Search results for "Cyclopropane"

showing 10 items of 104 documents

Autophagy as a rescue mechanism in efavirenz-induced mitochondrial dysfunction: a lesson from hepatic cells.

2011

Efavirenz (EFV) is the most widely used non-nucleoside reverse transcriptase inhibitor applied in highly active antiretroviral therapy (HAART), the combined pharmacological treatment of the human immunodeficiency virus infection. Its use has been associated with the development of several adverse events including hepatotoxicity. The molecular pathogenesis of this effect is poorly understood but recent reports have highlighted features of mitochondrial dysfunction in hepatic cells exposed to clinically relevant concentrations of EFV. In this study, we investigated the activation of autophagy and, in particular, mitophagy, in human hepatic cells exposed to EFV. We detected the presence of alt…

CyclopropanesEfavirenzCell SurvivalMitochondrionBiologyModels Biologicalchemistry.chemical_compoundMitophagymedicineAutophagyHumansMolecular BiologyReverse-transcriptase inhibitorAutophagyCell BiologyBenzoxazinesMitochondriachemistryApoptosisAlkynesImmunologyCancer researchHepatic stellate cellHepatocytesReverse Transcriptase InhibitorsHomeostasismedicine.drugAutophagy
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Compromising mitochondrial function with the antiretroviral drug efavirenz induces cell survival-promoting autophagy

2011

Hepatotoxicity is a very common side effect associated with the pharmacological treatment of human immunodeficiency virus (HIV) infection and its pathogenesis is poorly understood. Efavirenz (EFV) is the most widely used nonnucleoside reverse transcriptase inhibitor administered for the control of HIV and some of its toxic effects in hepatic cells have been recently shown to display features of mitochondrial dysfunction. Here we studied the activation of autophagy and, in particular, mitophagy, the main mitochondrial turnover mechanism, in human hepatic cells treated with clinically relevant concentrations of this drug. EFV-treated cells had altered mitochondria, characterized by a relative…

CyclopropanesEfavirenzHepatologyAnti-HIV AgentsCell SurvivalMitochondrial TurnoverAutophagyVacuoleMitochondrionBiologyBenzoxazinesMitochondriaCell biologychemistry.chemical_compoundchemistryApoptosisAlkynesMitophagyAutophagyCancer researchHepatic stellate cellHumansChemical and Drug Induced Liver InjuryHeLa CellsHepatology
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ER stress in human hepatic cells treated with Efavirenz: Mitochondria again

2013

Background & Aims ER stress is associated with a growing number of liver diseases, including drug-induced hepatotoxicity. The non-nucleoside analogue reverse transcriptase inhibitor Efavirenz, a cornerstone of the multidrug strategy employed to treat HIV1 infection, has been related to the development of various adverse events, including metabolic disturbances and hepatic toxicity, the mechanisms of which remain elusive. Recent evidence has pinpointed a specific mitochondrial effect of Efavirenz in human hepatic cells. This study assesses the induction of ER stress by Efavirenz in the same model and the implication of mitochondria in this process. Methods Primary human hepatocytes and Hep3B…

CyclopropanesEfavirenzXBP1Anti-HIV AgentsMitochondria LiverMitochondrionBiologyPharmacologyModels BiologicalCell Linechemistry.chemical_compoundMicroscopy Electron TransmissionDownregulation and upregulationHumansSide effectsEndoplasmic Reticulum Chaperone BiPCells CulturedHepatologyEndoplasmic reticulumHepatotoxicityATF4HIVEndoplasmic Reticulum StressHIV Reverse TranscriptaseBenzoxazinesMitochondriachemistryAlkynesHepatocytesHepatic stellate cellUnfolded protein responseReverse Transcriptase InhibitorsThapsigarginCalciumEfavirenzER stressBiomarkersJournal of Hepatology
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A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

2008

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1-tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2-fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, st…

CyclopropanesFluorine RadioisotopesStaining and LabelingStereochemistryOrganic ChemistryRadiosynthesisEsterasesStereoisomerismBiochemistryEsteraseStreptomycesSubstrate SpecificityCyclopropaneKinetic resolutionchemistry.chemical_compoundchemistryYield (chemistry)Ethyl acrylateOrganic chemistryStereoselectivityPhysical and Theoretical ChemistryEnantiomerTolueneOrganic & Biomolecular Chemistry
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Roflumilast N-oxide reverses corticosteroid resistance in neutrophils from patients with chronic obstructive pulmonary disease

