1672-58-8

Basic information

• Product Name: N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide
• Synonyms: N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide;4-CARBOXAMIDO-1,2-DIHYDRO-1,5-DIMETHYL-2-PHENYL-3H-PYRAZOLE-3-ONE;4-Carboxamido-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one;carboxamidoantipyrine;1,2-Dihydro-4-formylamino-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one;1,5-Dimethyl-2-phenyl-4-(formylamino)-1,2-dihydro-3H-pyrazole-3-one;4-Formylaminoantipyrin;N-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)formamide
• CAS NO: 1672-58-8
• Molecular Formula: C12H13N3O2
• Molecular Weight: 231.25052
• EINECS: 216-808-3
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 1672-58-8.mol
• Article Data: 36

Chemical Properties

• Melting Point: 189-192?C
• Boiling Point: 400.1°Cat760mmHg
• Flash Point: 195.8°C
• Appearance: /
• Density: 1.29±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Refrigerator
• PKA: 12.72±0.20(Predicted)
• BRN: 217665
• CAS DataBase Reference: N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide(1672-58-8)
• EPA Substance Registry System: N-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)formamide(1672-58-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/22
• WGK Germany: 3
• Hazardous Substances Data: 1672-58-8(Hazardous Substances Data)

Usage

Chemical Properties

Light Tan Solid

Uses

A metabolite of Dipyrone, a nonsteroidal anti-inflammatory drug.

Definition

ChEBI: A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a formaylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It is a metabolite of aminophenazone.

InChI:InChI=1/C12H13N3O2/c1-9-11(13-8-16)12(17)15(14(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3,(H,13,16)

Upstream product

• 42513-41-7 (Z)-1-chlorotetradec-9-ene 
• 127-08-2 potassium acetate 
• 592-41-6 1-hexene 
• 50816-18-7 9-decen-1-yl acetate 
• 29541-97-7 9-acetoxynonal 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 31608-22-7 4-bromo-1-(2-tetrahydropyranyloxy)butane 
• 108-24-7 acetic anhydride 
• 64275-63-4 1-bromo-dec-5c-ene 
• 72194-91-3 9‐tetradecen‐1‐ol 
• 2695-48-9 8-Bromo-1-octene 
• 50816-19-8 8-bromooctanol 
• 105866-20-4 Acetic acid (E)-9-benzenesulfonyl-tetradec-9-enyl ester 
• 117952-77-9 8-bromo-1-(1-butoxyethoxy)octane 

Downstream Products

• 43200-52-8 4-{[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-formyl-amino]-methyl}-4-methyl-morpholin-4-ium; iodide 

Relevant articles and documents

IDENTIFICATION OF IMPURITIES IN TECHNICAL-GRADE AMIDOPYRINE BY MASS-SPECTROMETRIC METHODS

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Oxidative degradation of sulpyrine by molecular oxygen

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Cytochrome P450 1A2 is the most important enzyme for hepatic metabolism of the metamizole metabolite 4-methylaminoantipyrine

Aims: Metamizole (dipyrone) is a prodrug not detectable in serum or urine after oral ingestion. The primary metabolite, 4-methylaminoantipyrine (4-MAA), can be N-demethylated to 4-aminoantipyrine (4-AA) or oxidized to 4-formylaminoantipyrine (4-FAA) by cytochrome P450 (CYP)-dependent reactions. We aimed to identify the CYPs involved in 4-MAA metabolism and to quantify the effect of CYP inhibition on 4-MAA metabolism. Methods: We investigated the metabolism of 4-MAA in vitro using CYP expressing supersomes and the pharmacokinetics of metamizole in the presence of CYP inhibitors in male subjects. Results: The experiments in supersomes revealed CYP1A2 as the major CYP for 4-MAA N-demethylation and 4-FAA formation with CYP2C19 and CYP2D6 contributing to N-demethylation. In the clinical study, we investigated the influence of ciprofloxacin (CYP1A2 inhibitor), fluconazole (CYP2C19 inhibitor) and the combination ciprofloxacin/fluconazole on the pharmacokinetics of metamizole in n =?12 male subjects in a randomized, placebo-controlled, double-blind study. The geometric mean ratios for the area under the concentration–time curve of 4-MAA after/before treatment were 1.17 (90% CI 1.09–1.25) for fluconazole, 1.51 (90% CI 1.42–1.60) for ciprofloxacin and 1.92 (90% CI 1.81–2.03) for ciprofloxacin/fluconazole. Fluconazole increased the half-life of 4-MAA from 3.22 hours by 0.47 hours (95% CI 0.13–0.81, P .05), ciprofloxacin by 0.69 hours (95% CI 0.44–0.94, P .001) and fluconazole/ciprofloxacin by 2.85 hours (95% CI 2.48–3.22, P .001). Conclusion: CYP1A2 is the major CYP for the conversion of 4-MAA to 4-AA and 4-FAA. The increase in 4-MAA exposure by the inhibition of CYP1A2 and by the combination CYP1A2/CYP2C19 may be relevant for dose-dependent adverse reactions of 4-MAA.

Method for synthesizing grassland spodoptera litura sex pheromone active ingredients

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing grassland spodoptera litura sex pheromone active ingredients (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. The method comprises the steps: using bromo-alcohol as a starting raw material; and firstly generating hydroxyl phosphonium salt with triphenylphosphine, then respectively carrying out Wittig coupling reaction with propionaldehyde and valeraldehyde to generate Z-type enol, and finally carrying out acetylation reaction with acetic anhydride to prepare (Z)-9-dodecene-1-alcohol acetate, (Z)-9-tetradecene-1-alcohol acetate and (Z)-11-hexadecene-1-alcohol acetate. According to the method, hydroxyl phosphonium salt is used for Wittig reaction, two steps of hydroxyl protection and deprotection are omitted, the synthetic route is simplified, and the method has the advantages of being environmentally friendly and the like.