent. It is used in the treatment of AMYOTROPHIC LATERAL SCLEROSIS and STROKE.

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3.3 Methods of Manufacturing
CONDENSATION OF PHENYLHYDRAZINE WITH ETHYL ACETOACETATE|BY CONDENSATION OF PHENYLHYDRAZINE WITH ETHYLACETOACETATE.
3.4 Purification Methods
Crystallise the pyrazolone from hot H2O, EtOH or EtOH/water (1:1). It complexes with metals. [Veibel et al. Acta Chim Scand 6 1066 1952, Beilstein 24 II 9, 24 III/IV 71.] 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Preparation Products And Raw materials Preparation Products
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3.5 Usage
antioxidant, lipoxygenase inhibitor
4. Safety and Handling
4.1 Safety Profile
Moderately toxic by ingestion andintraperitoneal routes. An eye irritant. When heated todecomposition it emits toxic fumes of NOx.
4.2 Report

NCI Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NCITR* ?? National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-141 ,1978. . Reported in EPA TSCA Inventory.

4.3 Safety

Moderately toxic by ingestion and intraperitoneal routes. An eye irritant. When heated to decomposition it emits toxic fumes of NOx.
Safety Information of Norphenazone (CAS NO.89-25-8):
Hazard Codes: Xi
Risk Statements: 36/37/38:? Irritating to eyes, respiratory system and skin?
Safety Statements: 26-36
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
WGK Germany:?1

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4.4 Specification

?Norphenazone, its CAS NO. is 89-25-8, the synonyms are 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one ; 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one?.

4.5 Toxicity
LD50 orl-rat: 3500 mg/kg LONZA# 08FEB79
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Skin sensitization, Category 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H317 May cause an allergic skin reaction

H413 May cause long lasting harmful effects to aquatic life
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P273 Avoid release to the environment.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in CDCl3  
1H NMR : 400 MHz in DMSO-d6  
IR : KBr disc  
IR : nujol mull  
Mass  
7. Synthesis Route
89-25-8Total: 50 Synthesis Route
 
