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Chemical Compound Review:

SureCN5023104 1-acetamido-4-sulfooxy-benzene

Synonyms: CHEBI:32635, AC1L36H7, 10066-90-7, UNII-S6002H6J9F, Paracetamol sulfate, ...

Pang, K.S. et al., Hutabarat, R.M. et al., Reiter, C. et al., Würthwein, G. et al., Alberti, A. et al., et al.

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Disease relevance of Acetaminophen sulfate ester

Of the mechanisms that may be responsible for these differences, the most likely is enhanced activity (in subjects with cystic fibrosis) of the transferases that mediate the metabolism of acetaminophen to acetaminophen sulfate and acetaminophen glucuronide, respectively [1].

High impact information on Acetaminophen sulfate ester

Acetaminophen uptake and conversion in the perfused rat liver to acetaminophen sulfate was studied with the multiple indicator dilution technique (MID) [2].
The liver cells exhibited a concomitant very low permeability to product acetaminophen sulfate, leading to protracted product outflow curves [2].
The [3H]acetaminophen curve exhibited an early high peak, paralleling that for red cells and varying with hematocrit, followed by a prolonged decline, with the late appearance of acetaminophen sulfate product; the early peak disappeared when red cells were absent from the dose and perfusate [2].
METHODS: Utilizing the biochemical characteristics of paracetamol we evaluated by high performance liquid chromatography, the urine paracetamol-sulfate/paracetamol-glucuronide (PS/PG) ratio in all subjects following administration of this drug [3].
There were significant correlations between the activities of both the TS and TL forms of platelet PST and the excretion of acetaminophen sulfate expressed as a percentage of the dose of the drug (r = 0.62, P less than 0.001; r = 0.456, P less than 0.02) [4].

Biological context of Acetaminophen sulfate ester

The formation of acetaminophen sulfate is describable by Michaelis-Menten kinetics, with a Vmax of about 6.5 mumol/min/kg and an in vivo KM (referenced to plasma) of about 100 microM.(ABSTRACT TRUNCATED AT 250 WORDS)[5]
The disposition of the two major metabolites of acetaminophen, acetaminophen glucuronide (A-G) and acetaminophen sulfate (A-S), was studied in nine chronically catheterized fetal lambs during the third trimester [6].
The aim of this study was to compare the pharmacokinetics of paracetamol (PCM) and its metabolites [paracetamol glucuronide (PCM-G), paracetamol sulfate (PCM-S), and paracetamol cysteine (PCM-C)] in 16 patients with 16 normal subjects [7].

Anatomical context of Acetaminophen sulfate ester

Multiple forms of aryl sulfotransferase for acetaminophen sulfate conjugation in rat liver cytosol [8].

Associations of Acetaminophen sulfate ester with other chemical compounds

Rats on a low protein diet excreted a larger percentage of the administered dose as the glucuronide conjugate (34.6 vs. 12.3%) and a smaller percentage as acetaminophen sulfate (41.0 vs. 70.1%) [9].
The effects of phenobarbital (Pb)-pretreatment and bilateral renal ligation on the disposition of acetaminophen, acetaminophen glucuronide (AG) and acetaminophen sulfate (AS) were examined in serum, bile and urine of rats [10].
Sparse serum (37 samples; 4-7 per patient) and urine samples (27 samples; 0-15 per patient) were analyzed for paracetamol, paracetamol-glucuronide, paracetamol-sulfate, paracetamol-mercapturate and paracetamol-cysteine using capillary electrophoresis [11].

Gene context of Acetaminophen sulfate ester

Multiple mechanisms are involved in the biliary excretion of acetaminophen sulfate in the rat: role of Mrp2 and Bcrp1 [12].
Clearance (CL/F) of APAP and renal (CLR) and formation (CLf) clearance of acetaminophen glucuronide (AG) and acetaminophen sulfate (AS) were determined in CF-knockout mice following administration of APAP (50 mg/kg, intraperitoneal) [13].

Analytical, diagnostic and therapeutic context of Acetaminophen sulfate ester

The hepatocytic entry of acetaminophen sulfate conjugate was examined in the rat liver, perfused with red cells with and without albumin, by use of the multiple-indicator dilution technique [14].
Acetaminophen sulfate is greater than 50% protein bound, as determined by equilibrium dialysis and ultrafiltration [15].
Pharmacokinetics of acetaminophen sulfate after oral administration in rats: analysis of plasma profiles exhibiting a non-linear second peak [16].
Hemodilution with 40 ml/kg of Fluosol or saline reduced the acetaminophen Vd and the acetaminophen sulfate ClM at 48 or 72 h, respectively [17].

