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Simultaneous determination of clopidogrel,2-oxo-clopidogrel,and the thiol metabolite of clopidogrel in human plasma by LC-MS/MS

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The Journal of Biomedical Research 2022年第2期36卷 109-119页

作者： Lei Xu Ran Li Juan Li Zhou Dong Jiaxin Zong Chuchu Tan Zekang Ye Lu Shi Xiaoxuan Gong Chunjian Li Department of Cardiology the First Affiliated Hospital of Nanjing Medical UniversityNanjingJiangsu 210009China Department of Cardiology the Affiliated Sir Run Run Hospital of Nanjing Medical UniversityNanjing Jiangsu 210009China Cardiovascular Center the Second Affiliated Hospital of Nanjing Medical UniversityNanjingJiangsu 210003China

clopidogrel is a pro-drug which needs two-step metabolism to produce the active thiol metabolite.This study aimed to explore an efficient method to simultaneously determine the plasma clopidogrel,2-oxo-clopidogrel(2-Oxo-CLP),and the clopidogrel active metabolite(CAM).A high-throughput liquid chromatography tandem mass spectrometry(LC-MS/MS)was therefore developed.The analytes were extracted from plasma by using methyl tert-butyl ether(MTBE).Chromatographic separation was performed on a C18 column under an isocratic elution,accompanied with acetonitrile and deionized water containing 0.1%formic acid.After optimizing the condition of LC-MS/MS,a stable linearity was observed in the standard curves over the concentration ranges of 0.05 to 50.0 ng/mL for clopidogrel,0.5 to 50.0 ng/mL for 2-Oxo-CLP,and 0.5 to 100 ng/mL for clopidogrel active metabolite derivative(CAMD).The retention time was 4.78 minutes,3.79 minutes,3.59 minutes,and 4.82 minutes for clopidogrel,2-Oxo-CLP,CAMD,and internal standard,respectively.Both the relative standard deviation and the relative error were within the requirement of operating criteria.No significant degradation of clopidogrel,2-Oxo-CLP,and CAMD occurred under different storage conditions.This method was successfully validated in 3 patients with coronary artery disease.The results showed that the current LC-MS/MS method was efficient for simultaneously detecting clopidogrel,2-Oxo-CLP,and CAM with fine linearity,accuracy,precision,and stability.

关键词： clopidogrel drug metabolites liquid chromatography tandem mass spectrometry coronary artery disease

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Safety of early surgery for geriatric hip fracture patients taking clopidogrel:a retrospective case-control study of 120 patients in China

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Chinese Medical Journal 2021年第14期134卷 1720-1725页

作者： Ming-Hui Yang Bo Li Dong-Chen Yao Yan Zhou Wen-Chao Zhang Geng Wang Ping Zhang Shi-Wen Zhu Xin-Bao Wu Department of Orthopedics and Traumatology Beijing Jishuitan HospitalPeking University Fourth School of Clinical MedicineBeijing 100035China Department of Anesthesiology Beijing Jishuitan HospitalPeking University Fourth School of Clinical MedicineBeijing 100035China Department of Geriatric Medicine Beijing Jishuitan HospitalPeking University Fourth School of Clinical MedicineBeijing 100035China

Background:Geriatric hip fracture patients receiving clopidogrel are a surgical challenge.In China,most of these patients undergo delayed surgical treatment after clopidogrel withdrawal for at least 5 to 7 days.However,delayed surgery is associated with increased complications and mortality in the older adults.This retrospective paralleled comparison study investigated the safety of early surgery for geriatric hip fracture patients within 5 days of clopidogrel withdrawal.Methods:Acute hip fracture patients(≥65 years)who were hospitalized in the orthogeriatric co-management ward of Beijing Jishuitan Hospital between November 2016 and April 2018 were retrospectively reviewed.Sixty patients taking clopidogrel before injury and discontinuedclopidogrel group.The control group constituted 60 patients not taking antiplatelet or anticoagulant drugs and matched 1:1 with the clopidogrel group for sex,fracture type,operative procedure,and time from injury to operation(±10 h).The primary outcome was perioperative blood loss and the secondary outcomes were transfusion requirement,complications,and mortality.The Student’s t test or Wilcoxon signed rank sum test was used for continuous variables and the Chi-square test was used for categorical variables.Results:Age,body mass index,American Society of Anesthesiologists score,and percentage undergoing general anesthesia were comparable between the groups(P>0.050).The percentages of patients with coronary heart disease(61.7%vs.18.3%;Pclopidogrel vs.control groups,respectively.The median clopidogrel discontinuation time before operation was 73.0(range:3.0–120.0)h.There was no significant difference in the estimated perioperative blood loss between the clopidogrel group(median:745 mL)and control group(median:772 mL)(P=0.866).The intra-operative transfusion rate was higher in the clopidogrel group(22/60,36.7%)than that in the control group(12/60,20.0%)(P<0.

