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Investigation into the structures and physicochemical properties of multi-component crystals of voriconazole

Chinese Chemical Letters 2023年第6期34卷 504-511页

作者： Hong-Mei Yu Bao-Xi Zhang Wen-Hui Xing Mei-Ju Liu Feng-Feng Wang Ning-Bo Gong Li Zhang Yang Lu Guan-Hua Du Beijing Key Laboratory of Polymorphic Drugs Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China National Institutes for Food and Drug Control Beijing 102629China Beijing City Key Laboratory of Drug Target Identification and Drug Screening Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

voriconazole(VZL)is a second-generation and broad-spectrum triazole against fungal infections.Being a BCS(biopharmaceutics classification system)class II compound,the poor aqueous solubility has limited its bioavailability and clinical efficacy.Aims to overcome this disadvantage,a cocrystallization strategy based on crystal engineering principles has resulted in five new multi-component crystals of VZL with maleic acid,L-tartaric,protocatechuic,gallic,and 3,5-dinitrobenzoic acids.Structure analysis revealed that the hydroxyl/carboxylic acid···triazole N_(3)hydrogen bonding interaction appears as a main supramolecular heterosynthon in the VZL multi-component crystals with organic acids.And VZL molecule has a flexible conformation in each of the five multi-component structures.The newly synthesized multi-component crystals showed impressive solubility improvement compared to that of the raw material of VZL.Molecular electrostatic potential surfaces(MEPS)analysis based on density functional(DFT)calculations revealed that hydrogen bond interactions in cocrystals mainly involved pairwise interactions in the global maxima and minima sites,but this rule is not always followed.This study indicates the potential of cocrystals to improve the solubility and dissolution rate of VZL.

关键词： Multi-component crystal voriconazole Solubility Dissolution Stability

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voriconazole in an infant with cryptococcal meningitis

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Chinese Medical Journal 2008年第3期121卷 286-288页

作者： SHEN Yin-zhong WANG Jiang-rong LU Hong-zhou Department of Infectious Diseases Shanghai Public HealthClinical Center Fudan University Shanghai 201508 China

Cryptococcus neoformans （C. neoformans） is the most common cause of fungal meningitis worldwide.1 Cryptococcal meningitis is an opportunistic infection commonly found in immunocompromised hosts, especially HIV-infected adults. It also occurs in apparently immunocompetent individuals. Rarely has it been reported in children, and it is almost nonexistent in infants. voriconazole is a member of a second generation of antifungal triazoles with broad spectrum antifungal activity, oral and parenteral bioavailability and a favorable safety profile in adults.3 This patient shows improved in vitro activity against C. neoformans when compared to fluconazole and it has been used successfully in about half the patients with refractory cryptococcosis.4 However, the efficacy and safety of voriconazole as a antifungal agent in children with cryptococcal meningitis have not been well assessed, This report described cryptococcal meningitis in a 13-day-old premature neonate who recovered without overt toxicity after voriconazole was added to an antifungal regimen that included amphotericin B and flucytosine. We focused on the response of this child with cryptococcal meningitis to voriconazole.

关键词： voriconazole cryptococcal meningitis child

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CYP2C19 Genotyping Plus Therapeutic Drug Monitoring Dependent voriconazole Treatment for Invasive Pulmonary Aspergillosis in a Patient with Liver Failure

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Infectious Diseases & Immunity 2022年第2期2卷 125-128页

作者： Chuan Shen Qian Zhao Ziyue Li Wei Wang Yalin Zhao Lingya Kong Jing Xie Caiyan Zhao Department of Infectious Disease Third Affiliated Hospital of Hebei Medical UniversityShijiazhuang 050051China Clinical Research Center for Infectious Disease of Hebei Province Shijiazhuang 050051China Office of Quality Management and Control in Healthcare Third Affiliated Hospital of Hebei Medical UniversityShijiazhuang 050051China

Invasive pulmonary aspergillosis(IPA)is a lethal infectious disease with high mortality in patients with liver failure.Early recognition of the risk factors prompting earlier diagnosis and treatment may improve the outcomes.voriconazole is recommended as the first-line drug for IPA,but hepatotoxicity limits its use in the context of liver diseases.We report a case of a 63-year-old female who was admitted to the Third Affiliated Hospital of Hebei Medical University due to IPA after glucocorticoid therapy for liver failure.The polymorphism of cytochrome P450(CYP)isoenzymes showed CYP2C19∗1/∗2 genotype associated with intermediate metabolism of voriconazole.However,the patient developed side effects such as skin rash,vomiting,hyperbilirubinemia,and alteration of consciousness,even if she received half of the recommended dosage for voriconazole.Therapeutic drug monitoring(TDM)was applied to guide the dosage adjustment of voriconazole in this patient,and consequently,the patient presented a favorable outcome.In conclusion,genotyping screening plus TDM dependent individualized treatment of voriconazole may improve the survival of liver failure patient with IPA.

