Phenacetin-13C

Names

[ Name ]:
Phenacetin-13C

[Synonym ]:
N-(4-Ethoxy-1-13C-phenyl)acetamide
MFCD00083951
N-4-((1-13C)Ethoxy)phenylacetamide
Phenacetin-13C1 (ethoxy-1-13C)
p-Acetophenetidide-ethoxy-1-13C
(<1-13C>ethoxy)phenacetin
Phenacetin-ethoxy-1-13C

Biological Activity

[Description]:

Phenacetin-13C is the 13C labeled Phenacetin[1]. Phenacetin (Acetophenetidin) is a non-opioid analgesic/antipyretic agent. Phenacetin is a selective COX-3 inhibitor. Phenacetin is used as probe of cytochrome P450 enzymes CYP1A2 in human liver microsomes and in rats[2][3][4].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[In Vitro]

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs[1].

[References]

[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216.

[2]. Chandrasekharan NV, et al. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31.

[3]. Xiao-Meng He, et al. Effects of long-term smoking on the activity and mRNA expression of CYP isozymes in rats. J Thorac Dis. 2015 Oct 7(10): 1725–1731.

[4]. Na Gao, et al. Inhibition of Baicalin on Metabolism of Phenacetin, a Probe of CYP1A2, in Human Liver Microsomes and in Rats. PLoS One. 2014 9(2): e89752.

Chemical & Physical Properties

[ Density]:
1.099g/cm3

[ Melting Point ]:
134-136ºC(lit.)

[ Molecular Formula ]:
C₁₀H₁₃NO₂

[ Molecular Weight ]:
180.20800

[ Exact Mass ]:
180.09800

[ PSA ]:
38.33000

[ LogP ]:
2.11670

[ Index of Refraction ]:
1.548

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H350

[ Precautionary Statements ]:
P201-P308 + P313

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
45-46-20/21/22

[ Safety Phrases ]:
53-22-36/37/39-45

[ RIDADR ]:
UN 3077 9 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Gastroenterology 72 , 1033, (1977)