Retrovirus HIV (humans) Animal viruses resulting in cancer / AIDS 15-39%

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Presentation transcript:

Retrovirus HIV (humans) Animal viruses resulting in cancer / AIDS 15-39%

Stages of replication - RNA virus Alternative C: Retrovirus; (+) RNA virus Specific retroviral drugs Reverse transcriptase inhibitors Nucleosides (NRTIs) Non-nucleosides (NNRTIs) Protease inhibitors

Nucleoside Reverse Transcriptase Inhibitors Nucleoside analogs without 3’ OH - DNA chain termination Pro-drugs - Phosphorylated by kinases in vivo Zidovudine (AZT) Retrovir® Trizivir® Kombi prep. Stavudine Zerit® Zalcitabine (ddC)Lamividine (3TC) Epivir® Trizivir® Compivir ® Kombi prep. Didanosine (ddI) Videx® Abacavir (ABC) Trizivir® Kombi prep.

Abacavir (ABC) Carbocyclic nucleoside analog Carbovir, studied in the 1980s (Too toxic) Aristeromycin Streptomyces citricolor Cytotoxic

Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTI) Efavirenz / Sustiva Stocrin® Nevirapin Viramune® J Med Chem 2004, 5923 FDA 1998 Already resistance activity resist strains Wild type RT mutated Binds directly to TR

Non-Nucleoside everse Transcriptase Inhibitors (NNRTI) Cytotox. Geir Andresen Weak antiviral

Protease Inhibitors Solomon “oppgitt emne” Dec. 10th The HIV-1 protease is an enzyme crucial for the maturation and assembly of infectious viral particles

Science 1990, 249, 527 The two subunits are rotated 180 from each other J. Med. Chem. 1990,33, 2687 Design of C2 sym. comp. as TS(Intermed) analog of Phe-Pro cleavage (Type 1 comp. did not lead to drugs) X-ray: HIV-1 protease - C2 symmetric homodimeric -Not C2-sym. in related human proteases!

Ritonavir Norvir® -Bad water sol. and oral bioavail. -X-ray indicate modification of Cbz allowed M w >500! -Somewhat lower Mw -Thiazol instead of pyridine -FDA March 1996, now many resistant strains -Ritonavir inhib. 3A4 isozyme of CypP450 Used in combi. with other protease inhib. to suppress their metab.

Saquinavir (green) bound to HIV-1 Protease Saquinavir Fortovase® Indinavir Crixivan® Nelfinavir Viracept® Amprenavir Agenerase® Lopinavir Kaletra®