Literature DB >> 29697468

4'-Ethynyl-2-fluoro-2'-deoxyadenosine, MK-8591: a novel HIV-1 reverse transcriptase translocation inhibitor.

Martin Markowitz1, Stefan G Sarafianos2.   

Abstract

PURPOSE OF REVIEW: 4'-Ethynyl-2-fluoro-2'-deoxyadenosine (EFdA) is a nucleoside reverse transcriptase inhibitor (NRTI) with a novel mechanism of action, unique structure, and amongst NRTIs, unparalleled anti-HIV-1 activity. We will summarize its structure and function, antiviral activity, resistance profile, and potential as an antiretroviral for use in the treatment and preexposure prophylaxis of HIV-1 infection. RECENT
FINDINGS: EFdA is active against wild-type (EC50 as low as 50 pmol/l) and most highly NRTI-resistant viruses. The active metabolite, EFdA-triphosphate, has been shown to have a prolonged intracellular half-life in human and rhesus (Rh) blood cells. As a result, single drug doses tested in simian immunodeficiency virus mac251-infected Rh macaques and HIV-1-infected individuals exhibited robust antiviral activity of 7-10 days duration. Preclinical studies of EFdA as preexposure prophylaxis in the Rh macaque/simian/human immunodeficiency virus low-dose intrarectal challenge model have shown complete protection when given in clinically relevant doses.
SUMMARY: EFdA is a novel antiretroviral with activity against both wild-type and NRTI-resistant viruses. As a result of the prolonged intracellular half-life of its active moiety, it is amenable to flexibility in dosing of at least daily to weekly and perhaps longer.

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Year:  2018        PMID: 29697468      PMCID: PMC6449048          DOI: 10.1097/COH.0000000000000467

Source DB:  PubMed          Journal:  Curr Opin HIV AIDS        ISSN: 1746-630X            Impact factor:   4.283


  28 in total

1.  4'-Ethynyl nucleoside analogs: potent inhibitors of multidrug-resistant human immunodeficiency virus variants in vitro.

Authors:  E I Kodama; S Kohgo; K Kitano; H Machida; H Gatanaga; S Shigeta; M Matsuoka; H Ohrui; H Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2001-05       Impact factor: 5.191

Review 2.  Mitochondrial toxicity induced by nucleoside-analogue reverse-transcriptase inhibitors is a key factor in the pathogenesis of antiretroviral-therapy-related lipodystrophy.

Authors:  K Brinkman; J A Smeitink; J A Romijn; P Reiss
Journal:  Lancet       Date:  1999-09-25       Impact factor: 79.321

3.  Mitochondrial toxicity of nucleoside analogue reverse transcriptase inhibitors: a looming obstacle for long-term antiretroviral therapy?

Authors:  Kees Brinkman; Thomas N. Kakuda
Journal:  Curr Opin Infect Dis       Date:  2000-02       Impact factor: 4.915

4.  2'-deoxy-4'-C-ethynyl-2-fluoroadenosine, a nucleoside reverse transcriptase inhibitor, is highly potent against all human immunodeficiency viruses type 1 and has low toxicity.

Authors:  Hiroshi Ohrui
Journal:  Chem Rec       Date:  2006       Impact factor: 6.771

5.  A mechanism of AZT resistance: an increase in nucleotide-dependent primer unblocking by mutant HIV-1 reverse transcriptase.

Authors:  P R Meyer; S E Matsuura; A M Mian; A G So; W A Scott
Journal:  Mol Cell       Date:  1999-07       Impact factor: 17.970

6.  2'-Deoxy-4'-C-ethynyl-2-fluoroadenosine: a nucleoside reverse transcriptase inhibitor with highly potent activity against all HIV-1 strains, favorable toxic profiles and stability in plasma.

Authors:  Hiroshi Ohrui; Satoru Kohgo; Hiroyuki Hayakawa; Eiichi Kodama; Masao Matsuoka; Tomohiro Nakata; Hiroyuki Mitsuya
Journal:  Nucleic Acids Symp Ser (Oxf)       Date:  2006

7.  Lamivudine (3TC) resistance in HIV-1 reverse transcriptase involves steric hindrance with beta-branched amino acids.

Authors:  S G Sarafianos; K Das; A D Clark; J Ding; P L Boyer; S H Hughes; E Arnold
Journal:  Proc Natl Acad Sci U S A       Date:  1999-08-31       Impact factor: 11.205

8.  2'-deoxy-4'-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants.

Authors:  Atsushi Kawamoto; Eiichi Kodama; Stefan G Sarafianos; Yasuko Sakagami; Satoru Kohgo; Kenji Kitano; Noriyuki Ashida; Yuko Iwai; Hiroyuki Hayakawa; Hirotomo Nakata; Hiroaki Mitsuya; Eddy Arnold; Masao Matsuoka
Journal:  Int J Biochem Cell Biol       Date:  2008-04-11       Impact factor: 5.085

9.  Potent activity of a nucleoside reverse transcriptase inhibitor, 4'-ethynyl-2-fluoro-2'-deoxyadenosine, against human immunodeficiency virus type 1 infection in a model using human peripheral blood mononuclear cell-transplanted NOD/SCID Janus kinase 3 knockout mice.

