Prodrugs and soft drugs

Pharmacological Reports

Volumn 58, Issue 5, 2006, Pages 599-613

  Stańczak, Andrzej ^a   Ferra, Anna ^a  

^a Medical University   (Poland)

Author keywords

ADEPT; Bioprecursos; Drug delivery system; GDEPT; Prodrugs; Soft drugs

Indexed keywords

ACETONE; ACICLOVIR; ADRENALIN; AMPICILLIN; BARBITURIC ACID DERIVATIVE; BROMAZEPAM; CLINDAMYCIN PHOSPHATE; CYCLOPHOSPHAMIDE; DIAZEPAM; DIPIVEFRINE; DRUG DERIVATIVE; ESTRONE; ETHYL LOFLAZEPATE; FAMCICLOVIR; FOSFESTROL; HALOPERIDOL; HALOPERIDOL DECANOATE; HETACILLIN; HEXOBARBITAL; LEVODOPA; MERCAPTOPURINE; METHENAMINE; NALTREXONE; PRODRUG; PROPRANOLOL; SOFT DRUG; TEMOPORFIN; TIRAPAZAMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALACICLOVIR;

CLINICAL TRIAL; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG DOSE REGIMEN; DRUG METABOLISM; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; ENZYME MECHANISM; HERPES SIMPLEX; HERPES ZOSTER; HUMAN; MALIGNANT NEOPLASTIC DISEASE; METABOLITE; NONHUMAN; PARKINSON DISEASE; PHYSICAL CHEMISTRY; REVIEW; STOMACH HEMORRHAGE; STOMACH IRRITATION; SUSTAINED DRUG RELEASE; URINARY TRACT INFECTION;

EID: 33750984794     PISSN: 22995684     EISSN: 22995684     Source Type: Journal    
DOI: None     Document Type: Review

References (41)

