Biopharmaceutic parameters, pharmacokinetics, transport and CYP-mediated drug interactions of IIIM-017: A novel nitroimidazooxazole analogue with anti-tuberculosis activity

European Journal of Pharmaceutical Sciences

Volumn 106, Issue , 2017, Pages 71-78

  Kour, Gurleen ^a,b   Singh, Parvinder Pal ^a   Bhagat, Asha ^a   Ahmed, Zabeer ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

Caco 2 permeability; Cytochrome P450; Nitrohydroimidazooxazole; P glycoprotein; Pharmacokinetics

Indexed keywords

ATENOLOL; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; DELAMANID; DIGOXIN; IIIM 017; ISONIAZID; MULTIDRUG RESISTANCE PROTEIN; OXAZOLE DERIVATIVE; PRETOMANID; PROPRANOLOL; RIFAMPICIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; 2-NITRO-6-(4-(TRIFLUOROMETHOXY)BENZYLOXY)-6,7-DIHYDRO-5H-IMIDAZO(2,1-B)(1,3)OXAZINE; NITROIMIDAZOLE DERIVATIVE; OPC-67683;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; CACO-2 CELL LINE; CELL MEMBRANE PERMEABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG INTERACTION; DRUG PENETRATION; DRUG PROTEIN BINDING; DRUG TRANSPORT; ENZYME INHIBITION; EQUILIBRIUM DIALYSIS; HUMAN; HUMAN CELL; IN VITRO STUDY; INTRINSIC CLEARANCE; LIPOPHILICITY; LIQUID CHROMATOGRAPHY; LIVER TOXICITY; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PERMEABILITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY; ANIMAL; BAGG ALBINO MOUSE; CHEMISTRY; COMPUTER SIMULATION; LIVER MICROSOME; METABOLISM; TRANSPORT AT THE CELLULAR LEVEL;

ANIMALS; ANTITUBERCULAR AGENTS; ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1; BIOLOGICAL TRANSPORT; CACO-2 CELLS; COMPUTER SIMULATION; DRUG INTERACTIONS; HUMANS; MICE, INBRED BALB C; MICROSOMES, LIVER; NITROIMIDAZOLES; OXAZOLES;

EID: 85020024939     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2017.05.053     Document Type: Article

References (40)

