Thermal decomposition mechanism of tenofovir disoproxil fumarate

Wu, C. H.; You, Jingsong; Wang, Xue Jie

doi:10.1007/s10973-017-6910-3

Cited by 12 publications

(9 citation statements)

References 13 publications

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“…This suggests lesser fiber stiffness when drugs are present, which is consistent with the different lipophilicity of drugs and polymer. Thermograms of liposomes-in-PVA fibers did not feature typical melting endotherms of drugs (TDF at 115 • C [34] and FTC 180 • C [35]) or lipids, thus suggesting good miscibility/incorporation of drugs and liposomes in the polymeric matrix. However, a small reduction in T m was observed upon drug/liposome addition, which was accompanied by a marked increase in the crystallinity of the polymeric matrix.…”

Section: Physicochemical and Mechanical Characterization Of Tdf/ftcloaded Fibersmentioning

confidence: 93%

Electrospun fibers for vaginal administration of tenofovir disoproxil fumarate and emtricitabine in the context of topical pre-exposure prophylaxis

Nunes

Bogas

Faria

et al. 2021

Journal of Controlled Release

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Women are particularly vulnerable to sexual HIV-1 transmission. Oral pre-exposure prophylaxis (PrEP) with tenofovir disoproxil fumarate and emtricitabine (TDF/FTC) is highly effective in avoiding new infections in men, but protection has only been shown to be moderate in women. Such differences have been associated, at least partially, to poor drug penetration of the lower female genital tract and the need for strict adherence to continuous daily oral intake of TDF/FTC. On-demand topical microbicide products could help circumvent these limitations. We developed electrospun fibers based on polycaprolactone (PCL fibers) or liposomes associated to poly(vinyl alcohol) (liposomes-in-PVA fibers) for the vaginal co-delivery of TDF and FTC, and assessed their pharmacokinetics in mice. PCL fibers and liposomes-in-PVA fibers were tested for morphological and physicochemical properties using scanning electron microscopy, differential scanning calorimetry and X-ray diffractometry. Fibers featured organoleptic and mechanical properties compatible with their suitable handling and vaginal administration. Fluorescent quenching of mucin in vitroused as a proxy for mucoadhesionwas intense for PCL fibers, but mild for liposomes-in-PVA fibers. Both fibers were shown safe in vitro and able to rapidly release drug content (15-30 min) under sink conditions. Liposomes-in-PVA fibers allowed increasing genital drug concentrations after a single intravaginal administration when compared to continuous daily treatment for five days with 25-times higher oral doses. For instance, the levels of tenofovir and FTC in vaginal lavage were around 4-and 29-fold higher, respectively. PCL fibers were also superior to oral treatment, although to a minor extent (approximately 2-fold higher drug concentrations in lavage). Vaginal tissue drug levels were generally low for all treatments, while systemic drug exposure was negligible in the case of fibers. These data suggest that proposed fibers may provide an interesting alternative or an ancillary option to oral PrEP in women.

show abstract

Section: Physicochemical and Mechanical Characterization Of Tdf/ftcloaded Fibersmentioning

confidence: 93%

Electrospun fibers for vaginal administration of tenofovir disoproxil fumarate and emtricitabine in the context of topical pre-exposure prophylaxis

Nunes

Bogas

Faria

et al. 2021

Journal of Controlled Release

View full text Add to dashboard Cite

show abstract

“…This suggests lesser fiber stiffness when drugs are present, which is consistent with the different lipophilicity of drugs and polymer. Thermograms of liposomes-in-PVA fibers did not feature typical melting endotherms of drugs (TDF at 115 °C [34] and FTC 180 °C [35]) or lipids, thus suggesting good miscibility/incorporation of drugs and liposomes in the polymeric matrix. However, a small reduction in Tm was observed upon drug/liposome addition, which was accompanied by a marked increase in the crystallinity of the polymeric matrix.…”

Section: Physicochemical and Mechanical Characterization Of Tdf/ftc-loaded Fibersmentioning

confidence: 93%

Electrospun fibers for vaginal administration of tenofovir disoproxil fumarate and emtricitabine in the context of topical pre-exposure prophylaxis

