Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats

Comparative Biochemistry and Physiology - C Toxicology and Pharmacology

Volumn 133, Issue 4, 2002, Pages 587-592

  Imamura, Yorishige ^a   Kaneko, Miho ^a   Takada, Hidenori ^a   Otagiri, Masaki ^a   Shimada, Hideaki ^a   Akita, Hiroyuki ^b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b TOHO UNIVERSITY   (Japan)

Author keywords

Acetohexamide; Active metabolite; Pharmacokinetic parameter; Rat; S( ) Hydroxyhexamide; Sex dependent pharmacokinetics; Sulfamethazine; Testectomy

Indexed keywords

ACETOHEXAMIDE; CYTOCHROME P450; CYTOCHROME P450 2C11; HYDROXYHEXAMIDE;

ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG ELIMINATION; DRUG STRUCTURE; FEMALE; HYDROXYLATION; KIDNEY CORTEX; KIDNEY SLICE; MALE; NONHUMAN; ORCHIECTOMY; OVARIECTOMY; PLASMA; PLASMA CLEARANCE; PRIORITY JOURNAL; RAT; SEX;

EID: 0036891121     PISSN: 15320456     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1532-0456(02)00177-1     Document Type: Article

References (21)

1. Akita H., Kurashima K., Nozawa M., Yamamura S., Seri K., Imamura Y. Determination of absolute configuration of a metabolite (-)-hydroxyhexamide from acetohexamide, syntheses of (-)- and (+)-hydroxyhexamides and (-)- and (+)-acetoxyhexamides. Tetrahedron: Asymmetry. 9:1998;4331-4340.
2. Akita H., Kurashima K., Nozawa M., et al. Enzymatic synthesis of (-)- and (+)-acetoxyhexamides and (-)- and (+)-hydroxyhexamides. Chem. Pharm. Bull. 47:1999;1164-1166.
3. Asada S., Nagamine S., Nakae H. Comparative pharmacokinetics of acetohexamide and its metabolite, hydroxyhexamide in laboratory animals. Chem. Pharm. Bull. 37:1989;760-765.
4. Field J.B., Ohta M., Boyle C., Remer A. Potentiation of acetohexamide hypoglycemia by phenylbutazone. New Eng. J. Med. 277:1967;889-894.
5. Galloway J.A., McMahon R.E., Culp H.W., Marshall F.J., Young E.C. Metabolism, blood levels and rate of excretion of acetohexamide in human subjects. Diabetes. 16:1967;118-127.
6. Hanada K., Fujisawa R., Kataoka R., Nagamura S., Ogata H. Sex-related differences in the renal disposition of the acidic metabolite of clentiazem in rat. Xenobiotica. 31:2001;725-731.
7. Henderson S.J., Lindup W.E. Renal organic acid transport: uptake by rat kidney slices of a furan dicarboxylic acid which inhibits plasma protein binding of ligands in uremia. J. Pharmacol. Exp. Ther. 263:1992;54-60.
8. Imamura Y., Kojima Y., Higuchi T., Akita H., Oishi T., Otagiri M. Stereoselective reduction of acetohexamide in cytosol of rabbit liver. J. Pharmacobio-Dyn. 12:1989;731-735.
9. Imamura Y., Nomura T., Katsuki Y., Kojima Y., Otagiri M. Mechanism of pharmacodynamic and pharmacokinetic interactions between acetohexamide and phenylbutazone in rabbits. Pharmacol. Toxicol. 67:1990;415-419.
10. Imamura Y., Sanai K., Seri K., Akita H. Hypoglycemic effect of S(-)-hydroxyhexamide, a major metabolite of acetohexamide, and its enantiomer R(+)-hydroxyhexamide. Life Sci. 69:2001;1947-1955.
11. Kato R., Kamataki T. Cytochrome P-450 as a determinant of sex difference of drug metabolism in the rat. Xenobiotica. 12:1982;787-800.
12. Kato R., Yamazoe Y. Hormonal regulation of cytochrome P450 in rat liver. Schenkman J.B., Greim H. Handbook of Experimental Pharmacology. 1993;447-459 Springer-Verlag, Berlin Heidelberg.
13. McMahon R.E., Marshall F.J., Culp H.W. The nature of the metabolites of acetohexamide in the rat and the human. J. Pharmacol. Exp. Ther. 149:1965;272-279.
14. Morgan E.T., MacGeoh C., Gustafsson J.-Å. Sexual differentiation of cytochrome P-450 in rat liver: evidence for a constitutive isozyme as the male-specific 16α-hydroxylase. Mol. Pharmacol. 27:1985;471-479.
15. Pritchard J.B., Miller D.S. Comparative insights into the mechanisms of renal organic anion and cation secretion. Am. J. Physiol. 261:1991;R1329-R1340.
16. Ryan D.E., Levin W. Age- and gender-related expression of rat liver cytochrome P450. Schenkman J.B., Greim H. Handbook of Experimental Pharmacology. 1993;461-476 Springer-Verlag, Berlin Heidelberg.
17. Seri K., Sanai K., Kurashima K., Imamura Y., Akita H. (R)-ACX is a novel sulfonylurea compound with potent, quick and short-lasting hypoglycemic activity. Eur. J. Pharmacol. 389:2000;253-256.
18. Takagishi Y., Sato K., Tomita K., Sakamoto T. High-performance liquid chromatographic determination of acetohexamide and its metabolite, hydroxyhexamide. Yakugaku Zasshi. 99:1979;961-963.
19. Ullrich K.J., Rumrich G. Contraluminal transport systems in the proximal renal tubule involved in secretion of organic anions. Am. J. Physiol. 254:1988;F426-F453.
20. Witkamp R.F., Nijmeijer S.M., Yun H., Noordhoek J., van Miert A.S. Sulfamethazine as a model compund to assess sex hormone-dependent cytochrome P-450 activity in rats. Drug Metab. Dispos. 21:1993;441-446.
21. Waxman D.J., Dannan G.A., Guengerich F.P. Regulation of rat hepatic cytochrome P-450: age-dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isoenzymes. Biochemistry. 24:1985;4409-4417.