关键词： Hip fracture clopidogrel Blood loss Blood transfusion Complication Mortality

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clopidogrel delays and can reverse diabetic nephropathy pathogenesis in type 2 diabetic db/db mice

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World Journal of Diabetes 2022年第8期13卷 600-612页

作者： Hong-Qin Li Nian Liu Zong-Yu Zheng Hao-Lin Teng Jin Pei Department of Biopharmacy Jilin University School of Pharmaceutical SciencesChangchun 130021Jilin ProvinceChina Department of Urology The First Hospital of Jilin UniversityChangchun 130021Jilin ProvinceChina

BACKGROUND Diabetic nephropathy(DN)is the principal cause of end-stage renal disease.Previous studies have shown that clopidogrel can prevent the early progression of renal injury.AIM To elucidate whether clopidogrel is beneficial against DN by using a db/db mouse model.METHODS db/db mice with a higher urinary albumin/creatinine ratio(ACR)relative to ageand sex-matched wild-type control mice were randomly allocated to clopidogrel and vehicle treatment groups.clopidogrel was administered at doses of 5,10,and 20 mg/kg by gavage for 12 wk.Body mass,blood glucose level,and urinary creatinine and albumin concentrations in each group were measured before and after the intervention.Renal fibrosis was evaluated using periodic acid-Schiff and Masson’s trichrome staining.The renal protein expression of tumor necrosis factor-α(TNF-α),interleukin-1β(IL-1β),and F4/80 was assessed using immunohistochemistry.Urinary TNF-α,monocyte chemoattractant protein-1(MCP-1),and IL-6 levels were analyzed using enzyme-linked immunosorbent assay;TNF-αand IL-1βmRNA expression was measured using real-time quantitative polymerase chain reaction.The protein expression of fibronectin(FN)and collagen I was assessed using immunohistochemistry.RESULTS clopidogrel treatment did not affect the body mass or blood glucose level of the db/db mice;however,it increased bleeding time and reduced urinary ACR in a dose-dependent manner.Immunohistochemical staining revealed an amelioration of renal fibrosis,significantly lower deposition of FN and collagen I,and significantly lower expression of the proinflammatory cytokines TNF-αand IL-1βand lower levels of urinary TNF-αand MCP-1 in the clopidogrel-treated db/db mice(Pclopidogrel significantly reduced macrophage infiltration into the glomeruli of the db/db mice.CONCLUSION clopidogrel significantly reduced renal collagen deposition and fibrosis and prevented renal dysfunction in db/db mice,most likely through inhibition of renal macrophage infiltration and the associated inflammation.

关键词： Diabetes clopidogrel Inflammation Fibronectin Diabetic nephropathy

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clopidogrel improves aspirin response after off-pump coronary artery bypass surgery

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The Journal of Biomedical Research 2014年第2期28卷 108-113页

作者： Xuezhong Wang Xiaoxuan Gong Tiantian Zhu Qiu Zhang Yangyang Zhang Xiaowei Wang Zhijian Yang Chunjian Lia Department of Cardiology the First Affiliated HospitalNanjing Medical University Department of Cardiology Maanshan people's Hospital Department of Cardiology Jiangning People's Hospital Department of Cardiology the Second People's Hospital of Changzhou City Department of Cardiac-thoracic Surgery the First Affiliated HospitalNanjing Medical University