1. Akarada M, Ohmari M, Harada K, Araki N, Saithoh T, Fuijmura A: Different accumulation of termocapril and enalapril during repeated dosing in elderly patients. Br J Clin Pharmacol, 2005, 49, 489.
2. Albert A: Chemical aspects of selective toxicity. Nature, 1958, 182, 421-423.
3. Berner, Bret: United States Patent Application 20040185105, US Patent& Trademark.
4. Bödor N, Buchwald P: Soft drug design: general principles and recent applications. Med Res Rev, 2000, 20, 58-101.
5. Bodor N: Novel approaches for the design of membrane transport properties of drugs. In: design of biophamaceutical properties through proanugs and analogs. Roche EB Ed. Academy of Pharmaceutical Sciences: Washington 1977, 98-135.
6. Bonvier E, Thirot S, Schmidt F, Monneret C: A new paclitaxel prodrug for use in ADEPT strategy. Org Biomol Chem, 2003, 1, 3343-3352.
7. Borgman RJ, McPfillips JJ, Stietzel RE, Goodman IJ: Synthesis and pharmacology of centrally acting dopamine derivatives and analogs in relation to Parkinson's disease. J Med Chem, 1973, 16, 630-633.
8. Chambon JP, Perio A, Demarne H, Hallot A, Dantzer R, Roncucci R, Biziere K: Ethyl Loflazepate: a prodrug from the benzodiazepine series designed to dissociate anxiolytic and sedative activities. Arzneimittelforschung, 1985, 35, 1573-1577.
9. Chandrasetchar U, Giridhar T, Ashima KM: Synthesis, stereoselective enzymatic hydrolysis, and skin permeation of diastereomeric propranolol ester prodrug. J Pharm Sci., 2000, 88, 544-550.
10. DeMaster EG, Shirota FN, Nagasawa HT: Microsomal N-depropargylation of pargyline to propiolaldehyde an irreversible of mitochondrial aldehyde dehydrogenase. Adv Exp Med Biol, 1980, 132, 219-228.
11. Friend DR, Chang GW: A colon-specific drug-delivery system based on drug glycosides and the glycosides of colonic bacteria. J Med Chem, 1984, 27, 261-266.
12. Graffner-Nordberg M: Approaches to soft drug analogues of dihydrofolate reductase inhibitors. Design and synthesis. Doctoral thesis. Acta Univ Uppsala, 2001, abstr. 251.
13. Han H-K, Amidon GL: Targeted prodrug design to optimize drug delivery, AAPS PharmSci, 2000, 2, (http//www.pharmsci.org/) article 6, 1-11.
14. Huang JA, Buchwald P, Bodor N: Design and evaluation of new soft anticholinergic agents. Drug Dev Res, 1998, 43, 117-127.
15. IUPAC Pure & Appl. Chem., 1998, 70, 1129-1143.
16. Jiunn HL, Lu AYH: Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev, 1997, 49, 403-449.
17. Jounaidi Y, Waxman DJ: Combination of the bioreductive drug tirapazamine with the chemotherapeutic prodrug cyclophosphamide for P450/ P450-roductase-based on cancer drug therapy. Cancer Res, 2000, 60, 3761-3769.
18. Kline MY, Torgov BA, Mendelsohn ChG, Cerveny PD: Novel antitumor prodrugs designed for activation by matrix metalloproteinases-2 and -9. Mol Pharm, 2004, 1, 9-22.
19. Leong CH: Urinary tract infection. The Hong Kong Practitioner, 1978, 1, 1-6.
20. Luo JP, Hubbard JW, Midha KK: Studies on the mechanism of adsorption of depot neuroleptics: fluphenazine deconoate in sesame oil. Pharm Res, 1997, 14, 1079-1084.
21. Misiura K, Szymanowicz D, Kusnierczyk D, Wietrzyk J, Opolski A: Isophosphoramide mustard analogues as prodrugs for anticancer gene-directed enzyme-prodrug therapy (GDEPT). Acta Bioch Pol, 2002, 49, 169-176.
22. Nakamura M, Shirasawe E, Hikida M: Characterization of esterases involved in the hydrolysis of dipiveffin hydrochloride. Ophtalmic Res, 1993, 25, 46-51.
23. Patrick GL (Ed.): An Introduction to Medical Chemistry. 2nd edn., Oxford, 2001.
24. Paternotte J, Fan HJ, Screve P; Cleasen M, Tulkens PM, Sonveaux E: Synthesis and hydrolysis of basic and dibasic amicillin esters tailored for intracellular accumulation. Biorg Med Chem, 2001, 493-502.
25. Patterson AV, Saunders MP, Greco O: Prodrugs in genetic chemoradiotherapy. Curr Pharm Des, 2003, 9, 2131-2154.
26. Phadhya TA, Gluckman JL: Photodynamic therapy in otolaryngology. Curr Opin Otolaryngol Head Neck Surg 1997, 7, 57.
27. Rapaka RS (Ed.): Membranes and Barriers: Targeted Drug Delivery, NIDA Research Monograph 154 (1995), 1-264.
28. Reusser P: Antiviral therapy: current option and challenges. Schweiz Med Wochenschr, 2000,130, 101-112.
29. Robinson MA, Charlton ST, Garnier P, Wang XT, Davis SS, Perkins AC, Frier M et al.: LEAPT: lectin-directed enzyme-activated. prodrug therapy. Proc Natl Acad Sci USA, 2004, 101, 14527-14532.
30. Saunders NR, Habgood MD, Dziegielewska KM: Barrier mechanisms in the brain, 1. Adult brain. Clin Exp Pharm Phys, 1999, 26, 11-19.
31. Schwartz PS, Chen CS, Waxman DJ: Sustained P450 expression and prodrug activation in bolus cyclophosphamide - treated cultured tumor cells. Impact of prodrug schedule on P450 gene-directed prodrug therapy. Cancer Drug Therapy, 2003, 10, 571-582.
32. Stinchcomb AL, Hammel DC, Challapalli PVN, Paxton EW, Swaan PW, Klauser M: Naltrexone ester prodrug bioconversion in a human epidermis equivalent. Annual Meeting AAPA, Toronto, 2002. J Pharm Sci, 2002, 91, 2571-2578.
33. Surya H, Prakash R: Capping drugs: development of prodrugs-resonance. 2003, www.ias.a:c.in/resonance/Feb2003/Pdf/Feb2003/19-27.pdf.
34. Thorsteinsson T, Massan M, Kristinsson KG, Himarsson H, Loftsson J: Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds. J Med Chem, 2003, 46, 4173-4181.
35. Truelove JE, Hussain AA, Kostenbauder HB: Synthesis of 1-O-(2'-acetoxy)-bezoyl-alpha-D-2-deoxyglucopyrase, a novel aspirin prodrug. J Pharm Sci, 1980, 69, 231-232.
36. Tsujia YT: Kinetic approach to the development in bet-alactam antibiotics. Prodrugs (1). Simulaneous determination of hetacillin and ampicillin, and its application to the stability of hetacillin in aqueous solutions. Chem Pharm Bull, 1974, 22, 2434-2443.
37. Wentworth P, Datta A, Blakley D, Boyle T, Partridge LJ, Blackburn GM: Toward antibody-directed "abzyme" prodrug therapy, ADAPT: carbarnate prodrug activation by a catalytic antibody and its in vitro application to human tumor cell killing Proc Natl Acad Sci USA, 1996, 93, 799-803
38. Wermuth CG: Designing prodrugs and bioprecursors. In: Drug Design: Fact or Fantasy, Ed. Jolles G, Woolridge KRH, Academic Press, London, 1984, 47-72.
39. William AD: Suicide gene therapy. J Biomed Biotechnol, 2003, 1, 48-70.
40. Zajac M, Pawelczyk E: Chemistry of Drugs. Medical Academy, Poznań 2000.
41. Zins BJ, Sandborn WJ, McKinney JA, Mays DC, van Os EC, Tremaine WJ, Mahoney DW et al.: A dose-ranging study of azathioprine pharmacokinetics after single-dose administration of a delayed-release oral formulation. J Clin Pharm, 1997, 37, 38-46.