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A7302 Aldrich

4-Acetamidophenol

98%

Synonym: 4′-Hydroxyacetanilide, 4-Acetamidophenol, N-(4-Hydroxyphenyl)acetamide, N-Acetyl-4-aminophenol, APAP, Acetaminophen, Paracetamol

Purchase

Properties

assay   98%
mp   168-172 °C(lit.)
storage temp.   room temp

Description

Application

Analgesic.

Packaging

1 kg in poly bottle

250 g in poly bottle

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



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Acetaminophen

meets USP testing specifications, 98.0-102.0%, powder

Paracetamol
P0300000Paracetamol

European Pharmacopoeia (EP) Reference Standard

Phenacetin

≥98.0% (HPLC)

Phenacetin

97%

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36
WGK Germany 
1
RTECS 
AE4200000

Protocols & Articles

Protocols

Enzymatic Activity of Glucose-6-Phosphatase [EC 3.1.3.9]

Replaces enzyme assay procedure SSGLUC02. Document number and formatting changed to reflect current numbering and formatting guidelines. The procedure was modified to include a standard curve that re...
Keywords: Enzyme activity, Enzymology

Enzymatic Assay of 5’-Nucleotidase

1. OBJECTIVE To standardize a procedure for determining the enzymatic activity of 5’-Nucleotidase.
Keywords: Chromatography, Enzyme activity

Peer-Reviewed Papers

References

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Decreased glucuronidation and increased bioactivation of acetaminophen in Gilbert's syndrome. de Morais SM, Uetrecht JP, and Wells PG Gastroenterology 102(2), 577-86, (1992)

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UDP-glucuronosyltransferases and clinical drug-drug interactions. Tony K L Kiang et al Pharmacol. Ther. 106, 97-132, (2005)

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The modern pharmacology of paracetamol: therapeutic actions, mechanism of action, metabolism, toxicity and recent pharmacological findings. Graham GG, Davies MJ, Day RO, et al. Inflammopharmacology 21(3), 201-32, (2013)

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Metabolism and disposition of acetaminophen: recent advances in relation to hepatotoxicity and diagnosis. McGill MR and Jaeschke H Pharm. Res. 30(9), 2174-87, (2013)

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Single dose oral ibuprofen plus paracetamol (acetaminophen) for acute postoperative pain. Derry CJ, Derry S, and Moore RA Cochrane Database Syst. Rev. 6, CD010210, (2013)

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Paracetamol to induce ductus arteriosus closure: is it valid? Allegaert K, Anderson B, Simons S, et al. Arch. Dis. Child. 98(6), 462-6, (2013)

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Differential 12C-/13C-isotope dansylation labeling and fast liquid chromatography/mass spectrometry for absolute and relative quantification of the metabolome. Guo K and Li L Anal. Chem. 81(10), 3919-32, (2009)

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Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. Gustav Ahlin et al J. Med. Chem. 51, 5932-42, (2008)

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The human serum metabolome. Psychogios N, Hau DD, Peng J, et al. PLoS ONE 6(2), e16957, (2011)

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Effect of human glutathione S-transferase hGSTP1-1 polymorphism on the detoxification of reactive metabolites of clozapine, diclofenac and acetaminophen. Dragovic S, Venkataraman H, Begheijn S, et al. Toxicol. Lett. 224(2), 272-81, (2014)

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The human cerebrospinal fluid metabolome. Wishart DS, Lewis MJ, Morrissey JA, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 871(2), 164-73, (2008)

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Tolerability of paracetamol. Graham GG, Scott KF, and Day RO Drug Saf. 28(3), 227-40, (2005)

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Dose-dependent inhibition of platelet function by acetaminophen in healthy volunteers. Munsterhjelm E, Munsterhjelm NM, Niemi TT, et al. Anesthesiology 103(4), 712-7, (2005)

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QSAR study on permeability of hydrophobic compounds with artificial membranes. Masaaki Fujikawa et al Bioorg. Med. Chem. 15, 3756-67, (2007)

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The effect of aging on acetaminophen pharmacokinetics, toxicity and Nrf2 in Fischer 344 rats. Mach J, Huizer-Pajkos A, Cogger VC, et al. J. Gerontol. A. Biol. Sci. Med. Sci. 69(4), 387-97, (2014)