References

Disposition of drugs in cystic fibrosis. III. Acetaminophen. Hutabarat, R.M., Unadkat, J.D., Kushmerick, P., Aitken, M.L., Slattery, J.T., Smith, A.L. Clin. Pharmacol. Ther. (1991) [Pubmed]
Sulfation of acetaminophen by the perfused rat liver: the effect of red blood cell carriage. Pang, K.S., Barker, F., Simard, A., Schwab, A.J., Goresky, C.A. Hepatology (1995) [Pubmed]
Sulphation deficit in "low-functioning" autistic children: a pilot study. Alberti, A., Pirrone, P., Elia, M., Waring, R.H., Romano, C. Biol. Psychiatry (1999) [Pubmed]
Platelet phenol sulfotransferase activity: correlation with sulfate conjugation of acetaminophen. Reiter, C., Weinshilboum, R. Clin. Pharmacol. Ther. (1982) [Pubmed]
Effect of prevention of inorganic sulfate depletion on the pharmacokinetics of acetaminophen in rats. Lin, J.H., Levy, G. J. Pharmacol. Exp. Ther. (1986) [Pubmed]
Distribution and fate of acetaminophen conjugates in fetal lambs in utero. Wang, L.H., Rudolph, A.M., Benet, L.Z. J. Pharmacol. Exp. Ther. (1985) [Pubmed]
A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. Tankanitlert, J., Howard, T.A., Temsakulphong, A., Sirankapracha, P., Morales, N.P., Sanvarinda, Y., Fucharoen, P., Ware, R.E., Fucharoen, S., Chantharaksri, U. Eur. J. Clin. Pharmacol. (2006) [Pubmed]
Multiple forms of aryl sulfotransferase for acetaminophen sulfate conjugation in rat liver cytosol. Mizuma, T., Araya, H., Hayashi, M., Awazu, S. J. Pharmacobio-dyn. (1984) [Pubmed]
Disposition of acetaminophen in protein-calorie malnutrition. Jung, D. J. Pharmacol. Exp. Ther. (1985) [Pubmed]
Altered hepatobiliary disposition of acetaminophen metabolites after phenobarbital pretreatment and renal ligation: evidence for impaired biliary excretion and a diffusional barrier. Brouwer, K.L., Jones, J.A. J. Pharmacol. Exp. Ther. (1990) [Pubmed]
Pharmacokinetics of intravenous paracetamol in children and adolescents under major surgery. Würthwein, G., Koling, S., Reich, A., Hempel, G., Schulze-Westhoff, P., Pinheiro, P.V., Boos, J. Eur. J. Clin. Pharmacol. (2005) [Pubmed]
Multiple mechanisms are involved in the biliary excretion of acetaminophen sulfate in the rat: role of Mrp2 and Bcrp1. Zamek-Gliszczynski, M.J., Hoffmaster, K.A., Tian, X., Zhao, R., Polli, J.W., Humphreys, J.E., Webster, L.O., Bridges, A.S., Kalvass, J.C., Brouwer, K.L. Drug Metab. Dispos. (2005) [Pubmed]
Disposition of acetaminophen and indocyanine green in cystic fibrosis-knockout mice. Kulkarni, S.G., Pegram, A.A., Smith, P.C. AAPS PharmSci (2000) [Pubmed]
Uptake of a protein-bound polar compound, acetaminophen sulfate, by perfused rat liver. Goresky, C.A., Pang, K.S., Schwab, A.J., Barker, F., Cherry, W.F., Bach, G.G. Hepatology (1992) [Pubmed]
Renal clearance and serum protein binding of acetaminophen and its major conjugates in humans. Morris, M.E., Levy, G. Journal of pharmaceutical sciences. (1984) [Pubmed]
Pharmacokinetics of acetaminophen sulfate after oral administration in rats: analysis of plasma profiles exhibiting a non-linear second peak. Sawamoto, T., Kurosaki, Y., Kimura, T., Nakayama, T. Biol. Pharm. Bull. (1996) [Pubmed]
The effect of moderate hemodilution with fluosol-DA or normal saline on acetaminophen disposition in the rat. Shrewsbury, R.P., White, L.G. Experientia (1990) [Pubmed]

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