Phosphonate prodrugs: an overview and recent advances

USC-087 protects Syrian hamsters against lethal challenge with human species C adenoviruses

(2018) Karoly Toth et al.   ANTIVIRAL RESEARCH

Expansion of human γδ T cells for adoptive immunotherapy using a bisphosphonate prodrug

(2018) Yoshimasa Tanaka et al.   CANCER SCIENCE

The expanding role of prodrugs in contemporary drug design and development

(2018) Jarkko Rautio et al.   NATURE REVIEWS DRUG DISCOVERY

The Methylerythritol Phosphate Pathway: Promising Drug Targets in the Fight against Tuberculosis

(2018) Xu Wang et al.   ACS Infectious Diseases

MEPicides: α,β-Unsaturated Fosmidomycin Analogues as DXR Inhibitors against Malaria

(2018) Xu Wang et al.   JOURNAL OF MEDICINAL CHEMISTRY

Safety, pharmacokinetics and pharmacogenetics of a single ascending dose of pradefovir, a novel liver-targeting, anti-hepatitis B virus drug, in healthy Chinese subjects

(2017) Yanhua Ding et al.   Hepatology International

Synthesis and Evaluation of Asymmetric Acyclic Nucleoside Bisphosphonates as Inhibitors of Plasmodium falciparum and Human Hypoxanthine–Guanine–(Xanthine) Phosphoribosyltransferase

(2017) Petr Špaček et al.   JOURNAL OF MEDICINAL CHEMISTRY

Expanding the Antiviral Spectrum of 3-Fluoro-2-(phosphonomethoxy)propyl Acyclic Nucleoside Phosphonates: Diamyl Aspartate Amidate Prodrugs

(2017) Min Luo et al.   JOURNAL OF MEDICINAL CHEMISTRY

Phosphinophosphonates and Their Tris-pivaloyloxymethyl Prodrugs Reveal a Negatively Cooperative Butyrophilin Activation Mechanism

(2017) Rebekah R. Shippy et al.   JOURNAL OF MEDICINAL CHEMISTRY

The ProTide Prodrug Technology: From the Concept to the Clinic

(2017) Youcef Mehellou et al.   JOURNAL OF MEDICINAL CHEMISTRY

Kinetin Riboside and Its ProTides Activate the Parkinson’s Disease Associated PTEN-Induced Putative Kinase 1 (PINK1) Independent of Mitochondrial Depolarization

(2017) Laura Osgerby et al.   JOURNAL OF MEDICINAL CHEMISTRY

Synthesis and antiviral evaluation of base-modified deoxythreosyl nucleoside phosphonates

(2017) Chao Liu et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Switching from tenofovir disoproxil fumarate to tenofovir alafenamide coformulated with rilpivirine and emtricitabine in virally suppressed adults with HIV-1 infection: a randomised, double-blind, multicentre, phase 3b, non-inferiority study

(2017) Chloe Orkin et al.   Lancet HIV

Anti-Tumor Activity and Immunotherapeutic Potential of a Bisphosphonate Prodrug

(2017) Yoshimasa Tanaka et al.   Scientific Reports

MEPicides: potent antimalarial prodrugs targeting isoprenoid biosynthesis

(2017) Rachel L. Edwards et al.   Scientific Reports

A phase 1 randomized placebo-controlled safety and pharmacokinetic trial of a tenofovir disoproxil fumarate vaginal ring

(2016) Marla J. Keller et al.   AIDS

Tenofovir alafenamide: A novel prodrug of tenofovir for the treatment of Human Immunodeficiency Virus

(2016) Adrian S. Ray et al.   ANTIVIRAL RESEARCH

A new motif for inhibitors of geranylgeranyl diphosphate synthase

(2016) Benjamin J. Foust et al.   BIOORGANIC & MEDICINAL CHEMISTRY

The ProTides Boom

(2016) Youcef Mehellou   ChemMedChem

Design and Synthesis of Fluorescent Acyclic Nucleoside Phosphonates as Potent Inhibitors of Bacterial Adenylate Cyclases

