MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 561575 | Name: Phenacetin
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenacetin is an analgesic used in research as the preferred marker for detecting CYP1A2-based inhibition potential in vitro.

Chemical Structure

Phenacetin
Phenacetin
CAS#62-44-2

Theoretical Analysis

MedKoo Cat#: 561575

Name: Phenacetin

CAS#: 62-44-2

Chemical Formula: C10H13NO2

Exact Mass: 179.0946

Molecular Weight: 179.22

Elemental Analysis: C, 67.02; H, 7.31; N, 7.82; O, 17.85

Price and Availability

Size Price Availability Quantity
25g USD 165.00
500g USD 305.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Phenacetin; Acetophenetidin;
IUPAC/Chemical Name
N-(4-Ethoxyphenyl)acetamide
InChi Key
CPJSUEIXXCENMM-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CC(NC1=CC=C(OCC)C=C1)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenacetin is a selective COX-3 inhibitor.
In vitro activity:
In the present experiments, cell proliferative and cytotoxic effects on the nasal mucosa were examined after short-term phenacetin administration. Two-week daily gavage treatment of rats with phenacetin at 100, 625, or 1250 mg/kg/day increased olfactory epithelial cell replication 62.4, 174, or 763%, respectively. The dose-response relationship for cell proliferation was similar to that of nasal tumor formation. These data suggest that the primary site of phenacetin toxicity within the nose is the olfactory mucosa, with restorative cell proliferation being confined to the epithelial cell layer. Reference: Toxicol Appl Pharmacol. 1989 Mar 15;98(1):100-12. https://pubmed.ncbi.nlm.nih.gov/2929018/
In vivo activity:
Phenacetin administration for 52 weeks in males significantly increased gpt (point mutations) mutant frequency (MF) in the kidney, the target organ of carcinogenesis. In the liver, the nontarget organ of carcinogenesis, gpt MFs were significantly elevated in phenacetin treatment groups of both genders during 26- and 52-week treatments. Furthermore, sensitive to P2 interference (Spi(-)deletions) MF increased in the liver of both genders following 52-week treatment. MFs were higher after treatment for 52 weeks than after treatment for 26 weeks. Frequencies of phenacetin-induced mutations were higher in the liver than in the kidney, suggesting that the intensity of genotoxicity does not necessarily correlate with the induction of tumor formation. Reference: Toxicology. 2014 Oct 3;324:10-7. https://pubmed.ncbi.nlm.nih.gov/25047350/
Solvent mg/mL mM comments
Solubility
DMSO 68.0 379.42
Ethanol 36.0 200.00
Water 0.7 3.99
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 179.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Bogdanffy MS, Mazaika TJ, Fasano WJ. Early cell proliferative and cytotoxic effects of phenacetin on rat nasal mucosa. Toxicol Appl Pharmacol. 1989 Mar 15;98(1):100-12. doi: 10.1016/0041-008x(89)90138-5. PMID: 2929018. 2. Johansson SL, Radio SJ, Saidi J, Sakata T. The effects of acetaminophen, antipyrine and phenacetin on rat urothelial cell proliferation. Carcinogenesis. 1989 Jan;10(1):105-11. doi: 10.1093/carcin/10.1.105. PMID: 2910518. 3. Kawamura Y, Hayashi H, Masumura K, Numazawa S, Nohmi T. Genotoxicity of phenacetin in the kidney and liver of Sprague-Dawley gpt delta transgenic rats in 26-week and 52-week repeated-dose studies. Toxicology. 2014 Oct 3;324:10-7. doi: 10.1016/j.tox.2014.07.003. Epub 2014 Jul 15. PMID: 25047350. 4. Luijten M, Speksnijder EN, van Alphen N, Westerman A, Heisterkamp SH, van Benthem J, van Kreijl CF, Beems RB, van Steeg H. Phenacetin acts as a weak genotoxic compound preferentially in the kidney of DNA repair deficient Xpa mice. Mutat Res. 2006 Apr 11;596(1-2):143-50. doi: 10.1016/j.mrfmmm.2005.12.011. Epub 2006 Feb 7. PMID: 16464479.
In vitro protocol:
1. Bogdanffy MS, Mazaika TJ, Fasano WJ. Early cell proliferative and cytotoxic effects of phenacetin on rat nasal mucosa. Toxicol Appl Pharmacol. 1989 Mar 15;98(1):100-12. doi: 10.1016/0041-008x(89)90138-5. PMID: 2929018. 2. Johansson SL, Radio SJ, Saidi J, Sakata T. The effects of acetaminophen, antipyrine and phenacetin on rat urothelial cell proliferation. Carcinogenesis. 1989 Jan;10(1):105-11. doi: 10.1093/carcin/10.1.105. PMID: 2910518.
In vivo protocol:
1. Kawamura Y, Hayashi H, Masumura K, Numazawa S, Nohmi T. Genotoxicity of phenacetin in the kidney and liver of Sprague-Dawley gpt delta transgenic rats in 26-week and 52-week repeated-dose studies. Toxicology. 2014 Oct 3;324:10-7. doi: 10.1016/j.tox.2014.07.003. Epub 2014 Jul 15. PMID: 25047350. 2. Luijten M, Speksnijder EN, van Alphen N, Westerman A, Heisterkamp SH, van Benthem J, van Kreijl CF, Beems RB, van Steeg H. Phenacetin acts as a weak genotoxic compound preferentially in the kidney of DNA repair deficient Xpa mice. Mutat Res. 2006 Apr 11;596(1-2):143-50. doi: 10.1016/j.mrfmmm.2005.12.011. Epub 2006 Feb 7. PMID: 16464479.
1: Furihata C, Watanabe T, Suzuki T, Hamada S, Nakajima M. Collaborative studies in toxicogenomics in rodent liver in JEMS·MMS; a useful application of principal component analysis on toxicogenomics. Genes Environ. 2016 Aug 1;38:15. doi: 10.1186/s41021-016-0041-0. eCollection 2016. Review. PubMed PMID: 27482301; PubMed Central PMCID: PMC4968012. 2: Broséus J, Gentile N, Esseiva P. The cutting of cocaine and heroin: A critical review. Forensic Sci Int. 2016 May;262:73-83. doi: 10.1016/j.forsciint.2016.02.033. Epub 2016 Feb 26. Review. PubMed PMID: 26974713. 3: Fukami T. [Role of Human Orphan Esterases in Drug-induced Toxicity]. Yakugaku Zasshi. 2015;135(11):1235-44. doi: 10.1248/yakushi.15-00186. Review. Japanese. PubMed PMID: 26521872. 4: Jones HE, Suarez Ordoñez R, Browne T. Little Fly Wing: a new drug of concern in Argentina. Addiction. 2015 Sep;110(9):1534-5. doi: 10.1111/add.13000. Epub 2015 Jul 14. Review. PubMed PMID: 26171755. 5: Brune K, Renner B, Tiegs G. Acetaminophen/paracetamol: A history of errors, failures and false decisions. Eur J Pain. 2015 Aug;19(7):953-65. doi: 10.1002/ejp.621. Epub 2014 Nov 27. Review. PubMed PMID: 25429980. 6: Pijls KE, de Vries H, Nikkessen S, Bast A, Wodzig WK, Koek GH. Critical appraisal of 13C breath tests for microsomal liver function: aminopyrine revisited. Liver Int. 2014 Apr;34(4):487-94. doi: 10.1111/liv.12451. Epub 2014 Jan 16. Review. PubMed PMID: 24428683. 7: Yates DR, Catto JW. Distinct patterns and behaviour of urothelial carcinoma with respect to anatomical location: how molecular biomarkers can augment clinico-pathological predictors in upper urinary tract tumours. World J Urol. 2013 Feb;31(1):21-9. doi: 10.1007/s00345-012-0946-6. Epub 2012 Sep 18. Review. PubMed PMID: 22986906. 8: Ram N, Kalász H, Adeghate E, Darvas F, Hashemi F, Tekes K. Medicinal chemistry of drugs with active metabolites (N-, O-, and S-desalkylation and some specific oxidative alterations). Curr Med Chem. 2012;19(33):5683-704. Review. PubMed PMID: 22934779. 9: Fukami T, Yokoi T. The emerging role of human esterases. Drug Metab Pharmacokinet. 2012;27(5):466-77. Epub 2012 Jul 17. Review. PubMed PMID: 22813719. 10: Bosetti C, Rosato V, Gallus S, La Vecchia C. Aspirin and urologic cancer risk: an update. Nat Rev Urol. 2012 Jan 24;9(2):102-10. doi: 10.1038/nrurol.2011.219. Review. PubMed PMID: 22270135. 11: Hunter L, Gordge L, Dargan PI, Wood DM. Methaemoglobinaemia associated with the use of cocaine and volatile nitrites as recreational drugs: a review. Br J Clin Pharmacol. 2011 Jul;72(1):18-26. doi: 10.1111/j.1365-2125.2011.03950.x. Review. PubMed PMID: 21352269; PubMed Central PMCID: PMC3141183. 12: Murta-Nascimento C, Schmitz-Dräger BJ, Zeegers MP, Steineck G, Kogevinas M, Real FX, Malats N. Epidemiology of urinary bladder cancer: from tumor development to patient's death. World J Urol. 2007 Jun;25(3):285-95. Review. PubMed PMID: 17530260. 13: Janković S, Radosavljević V. Risk factors for bladder cancer. Tumori. 2007 Jan-Feb;93(1):4-12. Review. PubMed PMID: 17455864. 14: Nista EC, Fini L, Armuzzi A, Candelli M, Zocco MA, Cazzato IA, Merra G, Finizio R, Miele L, Grieco A, Gasbarrini G, Gasbarrini A. 13C-breath tests in the study of microsomal liver function. Eur Rev Med Pharmacol Sci. 2004 Jan-Feb;8(1):33-46. Review. PubMed PMID: 15209153. 15: Otto T, Rübben H. [Prevention of bladder cancer]. Urologe A. 2004 May;43(5):562-4. Review. German. PubMed PMID: 15150694. 16: Yun EJ, Meng MV, Carroll PR. Evaluation of the patient with hematuria. Med Clin North Am. 2004 Mar;88(2):329-43. Review. PubMed PMID: 15049581. 17: Botting R. Antipyretic therapy. Front Biosci. 2004 Jan 1;9:956-66. Review. PubMed PMID: 14766422. 18: Fox JM, Siebers U. Caffeine as a promoter of analgesic-associated nephropathy--where is the evidence? Fundam Clin Pharmacol. 2003 Jun;17(3):377-92. Review. PubMed PMID: 12803578. 19: Baron JA. Epidemiology of non-steroidal anti-inflammatory drugs and cancer. Prog Exp Tumor Res. 2003;37:1-24. Review. PubMed PMID: 12795046. 20: Peuckmann V, Strumpf M, Zenz M, Bruera E. [Novel potential uses of thalidomide in the management of pain? A review of the literature]. Schmerz. 2003 Jun;17(3):204-10. Review. German. PubMed PMID: 12789488.