- Monograph ID
- M1317
- Title
- Acetaminophen
- CAS Registry Number
- 103-90-2
- CAS name
- N-(4-Hydroxyphenyl)acetamide
- UNII
- 362O9ITL9D
- Additional names
- 4′-hydroxyacetanilide; N-acetyl-p-aminophenol; p-acetamidophenol; p-acetaminophenol; p-acetylaminophenol; p-hydroxyacetanilide; paracetamol
- Trademark names
- Acamol (Volta); Alpiny (SS Pharm.); Alvedon (AstraZeneca); Anhiba (Abbott); Ben-u-ron (Novartis); Calpol (Pfizer); Calradol (Bayer); Captin (Krewel); Dafalgan (BMS); Datril (BMS); Dirox (Gramon); Disprol (Reckitt Benckiser); Doliprane (Sanofi-Aventis); Dolitabs (Sanofi-Aventis); Dolviran (Bayer); Efferalgan (BMS); Efferalganodis (UPSA); Enelfa (Dolorgiet); Expandox (Expanpharm); Fensum (Merckle); Geluprane (Sanofi-Aventis); Hedex (GSK); Malex (Ecosol); Mejoralito (GSK); Panadol (GSK); Panamax (Sanofi-Aventis); Panodil (GSK); Pasolind N (Stada); Perfalqan (BMS); Sanipirina (Bayer); Sedalito (Merck KGaA); Tempra (BMS); Tylenol (McNeil)
- Molecular formula
- C8H9NO2
- Molecular weight
- 151.17
- Percent composition
- C 63.56%, H 6.00%, N 9.27%, O 21.17%
- Standard InChI
- InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
- Standard InChIKey
- RZVAJINKPMORJF-UHFFFAOYSA-N
Properties
Large monoclinic prisms from water, mp 169-170.5 °C. d421 1.293. uv max (ethanol): 250 nm (ε 13800). Freely sol in alcohol. Sol in methanol, ethanol, dimethylformamide, ethylene dichloride, acetone, ethyl acetate, boiling water, 1N sodium hydroxide. Slightly sol in ether. Very slightly sol in cold water. Practically insol in petr ether, pentane, benzene. LD50 in mice (mg/kg): 338 orally, 500 i.p. See: G. A. Stramer et al., Toxicol. Appl. Pharmacol. 19, 20 (1971) DOI: 10.1016/0041-008X(71)90185-2 PMID: 5570565; D. C. Dahlin, S. D. Nelson, J. Med. Chem. 25, 885 (1982) DOI: 10.1021/jm00350a001 PMID: 7120276 .
Non-medical use
Manuf azo dyes, photographic chemicals.
References
Synthetic non-opiate analgesic. Prepn from p-nitrophenol: Morse, Ber. 11, 232 (1878); Tingle, Williams, Am. Chem. J. 37, 63 (1907); from p-aminophenol: Lumière et al., Bull. Soc. Chim. Fr.
Evaluation of renal effects: D. P. Sandler et al., N. Engl. J. Med. 320, 1238 (1989) PMID: 2651928.
Clinical trial in osteoarthritis: A. R. Temple et al., Clin. Ther. 28, 222 (2006) DOI: 10.1016/j.clinthera.2006.02.004 PMID: 16678643.
Molecular toxicology: P. D. Josephy, Drug Metab. Rev. 37, 581 (2005) DOI: 10.1080/03602530500205200 PMID: 16393886.
Comprehensive description: J. E. Fairbrother, Anal. Profiles Drug Subs. 3, 1-109 (1974).
Review of pharmacology: B. Ameer, D. J. Greenblatt, Ann. Intern. Med. 87, 202-209 (1977) PMID: 329728.
Review of mechanism of hepatotoxicity: L. P. James et al., Drug Metab. Dispos. 31, 1499-1506 (2003) DOI: 10.1124/dmd.31.12.1499 PMID: 14625346; of acetaminophen-induced acute liver failure: A. M. Larson et al., Hepatology 42, 1364-1372 (2005) DOI: 10.1002/hep.20948 PMID: 16317692.
Classifications
- Therapeutic category
- Analgesic; Analgesic (Non-opioids); Anilides; Antipyretic
- Therapeutic category (Vet.)
- Analgesic.
- Keywords
- Analgesic; antipyretic.