Nunes

Bogas

Faria

et al. 2021

Preprint

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Women are particularly vulnerable to sexual HIV-1 transmission. Oral pre-exposure prophylaxis (PrEP) with tenofovir disoproxil fumarate and emtricitabine (TDF/FTC) is highly effective in avoiding new infections in men, but protection has only been shown moderate in women. Such differences have been associated, at least partially, to poor drug penetration of the lower female genital tract and the need for strict adherence to continuous daily oral intake of TDF/FTC. On-demand topical microbicide products could help circumventing these limitations. We developed electrospun fibers based on polycaprolactone (PCL fibers) or liposomes associated to poly(vinyl alcohol) (liposomes-in-PVA fibers) for the vaginal co-delivery of TDF and FTC, and assessed their pharmacokinetics in mice. PCL fibers and liposomes-in-PVA fibers were tested for morphological and physicochemical properties using scanning electron microscopy, differential scanning calorimetry and X-ray diffractometry. Fibers featured organoleptic and mechanical properties compatible with their suitable handling and vaginal administration. Fluorescent quenching of mucin in vitro (used as a proxy for mucoadhesion) was intense for PCL fibers, but mild for liposomes-in-PVA fibers. Both fibers were shown safe in vitro and able to rapidly release drug content (15-30 min) under sink conditions. Liposomes-in-PVA fibers allowed increasing genital drug concentrations after a single intravaginal administration when compared to continuous daily treatment with 25-times higher oral doses. For instance, the levels of tenofovir and FTC in vaginal lavage were around 4- and 29-fold higher, respectively. PCL fibers were also superior to oral treatment, although to a minor extent (approximately 2-fold higher drug concentrations in lavage). Vaginal tissue drug levels were generally low for all treatments, while systemic drug exposure was negligible in the case of fibers. These data suggest that proposed fibers may provide an interesting alternative or an ancillary option to oral PrEP in women.

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“…One of the NRTIs, Tenofovir disoproxil fumarate (TDF, trade name Viread ® ) was researched and developed by Gilead Sciences, Inc. Its International Union of Pure and Applied Chemistry (IUPAC) name is Bis{[(isopropoxycarbonyl)oxy]methyl}({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl) phosphonate fumarate. TDF has been approved by the Food and Drug Administration (FDA) for the treatment of AIDS and hepatitis B, and it appears in the list of essential drugs of the World Health Organization (WHO) [ 4 ]. TDF is a precursor of Tenofovir (TFV).…”

Section: Introductionmentioning

confidence: 99%

Fast and Ultrasensitive Electrochemical Detection for Antiviral Drug Tenofovir Disoproxil Fumarate in Biological Matrices

et al. 2022

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Tenofovir disoproxil fumarate (TDF) is an antiretroviral medication with significant curative effects, so its quantitative detection is important for human health. At present, there are few studies on the detection of TDF by electrochemical sensors. This work can be a supplement to the electrochemical detection of TDF. Moreover, bare electrodes are susceptible to pollution, and have high overvoltage and low sensitivity, so it is crucial to find a suitable electrode material. In this work, zirconium oxide (ZrO2) that has a certain selectivity to phosphoric acid groups was synthesized by a hydrothermal method with zirconyl chloride octahydrate as the precursor. A composite modified glassy carbon electrode for zirconium oxide-chitosan-multiwalled carbon nanotubes (ZrO2-CS-MWCNTs/GCE) was used for the first time to detect the TDF, and achieved rapid, sensitive detection of TDF with a detection limit of sub-micron content. The ZrO2-CS-MWCNTs composite was created using sonication of a mixture of ZrO2 and CS-MWCNTs solution. The composite was characterized using scanning electron microscopy (SEM) and cyclic voltammetry (CV). Electrochemical analysis was performed using differential pulse voltammetry (DPV). Compared with single-material electrodes, the ZrO2-CS-MWCNTs/GCE significantly improves the electrochemical sensing of TDF due to the synergistic effect of the composite. Under optimal conditions, the proposed method has achieved good results in linear range (0.3~30 μM; 30~100 μM) and detection limit (0.0625 μM). Moreover, the sensor has the merits of simple preparation, good reproducibility and good repeatability. The ZrO2-CS-MWCNTs/GCE has been applied to the determination of TDF in serum and urine, and it may be helpful for potential applications of other substances with similar structures.

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Thermal decomposition mechanism of tenofovir disoproxil fumarate

Cited by 12 publications

References 13 publications

Electrospun fibers for vaginal administration of tenofovir disoproxil fumarate and emtricitabine in the context of topical pre-exposure prophylaxis

Electrospun fibers for vaginal administration of tenofovir disoproxil fumarate and emtricitabine in the context of topical pre-exposure prophylaxis

Electrospun fibers for vaginal administration of tenofovir disoproxil fumarate and emtricitabine in the context of topical pre-exposure prophylaxis

Fast and Ultrasensitive Electrochemical Detection for Antiviral Drug Tenofovir Disoproxil Fumarate in Biological Matrices

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