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Infiltrating monocyte-derived macrophages and resident kupffer cells display different ontogeny and functions in acute liver injury. Zigmond E, Samia-Grinberg S, Pasmanik-Chor M, et al. J. Immunol. 193(1), 344-53, (2014)

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Identification of patients at risk of anaphylactoid reactions to N-acetylcysteine in the treatment of paracetamol overdose. Schmidt LE Clin. Toxicol. (Phila.) 51(6), 467-72, (2013)

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Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Alessio Innocenti et al Bioorg. Med. Chem. 16, 7424-8, (2008)

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Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bram Baert et al Bioorg. Med. Chem. 15, 6943-55, (2007)

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Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. R Scott Obach et al Drug Metab. Dispos. 36, 1385-405, (2008)

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Physicochemical determinants of human renal clearance. Manthena V S Varma et al J. Med. Chem. 52, 4844-52, (2009)

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Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination. Manthena V S Varma et al J. Med. Chem. 53, 1098-108, (2010)

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[Pharmacokinetics of acetaminophen in individuals occupationally exposed to polyvinyl chloride modified with plasticizers]. Smilgin Z, Droździk M, Gawrońska-Szklarz B, et al. Med. Pr. 44(5), 423-9, (1993)

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ABCD: a simple mnemonic for the King's College Hospital criteria in paracetamol overdose. Kelham MD and Goundry AL Br. J. Hosp. Med. (Lond.) 75(12), 716, (2014)

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Comparative effectiveness of pharmacologic interventions for knee osteoarthritis: a systematic review and network meta-analysis. Bannuru RR, Schmid CH, Kent DM, et al. Ann. Intern. Med. 162(1), 46-54, (2015)

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How safe is paracetamol? Star K and Choonara I Arch. Dis. Child. 100(1), 73-4, (2015)

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Caffeine as an analgesic adjuvant for acute pain in adults. Derry CJ, Derry S, and Moore RA Cochrane Database Syst. Rev. 12, CD009281, (2014)

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Paracetamol exposure in pregnancy and early childhood and development of childhood asthma: a systematic review and meta-analysis. Cheelo M, Lodge CJ, Dharmage SC, et al. Arch. Dis. Child. 100(1), 81-9, (2015)

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[Paracetamol-codeine, an always actual choice for the treatment of pain]. Mattia C and Ferrari A Minerva Med. 105(6), 501-13, (2014)

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Gastrointestinal damage by non-steroidal anti-inflammatory drugs: updated clinical considerations. Pellicano R Minerva Gastroenterol. Dietol. 60(4), 255-61, (2014)

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S-adenosyl-l-methionine protection of acetaminophen mediated oxidative stress and identification of hepatic 4-hydroxynonenal protein adducts by mass spectrometry. Brown JM, Kuhlman C, Terneus MV, et al. Toxicol. Appl. Pharmacol. 281(2), 174-84, (2014)

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GSK2374697, a novel albumin-binding domain antibody (AlbudAb), extends systemic exposure of exendin-4: first study in humans--PK/PD and safety. O'Connor-Semmes RL, Lin J, Hodge RJ, et al. Clin. Pharmacol. Ther. 96(6), 704-12, (2014)

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Paracetamol-associated acute liver failure in Australian and New Zealand children: high rate of medication errors. Rajanayagam J, Bishop JR, Lewindon PJ, et al. Arch. Dis. Child. 100(1), 77-80, (2015)

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Ibuprofen with acetaminophen for postoperative pain control following tonsillectomy does not increase emergency department utilization. Bedwell JR, Pierce M, Levy M, et al. Otolaryngol. Head Neck Surg. 151(6), 963-6, (2014)

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OFIRMEV: an old drug becomes new again. Nishimoto RN Anesth. Prog. 61(3), 99-102, (2014)

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Targeting mitochondria with methylene blue protects mice against acetaminophen-induced liver injury. Lee KK, Imaizumi N, Chamberland SR, et al. Hepatology 61(1), 326-36, (2015)

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Deadly pain pills: everyday, 46 people in the U.S. die from legal pain pills. Here's how to avoid being a statistic. Consum. Rep. 79(9), 19-22, (2014)

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Using acetaminophen safely. Johns Hopkins Med. Lett. Health After 50 26(2), 1-2, (2014)