We sought to assess the incidence of aspirin resistance after off-pump coronary artery bypass （OPCAB） surgery, and investigate whether clopidogrel can improve aspirin response and be safely applied early after OPCAB surgery. Sixty patients who underwent standard OPCAB surgery were randomized into two groups. One group （30 patients） received mono-antiplatelet treatment （MAPT） with aspirin 100 mg daily and the other group received dual anfiplatelet treatment （DAPT） with aspirin 100 mg daily plus clopidogrel 75 mg daily. Platelet aggregations in response to arachi- donic acid （PLAA） and adenosine diphosphate （ADP）（PLADP） were measured preoperatively and on days 1 to 6, 8 and 10 after the antiplatelet agents were administered. A PLAA level above 20% was defined as aspirin resistance. Postoperative bleeding and other perioperative variables were also recorded. There were no significant differences between the two groups in baseline characteristics, average number of distal anastomosis, operation time, postoperative bleeding, ventilation time and postoperative hospital stay. However, the incidence of aspirin resistance was significantly lower in the DAPT group than that in the MAPT group on the first and second day after antiplatelet agents were given （62.1% vs, 32.1%, 34.5% vs. 10.7%, respectively, both P 〈 0.05）. There was no significant difference in postoperative complication between the two groups. DAPT with aspirin and clopidogrel can be safely applied to OPCAB patients early after the procedure. Moreover, clopidogrel reduces the incidence of OPCAB-related aspirin resistance.

关键词： aspirin clopidogrel aspirin resistance off-pump coronary artery bypass （OPCAB）

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Optimal strategy of switching from clopidogrel to ticagrelor in Chinese acute coronary syndrome patients with complicated coronary artery disease: the switching from clopidogrel to ticagrelor (SHIFT-CACS) study

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Chinese Medical Journal 2019年第19期132卷 2292-2299页

作者： Ying Yao Ping Wang Xiao-Zeng Wang Xin Zhao Wei Zhao Tie-Nan Zhou Lei Zhang Department of Cardiology Institute of Cardiovascular ResearchGeneral Hospital of Northern Theater CommandShenyangLiaoning 110840China Department of Clinical Pharmacy Shenyang Pharmaceutical UniversityShenyangLiaoning 110016China

Background:The dose and time point for switching from clopidogrel to ticagrelor remain controversial,especially for Chinese acute coronary syndrome(ACS)patients with complicated coronary artery disease(CAD).Hence,the purpose of this study was to further explore the optimal dose and time point for the switching strategy to balance the increase in platelet inhibition and the decrease in adverse events in Chinese ACS patients with complicated CAD managed by percutaneous coronary intervention(PCI).Methods:From July 2017 to December 2017,the prospective,randomized,open-label study(the SwitcHIng from clopidogrel to ticagrelor study)assigned the eligible Chinese ACS patients with complicated CAD managed by PCI(n=102)for 90 mg of ticagrelor at 12 h(T-90 mg-12 h),90 mg of ticagrelor at 24 h(T-90 mg-24h)or 180 mg ticagrelor at 24 h(T-180 mg-24 h)after the last dose of clopidogrel.The primary endpoint was the comparison of maximal platelet aggregation(MPA)values at 2 h after switching strategies among the three groups.In addition,the MPA values at baseline,8 h and before discharge and the rates of high ontreatment platelet reactivity were evaluated,the incidences of bleeding episodes and dyspnea during hospitalization and at 30-day follow-up in our study were also recorded.The MPA was measured by light transmittance aggregometry in our study.A repeatedmeasures analysis of variance(ANOVA)model and one-way ANOVA were used to compare data for the primary endpoint.Results:The MPA values were significantly decreased in the T-180 mg-24 h group compared with the T-90 mg-12 h group(P=0.017)and decreased numerically compared with the T-90 mg-24 h group(P=0.072)at 2 h.In particular,the MPA values were markedly reduced in the T-90 mg-24 h group compared with the T-90 mg-12 h group at 8 h after switching treatment(P=0.002).There was no significant difference among the three groups in all bleedings and dyspnea events.Conclusions:The optimal treatment strategy recommended in this study for Chinese ACS patients with complicated CAD manage

关键词： clopidogrel Drug substitution Pharmacology Ticagrelor

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Clinical outcomes and predictive model of platelet reactivity to clopidogrel after acute ischemic vascular events

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Chinese Medical Journal 2019年第9期132卷 1053-1062页

