Hostname: page-component-848d4c4894-nmvwc Total loading time: 0 Render date: 2024-06-28T23:27:28.315Z Has data issue: false hasContentIssue false
  • English
  • Français

HPLC analysis and pharmacokinetics of the enantiomers of R,S-oxazepam and R,S-temazepam with their corresponding glucuronide conjugates in urine and plasma of man

Published online by Cambridge University Press:  18 September 2015

T.B. Vree ,
A.M. Baars  and
E.W. Wuis
T.B. Vree*
Affiliation:
Afdeling Klinische Farmacie en Anesthesiologie, Academisch Ziekenhuis Nijmegen Sint Radboud, Geert Grooteplein Zuid 8, 6525 GA Nijmegen Anesthesiologie, Academisch Ziekenhuis Nijmegen Sint Radboud, Geert Grooteplein Zuid 8, 6525 GA Nijmegen
A.M. Baars
Affiliation:
Afdeling Klinische Farmacie en Anesthesiologie, Academisch Ziekenhuis Nijmegen Sint Radboud, Geert Grooteplein Zuid 8, 6525 GA Nijmegen
E.W. Wuis
Affiliation:
Afdeling Klinische Farmacie en Anesthesiologie, Academisch Ziekenhuis Nijmegen Sint Radboud, Geert Grooteplein Zuid 8, 6525 GA Nijmegen
*
Afdeling Klinische Farmacie, Academisch Ziekenhuis Nijmegen Sint Radboud Ziekenhuis, Geert Grooteplein Zuid 8, 6525 GA Nijmegen
Get access Rights & Permissions [Opens in a new window]

Summary

R,S-Oxazepam and R,S-temazepam can be separated in their enantiomers by means of a chiral AGP column. The corresponding R- and S-glucuronide conjugates can be separated on a normal reversed-phase C18 column. Man conjugates the S-enantiomer of oxazepam and temazepam both better than the R-enantiomer. The urinary recovery of the glucuronides following either R,S,-oxazepam or R,S-temazepam almost amounts to 100% of the dose administered.

Keywords

HPLC analysisoxazepamtemazepamenantiomersglucuronidespharmacokineticsHPLC analyseoxazepamtemazepamenantiomerenglucuronidenfarmacokinetiek
Type
Research Article
Information
Acta Neuropsychiatrica , Volume 2 , Issue 4 , December 1990 , pp. 95 - 100
Copyright
Copyright © Scandinavian College of Neuropsychopharmacology 1990

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Literatuur

1.Pasteur, L. In: Richardson, GM, ed. Memoirs by Pasteur, van't Hoff, Le Bel and Wislicenus. New York: American Book Company, 1901: 1–33.Google Scholar
2.Smith, DF. Introduction to stereopsychopharmacology. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984: 11–31.Google Scholar
3.Cannon, JG. Dopamine analog stereoisomers. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984: 117–41.Google Scholar
4.Hyttel, J, Arnt, J, Bogeso, KP. Antipsychotic drugs: configurational stereoisomers. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984: 143–214.Google Scholar
5.Martin, AR. Antipsychotic and antidepressant drugs: conformationally restricted stereoisomers. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984:255–83.Google Scholar
6.Nickolson, VJ, Pinder, RM. Antidepressant drugs: chiral stereoisomers. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984:215–53.Google Scholar
7.Rutledge, CO, Walters, DE, Grunewald, GL. Noradrenergic drugs: conformational preferences in uptake mechanisms. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984:79–117.Google Scholar
8.Triggle, DJ. Muscarinic cholinergic drugs: effects of stereoisomers. In: Smith, DF, ed. CRC handbook of stereoisomers: Drugs in psychopharmacology. Boca Raton: CRC Press, 1984: 31–67.Google Scholar
9.Fryer, I. Benzodiazepine ligand-receptor interactions. In: Costa, E, ed. The benzodiazepines: From molecular biology to clinical practice. New York: Raven Press, 1983:7–21.Google Scholar
10.Ariëns, EJ. Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Eur J Clin Pharmacol 1984; 26: 663–8.CrossRefGoogle ScholarPubMed
11.Ariëns, EJ, Wuis, EW, Veringa, EJ. Stereoselectivity of bioactive xenobiotics. A pre-pasteur attitude in medicinal chemistry, pharmacokinetics and clinical pharmacology. Biochem Pharmacol 1988; 37:9–18.CrossRefGoogle ScholarPubMed
12.Ariëns, EJ. Racemische therapeutica, probleemmiddelen. Pharm Weekbl 1990, 125:552–4.Google Scholar
13.Armstrong, DW. Optical isomer separation by liquid chromatography. Anal Chem 1987; 59:84A–91A.CrossRefGoogle ScholarPubMed
14.Smith, DF, Pirkle, WH. Stereoselective analysis of racemic psychotropic compounds by HPLC on chiral stationary phase. Psychopharmacology 1986; 89:392–3.CrossRefGoogle ScholarPubMed
15.Vree, TB, Beneken Kolmer, EWJ, Martea, M, Bosch, R, Shimoda, M. High-performance liquid chromatography of sulphadimethoxine and its N1 glucuronide N4-acetyl and N4-acetyl-N1-glucuronide metabolites in human plasma and urine. J Chromatogr 1990-526: 119–28.CrossRefGoogle ScholarPubMed
16.Vree, TB, Steegers-Theunissen, RPM, Baars, AM, Hekster, YA. Direct highperformance liquid chromatographic analysis of p-hydroxyphenyl-phenylhydantoin glucuronide, the final metabolite of phenytoin, in human serum and urine. J Chromatogr. 1990; 526:581–9.CrossRefGoogle ScholarPubMed
17.Ruelius, HW, Tio, CO, Knowles, JA, McHugh, SL, Schilings, RT, Sisenwine, SF. Diastereoisomeric glucuronidation of oxazepam. Isolation and stereoselective enzyme hydrolysis. Drug Metab Dispos 1979;7:40–3.Google Scholar
18.Seideman, P, Ericsson, O, Groningsson, K, von Bahr, C. Effect of Pentobarbital on the formation of diastereometric oxazepam glucuronides in man: Analysis by high performance liquid chromatography. Acta Pharmacol Toxicol 1981; 49: 200–4.CrossRefGoogle Scholar
19.Sisenwine, SF, Tio, CO, Hadley, FV, Liu, AL, Kimmel, B, Ruelius, HW. Species related differences in the stereoselective glucuronidation of oxazepam. Drug Metab Dispos 1982; 10: 605–8.Google ScholarPubMed
20.Mouelhi, M, Ruelius, HW, Fenselau, C, Dulik, DM. Species-dependent enantioselective glucuronidation of three 2-arylpropionic acids. Drug Metab Dispos 1987; 15:767–72.Google ScholarPubMed
21.Yost, GS, Finley, BL. Stereoselective glucuronidation as a probe of induced forms of UDP-glucuronyltransferase in rabbits. Drug Metab Dispos 1985; 13:5–8.Google ScholarPubMed
22.Cartwright, AC. Stereochemistry and safety, efficacy and quality issues: genesis of new regulations. Drug Information J 1990; 24: 115–6.CrossRefGoogle Scholar
23.Kumkumian, CS. Regulatory considerations concerning stereoisomers in drug products. Drug Information J 1990; 24: 125–7.CrossRefGoogle Scholar
24.Sheldon, RA. The industrial synthesis of pure enantiomers. Drug Information J 1990; 24: 129–39.CrossRefGoogle Scholar