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Hepatic DNA deposition drives drug-induced liver injury and inflammation in mice. Marques PE, Oliveira AG, Pereira RV, et al. Hepatology 61(1), 348-60, (2015)

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Clinical question: are non-steroidal anti-inflammatories superior to acetaminophen for sprains/strains? Wheeler H, Vonfeldt K, Kavanaugh A, et al. J. Okla. State Med. Assoc. 107(3), 109-10, (2014)

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[Molecular mechanism of acute acetaminophen intoxication]. Kondo T Chudoku. Kenkyu. 27(1), 3-9, (2014)

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Exercise stays central to treatment of osteoarthritis in latest advice. Berry L Nurs. Older People 26(3), 9, (2014)

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Intravenous acetaminophen and intravenous ketorolac for management of pediatric surgical pain: a literature review. Baley K, Michalov K, Kossick MA, et al. AANA J. 82(1), 53-64, (2014)

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Antenatal acetaminophen use and attention-deficit/hyperactivity disorder: an interesting observed association but too early to infer causality. Cooper M, Langley K, and Thapar A JAMA Pediatr. 168(4), 306-7, (2014)

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Effects of iron on the pharmacokinetics of paracetamol in saliva. Issa MM, Nejem RM, and Shanab AA Pak. J. Biol. Sci. 16(24), 2050-3, (2013)

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The postoperative analgesic effect of morphine and paracetamol in the patients undergoing laparotomy, using PCA method. Yaghoubi S, Pourfallah R, Barikani A, et al. Glob. J. Health Sci. 6(1), 207-14, (2014)

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Baccharis trimera improves the antioxidant defense system and inhibits iNOS and NADPH oxidase expression in a rat model of inflammation. Cruz Padua Bd, Rossoni Junior JV, de Brito Magalhaes CL, et al. Curr. Pharm. Biotechnol. 14(11), 975-84, (2013)

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[Paracetamol poisoning is getting more and more common. The Swedish Poison Information Centre raise the alarm--time for countermeasures]. Höjer J, Karlson-Stiber C, Landgren A, et al. Lakartidningen. 110(42), 1870-1, (2013)

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The application of clinical audit to improve pain control following third molar surgery. Catherine B and Rood JP Dent. Update 40(8), 659-60, 663-4, 667-8, (2013)

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Beware of paracetamol use in alcohol abusers: a potential cause of acute liver injury. Manchanda A, Cameron C, and Robinson G N. Z. Med. J. 126(1383), 80-4, (2013)

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[Effectiveness of analgesic combinations in the self-medication]. Morgenstern EC and Heintze K MMW Fortschr. Med. 155(9), 49-51, (2013)

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Rational prescribing. Meyer CR Minn. Med. 96(3), 4, (2013)

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Assessment and management of paracetamol poisoning in adults. Pettie J and Dow M Nurs. Stand. 27(45), 39-47; quiz 48, 50, (2013)

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Epidural versus continuous transversus abdominis plane catheter technique for postoperative analgesia after abdominal surgery. Rao Kadam V, Van Wijk RM, Moran JI, et al. Anaesth. Intensive Care 41(4), 476-81, (2013)

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How safe is acetaminophen? Kam RY HDA Now, 20-1, (2013)

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Temperature management in haematology patients with febrile neutropenia: a practice survey. Weinkove R, Clay J, and Wood C N. Z. Med. J. 126(1373), 62-73, (2013)

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Undetected Ultracet™ dependence in an adolescent with nonmalignant back pain. Khan NA, Sullivan MA, Vitale MG, et al. J. Opioid Manag. 9(3), 225-30, (2013)

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A review of warfarin dosing with concurrent acetaminophen therapy. Pinson GM, Beall JW, and Kyle JA J. Pharm. Pract. 26(5), 518-21, (2013)

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Acetaminophen induced gender-dependent liver injury and the involvement of GCL and GPx. Sheng Y, Liang Q, Deng Z, et al. Drug Discov. Ther. 7(2), 78-83, (2013)

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Pharmacokinetic evaluation of hydrocodone/acetaminophen for pain management. Singla A and Sloan P J. Opioid Manag. 9(1), 71-80, (2013)