(2016) Petra Břehová et al.   ChemMedChem

Targeting Cancer Cells with a Bisphosphonate Prodrug

(2016) Kenji Matsumoto et al.   ChemMedChem

Innovation in the pharmaceutical industry: New estimates of R&D costs

(2016) Joseph A. DiMasi et al.   JOURNAL OF HEALTH ECONOMICS

HMBPP Analog Prodrugs Bypass Energy-Dependent Uptake To Promote Efficient BTN3A1-Mediated Malignant Cell Lysis by Vγ9Vδ2 T Lymphocyte Effectors

(2016) Ashley M. Kilcollins et al.   JOURNAL OF IMMUNOLOGY

Discovery of Orally Available Prodrugs of the Glutamate Carboxypeptidase II (GCPII) Inhibitor 2-Phosphonomethylpentanedioic Acid (2-PMPA)

(2016) Pavel Majer et al.   JOURNAL OF MEDICINAL CHEMISTRY

Reduction Sensitive Lipid Conjugates of Tenofovir: Synthesis, Stability, and Antiviral Activity

(2016) Kyle E. Giesler et al.   JOURNAL OF MEDICINAL CHEMISTRY

Amidate Prodrugs of Deoxythreosyl Nucleoside Phosphonates as Dual Inhibitors of HIV and HBV Replication

(2016) Chao Liu et al.   JOURNAL OF MEDICINAL CHEMISTRY

Nucleoside Phosphate and Phosphonate Prodrug Clinical Candidates

(2016) Peter J. Thornton et al.   JOURNAL OF MEDICINAL CHEMISTRY

Next-Generation Reduction Sensitive Lipid Conjugates of Tenofovir: Antiviral Activity and Mechanism of Release

(2016) Kyle E. Giesler et al.   JOURNAL OF MEDICINAL CHEMISTRY

Structure–Activity Relationships of the MEPicides: N-Acyl and O-Linked Analogs of FR900098 as Inhibitors of Dxr from Mycobacterium tuberculosis and Yersinia pestis

(2016) Géraldine San Jose et al.   ACS Infectious Diseases

Efficacy and safety of tenofovir alafenamide versus tenofovir disoproxil fumarate given as fixed-dose combinations containing emtricitabine as backbones for treatment of HIV-1 infection in virologically suppressed adults: a randomised, double-blind, active-controlled phase 3 trial

(2016) Joel E Gallant et al.   Lancet HIV

Antimalarial activity of prodrugs of N-branched acyclic nucleoside phosphonate inhibitors of 6-oxopurine phosphoribosyltransferases

(2015) Dana Hocková et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Synthesis and antimalarial evaluation of prodrugs of novel fosmidomycin analogues

(2015) Ana Maria Faísca Phillips et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Synthesis and Evaluation of Novel Acyclic Nucleoside Phosphonates as Inhibitors ofPlasmodium falciparumand Human 6-Oxopurine Phosphoribosyltransferases

(2015) Martin M. Kaiser et al.   ChemMedChem

Bisamidate Prodrugs of 2-Substituted 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA, adefovir) as Selective Inhibitors of Adenylate Cyclase Toxin fromBordetella pertussis

(2015) Michal Česnek et al.   ChemMedChem

A Treatment Algorithm for the Management of Chronic Hepatitis B Virus Infection in the United States: 2015 Update

(2015) Paul Martin et al.   Clinical Gastroenterology and Hepatology

Twenty-eight day safety, antiviral activity, and pharmacokinetics of tenofovir alafenamide for treatment of chronic hepatitis B infection

(2015) Kosh Agarwal et al.   JOURNAL OF HEPATOLOGY

Prodrugs of Reverse Fosmidomycin Analogues

(2015) Karin Brücher et al.   JOURNAL OF MEDICINAL CHEMISTRY

First Crystal Structures of Mycobacterium tuberculosis 6-Oxopurine Phosphoribosyltransferase: Complexes with GMP and Pyrophosphate and with Acyclic Nucleoside Phosphonates Whose Prodrugs Have Antituberculosis Activity