关键词： Invasive pulmonary aspergillosis Liver failure Therapeutic drug monitoring voriconazole

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voriconazole-associated periostitis:Pathophysiology,risk factors,clinical manifestations,diagnosis,and management

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World Journal of Transplantation 2021年第9期11卷 356-371页

作者： Anthony J Guarascio Nitin Bhanot Zaw Min Department of Pharmacy Duquesne University School of PharmacyPittsburghPA 15282United States Division of Infectious Disease Medicine InstituteAllegheny General HospitalAllegheny Health NetworkPittsburghPA 15212United States

voriconazole use has been associated with osteoarticular pain and periostitis,likely due to high fluoride content in the drug formulation.This phenomenon has been described primarily with high dosage or prolonged course of voriconazole therapy in immunocompromised and transplant patient populations.Patients typically present with diffuse bony pains associated with elevated serum alkaline phosphatase and plasma fluoride levels in conjunction with radiographic findings suggestive of periostitis.We provide a comprehensive review of the literature to highlight salient characteristics commonly associated with voriconazole-induced periostitis.

关键词： voriconazole Periostitis Fluoride Fluorosis Alkaline phosphatase

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Remission of hepatotoxicity in chronic pulmonary aspergillosis patients after lowering trough concentration of voriconazole

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World Journal of Clinical Cases 2020年第20期8卷 4700-4707页

作者： Guo-Jie Teng Xiang-Rong Bai Lin Zhang Hong-Jun Liu Xiu-Hong Nie Department of Pulmonary and Critical Care Medicine Xuanwu Hospital Capital Medical UniversityBeijing 100053China Pharmacy Department Xuanwu Hospital Capital Medical UniversityBeijing 100053China Department of Evidence-based Medicine Xuanwu Hospital Capital Medical UniversityBeijingChinaBeijing 100053China

BACKGROUND Chronic pulmonary aspergillosis(CPA)is a rare syndrome that is often accompanied by gradual lung tissue destruction.voriconazole is usually employed as the first-line agent for CPA treatment.However,some patients can develop hepatotoxicity and often were forced to stop voriconazole treatment.AIM To record the improving trend of liver function and the therapeutic effects in patients after lowering the trough concentration of voriconazole.METHODS This study retrospectively analyzed 12 adult CPA patients who developed hepatotoxicity during the voriconazole treatment.In these patients,the oral dose was reduced to 3/4 or 1/2 of the standard dose(4 mg/kg,twice daily),and the lower limit of voriconazole trough concentration was maintained more than 0.5μg/m L.The trend of remission of liver toxicity after drug reduction in 12 patients was recorded.During the same period,25 patients who received standard doses served as the control group.Data from the two groups were collected and analyzed for different parameters such as demographic characteristics,underlying pulmonary disorders,laboratory tests,and therapeutic effect.The differences between the two groups were statistically compared.RESULTS Hepatotoxicity occurred in 12 patients within 28-65 d after oral voriconazole treatment.Hepatotoxicity was mainly manifested by the significantly increased level of gamma-glutamyltransferase and a slight increase of alanine aminotransferase and aspartate aminotransferase.The oral dose of voriconazole was reduced to approximately 3 mg/kg in seven patients and approximately 2 mg/kg in five patients.The average trough concentrations for the 12 patients before and after voriconazole oral dose reduction were 3.17±1.47μg/m L(1.5-6.0μg/m L)and 1.70±0.78μg/m L(0.6-3.3μg/m L),respectively(P=0.02).After lowering the trough concentrations,the hepatotoxicity was alleviated in all the patients.However,gamma-glutamyltransferase levels declined slowly.After 4 mo of treatment,7 of the 12 patients were successfully treated in the low troug

关键词： voriconazole Hepatotoxicity Chronic pulmonary aspergillosis CYP2C19 genotypes Reduction Trough concentration

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Argon laser photocoagulation versus intrastromal voriconazole injection in treatment of mycotic keratitis