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Morphine-sparing effect of intravenous paracetamol for post operative pain management following gynaecological surgery. Olonisakin RP, Amanor-Boadu SD, and Akinyemi AO Afr. J. Med. Med. Sci. 41(4), 429-36, (2012)

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Order in the house. Setting standards for treatment of acetaminophen toxicity. Frischknecht J Adv. NPs PAs 4(3), 34-6, (2013)

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Injectable paracetamol in children: yet more cases of 10-fold overdose. Prescrire Int. 22(135), 44-5, (2013)

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[The role of paracetamol in transition reactions of alpha-nitrogen and oxidative stress in the liver]. Polaniak R, Bułdak RJ, Birkner E, et al. Pol. Merkur. Lekarski 33(198), 346-8, (2012)

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[Severe paracetamol poisoning complicated with liver and renal failure--case report and review of literature]. Mietka-Ciszowska A, Stojakowska M, and Groszek B Prz. Lek. 69(8), 614-7, (2012)

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[Management of acute intoxication with paracetamol--Polish Medical Society, Section of Clinical Toxicology position statement]. Waldman W, Groszek B, Burda P, et al. Prz. Lek. 69(8), 466-9, (2012)

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Role of inflammation in the mechanism of acetaminophen-induced hepatotoxicity. Jaeschke H Expert Opin. Drug Metab. Toxicol. 1(3), 389-97, (2005)

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Single dose oral paracetamol (acetaminophen) for postoperative pain. Barden J, Edwards J, Moore A, et al. Cochrane Database Syst. Rev. (1), CD004602, (2004)

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CSF Glucose Concentrations in Infants with Febrile Convulsions and the Possible Effect of Acetaminophen. Mohammadi M, Mohebbi MR, and Naderi F Indian Pediatr. 40(12), 1183-6, (2003)

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Reduction of adverse effects from intravenous acetylcysteine treatment for paracetamol poisoning: a randomised controlled trial. Bateman DN, Dear JW, Thanacoody HK, et al. Lancet 383(9918), 697-704, (2014)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Outcomes and complications of intracranial pressure monitoring in acute liver failure: a retrospective cohort study. Karvellas CJ, Fix OK, Battenhouse H, et al. Crit. Care Med. 42(5), 1157-67, (2014)

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Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 18, 3593-6, (2008)

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The Japanese toxicogenomics project: application of toxicogenomics. Takeki Uehara et al Mol. Nutr. Food. Res. 54, 218-27, (2010)

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Bile analysis of drugs in postmortem cases. Vanbinst R, Koenig J, Di Fazio V, et al. Forensic Sci. Int. 128(1-2), 35-40, (2002)

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Fragment-based discovery of bromodomain inhibitors part 1: inhibitor binding modes and implications for lead discovery. Chun-Wa Chung et al J. Med. Chem. 55, 576-86, (2012)

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Hologram QSAR model for the prediction of human oral bioavailability. Tiago L Moda et al Bioorg. Med. Chem. 15, 7738-45, (2007)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Urinary excretion of acetaminophen and its metabolites as studied by proton NMR spectroscopy. Bales JR, Sadler PJ, Nicholson JK, et al. Clin. Chem. 30(10), 1631-6, (1984)

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Analgesic drugs in breast milk and plasma. Findlay JW, DeAngelis RL, Kearney MF, et al. Clin. Pharmacol. Ther. 29(5), 625-33, (1981)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential. Dennis J Pelletier et al J. Chem. Inf. Model. 47, 1196-205, (2007)

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Acetaminophen in cerebrospinal fluid in children. van der Marel CD, Anderson BJ, Pluim MA, et al. Eur. J. Clin. Pharmacol. 59(4), 297-302, (2003)

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Pharmacokinetic study of the fate of acetaminophen and its conjugates in rats. Watari N, Iwai M, and Kaneniwa N J. Pharmacokinet. Biopharm. 11(3), 245-72, (1983)

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Two-dimensional proton nuclear magnetic resonance "maps" of acetaminophen metabolites in human urine. Bales JR, Nicholson JK, and Sadler PJ Clin. Chem. 31(5), 757-62, (1985)

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Protective effects of acetaminophen on ibuprofen-induced gastric mucosal damage in rats with associated suppression of matrix metalloproteinase. Fukushima E, Monoi N, Mikoshiba S, et al. J. Pharmacol. Exp. Ther. 349(1), 165-73, (2014)