2013

Background Glucocorticoid functions are markedly impaired in patients with chronic obstructive pulmonary disease (COPD). The phosphodiesterase 4 inhibitor roflumilast N-oxide (RNO) is the active metabolite of roflumilast approved as a treatment to reduce the risk of exacerbations in patients with severe COPD. Objective We sought to characterize the differential effects of RNO versus corticosteroids and their potential additive/synergistic effect in neutrophils from patients with COPD, thus providing scientific rationale for the combination of roflumilast with corticosteroids in the clinic. Methods Peripheral blood neutrophils were isolated from patients with COPD (n = 32), smokers (n = 7), …

CyclopropanesLipopolysaccharidesMaleMAPK/ERK pathwaymedicine.medical_specialtyNeutrophilsPrimary Cell CultureImmunologyDrug ResistanceAminopyridinesGene ExpressionComplex MixturesDexamethasoneHistone DeacetylasesPhosphatidylinositol 3-KinasesPulmonary Disease Chronic ObstructiveGlucocorticoid receptorAdrenal Cortex HormonesInternal medicineTobaccomedicineHumansImmunology and AllergyMacrophage Migration-Inhibitory FactorsDexamethasoneActive metaboliteRoflumilastAgedCOPDbusiness.industryInterleukin-8Drug SynergismMiddle Agedmedicine.diseaseIntramolecular OxidoreductasesEndocrinologyMatrix Metalloproteinase 9BenzamidesMitogen-Activated Protein Kinase PhosphatasesFemaleMacrophage migration inhibitory factorPhosphodiesterase 4 InhibitorsbusinessBiomarkersGlucocorticoidmedicine.drugJournal of Allergy and Clinical Immunology
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Safety and Pharmacokinetics of Glecaprevir/Pibrentasvir in Adults With Chronic Genotype 1–6 Hepatitis C Virus Infections and Compensated Liver Disease

2019

Background: Untreated, chronic hepatitis C virus (HCV) infection may lead to progressive liver damage, which can be mitigated by successful treatment. This integrated analysis reports the safety, efficacy, and pharmacokinetics (PK) of the ribavirin-free, direct-acting, antiviral, fixed-dose combination of glecaprevir/pibrentasvir (G/P) in patients with chronic HCV genotype 1-6 infections and compensated liver disease, including patients with chronic kidney disease stages 4 or 5 (CKD 4/5). Methods: Data from 9 Phase II and III clinical trials, assessing the efficacy and safety of G/P treatment for 8-16 weeks, were included. The presence of cirrhosis was determined at screening using a liver …

CyclopropanesLiver CirrhosisMaleAminoisobutyric AcidsPyrrolidinesCirrhosisSustained Virologic Responseadverse eventHepacivirusmedicine.disease_causeGastroenterology0302 clinical medicine030212 general & internal medicinePathologie maladies infectieusesSulfonamidesmedicine.diagnostic_testLiver DiseasesPibrentasvirMicrobiologie et protistologie [entomologiephytoparasitolog.]Infectious DiseasesData Interpretation StatisticalLiver biopsyglecaprevir/pibrentasvirHCVDrug Therapy CombinationFemale030211 gastroenterology & hepatologycompensated cirrhosisMicrobiologie et protistologie [parasitologie hum. et anim.]Microbiology (medical)medicine.medical_specialtyGenotypeProlineLactams MacrocyclicHepatitis C virusAntiviral Agents03 medical and health sciencesLeucineQuinoxalinesInternal medicinemedicineHumansAdverse effectAgedbusiness.industryGlecaprevirHepatitis C Chronicmedicine.diseaseBenzimidazolesMicrobiologie et protistologie [bacteriol.virolog.mycolog.]Transient elastographybusinesschronic kidney diseaseKidney diseaseClinical Infectious Diseases
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Safety and efficacy of ombitasvir/paritaprevir/ritonavir/dasabuvir plus ribavirin in patients over 65 years with HCV genotype 1 cirrhosis

2018

Purpose: To analyse safety and efficacy of treatment based on ombitasvir/paritaprevir/ritonavir/dasabuvir plus ribavirin in the sub-group of GT1 patients older than 65 years. Methods: We collected data extracted from the ABACUS compassionate-use nationwide Italian programme, in patients with cirrhosis due to hepatitis C virus (HCV) Genotype-1 (GT1) or 4 and at high risk of decompensation. GT1-HCV-infected patients received once-daily ombitasvir/paritaprevir, with the pharmacokinetic enhancer ritonavir (25/150/100 mg) and twice-daily dasabuvir (250 mg) plus Ribavirin (RBV) (OBV/PTV/r + DSV + RBV) for 12 (GT1b) or 24 (GT1a) weeks. Endpoints were to evaluate safety and efficacy, the latter def…

