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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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F Jorquera et al.
The journals of gerontology. Series A, Biological sciences and medical sciences, 53(1), M14-M19 (1998-02-19)
Drug-metabolizing capacity is generally reduced in the elderly. The purpose of this investigation was to study antipyrine clearance and metabolite excretion in old subjects of both sexes. Saliva clearance of antipyrine and the production clearances of antipyrine metabolites were studied
H A Ali et al.
Human & experimental toxicology, 13(10), 658-662 (1994-10-01)
1. We measured the antipyrine clearance in 18 healthy Saudi subjects and determined the urinary excretion of three of its metabolites: 4-hydroxyantipyrine (4-OH AP), norantipyrine (NOR AP) and 3 hydroxymethylantipyrine (3-OHM AP) in 21 subjects. 2. The mean +/- SD
D Louden et al.
The Analyst, 125(5), 927-931 (2000-07-08)
A prototype flow injection analysis (FIA) system for the characterisation of compounds via a combination of diode array UV, 1H NMR, FT-IR spectroscopy and time-of-flight (TOF) mass spectrometry has been investigated using a number of pharmaceuticals and related compounds as
H A Ali et al.
Journal of hepatology, 22(1), 17-21 (1995-01-01)
Our aim was to study whether chronic hepatitis C affects the three metabolic pathways of the model drug antipyrine differently. We measured antipyrine clearance from saliva as well as urinary excretion of its main metabolites 4-hydroxy-antipyrine, 3-hydroxy-methyl-antipyrine, and nor-antipyrine in
K Janus et al.
Research in veterinary science, 63(1), 1-3 (1997-07-01)
The effect of four days water deprivation on the metabolism of antipyrine was studied in female Holstein-Friesian calves, aged 24 to 25 days, by measuring the antipyrine plasma clearance and the excretion of three major metabolites of antipyrine in urine.
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