The Importance of Stereochemistry in the Clinical Pharmacokinetics of the 2-Arylpropionic Acid Non-Steroidal Anti-Inflammatory Drugs

Hutt, Andrew J.; Caldwell, John

doi:10.2165/00003088-198409040-00007

Cited by 190 publications

(77 citation statements)

References 16 publications

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“…Profens (2-aryl propinoic acids), an important group of nonsteroidal antiinflammatory drugs, are pharmacologically active mainly in the (S)-enantiomer form (Hutt and Caldwell, 1984). For instance, (S)-ibuprofen [(S)-2(4-isobutylphenyl) propionic acid] is 160 times more potent than its antipode in inhibiting prostaglandin synthesis.…”

Section: Lipases In Resolution Of Racemic Acids and Alcoholsmentioning

confidence: 99%

Production, purification, characterization, and applications of lipases

Sharma

Chisti

Banerjee

2001

Biotechnology Advances

1,286

712

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Lipases (triacylglycerol acylhydrolases, EC 3.1.1.3) catalyze the hydrolysis and the synthesis of esters formed from glycerol and long-chain fatty acids. Lipases occur widely in nature, but only microbial lipases are commercially significant. The many applications of lipases include speciality organic syntheses, hydrolysis of fats and oils, modification of fats, flavor enhancement in food processing, resolution of racemic mixtures, and chemical analyses. This article discusses the production, recovery, and use of microbial lipases. Issues of enzyme kinetics, thermostability, and bioactivity are addressed. Production of recombinant lipases is detailed. Immobilized preparations of lipases are discussed. In view of the increasing understanding of lipases and their many applications in high-value syntheses and as bulk enzymes, these enzymes are having an increasing impact on bioprocessing. D

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Section: Lipases In Resolution Of Racemic Acids and Alcoholsmentioning

confidence: 99%

Production, purification, characterization, and applications of lipases

Sharma

Chisti

Banerjee

2001

Biotechnology Advances

1,286

712

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“…It contains an asymmetric centre at the carbon alpha to the carboxyl group and is administered as a racemic mixture. As with other arylpropionic acids, the pharmacologic activity, as measured by in vitro inhibition of prostaglandin synthesis, resides primarily in the Senantiomer (Grieg & Griffin, 1975;Hutt et al, 1984).…”

Section: Introductionmentioning

confidence: 99%

Stereoselective disposition of flurbiprofen in normal volunteers.

Knadler

Brater

Hall

1992

Brit J Clinical Pharma

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“…For ketoprofen, and the 2-arylpropionates in general, anti-inflammatory activity as determined by in vitro cyclo-oxygenase inhibition, resides almost exclusively with the Senantiomer (Hutt & Caldwell, 1984). With the exception of naproxen, all of the 2-arylpropionic acids in clinical use are marketed as the racemic forms.…”

Section: Introductionmentioning

confidence: 99%

The disposition of ketoprofen enantiomers in man.

Sallustio

Purdie

Whitehead

et al. 1988

Brit J Clinical Pharma

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1. The disposition of ketoprofen enantiomers was studied in 21 patients taking racemic ketoprofen (Orudis SR). 2. In each patient the plasma concentrations of the R‐ and S‐enantiomers were similar at all times over a 24 h dosing interval. The mean (+/‐ s.e. mean) time‐averaged plasma ketoprofen concentrations over the dosage interval were 0.76 (+/‐ 0.06) mg l‐1 for R‐ketoprofen and 0.78 (+/‐ 0.06) mg l‐1 for S‐ ketoprofen. 3. Creatinine clearances for the 21 patients ranged from 6‐ 162 ml min‐1. There was no correlation between creatinine clearance and time‐averaged plasma concentration for either R‐ or S‐ketoprofen. 4. Approximately 30% of the dose was recovered in urine (unconjugated + glucuronide conjugate) and this was made up of 43% R‐ketoprofen and 57% S‐ketoprofen. Because of incomplete urine recoveries of ketoprofen it was not possible to determine whether inversion from the R‐ to the S‐ enantiomer takes place in man. 5. The data suggest that in terms of total (bound + unbound) ketoprofen, half the concentration value derived by a non‐enantiospecific analysis would give a reasonable approximation of the pharmacologically active S‐enantiomer concentration in plasma.

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The Importance of Stereochemistry in the Clinical Pharmacokinetics of the 2-Arylpropionic Acid Non-Steroidal Anti-Inflammatory Drugs

Cited by 190 publications

References 16 publications

Production, purification, characterization, and applications of lipases

Production, purification, characterization, and applications of lipases

Stereoselective disposition of flurbiprofen in normal volunteers.

The disposition of ketoprofen enantiomers in man.

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