Authors:  Shinichiro Hattori; Kazuhiko Ide; Hirotomo Nakata; Hideki Harada; Shinya Suzu; Noriyuki Ashida; Satoru Kohgo; Hiroyuki Hayakawa; Hiroaki Mitsuya; Seiji Okada
Journal:  Antimicrob Agents Chemother       Date:  2009-06-22       Impact factor: 5.191

10.  Activity against human immunodeficiency virus type 1, intracellular metabolism, and effects on human DNA polymerases of 4'-ethynyl-2-fluoro-2'-deoxyadenosine.

Authors:  Hirotomo Nakata; Masayuki Amano; Yasuhiro Koh; Eiichi Kodama; Guangwei Yang; Christopher M Bailey; Satoru Kohgo; Hiroyuki Hayakawa; Masao Matsuoka; Karen S Anderson; Yung-Chi Cheng; Hiroaki Mitsuya
Journal:  Antimicrob Agents Chemother       Date:  2007-06-04       Impact factor: 5.191

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  28 in total

Review 1.  Evolving understanding of HIV-1 reverse transcriptase structure, function, inhibition, and resistance.

Authors:  Francesc Xavier Ruiz; Eddy Arnold
Journal:  Curr Opin Struct Biol       Date:  2020-01-11       Impact factor: 6.809

Review 2.  Review of Real-World Implementation Data on Emtricitabine-Tenofovir Disoproxil Fumarate as HIV Pre-exposure Prophylaxis in the United States.

Authors:  Jessica L Adams; Karishma Shelley; Melanie R Nicol
Journal:  Pharmacotherapy       Date:  2019-04-01       Impact factor: 4.705

Review 3.  The Promise of Long-Acting Antiretroviral Therapies: From Need to Manufacture.

Authors:  Howard E Gendelman; JoEllyn McMillan; Aditya N Bade; Benson Edagwa; Bhavesh D Kevadiya
Journal:  Trends Microbiol       Date:  2019-04-10       Impact factor: 17.079

4.  Development of Human Immunodeficiency Virus Type 1 Resistance to 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine Starting with Wild-Type or Nucleoside Reverse Transcriptase Inhibitor-Resistant Strains.

Authors:  Maria E Cilento; Aaron B Reeve; Eleftherios Michailidis; Tatiana V Ilina; Eva Nagy; Hiroaki Mitsuya; Michael A Parniak; Philip R Tedbury; Stefan G Sarafianos
Journal:  Antimicrob Agents Chemother       Date:  2021-09-13       Impact factor: 5.191

Review 5.  Advances in Long-Acting Agents for the Treatment of HIV Infection.

Authors:  Aadia I Rana; Jose R Castillo-Mancilla; Karen T Tashima; Raphael L Landovitz
Journal:  Drugs       Date:  2020-04       Impact factor: 9.546

6.  Extended-Duration MK-8591-Eluting Implant as a Candidate for HIV Treatment and Prevention.

Authors:  Stephanie E Barrett; Ryan S Teller; Seth P Forster; Li Li; Megan A Mackey; Daniel Skomski; Zhen Yang; Kerry L Fillgrove; Gregory J Doto; Sandra L Wood; Jose Lebron; Jay A Grobler; Rosa I Sanchez; Zhen Liu; Bing Lu; Tao Niu; Li Sun; Marian E Gindy
Journal:  Antimicrob Agents Chemother       Date:  2018-09-24       Impact factor: 5.191

Review 7.  Long-acting approaches for delivery of antiretroviral drugs for prevention and treatment of HIV: a review of recent research.

Authors:  Denise A Cobb; Nathan A Smith; Benson J Edagwa; JoEllyn M McMillan
Journal:  Expert Opin Drug Deliv       Date:  2020-07-06       Impact factor: 6.648

Review 8.  Avoiding Drug Resistance in HIV Reverse Transcriptase.

Authors:  Maria E Cilento; Karen A Kirby; Stefan G Sarafianos
Journal:  Chem Rev       Date:  2021-01-28       Impact factor: 60.622

9.  Antiviral nucleoside analogs.

Authors:  Vladimir E Kataev; Bulat F Garifullin
Journal:  Chem Heterocycl Compd (N Y)       Date:  2021-05-14       Impact factor: 1.277

10.  A Phase 1 Study to Evaluate the Drug Interaction Between Islatravir (MK-8591) and Doravirine in Adults Without HIV.

Authors:  Randolph P Matthews; Deanne Jackson Rudd; Kerry L Fillgrove; Saijuan Zhang; Charles Tomek; S Aubrey Stoch; Marian Iwamoto
Journal:  Clin Drug Investig       Date:  2021-06-21       Impact factor: 2.859

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