60-80-0
60-80-0 231 Suppliers
 
89-25-8
89-25-8 439 Suppliers
 
60-80-0
60-80-0 231 Suppliers
 
881-05-0
881-05-0 4 Suppliers
 
38604-70-5
38604-70-5
 
89-25-8
89-25-8 439 Suppliers
 
298-12-4
298-12-4 276 Suppliers
 
1672-63-5
1672-63-5 6 Suppliers
 
50871-97-1
50871-97-1
View all
8. Precursor and Product
precursor:
60-80-0
60-80-0
947-95-5
947-95-5
27991-08-8
27991-08-8
22123-17-7
22123-17-7
141-97-9
141-97-9
6078-46-2
6078-46-2
100-63-0
100-63-0
1128-54-7
1128-54-7
product:
1781-33-5
1781-33-5
6334-24-3
6334-24-3
7477-67-0
7477-67-0
1131-17-5
1131-17-5
4747-46-0
4747-46-0
1080-89-3
1080-89-3
881-05-0
881-05-0
1140-38-1
1140-38-1
1128-54-7
1128-54-7
41927-23-5
41927-23-5
9. Computed Properties
10.Other Information
Usage
3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS.
Merck
14,6713
BRN
609575
Description
Edaravone was marketed in Japan for improving neurologic recovery following acute brain infarction. Currently, several agents classified as neuroprotectants and acting by diverse mechanisms (inhibition of glutamate release, blockade of calcium channels, lazaroids) have been marketed for treating the outcomes of brain damage due to trauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radical scavenging activity to be introduced for this pathology. This previously described molecule (in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can be simply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevone is a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edema in the brain following ischemia by blocking the arachidonic acid cascade triggering peroxidative neurodegeneration. Interestingly, this agent has been shown to quench active oxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective during reperfusion following ischemic injury. As an additional indication, phase III trials started with edaravone for increasing the chance of recovery after subarachnoid hemorrhage.
View all
Description
MCI-186 is a free radical scavenger with diverse protective effects in vivo. Most notably, it reduces damage due to ischemia-reperfusion injury in lung, liver, and brain in animal models of transplant, infection, traumatic brain injury, and stroke. MCI-186 provides these protective effects, at least in part, by reducing reactive oxygen species, inhibiting apoptosis, and blocking nonenzymatic peroxidation and lipoxygenase activity.
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Chemical Properties
Off white to light yellow powder
Originator
Mitsubishi Pharma (Japan)
Uses
antioxidant, lipoxygenase inhibitor
Uses
Edaravone inhibits the disease activity in rheumatoid arthritis.
Definition
ChEBI: A pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively.
Brand name
Radicut
General Description
A free radical scavenger and antioxidant that reduces post-ischemic brain injury. Inhibits iron-dependent peroxidation in rat brain homogenates (IC50 = 15 μM). Inhibits mitochondrial permeability transition pore.
Storage Conditions
CONDENSATION OF PHENYLHYDRAZINE WITH ETHYL ACETOACETATE|BY CONDENSATION OF PHENYLHYDRAZINE WITH ETHYLACETOACETATE.
Dissociation Constants
7.0
Reactive Group
Amides and Imides
Reactivity Profile
Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
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Special Reports
DHEW/NCI; Bioassay of 1-Phenyl-3-methyl-5-pyrazolone for Possible Carcinogenicity (1978) Technical Rpt Series No. 141 DHEW Pub No. (NIH) 78-1396
Fire Hazards
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
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Personal Protective Equipment
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Livertox Summary
Edaravone is a free radical scavenger and neuroprotective agent used for therapy of amyotrophic lateral sclerosis. Edaravone is associated with a low rate of serum aminotransferase elevations during therapy but has not been linked to instances of clinically apparent, acute liver injury.
Drug Classes
Amyotrophic Lateral Sclerosis Agents
Mesh
Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)|Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)
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Absorption
The peak plasma concentration of the parent drug is reached at the end of infusion, without accumulation of the drug with multiple dosing regimen. The mean Cmax value in healthy male adults is 888ng/mL for intravenous infusion. The values of AUC and Cmax are increased in a dose-proportional relationship. The oral bioavailability in mouse studies is 38% of the I.V. delivery.|About 0.7-0.9% of the dose is excreted as unchanged drug and 71.0-79.9% of the dose is excreted as metabolites (mostly as glucuronide conjugates) through mainly renal elimination.|The mean Vd value following an intravenous infusion of a single 30mg dose is 18.5L/kg.|The mean total plasma drug clearance following an intravenous infusion of a single 30mg dose is 0.1L/min.
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Metabolism
Multiple renal and hepatic uridine diphosphate glucuronosyltransferase (UGT) isoforms catalyze glucuronidation reaction of edaravone to form glucuronide conjugates. Edaravone is also metabolized into sulfate conjugates via sulfotransferase activity, which is the main metabolite form predominantly found circulating in plasma. It is predicted that the sulfate conjugate is hydrolyzed back to edaravone, which is then converted to the glucuronide conjugate in the human kidney before excretion into the urine. These metabolites have no pharmacological activity.
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Biological Half Life
The mean terminal elimination half-life of edaravone is 4.5 to 6 hours and the half-lives of its metabolites are 2 to 2.8 hours.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
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Mesh Entry Terms
1 Phenyl 3 methyl 5 pyrazolone
Production
25,000 - 100,000 lb|(1976) 5.90X10+6 GRAMS (SALES)|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
Manufacturing Info
Synthetic dye and pigment manufacturing|3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-: ACTIVE
Use Classification
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Cosmetics -> Hair dyeing
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5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
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edaravone cas 89-25-8
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12. Related Questions
What are the Characteristics and Applications of Edaravone in Neurological Therapeutics?Introduction Edaravone, a potent free radical scavenger, has gained significant attention in the field of neurological therapeutics. Initially developed and approved in Japan for the treatment of acut..
What is the significance of continuous flow process production of 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one for patients with ALS?Research background 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one is a type of brain protective agent that can scavenge free radicals. It was approved in Japan in 2001 for improving brain function. Neuro..
What evidence supports the use of 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one as a neuroprotective agent?According to the WHO report, stroke ranked second among the causes of death or long-term and severe neurological disease worldwide in the past decade. The latest version of the "Guidelines for Diagnos..
What is the doctor's weapon? 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one has been developed in Japan since 1984. Clinical research started in 1987 and ended in 1996. It was launched in 2001, which lasted 17 years. 5-Methyl-2-phen..
13. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
10. Other Information
11. Toltal 408 Suppliers
12. Related Questions
13. Realated Product Infomation
 
 
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