CyclopropanesLiver CirrhosisMaleCirrhosis;Dasabuvir;Elderly;Ombitasvir;ParitaprevirCirrhosis; Dasabuvir; Elderly; Ombitasvir; Paritaprevir; Aged; Aged; 80 and over; Anilides; Antiviral Agents; Biomarkers; Carbamates; Female; Hepacivirus; Hepatitis C; Chronic; Humans; Liver Cirrhosis; Macrocyclic Compounds; Male; Ribavirin; Ritonavir; Sulfonamides; Treatment Outcome; Uracil; Drug Therapy; Combination; GenotypeParitaprevirCirrhosis Dasabuvir Elderly Ombitasvir Paritaprevir Microbiology (medical) Infectious DiseasesCirrhosis; Dasabuvir; Elderly; Ombitasvir; Paritaprevir; Aged; Aged 80 and over; Anilides; Antiviral Agents; Biomarkers; Carbamates; Female; Hepacivirus; Hepatitis C Chronic; Humans; Liver Cirrhosis; Macrocyclic Compounds; Male; Ribavirin; Ritonavir; Sulfonamides; Treatment Outcome; Uracil; Drug Therapy Combination; Genotype; Microbiology (medical); Infectious DiseasesHepacivirusGastroenterologychemistry.chemical_compound0302 clinical medicineElderly2-Naphthylamine80 and overMedicineAnilides030212 general & internal medicineChronicAged 80 and overSulfonamidesDasabuvirValineGeneral MedicineHepatitis CHepatitis CTreatment OutcomeInfectious DiseasesCirrhosisCombination030211 gastroenterology & hepatologyDrug Therapy CombinationFemaleDasabuvirMacrocyclic CompoundCirrhosis; Dasabuvir; Elderly; Ombitasvir; Paritaprevir; Microbiology (medical); Infectious Diseasesmedicine.drugHumanMicrobiology (medical)medicine.medical_specialtyMacrocyclic CompoundsProlineGenotypeLactams MacrocyclicSettore MED/12 - GASTROENTEROLOGIALiver CirrhosiSulfonamideAntiviral Agents03 medical and health sciencesDrug TherapyInternal medicineRibavirinHumansDecompensationUracilAgedHepatitisAntiviral AgentCirrhosiHepaciviruRitonavirbusiness.industryRibavirinSettore MED/09 - MEDICINA INTERNAAnilideBiomarkerHepatitis C Chronicmedicine.diseaseCirrhosis; Dasabuvir; Elderly; Ombitasvir; Paritaprevir; Aged; Aged 80 and over; Anilides; Antiviral Agents; Biomarkers; Carbamates; Female; Hepacivirus; Hepatitis C Chronic; Humans; Liver Cirrhosis; Macrocyclic Compounds; Male; Ribavirin; Ritonavir; Sulfonamides; Treatment Outcome; Uracil; Drug Therapy Combination; GenotypeOmbitasvirOmbitasvirchemistryParitaprevirCarbamateRitonavirCarbamatesbusinessBiomarkers
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Real-world experience with the all-oral, interferon-free regimen of ombitasvir/paritaprevir/ritonavir and dasabuvir for the treatment of chronic hepa…

2017

Summary Real-world studies are relevant to complement clinical trials on novel antiviral therapies against chronic hepatitis C; however, clinical practice data are currently limited. This study investigated effectiveness and safety of ombitasvir/paritaprevir/ritonavir (OBV/PTV/r)±dasabuvir (DSV)±ribavirin (RBV) for treatment of HCV genotype (GT) 1 and GT4 infection in a large real-world cohort. The German Hepatitis C Registry is an observational cohort study prospectively collecting clinical practice data on direct-acting antiviral therapies. Patients with GT1/4 infection treated with OBV/PTV/r±DSV±RBV were analysed. Effectiveness was assessed by sustained virologic response in 558 patients…

