Interspecies pharmacokinetics and in vitro metabolism of SQ109

British Journal of Pharmacology

Volumn 147, Issue 5, 2006, Pages 476-485

  Jia, Lee ^a   Noker, Patricia E ^b   Coward, Lori ^b   Gorman, Gregory S ^b   Protopopova, Marina ^c   Tomaszewski, Joseph E ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b SOUTHERN RESEARCH INSTITUTE   (United States)

^c SEQUELLA INC   (United States)

Author keywords

ADME; Antituberculosis; Diamine; Pharmacokinetics; SQ109

Indexed keywords

CARBON 14; COMPLEMENTARY DNA; CYTOCHROME; CYTOCHROME P450; CYTOCHROME P450 2C19; CYTOCHROME P450 2D6; DIAMINE; DRUG METABOLITE; N GERANYL N' (2 ADAMANTYL)ETHANE 1,2 DIAMINE; PLASMA PROTEIN; PROTEIN INHIBITOR; RECOMBINANT DNA; SQ 109; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BLOOD ANALYSIS; BLOOD SAMPLING; BODY SURFACE; COMPARATIVE STUDY; CONTROLLED STUDY; DEALKYLATION; DOG; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG ELIMINATION; DRUG FECES LEVEL; DRUG HALF LIFE; DRUG METABOLISM; DRUG OXIDATION; DRUG PROTEIN BINDING; DRUG TISSUE LEVEL; DRUG URINE LEVEL; EPOXIDATION; FEMALE; HUMAN; HUMAN CELL; INCUBATION TEMPERATURE; INCUBATION TIME; KIDNEY; LIQUID CHROMATOGRAPHY; LIVER; LIVER MICROSOME; LIVER MICROSOME METABOLISM; LUNG; MALE; MOUSE; NONHUMAN; PHENOTYPE; PRIORITY JOURNAL; RADIOACTIVITY; RAT; RODENT; SINGLE DRUG DOSE; SPECIES DIFFERENCE; SPLEEN; TANDEM MASS SPECTROMETRY;

ADAMANTANE; ANIMALS; ANTITUBERCULAR AGENTS; ARYL HYDROCARBON HYDROXYLASES; BLOOD PROTEINS; CYTOCHROME P-450 CYP2D6; DOGS; ENZYME INHIBITORS; ETHYLENEDIAMINES; FEMALE; HUMANS; MALE; METABOLIC CLEARANCE RATE; MICE; MIXED FUNCTION OXYGENASES; PROTEIN BINDING; RATS; RATS, INBRED F344; SPECIES SPECIFICITY; TISSUE DISTRIBUTION;

EID: 33644828189     PISSN: 00071188     EISSN: 14765381     Source Type: Journal    
DOI: 10.1038/sj.bjp.0706650     Document Type: Article

References (30)