(2015) Wai Soon Eng et al.   JOURNAL OF MEDICINAL CHEMISTRY

Tenofovir alafenamide versus tenofovir disoproxil fumarate, coformulated with elvitegravir, cobicistat, and emtricitabine, for initial treatment of HIV-1 infection: two randomised, double-blind, phase 3, non-inferiority trials

(2015) Paul E Sax et al.   LANCET

Correction of a genetic deficiency in pantothenate kinase 1 using phosphopantothenate replacement therapy

(2015) Stephen P. Zano et al.   MOLECULAR GENETICS AND METABOLISM

ProTides of N-(3-(5-(2′-deoxyuridine))prop-2-ynyl)octanamide as potential anti-tubercular and anti-viral agents

(2014) Christopher McGuigan et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Synthesis of Nucleoside Phosphate and Phosphonate Prodrugs

(2014) Ugo Pradere et al.   CHEMICAL REVIEWS

PMPA and PMEA prodrugs for the treatment of HIV infections and human papillomavirus (HPV) associated neoplasia and cancer

(2014) Fabrizio Pertusati et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Bisphosphonate prodrugs: Synthesis and biological evaluation in HuH7 hepatocarcinoma cells

(2014) Maelle Monteil et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Development of CMX001 (Brincidofovir) for the treatment of serious diseases or conditions caused by dsDNA viruses

(2014) Diana F Florescu et al.   Expert Review of Anti-Infective Therapy

Amidate Prodrugs of 9-[2-(Phosphonomethoxy)Ethyl]Adenine as Inhibitors of Adenylate Cyclase Toxin from Bordetella pertussis

(2013) Markéta Šmídková et al.   ANTIMICROBIAL AGENTS AND CHEMOTHERAPY

In vitro evaluation of 9-(2-phosphonylmethoxyethyl)adenine ester analogues, a series of anti-HBV structures with improved plasma stability and liver release

(2013) Sha Liao et al.   ARCHIVES OF PHARMACAL RESEARCH

The effect of chain length and unsaturation on Mtb Dxr inhibition and antitubercular killing activity of FR900098 analogs

(2013) Emily R. Jackson et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Evaluation of Novel Acyclic Nucleoside Phosphonates against Human and Animal Gammaherpesviruses Revealed an Altered Metabolism of Cyclic Prodrugs upon Epstein-Barr Virus Reactivation in P3HR-1 Cells

(2013) N. Coen et al.   JOURNAL OF VIROLOGY

CMX001 to Prevent Cytomegalovirus Disease in Hematopoietic-Cell Transplantation

(2013) Francisco M. Marty et al.   NEW ENGLAND JOURNAL OF MEDICINE

Design, synthesis, and biological evaluation of C1–phosphonamidate analogues of 2-deoxy-d-ribose-1-phosphate

(2013) Maurizio Quintiliani et al.   TETRAHEDRON

Design of potential bisubstrate inhibitors against Mycobacterium tuberculosis (Mtb) 1-deoxy-d-xylulose 5-phosphate reductoisomerase (Dxr)—evidence of a novel binding mode

(2013) Géraldine San Jose et al.   MedChemComm

Growth inhibition of Mycobacterium smegmatis by prodrugs of deoxyxylulose phosphate reducto-isomerase inhibitors, promising anti-mycobacterial agents

(2012) Sarah Ponaire et al.   EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Antibacterial and antitubercular activity of fosmidomycin, FR900098, and their lipophilic analogs

(2011) Eugene Uh et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Geranylgeranyl Diphosphate Synthase: An Emerging Therapeutic Target

(2011) A J Wiemer et al.   CLINICAL PHARMACOLOGY & THERAPEUTICS

Tyrosine-Based 1-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) Prodrugs: Synthesis, Stability, Antiviral Activity, and in Vivo Transport Studies