1. Artursson, P., Karlsson, J., Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelia (Caco-2) cells. Biochem. Biophys. Res. Commun. 175 (1991), 880–890.
2. Avdeef, A., Twsta, B., Physicochemical profiling in drug research: a brief survey of the state of the art of experimental techniques. Cell. Mol. Life Sci. 59:10 (2002), 1681–1689.
3. Balimane, P.V., Han, Y.-H., Chong, S., Current industrial practices of assessing permeability and P-glycoprotein interaction. AAPS J. 8 (2006), 1–13.
4. Barry, C.E., Crick, D.C., McNeil, M.R., Targeting the formation of the cell wall core of M. tuberculosis. Infect. Disord. Drug Targets 7 (2007), 182–202.
5. Brown, A.C., Parish, T., Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake. BMC Microbiol., 8, 2008, 78.
6. Coyne, K.M., Pozniak, A.L., Lamorde, M., Boffito, M., Pharmacology of second-line antituberculosis drugs and potential for interactions with antiretroviral agents. AIDS 23 (2009), 437–446.
7. Dashti, Y., Grkovic, T., Quinn, R.J., Predicting natural product value, an exploration of anti-TB drug space. Nat. Prod. Rep. 31 (2014), 990–998.
8. Eugene, Uh., Jackson, E.R., San Jose, G., Maddox, M., Lee, R.E., Boshoff, H.I., Dowd, C.S., Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs. Bioorg. Med. Chem. Lett. 21 (2011), 6973–6976.
9. Greiner, B., Eichelbaum, M., Fritz, P., The role of intestinal P-glycoprotein in the interaction of digoxin and rifampin. J. Clin. Invest. 104 (1999), 147–153.
10. Hidalgo, I.J., Raub, T.J., Borchardt, R.T., Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 96 (1989), 736–749.
11. Jackson, E.R., San Jose, G., Brothers, R.C., Edelstein, E.K., Sheldon, Z., Haymond, A., Johny, C., Boshoff, H.I., Couch, R.D., Dowd, C.S., The effect of chain length and unsaturation on Mtb Dxr inhibition and antitubercular killing activity of FR900098 analogs. Bioorg. Med. Chem. Lett. 24:2 (2014), 649–653.
12. Jones, H.M., Houston, J.B., Substrate depletion approach for determining in vitro metabolic clearance: time dependencies in hepatocyte and microsomal incubations. Drug Metab. Dispos. 32 (2004), 973–982.
13. Kmentova, I., Sutherland, H.S., Palmer, B.D., Blaser, A., Franzblau, S.G., Wan, B., Wang, Y., Ma, Z., Denny, W.A., Thompson, A.M., Synthesis and structure-activity relationships of aza and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1, 3]oxazine (PA-824). J. Med. Chem. 53 (2010), 8421–8439.
14. Koul, A., Arnoult, E., Lounis, N., Guillemont, J., Andries, K., The challenge of new drug discovery for tuberculosis. Nature 469 (2011), 483–490.
15. Lakshminarayana, S.B., Huat, T.B., Ho, P.C., Manjunatha, U.H., Dartois, V., Dick, T., Rao, S.P.S., Comprehensive physicochemical, pharmacokinetic and activity profiling of anti-TB agents. J. Antimicrob. Chemother. 70 (2015), 857–867.
16. Li, A.P., Reith, M.K., Rasmussen, A., Gorski, J.C., Hall, S.D., Xu, L., Kaminski, D.L., Cheng, L.K., Primary human hepatocytes as a tool for the evaluation of structure-activity relationship in cytochrome P450 induction potential of xenobiotics: evaluation of rifampin, rifapentine and rifabutin. Chem. Biol. Interact. 107 (1997), 17–30.
17. Lipinski, C.A., Lombardo, F., Dominy, B.W., Feeney, P.J., Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46 (2001), 3–26.
18. Makarov, V., Lechartier, B., Zhang, M., Neres, J., Sar, A.M., Raadsen, S.A., Hartkoorn, R.C., Ryabova, O.B., Vocat, A., Decosterd, L.A., Widmer, N., Bulcin, T., Bitter, W., Andries, K., Pojer, F., Dayson, P.J., Cole, S.T., Towards a new combination therapy for tuberculosis with next generation benzothiazinones. EMBO Mol. Med. 6 (2014), 372–383.
19. Matsumoto, M., Hashizume, H., Tomishige, T., Kawasaki, M., Tsubouchi, H., Sasaki, H., Shimokawa, Y., Komatsu, M., OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med., 3(11), 2006, e466.
