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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.)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
Metabolism of drugs. LIX. A new metabolite of antipyrine.
H Yoshimura et al.
Biochemical pharmacology, 17(8), 1511-1516 (1968-08-01)
Pharmacokinetics of antipyrine in calves after intravenous and oral administration.
K Janus et al.
Journal of veterinary pharmacology and therapeutics, 19(5), 408-410 (1996-10-01)
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
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
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