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How well can the Caco-2/Madin-Darby canine kidney models predict effective human jejunal permeability? Alex Avdeef et al J. Med. Chem. 53, 3566-84, (2010)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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Plasma and liver acetaminophen-protein adduct levels in mice after acetaminophen treatment: dose-response, mechanisms, and clinical implications. McGill MR, Lebofsky M, Norris HR, et al. Toxicol. Appl. Pharmacol. 269(3), 240-9, (2013)

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Paracetamol (acetaminophen) with or without an antiemetic for acute migraine headaches in adults. Derry S and Moore RA Cochrane Database Syst. Rev. 4, CD008040, (2013)

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Cellular apoptosis and cytotoxicity of phenolic compounds: a quantitative structure-activity relationship study. Cynthia D Selassie et al J. Med. Chem. 48, 7234-42, (2005)

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Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents. Suresh Khode et al Eur. J. Med. Chem. 44, 1682-8, (2009)

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Antimalarial dual drugs based on potent inhibitors of glutathione reductase from Plasmodium falciparum. Wolfgang Friebolin et al J. Med. Chem. 51, 1260-77, (2008)

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Secretory leukocyte protease inhibitor: a pivotal mediator of anti-inflammatory responses in acetaminophen-induced acute liver failure. Antoniades CG, Khamri W, Abeles RD, et al. Hepatology 59(4), 1564-76, (2014)

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Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species. Francisco J Prado-Prado et al Bioorg. Med. Chem. 18, 2225-31, (2010)

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The association between acetaminophen and asthma: should its pediatric use be banned? Martinez-Gimeno A and García-Marcos L Expert Rev. Respir. Med. 7(2), 113-22, (2013)

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Protein kinase C (PKC) participates in acetaminophen hepatotoxicity through c-jun-N-terminal kinase (JNK)-dependent and -independent signaling pathways. Saberi B, Ybanez MD, Johnson HS, et al. Hepatology 59(4), 1543-54, (2014)

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A single liquid-chromatographic procedure for therapeutic monitoring of theophylline, acetaminophen, or ethosuximide. Quattrone AJ and Putnam RS Clin. Chem. 27(1), 129-32, (1981)

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Determination of acetaminophen-protein adducts in mouse liver and serum and human serum after hepatotoxic doses of acetaminophen using high-performance liquid chromatography with electrochemical detection. Muldrew KL, James LP, Coop L, et al. Drug Metab. Dispos. 30(4), 446-51, (2002)

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Scottish and Newcastle antiemetic pre-treatment for paracetamol poisoning study (SNAP). Thanacoody HK, Gray A, Dear JW, et al. BMC Pharmacol. Toxicol. 14, 20, (2013)

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Acetaminophen use during pregnancy, behavioral problems, and hyperkinetic disorders. Liew Z, Ritz B, Rebordosa C, et al. JAMA Pediatr. 168(4), 313-20, (2014)

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Statistical analysis plan for the HEAT trial: a multicentre randomised placebo-controlled trial of intravenous paracetamol in intensive care unit patients with fever and infection. Young PJ, Weatherall M, Saxena MK, et al. Crit. Care Resusc. 15(4), 279-86, (2013)

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Interindividual variation in response to xenobiotic exposure established in precision-cut human liver slices. Jetten MJ, Claessen SM, Dejong CH, et al. Toxicology 323, 61-9, (2014)

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Sterile inflammation in acetaminophen-induced liver injury is mediated by Cot/tpl2. Sanz-Garcia C, Ferrer-Mayorga G, González-Rodríguez Á, et al. J. Biol. Chem. 288(21), 15342-51, (2013)

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Median effective dose (ED₅₀) of paracetamol and morphine for postoperative pain: a study of interaction. Zeidan A, Mazoit JX, Ali Abdullah M, et al. Br. J. Anaesth. 112(1), 118-23, (2014)

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Prediction of drug intestinal absorption by new linear and non-linear QSPR. Alan Talevi et al Eur. J. Med. Chem. 46, 218-28, (2011)