1. AMERICAN THORACIC SOCIETY DOCUMENTS. (2003). American Thoracic Society/Centers for Disease Control and Prevention/Infectious Diseases Society of America: Treatment of Tuberculosis. Am. J. Respir. Crit. Care Med., 167, 603-662.
2. BARRE, J., CHAMOUARD, J.M., HOUIN, G. & TILLEMENT, J.P. (1985). Equilibrium dialysis, ultrafiltration, and ultracentrifugation compared for determining the plasma-protein-binding characteristics of valproic acid. Clin. Chem., 31, 60-64.
3. BARRY III, C.E., SLAYDEN, R.A., SAMPSON, A.E. & LEE, R.E. (2000). Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs. Biochem. Pharmacol., 59, 221-231.
4. BJORNSSON, T.D., CALLAGHAN, J.T., EINOLF, H.J., FISCHER, V., GAN, L., GRIMM, S., KAO, J., KING, S.P., MIWA, G., NI, L., KUWAR, G., MCLEOD, J., OBACH, R.S., ROBERTS, S., ROE, A., SHAH, A., SNIKERIS, F., SULLIVAN, J.T., TWEEDIE, D., VEGA, J.M., WALSH, J. & WRIGHTON, S.A. (2003). The conduct of in vitro and in vivo drug-drug interaction studies: a pharmaceutical research and manufacturers of America (PhRMA) perspective. Drug Metab. Dispos., 31, 815-832.
5. BOULTON, D.W., WALLE, U.K. & WALLE, T. (1998). Extensive binding of the bioflavonoid quercetin to human plasma proteins. J. Pharm. Pharmacol., 50, 243-250.
6. BOXENBAUM, H. (1980). Interspecies variation in liver weight, hepatic blood flow and antipyrine intrinsic clearance in extrapolation of data to benzodiazepines and phenytoin. J. Pharmacokinet. Biopharmacol., 8, 165-176.
7. DAVIES, B. & MORRIS, T. (1993). Physiological parameters in laboratory animals and humans. Pharm. Res., 10, 1093-1095.
8. DONAHUE, S.R., FLOCKHART, D.A., ABERNETHY, D.R. & KO, J. (1997). Ticlopidine inhibition of phenytoin metabolism mediated by potent inhibition of CYP2C19 Clin. Pharmacol. Ther., 62, 572-577.
9. HA-DUONG, N.T., DIJOLS, S., MACHEREY, A.C., DANSETTE, P.M. & MANSUY, D. (2001). Inhibition by ticlopidine and its derivatives of human liver cytochrome p450. Mechanism-based inactivation of CYP 2C19 by ticlopidine. Adv. Exp. Med. Biol., 500, 145-148.
10. JIA, L., BONAVENTURA, C., BONAVENTURA, J. & STAMLER, J.S. (1996). S-nitrosohaemoglobin: a dynamic activity of blood involved in vascular control. Nature, 380, 221-226.
11. JIA, L., COWARD, L., GORMAN, S.G., NOKER, P. & TOMASZEWSKI, E.J. (2005a). Pharmacoproteomic effects of isoniazid, ethambutol, and N-geranyl-N′-(2-adamantyl)ethane-1,2-diamine (SQ109) on Mycobacterium tuberculosis H37Rv. J. Pharmacol. Exp. Ther., 315, 905-911.
12. JIA, L., TOMASZEWSKI, J., HANRAHAN, C., COWARD, L., NOKER, P., GORMAN, G., NIKONENKO, B. & PROTOPOPOVA, M. (2005b). Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br. J. Pharmacol., 144, 80-87.
13. JIA, L., TOMASZEWSKI, J.E., NOKER, P.E., GORMAN, G.S., GLAZE, E. & PROTOPOPOVA, M. (2005c). Simultaneous estimation of pharmacokinetic properties in mice of three anti-tubercular ethambutol analogues obtained from combinatorial lead optimization. J. Pharm. Biomed. Anal., 37, 793-799.
14. JIA, L., WONG, H., WANG, Y., GARZA, M. & WEITMAN, S.D. (2003). Carbendazim: disposition, cellular permeability, metabolite identification and pharmacokinetic comparison with its nanoparticle. J. Pharm. Sci., 92, 161-172.
15. KARIV, I., CAO, H. & OLDENBURG, K.R. (2001). Development of a high throughput equilibrium dialysis method. J. Pharm. Sci., 90, 580-587.
16. KOSTIAINEN, R., KOTIAHO, T., KUURANNE, T. & AURIOLA, S. (2003). Liquid chromatography/ atmospheric pressure ionization-mass spectrometry in drug metabolism studies. J. Mass Spectrom., 38, 357-372.
17. LEE, R., PROTOPOPOVA, M., CROOKS, E., SLAYDEN, R., TERROT, M. & BARRY, C. (2003). Combinatorial lead optimization of [1,2]-diamines based on ethambutol as potential anti-tuberculosis preclinical candidates. J. Combin. Chem., 5, 172-187.
18. LIN, J.H. (1995). Species similarities and differences in pharmacokinetics. Drug. Metab. Dispos., 23, 1008-1021.
19. MARTINEZ, M., AMIDON, G., CLARKE, L., JONES, W.W., MITRA, A. & RIVIERE, J. (2002). Applying the biopharmaceutics classification system to veterinary pharmaceutical products. Part II. Physiological considerations. Adv. Drug Deliv. Rev., 54, 825-850.
20. MULLER, M., PENA, A.D. & DERENDORF, H. (2004). Issues in pharmacokinetics and pharmacodynamics of anti-infective agents: distribution in tissue. Antimicrob. Agents Chemother., 48, 1441-1453.
21. NATIONAL RESEARCH COUNCIL. (1996). Guide for the Care and Use of Laboratory Animals. Washington, DC: National Academy Press.
22. PANG, K.S. & GILLETTE, J.R. (1978). Theoretical relationships between area under the curve and route of administration of drugs and their precursors for evaluating sites and pathways of metabolism. J. Pharm. Sci., 67, 703-704.
23. PARKINSON, A. (1996). Biotransformation of xenobiotics. In: Casarett & Doull's Toxicology: The Basic Science of Poisons. ed. Klaassen, C. pp. 113-186. New York: McGraw-Hill.
24. ROWLAND, M. & TOZER, T.N. (1995). Clinical Pharmacokinetics Concepts and Applications, pp. 20-21. Media: Lippincott Williams & Wilkins.
25. RUBIN, E.J. (2005). Toward a new therapy for tuberculosis. N. Engl. J. Med., 352, 933-934.
26. RYAN, D.M. (1993). Pharmacokinetics of antibiotics in natural and experimental superficial compartments in animals and humans. J. Antimicrob. Chemother., 31 (Suppl D), 1-6.
27. SCHLICHTING, I., BERENDZEN, J., CHU, K., STOCK, A.M., MAVES, S.A., BENSON, D.E., SWEET, R.M., RINGE, D., PETSKO, G.A. & SLIGAR, S.G. (2000). The catalytic pathway of cytochrome P450cam at atomic resolution. Science, 287, 1615-1622.
28. TATEISHI, T., KUMAI, T., WATANABE, M., NAKURA, H., TANAKA, M. & KOBAYASHI, S. (1999). Ticlopidine decreases the in vivo activity of CYP2C19 as measured by omeprazole metabolism. Br. J. Clin. Pharmacol., 47, 454-457.
29. TUCKER, G.T., HOUSTON, J.B. & HUANG, S.M. (2001). Optimizing drug development: strategies to assess drug metabolism/transporter interaction potential - toward a consensus. Pharm. Res., 18, 1071-1080.
30. WILLIAMS, D.L.H. (1988). Nitrosation. New York: Cambridge University Press.