(2011) Valeria M. Zakharova et al.   JOURNAL OF MEDICINAL CHEMISTRY

Phosphoramidate ProTides of the Anticancer Agent FUDR Successfully Deliver the Preformed Bioactive Monophosphate in Cells and Confer Advantage over the Parent Nucleoside

(2011) Christopher McGuigan et al.   JOURNAL OF MEDICINAL CHEMISTRY

Development of Hexadecyloxypropyl Tenofovir (CMX157) for Treatment of Infection Caused by Wild-Type and Nucleoside/Nucleotide-Resistant HIV

(2010) E. R. Lanier et al.   ANTIMICROBIAL AGENTS AND CHEMOTHERAPY

Discovery of GS-9131: Design, synthesis and optimization of amidate prodrugs of the novel nucleoside phosphonate HIV reverse transcriptase (RT) inhibitor GS-9148

(2010) Richard L. Mackman et al.   BIOORGANIC & MEDICINAL CHEMISTRY

A prodrug approach towards the development of tricyclic-based FBPase inhibitors

(2010) Tomoharu Tsukada et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Synthesis of Ester Prodrugs of 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as Anti-Poxvirus Agents

(2010) Marcela Krečmerová et al.   JOURNAL OF MEDICINAL CHEMISTRY

Discovery of a β-d-2′-Deoxy-2′-α-fluoro-2′-β-C-methyluridine Nucleotide Prodrug (PSI-7977) for the Treatment of Hepatitis C Virus

(2010) Michael J. Sofia et al.   JOURNAL OF MEDICINAL CHEMISTRY

Serine Side Chain-Linked Peptidomimetic Conjugates of Cyclic HPMPC and HPMPA: Synthesis and Interaction with hPEPT1†

(2010) Larryn W. Peterson et al.   MOLECULAR PHARMACEUTICS

Design and Synthesis of Dually Branched 5′-Norcarbocyclic Adenosine Phosphonodiester Analogue as a New Anti-HIV Prodrug

(2010) Chang Hyun Oh et al.   NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS

Synthesis and Early Development of Hexadecyloxypropyl-cidofovir: An Oral Antipoxvirus Nucleoside Phosphonate

(2010) Karl Y. Hostetler   Viruses-Basel

Aryloxy Phosphoramidate Triesters: a Technology for Delivering Monophosphorylated Nucleosides and Sugars into Cells

(2009) Youcef Mehellou et al.   ChemMedChem

Nucleotide Analogue Prodrug Tenofovir Disoproxil Enhances Lymphoid Cell Loading following Oral Administration in Monkeys

(2009) Lucie Durand-Gasselin et al.   MOLECULAR PHARMACEUTICS

Pivaloyloxymethyl-modified isoprenoid bisphosphonates display enhanced inhibition of cellular geranylgeranylation

(2008) Andrew J. Wiemer et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Discovery of Phosphonic Diamide Prodrugs and Their Use for the Oral Delivery of a Series of Fructose 1,6-Bisphosphatase Inhibitors

(2008) Qun Dang et al.   JOURNAL OF MEDICINAL CHEMISTRY

Prodrugs of Phosphates and Phosphonates

(2008) Scott J. Hecker et al.   JOURNAL OF MEDICINAL CHEMISTRY

Pradefovir: A Prodrug That Targets Adefovir to the Liver for the Treatment of Hepatitis B

(2008) K. Raja Reddy et al.   JOURNAL OF MEDICINAL CHEMISTRY

Synthesis and Biological Evaluation of a Series of Liver-Selective Phosphonic Acid Thyroid Hormone Receptor Agonists and Their Prodrugs

(2008) Serge H. Boyer et al.   JOURNAL OF MEDICINAL CHEMISTRY

Your Prodrug Releases Formaldehyde: Should You Be Concerned? No!

(2008) Sundeep S. Dhareshwar et al.   JOURNAL OF PHARMACEUTICAL SCIENCES

Serine Peptide Phosphoester Prodrugs of Cyclic Cidofovir: Synthesis, Transport, and Antiviral Activity

(2008) Ulrika Eriksson et al.   MOLECULAR PHARMACEUTICS