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Antipyrine

Antipyrine structure

CAS No:
60-80-0
Formula:
C11H12N2O
Chemical Name:
Antipyrine
Synonyms:
3H-Pyrazol-3-one,1,2-dihydro-1,5-dimethyl-2-phenyl-;Antipyrine;1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one;Analgesine;Anodynine;Dimethyloxychinizin;Dimethyloxyquinazine;2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one;2,3-Dimethyl-1-phenyl-5-pyrazolone;Fenazone;Oxydimethylquinazine;Parodyne;Phenazone;1-Phenyl-2,3-dimethyl-5-pyrazolone;Sedatine;Phenazone (pharmaceutical);Azophen;Phenylone;Antipyrin;Phenazon;Antipirin;Phenylon;Anodynin;Pyrazophyl;Sedatin;Methozin;Apirelina;Azophene;Analgesin;Dentigoa N;Eu-Med mono;1,5-Dimethyl-2-phenyl-1,2-dihydropyrazol-3-one;NSC 7945;1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one;1,5-Dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one;1,5-Dimethyl-2-phenylpyrazol-3-one;1,5-Dimethyl-2-phenyl-1H-pyrazol-3(2H)-one;123175-91-7;5779-41-9
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

White Powder

Solid|COLOURLESS CRYSTALS OR WHITE POWDER.

Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at C-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.|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)

Antipyrine Basic Attributes

Molecular Weight：

188.23

Exact Mass：

188.23

BRN：

157775

EC Number：

200-486-6

UNII：

T3CHA1B51H

ICSC Number：

0376

NSC Number：

755874|7945

DSSTox ID：

DTXSID6021117

ATC Code：

N - Nervous system|S - Sensory organs

HScode：

29331190

Characteristics

PSA：

23.6

XLogP3：

0.4

Appearance：

White Crystalline Powder

Density：

1.19 g/cm³

Melting Point：

113 °C

Boiling Point：

319 °C

Flash Point：

109.4ºC

Refractive Index：

1.553

Water Solubility：

H2O: 1000 g/L (20 ºC)

Storage Conditions：

Refrigerator

Toxicity：

Oral-rat LD50: 1705 mg/kg; Oral-Mouse LD50: 1310 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxide fumes

PKA：

1.4None

Dissociation Constants：

1.4

Collision Cross Section：

137.7 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]|137.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|135.59 Å² [M+H]+

Physical Dangers：

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3249

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36-37/39

RTECS Number：

CD2450000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

Stable. Incompatible with ammonia, strong acids, alkalies, strong oxidizing agents, metallic salts, phenol.

Precautionary statement(s)：

P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302

Fire Hazards：

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 243 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fire Fighting：

Use water spray, powder, foam, carbon dioxide.

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.

Safe Storage：

Separated from strong oxidants.

Inhalation Risk：

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.

Effects of Short Term Exposure：

May cause mechanical irritation to the eyes and respiratory tract.

Effects of Long Term Exposure：

The substance may have effects on the blood. This may result in anaemia.

Fire Prevention：

NO open flames.

Exposure Prevention：

PREVENT DISPERSION OF DUST!

Inhalation Prevention：

Use ventilation, local exhaust or breathing protection.

Skin Prevention：

Protective gloves.

Eye Prevention：

Wear safety spectacles.

Toxicity

Toxicity class：

moderately toxic

Drug Information

Drug Indication：

Antipyrine is an analgesic often used to test effects of other drugs on liver enzymes. In combination with benzocaine in otic solutions, antipyrine is indicated for the symptomatic relief of acute otitis media arising from various etiologies.

Pharmacology：

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)

MeSH：

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. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Metabolism/Metabolites：

Antipyrine has known human metabolites that include 3-hydroxy-methylantipyrine, 4-hydroxy-antipyrine, and Norantipyrine.

Mechanism of Action：

Antipyrine 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.

First Aid：

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).

MeSH Entry Terms：

Anodynin

Exposure Routes：

The substance can be absorbed into the body by inhalation of dust and by ingestion.

Symptoms：

Cough.

No acute symptoms expected.

Redness.

Antipyrine Use and Manufacturing

Methods of Manufacturing

From 1-phenyl-3-methylpyrazolone-5 by methylation and hydrolysis. In a dry methylation tank, add pyrazolone, and then add dimethyl sulfate, heat to 160 ℃, react for 6 hours, and boil for 2 hours with heated water. Put the methylation reactant into a hydrolysis tank containing sodium hydroxide solution, and stir at 100-110°C for 3 hours for hydrolysis. Put the antipyrine oil layer in a crystallization tank, dilute with distilled water, stir, and cool the temperature to below 10℃. Crystals are precipitated, spin-filtered, washed with water, and spin-dried to obtain crude antipyrine. The crude product is recrystallized with distilled water and the activated carbon is decolorized to obtain the finished product. Methylation operation can also use methyl chloride or methyl bromide as raw materials, make such methylation reagents into methanol solution, and slightly react with 1-naphthyl-3-methylpyridone in a stirring reaction. Then methanol was distilled off, the reaction was dissolved in water, made slightly alkaline with sodium hydroxide, antipyrine was extracted with benzene, recrystallized from benzene, and finally refined with activated carbon and water. Another method is to use equimolar N, N-phenylmethylhydrazine and ethyl acetoacetate to heat and reflux on an oil bath at 130-160°C. Antipyrine was extracted from the thick oily liquid with boiling water, and then the water was evaporated to obtain crystals.

Uses

Analgesic

Manufacturing Info：

3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: ACTIVE

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:188.23
XLogP3:0.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:188.094963011
Monoisotopic Mass:188.094963011
Topological Polar Surface Area:23.6
Heavy Atom Count:14
Complexity:267
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

It has antipyretic, analgesic, anti-inflammatory and anti-rheumatic effects. The analgesic effect is mainly achieved by inhibiting the synthesis of prostaglandins and other pain-sensitive substances; the antipyretic effect is achieved through the hypothalamus temperature regulation center, thereby enhancing the heat dissipation process (peripheral vasodilation, increased and accelerated blood flow, and sweating), rather than inhibiting the heat production process.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Migraine Tablets
Ingredients	Each tablet contains the following active ingredients: 0.27g of antipyrine and 27mg of caffeine.
Indication	Not yet clear.
Specifications	Antipyrine 0.27g, Caffeine 27mg
Manufacturer	Jilin Galaxy Pharmaceutical Co., Ltd.

Migraine Tablets
Ingredients	Each tablet contains the following active ingredients: 0.27g of antipyrine and 27mg of caffeine.
Indication	Not yet clear.
Specifications	Antipyrine 0.27g, Caffeine 27mg
Manufacturer	Changchun Dazheng Tec-Phar Co., Ltd.

Compound aminopyrine injection
Ingredients	This product is a compound preparation of aminopyrine, antipyrine and barbiturate.
Specifications	2ml
Manufacturer	Shandong Xinhua Pharmaceutical Company Limited

See More Related Drugs

Registered Holders

Beijing Jingfeng Pharmaceutical (Shandong) Co., Ltd.

China
Active
Hebei Jiheng Pharmaceutical Co., Ltd.

China
Active
Zhejiang Haisen Pharmaceutical Co., Ltd.

China
Active

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