作者： Qi Ma Guang-Zhong Chen Yu-Hu Zhang Li Zhang Li-An Huang Department of Neurology The First Affiliated HospitalJinan UniversityGuangzhouGuangdong 510632China Guangdong Geriatrics Institute Guangdong Provincial People's HospitalGuangdong Academy of Medical SciencesGuangzhouGuangdong 510080China Department of Neurosurgery Guangdong Provincial People's HospitalGuangdong Academy of Medical SciencesGuangzhouGuangdong 510080China Department of Neurology Guangdong Provincial People's HospitalGuangdong Academy of Medical SciencesGuangzhouGuangdong 510080China

Background:High on-treatment platelet reactivity (HTPR) has been suggested as a risk factor for patients with ischemic vascular disease.We explored a predictive model of platelet reactivity to clopidogrel and the relationship with clinical outcomes.Methods:A total of 441 patients were included.Platelet reactivity was measured by light transmittance aggregometry after receiving dual antiplatelet therapy.HTPR was defined by the consensus cutoff of maximal platelet aggregation >46% by light transmittance aggregometry.CYP2C19 loss-of-function polymorphisms were identified by DNA microarray analysis.The data were compared by binary logistic regression to find the risk factors.The primary endpoint was major adverse clinical events (MACEs),and patients were followed for a median time of 29 months.Survival curves were constructed with Kaplan-Meier estimates and compared by logrank tests between the patients with HTPR and non-HTPR.Results:The rate of HTPR was 17.2%.Logistic regression identified the following predictors of HTPR:age,therapy regimen,body mass index,diabetes history,CYP2C19^*2,or CYP2C19^*3 variant.The area under the curve of receiver operating characteristic for the HTPR predictive model was 0.793 (95% confidence interval:0.738–0.848).Kaplan-Meier analysis showed that patients with HTPR had a higher incidence of MACE than those with non-HTPR (21.1% vs.9.9%;χ^2 = 7.572,P = 0.010).Conclusions:Our results suggest that advanced age,higher body mass index,treatment with regular dual antiplatelet therapy,diabetes,and CYP2C19^*2 or CYP2C19^*3 carriers are significantly associated with HTPR to clopidogrel.The predictive model of HTPR has useful discrimination and good calibration and may predict long-term MACE.

关键词： High on-treatment platelet reactivity clopidogrel CYP2C19 Light transmittance aggregometry Ischemic vascular events

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Development and validation of an HPLC–MS/MS method to determine clopidogrel in human plasma

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Acta Pharmaceutica Sinica B 2016年第1期6卷 55-63页

作者： Gangyi Liu Chunxia Dong Weiwei Shen Xiaopei Lu Mengqi Zhang Yuzhou Gui Qinyi Zhou Chen Yu Central Laboratory Shanghai Clinical CenterChinese Academy of Sciences/Central LaboratoryShanghai Xuhui Central Hospital State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Science

A quantitative method for clopidogrel using online-SPE tandem LC–MS/MS was developed and fully validated according to the well-established FDA guidelines.The method achieves adequate sensitivity for pharmacokinetic studies,with lower limit of quantifications(LLOQs)as low as 10 pg/m L.Chromatographic separations were performed on reversed phase columns Kromasil Eternity-2.5-C18-UHPLC for both methods.Positive electrospray ionization in multiple reaction monitoring(MRM)mode was employed for signal detection and a deuterated analogue(clopidogrel-d_4)was used as internal standard(IS).Adjustments in sample preparation,including introduction of an online-SPE system proved to be the most effective method to solve the analyte back-conversion in clinical samples.Pooled clinical samples(two levels)were prepared and successfully used as real-sample quality control(QC)in the validation of back-conversion testing under different conditions.The result showed that the real samples were stable in room temperature for 24 h.Linearity,precision,extraction recovery,matrix effect on spiked QC samples and stability tests on both spiked QCs and real sample QCs stored in different conditions met the acceptance criteria.This online-SPE method was successfully applied to a bioequivalence study of75 mg single dose clopidogrel tablets in 48 healthy male subjects.

