Stereoselectivity in the Placental Transfer and Kinetic Disposition of Racemic Bupivacaine Administered to Parturients with or Without a Vasoconstrictor

Chirality

Volumn 16, Issue 2, 2004, Pages 65-71

  Papini, Olga ^a   Silva Mathes, Ângelo Do Carmo ^a   Da Cunha, Sergio Pereira ^a   Lanchote, Vera Lucia ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Bupivacaine; Enantiomers; Parturients; Pharmacokinetics; Placental transfer

Indexed keywords

ADRENALIN; BUPIVACAINE;

ADULT; ARTICLE; CONTROLLED STUDY; DELIVERY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG DISPOSITION; DRUG DISTRIBUTION; DRUG TRANSPORT; EPIDURAL ANESTHESIA; FEMALE; GESTATIONAL AGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LABOR; MATERNAL BLOOD; NORMAL HUMAN; OBSTETRIC ANESTHESIA; PLACENTAL TRANSFER; PRIORITY JOURNAL; STEREOCHEMISTRY; ULTRAVIOLET RADIATION; UMBILICAL CORD BLOOD; VASOCONSTRICTION; VENOUS BLOOD;

ADOLESCENT; ADULT; BUPIVACAINE; EPINEPHRINE; FEMALE; FETAL BLOOD; HUMANS; KINETICS; MATERNAL AGE; MATERNAL-FETAL EXCHANGE; PARTURITION; PREGNANCY; STEREOISOMERISM; VASOCONSTRICTOR AGENTS;

EID: 1642579596     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10308     Document Type: Article

References (30)

