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About This Item
Linear Formula:
CH3CONHC6H4OC2H5
CAS Number:
Molecular Weight:
179.22
Beilstein:
1869238
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
grade
pharmaceutical primary standard
API family
phenacetin
manufacturer/tradename
USP
mp
133-136 °C (lit.)
application(s)
pharmaceutical (small molecule)
format
neat
SMILES string
CCOc1ccc(NC(C)=O)cc1
InChI
1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
InChI key
CPJSUEIXXCENMM-UHFFFAOYSA-N
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General description
Phenacetin Melting Point Standard (Phenacetin) is a lipid-soluble drug with moderate solubility with aqueous solvents. Its oral absorption is based on formulation factors like particle size. Its major metabolic route is O-dealkylation to paracetamol and its minor pathways are deacetylation and hydroxylation to form pphenetidine, 2-hydroxyphenetidine, 2- and 3-hydroxyphenacetin and N-hydroxyphenacetin.
Application
Phenacetin Melting Point Standard USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia.
Biochem/physiol Actions
Substrate of CYP1A2 and CYP2D6.
Analysis Note
These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.
Other Notes
Sales restrictions may apply.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Carc. 1B
Storage Class Code
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
涉药品监管产品
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Kinetics and metabolism of paracetamol and phenacetin
Prescott, L.F.
British Journal of Clinical Pharmacology (1980)
V M Buckalew
American journal of kidney diseases : the official journal of the National Kidney Foundation, 28(1 Suppl 1), S7-13 (1996-07-01)
Six epidemiologic studies in the United States and Europe indicate that habitual use of phenacetin is associated with the development of chronic renal failure and end-stage renal disease (ESRD), with a relative risk in the range of 4 to 19.
Phenacetin abuse: a review.
G Carro-Ciampi
Toxicology, 10(4), 311-339 (1978-08-01)
Analgesic nephropathy: a reassessment of the role of phenacetin and other analgesics.
L F Prescott
Drugs, 23(1-2), 75-149 (1982-01-01)
J A Hinson
Environmental health perspectives, 49, 71-79 (1983-03-01)
Phenacetin can be metabolized to reactive metabolites by a variety of mechanisms. (1) Phenacetin can be N-hydroxylated, and the resulting N-hydroxyphenacetin can be sulfated or glucuronidated. Whereas phenacetin N-O sulfate immediately rearranges to form a reactive metabolite which may covalently
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