Acetaminophen

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. [3] 33, 785 (1905); Fierz-David, Kuster, Helv. Chim. Acta 22, 94 (1939); Wilbert, De Angelis, US 2998450 (1961 to Warner-Lambert); Bergmann, DE 453577; Chem. Zentralbl. 1928, I, 2663; Frdl. 16, 238; from p-hydroxyacetophenone hydrazone: Pearson et al., J. Am. Chem. Soc. 75, 5907 (1953).

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.