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Prediction of dose-hepatotoxic response in humans based on toxicokinetic/toxicodynamic modeling with or without in vivo data: a case study with acetaminophen. Péry AR, Brochot C, Zeman FA, et al. Toxicol. Lett. 220(1), 26-34, (2013)

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The case of drug causation of childhood asthma: antibiotics and paracetamol. Heintze K and Petersen KU Eur. J. Clin. Pharmacol. 69(6), 1197-209, (2013)

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Synthesis and evaluation of paracetamol esters as novel fatty acid amide hydrolase inhibitors. Valentina Onnis et al J. Med. Chem. 53, 2286-98, (2010)

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Opioid-sparing effects of perioperative paracetamol and nonsteroidal anti-inflammatory drugs (NSAIDs) in children. Wong I, St John-Green C, and Walker SM Paediatr. Anaesth. 23(6), 475-95, (2013)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Synthesis, biological evaluation and docking studies of novel benzopyranone congeners for their expected activity as anti-inflammatory, analgesic and antipyretic agents. Amal A M Eissa et al Bioorg. Med. Chem. 17, 5059-70, (2009)

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A randomised controlled trial of parecoxib, celecoxib and paracetamol as adjuncts to patient-controlled epidural analgesia after caesarean delivery. Paech MJ, McDonnell NJ, Sinha A, et al. Anaesth. Intensive Care 42(1), 15-22, (2014)

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Temperature management in patients with acute neurological lesions: an Australian and New Zealand point prevalence study. Saxena MK, Taylor CB, Hammond NE, et al. Crit. Care Resusc. 15(2), 110-8, (2013)

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Micellar electrokinetic capillary chromatography as a powerful tool for pharmacological investigations without sample pretreatment: a precise technique providing cost advantages and limits of detection to the low nanomolar range. Kunkel A and Wätzig H Electrophoresis 20(12), 2379-89, (1999)

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Homology modeling and molecular dynamics of CYP1A1 and CYP2B1 to explore the metabolism of aryl derivatives by docking and experimental assays. Martha C Rosales-Hernández et al Eur. J. Med. Chem. 45, 4845-55, (2010)

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Determination of log D via automated microfluidic liquid-liquid extraction. Muhammad Alimuddin et al J. Med. Chem. 51, 5140-2, (2008)

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Antinociceptive properties of caffeic acid derivatives in mice. Fátima de Campos Buzzi et al Eur. J. Med. Chem. 44, 4596-602, (2009)

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Ibuprofen, paracetamol, and steam for patients with respiratory tract infections in primary care: pragmatic randomised factorial trial. Little P, Moore M, Kelly J, et al. BMJ 347, f6041, (2013)

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Effect of paracetamol use on the modification of the development of asthma by reactive oxygen species genes. Kang SH, Jung YH, Kim HY, et al. Ann. Allergy Asthma Immunol. 110(5), 364-369.e1, (2013)

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Toxin-induced hepatic injury. Lopez AM and Hendrickson RG Emerg. Med. Clin. North Am. 32(1), 103-25, (2014)

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Design, synthesis and analgesic properties of novel conformationally-restricted N-acylhydrazones (NAH). Arthur E Kümmerle et al Bioorg. Med. Chem. Lett. 19, 4963-6, (2009)

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Nonsteroidal anti-inflammatory drugs and their analogues as inhibitors of aldo-keto reductase AKR1C3: new lead compounds for the development of anticancer agents. Stanislav Gobec et al Bioorg. Med. Chem. Lett. 15, 5170-5, (2005)

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Acetaminophen-related hepatotoxicity. Bunchorntavakul C and Reddy KR Clin. Liver Dis. 17(4), 587-607, viii, (2013)

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Determination of permeability and lipophilicity of pyrazolo-pyrimidine tyrosine kinase inhibitors and correlation with biological data. Elena Dreassi et al Eur. J. Med. Chem. 44, 3712-7, (2009)

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Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1. Peter J McNamara et al Antimicrob. Agents Chemother. 53, 1898-906, (2009)

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Protective properties of 2-acetylcyclopentanone in a mouse model of acetaminophen hepatotoxicity. Zhang L, Gavin T, Geohagen BC, et al. J. Pharmacol. Exp. Ther. 346(2), 259-69, (2013)