20. Munagala, K.G., Yempalla, K.R., Singh, S., Sharma, S., Kalia, N.P., Rajput, V.S., Kumar, S., Sawant, S.D., Khan, I.A., Vishwakarma, R.A., Singh, P.P., Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: in vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation. Org. Biomol. Chem. 13 (2015), 3610–3624.
21. National Library of Medicine, PA-824-CL-007: Phase IIa Evaluation of Early Bactericidal Activity in Pulmonary tuberculosis. 2014, National Library of Medicine, National Institutes of Health, Bethesda, MD.
22. O'Shea, R., Moser, H.E., Physicochemical properties of antibacterial compounds: implications for drug discovery. J. Med. Chem. 51 (2008), 2871–2878.
23. Pritchard, J.F., Jurima-Romet, M., Reimer, M.L., Mortimer, E., Rolfe, B., Cayen, M.N., Making better drugs: decision gates in non-clinical drug development. Nat. Rev. Drug Discov. 2 (2003), 542–553.
24. Riesenman, C., Antidepressant drug interactions and the cytochrome P450 system: a critical appraisal. Pharmacotherapy 15 (1995), 84S–99S.
25. Rivers, E.C., Mancera, R.L., New anti-tuberculosis drugs with novel mechanisms of action. Curr. Med. Chem. 15 (2008), 1956–1967.
26. Ryan, N.J., Lo, J.H., Delamanid: first global approval. Drugs 74 (2014), 1041–1045.
27. Sasaki, H., Haraguchi, Y., Itotani, M., Kuroda, H., Hashizume, H., Tomishige, T., Kawasaki, M., Matsumoto, M., Komatsu, M., Tsubouchi, H., Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2, 3-dihydroimidazo[2,1-b]oxazoles. J. Med. Chem. 49 (2006), 7854–7860.
28. Schaberg, T., Rebhan, K., Lode, H., Risk factors for side-effects of isoniazid, rifampin and pyrazinamide in patients hospitalized for pulmonary tuberculosis. Eur. Respir. J. 9 (1996), 2026–2030.
29. Segel, I., Behavior analysis of rapid equilibrium and steady-state systems. Segel, I., (eds.) Enzyme Kinetics, 1975, John Wiley and Sons, New York, 54–55.
30. Shen, W.W., Cytochrome P450 monooxygenases and interactions of psychotropic drugs: a five-year update. Int. J. Psychiatry Med. 25 (1995), 277–290.
31. Somogyi, A., Muirhead, M., Pharmacokinetic interactions of cimetidine. Clin. Pharmacokinet. 12 (1987), 321–366.
32. Takacs-Novak, K., Physicochemical profiling in drug research and development. Mandic, Z., (eds.) Physico-Chemical Methods in Drug Discovery and Development, International Association of Physical Chemists (IAPC) Publishing, 2012, Zagreb, Croatia, 2–52.
33. US DHHS, FDA, CDERR, Guidance for Industry: Bioanalytical Method Validation, US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research and Center for Veterinary Medicine. 2001.
34. Veber, D.F., Johnson, S.R., Cheng, H.Y., Smith, B.R., Ward, K.W., Kopple, K.D., Molecular properties that influence the oral bioavailability of drug candidates. J. Med. Chem. 45 (2002), 2615–2623.
35. World Health Organization, Global tuberculosis report. WHO/HTM/TB/2015.22, 2015, WHO, Geneva, Switzerland.
36. Yan, Z., Caldwell, G.W., Optimization in drug discovery: in vitro methods. Kang, Y.J., (eds.) Methods in Pharmacology and Toxicology, 2004, Humana Press, Totowa, NJ.
37. Yee, D., Valiquette, C., Pelletier, M., Parisien, I., Rocher, I., Menzies, D., Incidence of serious side effects from first-line antituberculosis drugs among patients treated for active tuberculosis. Am. J. Respir. Crit. Care Med. 167 (2003), 1472–1477.
38. Yempalla, K.R., Munagala, G., Singh, S., Kour, G., Sharma, S., Chib, R., Kumar, S., Wazir, P., Singh, G.D., Raina, S., Bharate, S.S., Khan, I.A., Vishwakarma, R.A., Singh, P.P., Synthesis and biological evaluation of polar functionalities containing nitrodihydroimidazooxazoles as anti-TB agents. ACS Med. Chem. Lett. 6:10 (2015), 1059–1064.
39. Zhang, L., Strong, J.M., Qiu, W., Lesko, L.J., Huang, S.-M., Scientific perspectives on drug transporters and their role in drug interactions. Mol. Pharm. 3 (2006), 62–69.
40. Zumla, A., Nahid, P., Cole, S.T., Advances in the development of new tuberculosis drugs and treatment regimens. Nat. Rev. Drug Discov. 12 (2013), 388–404.