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International Journal of Ophthalmology(English edition) 2016年第2期9卷 225-229页

作者： Mohammad M.Khater Mohammad S.El-Shorbagy Adel A.Selima Department of Ophthalmology Tanta University Hospital

AIM： To compare argon laser photocoagulation and intrastromal injection of voriconazole as adjunctive treatment modalities in cases of resistant mycotic corneal ulcers. METHODS： Two groups each of them included 20 cases of resistant mycotic corneal ulcers. Both groups treated with local and systemic specific antimicrobial drugs guided with culture and sensitivity results. In one group argon laser photocoagulation was used as an adjunctive therapy to the specific antifungal drugs and in the other group, intrastromal injection of voriconazole was done besides the specific antifungal drugs. The 40 cases included in the study were proven according to culture and sensitivity to be 28 cases with pure fungal results and 12 cases with mixed （fungal and bacterial）. In argon laser group, argon laser irradiation of the corneal ulcer was performed using argon laser 532 nm wavelength （Carl Zeiss LSL 532s AG; Meditec, Inc.） after fluorescein staining. In the other group, voriconazole solution （500 pg/mL） was prepared and injected in the corneal stroma. All cases were followed up for 3mo after healing was achieved. RESULTS： Complete healing of the epithelial defect and resolution of stromal infiltration with no adverse effects were achieved in argon laser group in duration ranged from 2-4wk in 90% of cases. In voriconazole group 4 cases needed amniotic membrane graft due to thinning and 16 cases healed in duration ranged from 2- 6wk （80% of cases）. CONCLUSION： Argon superior to intrastromal treatment of resistant fungal laser photocoagulation is voriconazole injection in corneal ulcers.

关键词： mycotic keratitis argon laser voriconazole

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Evidence of voriconazole pharmacokinetic variability in children and adolescents with haematological disease: proposal for therapeutic drug monitoring optimisation

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Toxicology Advances 2023年第1期5卷 16-23页

作者： Pauline Lancia Yves Medard Evelyne Jacqz-Aigrain Tiphaine Adam de Beaumais Department of Biological Pharmacology and Pharmacogenetics Saint-Louis HospitalAPHPParis 75011France Department of Education and Training Paris UniversityParis 75013France

Objective:voriconazole(VCZ)is a triazole antifungal agent widely used in immunocompromised patients with suspected or proven invasive fungal infections.The achievement of therapeutic range(1-5 mg/L)is essential to maximize VCZ efficacy,as its pharmacokinetics is characterized by a wide inter-and intra-individual variability.This study aims to quantify the variability of VCZ trough concentrations in children and adolescents with haematological diseases and optimize therapeutic drug monitoring in clinical practice.Methods:We analysed the monitoring concentrations of all children(<18 years old)treated with VCZ in the Haematology Department of Robert DebréHospital between January 2014 and December 2016.Demographic,clinical data,and VCZ dosing and monitoring concentrations measured by high-performance liquid chromatography with ultraviolet detection(HPLC-UV)were analysed.Non-parametric tests were performed using SPSS IBM 24.0.Results:380 trough VCZ concentrations at steady-state(Ctrough,ss)were available in 79 children:45.6%had first Ctrough,ss in the therapeutic range at first monitoring,46.8%had Ctrough,ss below 1 mg/L and 7.6%had Ctrough,ss over 5 mg/L.Forty-one patients were treated with recommended doses but only 53%of them reached the therapeutic range.There was no impact of age,sex,biological parameters,or indication of VCZ on Ctrough,ss values.The number of Ctrough,ss in the therapeutic range increases with the number of monitoring per patient following dosage adaptations.Conclusion:The wide inter-and intra-individual variability of VCZ trough concentrations at recommended doses confirm the need to standardize VCZ monitoring and identify factors to be considered to prospectively adapt treatment for each patient.

