Grundinformationen
- Standard-SMILES
Cc1cc(=O)n(-c2ccccc2)n1C- InChIKey
VEQOALNAAJBPNY-UHFFFAOYSA-N- Summenformel
- C11H12N2O
- Durchschnittliche Molmasse
- 188,23 g/mol
- Monoisotopische Masse
- 188,094963
Überblick
Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, a xenobiotic, a cyclooxygenase 3 inhibitor and an environmental contaminant.
Namen und Bezeichner
- Bevorzugter Name
- Antipyrine
- IUPAC
- 1,5-dimethyl-2-phenylpyrazol-3-one
- Lokaler Name
- Antipyrine
- Englischer Name
- Antipyrine
- Summenformel
- C11H12N2O
- Molmasse
- 188.23
Namen und Synonyme
antipyrinePhenazone60-80-0AnalgesineAntipyrinFenazoneAntipyrinumPhenazonum2,3-Dimethyl-1-phenyl-5-pyrazoloneFenazona3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one
Weitere Namen anzeigen
AntipirinANTIPYRENEPhenozoneAntypirine
1,5-dimethyl-2-phenylpyrazol-3-one1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-oneDTXSID6021117CHEBI:312251,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-oneT3CHA1B51HDTXCID401117
Datenbank-Bezeichner
- CAS
60-80-0- PubChem CID
- 2206
- DTXSID
DTXSID6021117- ChEMBL
CHEMBL277474- ChEBI
CHEBI:31225- UNII
- T3CHA1B51H
- EC Number
- 200-486-6
- Nikkaji
- J2.340J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,4
- Polarare Oberfläche (TPSA)
- 23,6 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 266
Experimentelle und physikochemische Eigenschaften
Chemical ClassesPharmaceutical
Drugs
DEA NFLIS-Drug Category -> Analgesics
Pharmaceuticals -> Listed in ZINC15
Drug
Pharmaceuticals -> Metabolite of Metamizole
SpringerMaterials PropertiesCrystal structure
LogP
0.38
0,23
0.42
DensityRelative density (water = 1): 1.19
Solubility
4.74e+01 g/L
Solubility in water: very good
25.2 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Inflammatory Agents, Non-Steroidal
Pharmaceuticals
Boiling Point319 °C
Melting Point
114 °C
113 °C
Physical Description
Solid
COLOURLESS CRYSTALS OR WHITE POWDER.
Ionization Efficiency
Positive
3.15
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Dissociation Constants1.4
Physikochemische Eigenschaften
- Schmelzpunkt
- 109 · 109-111 °C(lit.)
- Siedepunkt
- 319 °C · 319 °C
- Dichte
- 1 · 1,19 g/cm3
- Brechungsindex
- 1.585 · 1.5850 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 2 O: · H2O: soluble1 gm in less than 1ml
- Aggregatzustand
- Crystalline Powder
- pka
- 1.4 · pKa 1.4 (Uncertain)
- Farbe
- White
- Biologische Quelle
- rabbit
- Wasserlöslichkeit
- 1000 g/L · 1000 g/L (20 ºC)
- Merck
- 14 · 14,716
- BRN
- 157775 · 157775
- Stabilität
- Stable. Incompatible with ammonia, strong acids, alkalies, strong oxidizing agents, metallic salts, phenol.
- InChI
- 1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
- InChIKey
- VEQOALNAAJBPNY-UHFFFAOYSA-N
- SMILES
- CN1N(C(=O)C=C1C)c2ccccc2
- LogP
- 0.38 · 0.380
- CAS Datenbank
- 60 · 60-80-0(CAS DataBase Reference)
- NIST chemische Informationen
- Antipyrine(60-80-0)
- EPA chemische Informationen
- Antipyrine (60-80-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (1 of 184) of reports.
Warning
H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 184 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
REACH registered substance: Phenazone (EC: 200-486-6)
3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes of nitrogen oxides. Reacts with strong oxidants.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Hazard Classes and CategoriesAcute Tox. 4 (99.5%)
Sicherheit und Schutzausrüstung
Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures
Fresh air, rest.
Rinse skin with plenty of water or shower.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Rinse mouth. Seek medical attention if you feel unwell.
Safe StorageSeparated from strong oxidants.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT DISPERSION OF DUST!
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation, local exhaust or breathing protection.
Effects of Long Term ExposureThe substance may have effects on the blood. This may result in anaemia.
Toxikologische Informationen
Exposure RoutesThe substance can be absorbed into the body by inhalation of dust and by ingestion.
Signs and Symptoms
Cough.
No acute symptoms expected.
Redness.
No acute symptoms expected.
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
USGS Health-Based Screening Levels for Evaluating Water-Quality
Antipyrine
Pharmaceutical
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Sicherheitsdaten
- F
- 10
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- 3249
- hs_code
- 29331190
- RTECS-Nr.
- CD2450000
- risk_code
- 22-36/37/38
- Toxizität
- LD50 orally in rats: 1.8 g/kg (Hart)
- hazard_code
- Xn
- safety_code
- 26-36-37/39
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
S - Sensory organs
QS - Sensory organs
QN - Nervous system
Pharmacodynamics
Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)
Mechanism of ActionAntipyrine is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1, COX-2, and COX-3 enzymes involved in prostaglandin (PG) synthesis.
Metabolism/MetabolitesAntipyrine has known human metabolites that include Norantipyrine, 3-hydroxy-methylantipyrine, and 4-hydroxy-antipyrine.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Cellular LocationsCytoplasm
Metabolite PathwaysAntipyrine Action Pathway
Verwendung und Herstellung
UsesUse (kg) in Switzerland (2009): >25
Use ClassificationPharmaceuticals
General Manufacturing Information3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: ACTIVE
Anwendungen
HistoryAntipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.
VerwendenAntipyrine has been used for immunoblotting. It has also been used as an internal reference marker for studying the transport characteristics of platinum-containing drug, cisplatin in the human placenta in vitro. 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)
Darstellung
synthetischeAntipyrine (1) was prepared from the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with methyl iodide in methanol or in acetonitrile containing sodium bicarbonate in water in 58% yield. The reaction of 1-methyl-2-phenylhydrazine (2) with methyl 3-oxobutanoate (3) in acetonitrile gave 1 and pyrazolone 4 . Krohn has been reported the synthesis of 1 from the reaction of 5 with dimethyl sulfate in 71% yield. The reaction of pyrazolone 6 with methanol in the presence of triphenylphosphine afforded 1 (14%) and pyrazole 7 (53%). The same reaction was reported by Pegurier et al by heating the reactants in methanol containing calcium monoxide. Knorr early reported also, the synthesis of antipyrine from heating of 1-phenyl-5-ethoxy-3- methylpyrazole (8) with methyl iodide in methanol.
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Ergänzende Hinweise
DefinitionChEBI: Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic and an environmental contaminant.
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