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The long and winding road of non steroidal antinflammatory drugs and paracetamol in cancer pain management: a critical review. Mercadante S and Giarratano A Crit. Rev. Oncol. Hematol. 87(2), 140-5, (2013)

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New analgesics synthetically derived from the paracetamol metabolite N-(4-hydroxyphenyl)-(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enamide. Christian Sinning et al J. Med. Chem. 51, 7800-5, (2008)

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Synthesis and in vivo evaluation of non-hepatotoxic acetaminophen analogs. Anthony L Vaccarino et al Bioorg. Med. Chem. 15, 2206-15, (2007)

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The geminal dimethyl analogue of Flurbiprofen as a novel Abeta42 inhibitor and potential Alzheimer's disease modifying agent. Nicholas Stock et al Bioorg. Med. Chem. Lett. 16, 2219-23, (2006)

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Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models. Naomi L Kruhlak et al Toxicol. Mech. Methods 18, 217-27, (2008)

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A patient with acute liver failure and extreme hypoglycaemia with lactic acidosis who was not in a coma: causes and consequences of lactate-protected hypoglycaemia. Oldenbeuving G, McDonald JR, Goodwin MI, et al. Anaesth. Intensive Care 42(4), 507-11, (2014)

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First-principle, structure-based prediction of hepatic metabolic clearance values in human. Haiyan Li et al Eur. J. Med. Chem. 44, 1600-6, (2009)

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Noninvasive determination of acetaminophen disposition in Down's syndrome. Griener JC, Msall ME, Cooke RE, et al. Clin. Pharmacol. Ther. 48(5), 520-8, (1990)

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Neural computational prediction of oral drug absorption based on CODES 2D descriptors. A Guerra et al Eur. J. Med. Chem. 45, 930-40, (2010)

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QSAR-based permeability model for drug-like compounds. Rafael Gozalbes et al Bioorg. Med. Chem. 19, 2615-24, (2011)

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Effect of the glucagon-like peptide-1 receptor agonist lixisenatide on postprandial hepatic glucose metabolism in the conscious dog. Moore MC, Werner U, Smith MS, et al. Am. J. Physiol. Endocrinol. Metab. 305(12), E1473-82, (2013)

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Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. Xiaofan Sui et al Eur. J. Med. Chem. 44, 4455-60, (2009)

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Synthesis of new 1-phenyl-3-{4-[(2E)-3-phenylprop-2-enoyl]phenyl}-thiourea and urea derivatives with anti-nociceptive activity. Lorena dos Santos et al Bioorg. Med. Chem. 16, 8526-34, (2008)

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Synthesis, hydrolyses and dermal delivery of N-alkyl-N-alkyloxycarbonylaminomethyl (NANAOCAM) derivatives of phenol, imide and thiol containing drugs. Susruta Majumdar et al Bioorg. Med. Chem. Lett. 16, 3590-4, (2006)

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Synthesis and pharmacological evaluation of N-phenyl-acetamide sulfonamides designed as novel non-hepatotoxic analgesic candidates. Maria Letícia de Castro Barbosa et al Eur. J. Med. Chem. 44, 3612-20, (2009)

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The effect of acetaminophen on the expression of BCRP in trophoblast cells impairs the placental barrier to bile acids during maternal cholestasis. Blazquez AG, Briz O, Gonzalez-Sanchez E, et al. Toxicol. Appl. Pharmacol. 277(1), 77-85, (2014)

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Use of a systems model of drug-induced liver injury (DILIsym(®)) to elucidate the mechanistic differences between acetaminophen and its less-toxic isomer, AMAP, in mice. Howell BA, Siler SQ, and Watkins PB Toxicol. Lett. 226(2), 163-72, (2014)

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A practical deuterium-free NMR method for the rapid determination of 1-octanol/water partition coefficients of pharmaceutical agents. Huaping Mo et al Bioorg. Med. Chem. Lett. 20, 6712-5, (2010)

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Tramadol and acetaminophen combination for chronic non-cancer pain. Farquhar-Smith P and Gubbay A Expert Opin. Pharmacother. 14(16), 2297-304, (2013)

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Preliminary studies of 3,4-dichloroaniline amides as antiparasitic agents: structure-activity analysis of a compound library in vitro against Trichomonas vaginalis. Padraick J Dornbush et al Bioorg. Med. Chem. Lett. 20, 5299-301, (2010)