1. Burm AGL, Van Der Meer AD, Van Kleef JW, Zeijlmans PWM, Groen K Pharmacokinetics of the enantiomers of bupivacaine following intravenous administration of the racemate. Br J Clin Pharmacol 1994;38:125-129.
2. Sidebotham DA, Schug SA. Stereochemistry in anaesthesia. Clin Exp Pharmacol Physisiol 1997;24:126-130.
3. Cox CR, Faccenda KA, Gilhooly C, Bannister J, Scott NB, Morrison LMM. Extradural S (-)-bupivacaine: comparison with racemic RS-bupivacaine. Br J Anaesth 1998;80:289-293.
4. Cox CR, Checketts MR, Makenzie N, Scott NB, Bannister J. Comparison of S(-)-bupivacaine with racemic (RS)-bupivacaine in supraclavicular brachial plexus block. Br J Anaesth 1998;80:594-598.
5. Santos AC, Karpel B, Noble G. The placental transfer and fetal effects of levobupivacaine, racemic bupivacaine, and ropivacaine. Anesthesiology 1999;90:1698-1703.
6. Bader AM, Tsen LC, Camann WR, Nephew E, Datta S. Clinical effects and maternal fetal plasma concentrations of 0.5% epidural levobupivacaine versus bupivacaine for cesarean delivery. Anesthesiology 1999;90:1596-1601.
7. Tucker GT. Pharmacokinetics of local anaesthetics. Br J Anaesth 1986;58:717-731.
8. Denson DD, Knapp RM, Turner P, Thompson GA. Serum bupivacaine concentrations in term parturients following continuous epidural analgesia for labor and delivery. Ther Drug Monit 1984;6:393-398.
9. Fawcett JP, Kennedy J, Kumar A, Ledger R, Zacharias M. Stereoselective urinary excretion of bupivacaine and its metabolites during epidural infusion. Chirality 1999;11:50-55.
10. Thomas J, Long G, Moore G, Morgan D. Plasma protein binding and placental transfer of bupivacaine. Clin Pharmacol Ther 1975;19:426-434.
11. Magno R, Berlin A, Karlsson K, Kjellmer I. Placental transfer and neonatal elimination of bupivacaine following epidural analgesia for elective cesarean section. Acta Anaesth Scand 1976;20:141-146.
12. Kuhnert PM, Kuhnert BR, Stitts JM, Gross TL. The use of a selected ion monitoring technique to study the disposition of bupivacaine in mother, fetus, and neonate following epidural anesthesia for cesarean section. Anesthesiology 1981;55:611-617.
13. Kuhnert BR, Zuspan KJ, Kuhnert PM, Syracuse CD, Brown DE. Bupivacaine disposition in mother, fetus, and neonate after spinal anesthesia for cesarean section. Anesth Analg 1987;66:407-412.
14. Reynolds F, Laishley R, Morgan B, Lee A. Effect of time and adrenaline on the feto-maternal distribution of bupivacaine. Br J Anaesth 1989;62:509-514.
15. Ledan C, Collet D, Vincelot A, Debord J, Lachatre G, Feiss P. Pharmacocinétique de la bupivacaïne administrée par voie péridurale ou sous-arachoïdienne pour césarienne réglée. Ann Fr Anesth Réanim 1993;12:552-559.
16. Loftus J, Hill H, Cohen SE. Placental transfer and neonatal effects of epidural sufentanil and fentanyl administered with bupivacaine during labor. Anesthesiology 1995;83:300-308.
17. Decocq G, Brazier M, Hary L, Hubau C, Fortaine MR, Gondry J, Andréjak M. Serum bupivacaine concentrations and transplacental transfer following repeated epidural administrations in term parturients during labour. Fundam Clin Pharmacol 1997;11:365-370.
18. Fernando R, Bonello E, Gill P, Urquhart J, Reynolds F, Morgan B. Neonatal welfare and placental of fentanyl and bupivacaine during ambulatory combined spinal epidural analgesia for labour. Anaesthesia 1997;52:517-524.
19. Johnson RF, Cahana A, Olenick M, Herman N, Paschall RL, Minzter B, Ramasubramanian R, Gonzalez H, Downing JW. A comparison of the placental transfer of ropivacaine versus bupivacaine. Anesth Analg 1999;89:703-708.
20. Johnson RF, Herman N, Arney TL, Gonzalez H, Johonson V, Dowing JW. Bupivacaine transfer across the human term placenta. A study using the dual perfused human placental model. Anesthesiology 1995;82:459-468.
21. Johnson RF, Herman NL, Johnson V, Arney TL, Paschall RL, Downing JW. Effects of fetal pH on local anesthetic transfer across the human placenta. Anesthesiology 1996;85:608-615.
22. Clark BJ, Hamdi A, Berrisford RG, Sabanathan S, Mearns AJ. Reversed-phase and chiral high-performance liquid chromatographic assay of bupivacaine and its enantiomers in clinical samples after continuous extrapleural infusion. J Chromatogr 1991;552:383-390.
23. Downig JW, Johnson HV, Gonzalez HF, Arney TL, Herman NL, Johnson RF. The pharmacokinetics of epidural lidocaine and bupivacaine during cesarean section. Anesth Analg 1997;84:527-532.
24. Walhagen A, Edholm L-E. Coupled-column chromatography on immobilized protein phases for direct separation and determination of drug enantiomers in plasma. J Chromatogr 1989;473:371-379.
25. Abraham I, Fawcett JP, Kennedy J, Kumar A, Ledger R. Simultaneous analysis of lignocaine and bupivacaine enantiomers in plasma by high-performance liquid chromatography. J Chromatogr B 1997;703:203-208.
26. Gu XK, Fryris B, Mather LE. High-performance liquid chromatographic separation and nanogram quantitation of bupivacaine enantiomers in blood. J Chomatogr B 1998;719:135-140.
27. Polley LS, Columb MO, Vaughton NN, Wagner DS, Van De Ven CJM. Effect of epidural epinephrine on the minimum local analgesic concentration of epidural bupivacaine in labor. Anesthesiology 2002;96:1123-1128.
28. Loebstein R, Lalkin A, Koren G. Pharmacokinetic changes during pregnancy and their clinical relevance. Clin Pharmacokinet 1997;33:328-343.
29. Thomas JM, Schug SA. Recent advances in the pharmacokinetics of local anaesthetics. Clin Pharmacokinet 1999;36:67-83.
30. Mather LE, Huang YF, Veering B, Pryor ME. Systemic and regional pharmacokinetics of levobupivacaine and bupivacaine enantiomers in sheep. Anesth Analg 1998;86:805-811.