CyclopropanesLiver CirrhosisMaleHepacivirusSeverity of Illness IndexCohort Studieschemistry.chemical_compound0302 clinical medicine2-NaphthylamineGermanyMedicineAnilides030212 general & internal medicineSulfonamidesDasabuvirValineHepatitis CMiddle AgedViral LoadInfectious DiseasesTreatment Outcome030211 gastroenterology & hepatologyDrug Therapy CombinationFemalemedicine.drugAdultmedicine.medical_specialtyMacrocyclic CompoundsGenotypeProlineLactams Macrocyclic03 medical and health sciencesVirologyOmbitasvir/paritaprevir/ritonavirInternal medicineHumansUracilAgedRitonavirHepatologybusiness.industryHepatitis C Chronicmedicine.diseaseVirologyOmbitasvirDiscontinuationRegimenchemistryParitaprevirRitonavirCarbamatesbusinessJournal of viral hepatitis
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Safety and efficacy of a fixed-dose combination regimen of grazoprevir, ruzasvir, and uprifosbuvir with or without ribavirin in participants with and…

2017

Background There is a need for hepatitis C virus (HCV) therapies with excellent efficacy across genotypes and in diverse populations. Part A of the C-CREST-1 and C-CREST-2 trials led to the selection of a three-drug regimen of grazoprevir (MK-5172; an HCV NS3/4A protease inhibitor; 100 mg/day) plus ruzasvir (MK-8408; an NS5A inhibitor; 60 mg/day) plus uprifosbuvir (MK-3682; an HCV NS5B polymerase inhibitor; 450 mg/day). Part B of the studies tested this combination as a single formulation in different treatment durations in a broader population. Methods Part B of these randomised, phase 2, open-label clinical trials enrolled individuals from 15 countries who were chronically infected with H…

CyclopropanesLiver CirrhosisMalePyrrolidinesSustained Virologic ResponseGastroenterologychemistry.chemical_compound0302 clinical medicinePegylated interferonGenotype030212 general & internal medicineSulfonamideseducation.field_of_studyGastroenterologyHepatitis CMiddle Aged10219 Clinic for Gastroenterology and HepatologyGrazoprevirHCVFemale030211 gastroenterology & hepatologymedicine.drugAdultmedicine.medical_specialtyGenotypePopulationFixed-dose combination610 Medicine & healthAntiviral AgentsHeterocyclic Compounds 4 or More RingsDrug Administration Schedule03 medical and health sciencesQuinoxalinesInternal medicineRibavirinmedicineHumans2715 GastroenterologyeducationUridinetherapyHepatologybusiness.industryRibavirinHepatitis C Chronicmedicine.diseaseAmidesThiazolesRegimenchemistryImmunology2721 HepatologyCarbamatesbusiness
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Real-world effectiveness of ombitasvir/paritaprevir/ritonavir±dasabuvir±ribavirin in patients with hepatitis C virus genotype 1 or 4 infection: A met…

2017

The direct-acting antiviral regimen of ombitasvir (OBV)/paritaprevir (PTV)/ritonavir (r) ± dasabuvir (DSV) ± ribavirin (RBV) demonstrated high rates of sustained viral response at post-treatment week 12 (SVR12) in clinical trials for treatment of hepatitis C virus (HCV) genotypes (GT) 1 and 4. To confirm the effectiveness of this regimen in the real world, we conducted meta-analyses of published literature on 30 April 2016. Freeman-Tukey transformation determined the SVR rate within GTs 1a, 1b, and 4, as well as specific SVR rates by cirrhosis or prior treatment experience status. Rates of virologic relapse, hepatic decompensation, drug discontinuation, and serious adverse events were also …

CyclopropanesLiver CirrhosisSustained Virologic ResponseHCV genotypes 1 and 4ComorbidityHepacivirusmedicine.disease_causeGastroenterologymeta-analysichemistry.chemical_compound0302 clinical medicineAnilides030212 general & internal medicineSulfonamidesDasabuvirValineHepatitis CViral LoadHepatitis Creal-world effectiveneInfectious DiseasesTreatment Outcome2D; 3D; HCV genotypes 1 and 4; hepatitis C; meta-analysis; real-world effectiveness; Hepatology; Infectious Diseases; Virology030211 gastroenterology & hepatologyDrug Therapy Combinationmedicine.drug3Dmedicine.medical_specialtyMacrocyclic CompoundsGenotypeProlineHepatitis C virusLactams MacrocyclicInfectious DiseaseAntiviral Agents03 medical and health sciencesInternal medicineVirologyRibavirinmedicineHumans2DRitonavirHepatologybusiness.industryRibavirinmedicine.diseaseOmbitasvirRegimenchemistryParitaprevirImmunologyRitonavirCarbamatesbusinessJournal of viral hepatitis
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