关键词： clopidogrel Online-SPE LC–MS/MS Back-conversion Bioequivalence Deuterated analogue Real samples stability FDA guidelines

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Head to Head Comparison of Two Point-of-care Platelet Function Tests Used for Assessment of On-clopidogrel Platelet Reactivity in Chinese Acute Myocardial Infarction Patients Undergoing Percutaneous Coronary Intervention

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Chinese Medical Journal 2016年第19期129卷 2269-2274页

作者： Yi Yao Jia-Hui Zhang Xiao-Fang Tang Chen He Yuan-Liang Ma Jing-Jing Xu Ying Song Ru Liu Xian-Min Meng Lei Song Miao Wang Run-Lin Gao Jin-Qing Yuan Department of Cardiology State Key Laboratory of Cardiovascular Disease Fuwai Hospital National Center for Cardiovascular Diseases Chinese Academy of Medical Sciences and Peking Union Medical College Beijing 100037 China Department of Central Laboratory State Key Laboratory of Cardiovascular Disease Fuwai Hospital National Center for Cardiovascular Diseases Chinese Academy of Medical Sciences and Peking Union Medical College Beijing 100037 China

Background：Platelet function tests are widely used in clinical practice to guide personalized antiplatelet therapy.In China,the thromboelastography （TEG） test has been well accepted in clinics,whereas VerifyNow,mainly used for scientific research,has not been used in routine clinical practice.The aim of the current study was to compare these two point-of-care platelet function tests and to analyze the consistency between the two tests for evaluating on-clopidogrel platelet reactivity in Chinese acute myocardial infarction patients undergoing percutaneous coronary intervention （PCI）.Methods：A total of 184 patients admitted to Fuwai Hospital between August 2014 and May 2015 were enrolled in the study.On-clopidogrel platelet reactivity was assessed 3 days after PCI by TEG and VerifyNow using adenosine diphosphate as an agonist.Based on the previous reports,an inhibition of platelet aggregation （IPA）〈30% for TEG or a P2Y12 reaction unit （PRU）〉230 for VerifyNow was defined as high on-clopidogrel platelet reactivity （HPR）.An IPA 〉70% or a PRU 〈178 was defined as low on-clopidogrel platelet reactivity （LPR）.Correlation and agreement between the two methods were analyzed using the Spearman correlation coefficient （r） and kappa value （κ）,respectively.Results：Our results showed that VerifyNow and TEG had a moderate but significant correlation in evaluating platelet reactivity （r =-0.511）.A significant although poor agreement （κ =0.225） in identifying HPR and a significantly moderate agreement in identifying LPR （κ =0.412） were observed between TEG and VerifyNow.By using TEG as the reference for comparison,the cutoffvalues of VerifyNow for the Chinese patients in this study were identified as PRU 〉205 for HPR and PRU 〈169 for LPR.Conclusions：By comparing VerifyNow to TEG which has been widely used in clinics,VerifyNow could be an attractive alternative to TEG for monitoring on-clopidogrel platelet reactivity in Chinese patients.

关键词： Blood Platelets clopidogrel Thromboelastography VerifyNow

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Efficacy of Leflunomide, Telmisartan, and clopidogrel for Immunoglobulin A Nephropathy： A Randomized Controlled Trial

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Chinese Medical Journal 2016年第16期129卷 1894-1903页

作者： Jie Wu Shu-Wei Duan Xue-Feng Sun Wen-Ge Li Ya-Ping Wang Wen-Hu Liu Jian-Rong Zhang Li-De Lun Xue-Mei Li Chun-Hua Zhou Ji-Jun Li Shu-Wen Liu Yuan-Sheng Xie Guang-Yan Cai Lu Ma Wen Huang Hua Wu Qiang Jia Xiang-Mei Chen Department of Nephrology Chinese People's Liberation Army General Hospital Chinese People's Liberation Army Institute of Nephrology State Key Laboratory of Kidney Diseases National Clinical Research Center for Kidney Diseases Beijing 100853 China Department of Nephrology China-Japan Friendship Hospital Beijing 100029 China Department of Nephrology PLA Army General Hospital Beijing 100700 China Department of Nephrology Beijing Friendship Hospital Capital Medical University Beijing 100050 China Department of Nephrology General Hospital of Chinese People's Armed Police Forces Beijing 100039 China Department of Nephrology Air Force General Hospital of People's Liberation Army Beijing 100142 China Department of Nephrology Peking Union Medical College Hospital Chinese Academy of Medical Sciences Beijing 100730 China Department of Nephrology Navy General Hospital Beijing 100048 China Department of Nephrology First Affiliated Hospital of General Hospital of People's Liberation Army Beijing 100048 China Treatment Center for Kidney Disease No. 281 Hospital of Beijing Military Region Qinhuangdao Hebei 066100 China Department of Nephrology Beijing Tongren Hospital Capital Medical University Beijing 100730 China Department of Nephrology Beijing Hospital Beijing 100730 China Department of Nephrology Xuanwu Hospital Capital Medical University Beijing 100053 China