关键词： voriconazole pharmacokinetics variability therapeutic drug monitoring paediatric haematology

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Determination of voriconazole in Human Plasma by Liquid Chromatography Tandem Mass Spectrometry: Application in Therapeutic Drug Monitoring

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American Journal of Analytical Chemistry 2023年第9期14卷 378-389页

作者： Waleed Alhussaini Ezzeldeen Ghanem Magd Alsahly Amani Kurdi Eman Alharbi Imadul Islam Majed Aljeraisy Department of Pharmaceutical Analysis King Abdullah International Medical Research Center King Saud bin Abdulaziz University for Health Sciences Ministry of the National Guard—Health Affairs Riyadh Saudi Arabia Research Office King Abdullah International Medical Research Center King Saud bin Abdulaziz University for Health Sciences Ministry of the National Guard—Health Affairs Riyadh Saudi Arabia

A sensitive, accurate and robust Liquid Chromatography Tandem Mass Spectrometry method has been developed and validated to measure voriconazole trough levels in human plasma. The plasma samples were mixed with fluconazole as an Internal Standard and directed to protein precipitation and drug extraction. An aliquot of 1 μl was injected into the chromatographic system and separated by the Acquity BEH C18 column at a flow rate of 0.30 ml/min in a gradient mobile phase consisting of acetonitrile, Ultrapure water (UPW), methanol and formic acid. voriconazole was detected by a Triple Quadrupole Detector (TQD) operating on Multiple Reaction Monitoring (MRM) and a positive ion mode Electrospray ionization (ESI) Q1 mass: 350.1 m/z, Q3 mass: 281.1 m/z. Method linearity of the calibration curve (0.10 - 8.00 μg/ml) indicated a correlation coefficient r ≥ 0.99. The intra and inter-assay accuracy was within 85% - 115% and the intra and inter-assay precision was ≤5.76%. voriconazole recovery percentage was between 97.69 - 119.62%. The method was successively applied in routine voriconazole TDM.

关键词： voriconazole Human Plasma Liquid Chromatography Tandem Mass Spectrometry Therapeutic Drug Monitoring

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Therapeutic Drug Monitoring of Vancomycin and voriconazole by Liquid Chromatography-Tandem Mass Spectrometric Method

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Chemical Research in Chinese Universities 2017年第3期33卷 339-342页

作者： LI Yanyan YIN Lei LI Yanhua SUN Zhihui ZHAO Xiaojun GAO Mingyue WANG Hongliang The First Hospital of Jilin University Changchun 130021 P. R. China School of Life Science Jilin University Changchun 130012 R R. China

A reliable liquid chromatography-tandem mass spectrometric（LC-MS/MS） method was developed and va- lidated for the simultaneous determination of vancomycin and voriconazole in human plasma. The analytes and internal standard 10-hydroxycarbazepine were separated at a flow rate of 0.9 mL/min using a Zorbax SB-C18 column （50 min×4.6 mm, 2.7 μm）. Positive ion electrospray ionization was used to detect vancomycin, voriconazole and intrenal standard（IS） 10-hydroxycarbazepine followed by multiple reaction monitoring（MRM） of the transition at m/z 725.5→144.2, 350.3→281.0 and 253.1→208.0, respectively. The total run time for both vancomycin and voriconazole samples was 5 min; 0.30μg/mL was the lower limit of quantification. The precision of intraday and interday was no more than 12.4%. The method was successfully and resoundingly applied in therapeutic drug monitoring of 156 patients treated with vancomycin and voriconazole.

关键词： Liquid chromatography-tandem mass spectrometry（LC-MS/MS） Vancomycin voriconazole Therapeutic drug monitoring

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Efficacy of voriconazole on leishmaniasis by Leishmania major: An in vitro and in vivo study

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Asian Pacific Journal of Tropical Medicine 2018年第10期11卷 562-569页

作者： Ahmad Oryan Somayeh Bahrami Effat Bemani Department of Pathology School of Veterinary Medicine Shiraz University Department of Parasitology Faculty of Veterinary Medicine Shahid Chamran University of Ahvaz

Objective: To appraise the activity of voriconazole against Leishmania major(L. major) in vitro and its effectiveness on wound regeneration in cutaneous leishmaniasis in BALB/c mice Methods: The IC_(50) of voriconazole against promastigotes and intra-macrophage amastigotes of L. major was investigated in vitro. The in vivo study was performed by treating the L. major infected BALB/c mice. When the wounds appeared in the base of tail, treatment was started by administration of 30 mg/kg voriconazole for 28 consecutive days orally. Results: The IC_(50) of voriconazole against promastigotes and intra-macrophage amastigotes were 0.74 and 0.89μM, respectively. voriconazole decreased lipid peroxidation and IL-6 level. Histopathologica findings indicated accelerated healing in the voriconazole treated group compared to other groups. Conclusions: Our results demonstrate that voriconazole can be an option in treating the cutaneous leishmaniasis by L. major.

关键词： Leishmania major Wound healing Azoles voriconazole Histopathology

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