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Ethical dilemmas in psychiatric evaluations in patients with fulminant liver failure. Appel J and Vaidya S Curr. Opin. Organ Transplant. 19(2), 175-80, (2014)

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Asthma and paracetamol: could we really know what happens between them? Moral L, Marco N, Fuentes MJ, et al. Allergol. Immunopathol. (Madr.) 41(4), 261-4, (2013)

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Acetaminophen enhances cisplatin- and paclitaxel-mediated cytotoxicity to SKOV3 human ovarian carcinoma. Wu YJ, Neuwelt AJ, Muldoon LL, et al. Anticancer Res. 33(6), 2391-400, (2013)

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Removal of endocrine disrupting compounds in a lab-scale anaerobic/aerobic sequencing batch reactor unit. Muz M, Ak S, Komesli OT, et al. Environ. Technol. 35(9-12), 1055-63, (2014)

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A new flavonoid C-glycoside from Solanum elaeagnifolium with hepatoprotective and curative activities against paracetamol-induced liver injury in mice. Hawas UW, Soliman GM, Abou El-Kassem LT, et al. Z. Naturforsch. C 68(1-2), 19-28, (2013)

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Development of new formulation and its evaluation by capillary electrophoresis of tablets containing tramadol hydrochloride and paracetamol. Ciurba A, Hancu G, Cojocea LM, et al. Pharm. Dev. Technol. 19(7), 833-8, (2014)

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Effect of aqueous extract of Dicranopteris linearis leaves against paracetamol and carbon tetrachloride-induced liver toxicity in rats. Ismail NA, Shamsahal-Din NS, Mamat SS, et al. Pak. J. Pharm. Sci. 27(4), 831-5, (2014)

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Synthesis, kinetics and pharmacological evaluation of mefenamic acid mutual prodrug. Shah K, Shrivastava SK, and Mishra P Acta Pol. Pharm. 70(5), 905-11, (2013)

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Acetaminophen: a possible alternative to ibuprofen in patent ductus arteriosus closure. DeMauro SB and Wright CJ J. Pediatr. 165(1), 209-10, (2014)

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PKCs: pernicious kinase culprits in acetaminophen pathogenesis. Ju C and Roth RA Hepatology 59(4), 1229-31, (2014)

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FDA asks physicians to stop prescribing high-dose acetaminophen products. Mitka M JAMA 311(6), 563, (2014)

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Co-administering diclofenac with intravenous paracetamol or Hartmann's solution. Madden GB Anaesthesia 69(2), 191-2, (2014)

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When is research clinical advice? Interpreting an exploratory study of paracetamol overdose. Isbister GK and Duffull SB Clin. Toxicol. (Phila.) 51(10), 1242, (2013)

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Understanding probability and exposure in paracetamol overdose risk assessment. Isbister GK and Duffull SB Clin. Toxicol. (Phila.) 51(10), 1240, (2013)

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Apoptosis or necrosis in acetaminophen-induced acute liver failure? New insights from mechanistic biomarkers*. McGill MR and Jaeschke H Crit. Care Med. 41(11), 2653-4, (2013)

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The ability of a retrospective review of electronic health records to fully capture the frequency of supratherapeutic dosing of acetaminophen. Charpiat B JAMA Intern. Med. 173(11), 1035-6, (2013)

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Clinical inquiry. How can pregnant women safely relieve low-back pain? Clemente-Fuentes RJ, Pickett H, and Carney M J. Fam. Pract. 62(5), 260-8, (2013)

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Two cases of corneal abrasions in children exposed to liquid detergent capsules. Lasnier O, El-Hadad C, and Superstein R Can. J. Ophthalmol. 48(2), e29-30, (2013)

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Merck 14,47

Beil. 13,IV,1091

Aldrich MSDS 1, 6:B / Corp MSDS 1 (1), 11:A / FT-IR 1 (2), 358:B / FT-IR 2 (2), 2969:C / FT-NMR 1 (2), 1365:B / IR-Spectra (2), 934:H / IR-Spectra (3), 1068:H / NMR-Reference 2 (2), 337:C / RegBook 1 (2), 1997:M / Sax 6, 1555 / Sigma FT-IR 1 (2), 238:A / Structure Index 1, 319:D:5

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