Background： The efficacy and safety of telmisartan combined with clopidogrel, leflunomide, or both drugs for immunoglobulin A nephropathy （IgAN） are unclear. This study was designed to evaluate the efficacy and safety of telmisartan combined with clopidogrel, leflunomide, or both drugs for IgAN. Methods： It is a multicenter, prospective, double-dummy randomized controlled trial. Primary IgAN patients were recruited in 13 renal units across Beijing, China, from July 2010 to June 2012. After a 4-week telmisartan （80 mg/d） wash-in, 400 patients continuing on 80 mg/d telmisartan were randomly assigned to additionally receive placebo （Group A）, 50 mg/d clopidogrel （Group B）, 20 mg/d leflunomide （Group C）, or 50 mg/d clopidogrel and 20 mg/d leflunomide （Group D）. The 24-week intervention was completed by 360 patients. The primary endpoint was change in 24-h proteinuria at 24 weeks. A linear mixed-effect model was used to analyze the changes at 4, 12, and 24 weeks. Generalized estimating equations were used to evaluate changes in hematuria grade. This trial was registered at the Chinese Clinical Trial Registry. Results： The effects oftelmisartan combined with leflunomide on changes in proteinuria （0.36 [95% confidence interval （CI） 0.18 0.55] g/d, P 〈 0.001）, in serum uric acid （76.96 [95% CI 57.44-96.49] μmol/L, P 〈 0.001）, in serum creatinine （9.49 [95% CI 6.54-12.44]μmol/L, P 〈 0.001）, and in estimated glomerular filtration rate （-6.72 [95% CI-9.46 to -3.98] ml.min -1. 1.73 m -2, p 〈 0.001） were statistically significant, whereas they were not statistically significant on changes in systolic and diastolic blood pressure and weight （P 〉 0.05）.Telmisartan combined with clopidogrel had no statistical effect on any outcome, and there was no interaction between the interventions. No obvious adverse reactions were observed. Conclusions： Telmisartan combined with leflunomide, not clopidogrel, is safe and effective for decreasing proteinuria in certain IgAN patients.

关键词： clopidogrel Immunoglobulin A Nephropathy Leflunomide Randomized Controlled Trial

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Pre-treatment with puerarin affects pharmacokinetics of warfarin, but not clopidogrel, in experimental rats

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Chinese Journal of Natural Medicines 2015年第4期13卷 257-263页

作者： LIU An-Chang ZHAO Li-Xia YU Shu-Wen LOU Hong-Xiang Qilu hospital of Shandong University Jinan Central Hospital Affiliated to Shandong University School of Pharmaceutical Sciences Shandong University

The present study was designed to determine the effects of puerarin pre-treatment on the pharmacokinetics of the oral anticoagulant agent warfarin and the antiplatelet agent clopidogrel in rats. In the treatment group, rats was gavaged with warfarin or clopidogrel after repeated treatment with puerarin at intraperitoneal doses of 20, 60, or 200 mg·kg-1 for 7 days, while rats in the control group were administrated only with the same dose warfarin or clopidogrel. Plasma samples were obtained at the prescribed times and analyzed by liquid chromatography tandem mass spectrometry(LC-MS/MS). The results showed that rats treated with puerarin at all the test doses of 20, 60 and 200 mg·kg-1 were found to affect the pharmacokinetics of warfarin, but not clopidogrel, suggesting a potential herb-drug interaction between puerarin and warfarin.

关键词： Puerarin Warfarin clopidogrel Pharmacokinetics Drug interaction

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