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109428

Sigma-Aldrich

4-Hydroxyantipyrine

99%

Synonym(s):

4-Hydroxy-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one, NSC 174055

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
1672-63-5
Molecular Weight:
204.23
MDL number:
MFCD00003143
UNSPSC Code:
12352100
PubChem Substance ID:
24846917
NACRES:
NA.22

Assay

99%

mp

184-186 °C (lit.)

functional group

ketone

SMILES string

CN1N(c2ccccc2)C(=O)C(O)=C1C

InChI

1S/C11H12N2O2/c1-8-10(14)11(15)13(12(8)2)9-6-4-3-5-7-9/h3-7,14H,1-2H3

InChI key

SKVPTPMWXJSBTF-UHFFFAOYSA-N

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General description

4-Hydroxyantipyrine is formed during oxidative deamination of aminopyrine. It is a metabolite of antipyrine.

Application

4-Hydroxyantipyrine was used to study the relationships between the metabolism of antipyrine, hexobarbitone and theophylline in man. It was used in a study on flow injection analysis system for the characterisation of pharmaceutical compounds via combination of diode array UV, 1H NMR, FT-IR spectroscopy and time-of-flight mass spectrometry.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000281830
0000231851
0000219245
0000281830
0000231851

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G Engel et al.
Clinical pharmacology and therapeutics, 59(6), 613-623 (1996-06-01)
Antipyrine has been widely used as a probe drug for human oxidative drug metabolism. To evaluate the role of antipyrine as a model drug, we have identified the cytochrome P450 enzymes involved in 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. We used
Reaction of drugs with nitrous acid as a source of carcinogenic nitrosamines.
W Lijinsky
Cancer research, 34(1), 255-258 (1974-01-01)
S B Seredenin et al.
Biulleten' eksperimental'noi biologii i meditsiny, 110(11), 491-493 (1990-11-01)
Antipyrine oxidation was studied in C57BL/6 and BALB/c inbred mice. It was found that C57BL/6 are weak oxidant but BALB/c are strong oxidants of antipyrine. Animals F1 hybrids inherited the high capacity of antipyrine oxidation.
M Monshouwer et al.
Xenobiotica; the fate of foreign compounds in biological systems, 25(5), 491-499 (1995-05-01)
1. In order to investigate the effect of a bacterial acute phase response model on drug disposition in vivo, plasma clearances of antipyrine, caffeine, paracetamol and indocyanine green were investigated in the healthy and Actinobacillus pleuropneumoniae-infected pig. 2. Indocyanine green
R P Shrewsbury et al.
Research communications in chemical pathology and pharmacology, 67(3), 411-414 (1990-03-01)
Two reports of antipyrine disposition in rats after hemodilution with 20, 40, or 80 ml/kg of Fluosol-DA are evaluated to determine if the extent of hemodilution influenced cytochrome P-450 mediated antipyrine metabolism. Alterations in antipyrine clearance (Cl) and 3-hydroxymethylantipyrine (3OHME)
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