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固态药物痕量晶体定量技术的研究进展

丁甜甜, 苏美玲, 钱帅, 张建军, 高缘, 魏元锋

丁甜甜,苏美玲,钱帅,等. 固态药物痕量晶体定量技术的研究进展[J]. 中国药科大学学报,2024,55(2):181 − 193. DOI: 10.11665/j.issn.1000-5048.2023081404
引用本文: 丁甜甜,苏美玲,钱帅,等. 固态药物痕量晶体定量技术的研究进展[J]. 中国药科大学学报,2024,55(2):181 − 193. DOI: 10.11665/j.issn.1000-5048.2023081404
DING Tiantian, SU Meiling, QIAN Shuai, et al. Progress of research on quantitative techniques for trace amount of crystals in solid state drugs[J]. J China Pharm Univ, 2024, 55(2): 181 − 193. DOI: 10.11665/j.issn.1000-5048.2023081404
Citation: DING Tiantian, SU Meiling, QIAN Shuai, et al. Progress of research on quantitative techniques for trace amount of crystals in solid state drugs[J]. J China Pharm Univ, 2024, 55(2): 181 − 193. DOI: 10.11665/j.issn.1000-5048.2023081404

固态药物痕量晶体定量技术的研究进展

基金项目: 国家自然科学基金项目(No. 82373824, No. 82104401, No. 82274217, No. 82204636);中央高校基本科研业务费重点项目(No. 2632021ZD15)
详细信息
    通讯作者:

    魏元锋: Tel:15251756256 E-mail:weiyuanfengyuer@yeah.net

  • 中图分类号: R944

Progress of research on quantitative techniques for trace amount of crystals in solid state drugs

Funds: This study was supported by the National Natural Science Foundation of China (No. 82373824, No. 82104401, No. 82274217, No. 82204636) and the Key Project of the Fundamental Research Funds for the Central Universities (No. 2632021ZD15)
  • 摘要:

    晶型是影响药物理化性质的关键因素,进而影响药物的体内药效、安全性及稳定性。固态药物的晶型研究对于药物的生产工艺开发、质量控制、临床疗效评价等至关重要。化学计量学方法与分析检测技术的联合应用,表现出对大量多维数据极强的分析能力,为痕量晶体(< 1%)的定量检测提供了可能。同时,利用过程分析技术(process analytical technology,PAT)对制剂制备过程中的晶体含量进行实时监测,可进一步实现对制剂质量的控制,并作为支撑晶型专利保护的核心技术。本文概述了晶体定性定量分析技术和化学计量学方法联合应用于痕量晶体的定量测定,以期为药品的生产和质量控制提供指导。

    Abstract:

    It is well-known that crystal form of a drug is a key factor impacting the physicochemical properties of the drug, which in turn affects its in vivo efficacy, safety and stability. The study on crystal forms of solid-state drugs is crucial for drug quality control, selection of production process and evaluation of clinical efficacy. The combination of chemometric and analytical techniques exhibited its great ability to analyze a large amount of multidimensional data, providing the possibility for quantification of trace amount of crystals (< 1%). Meanwhile, using the process analytical technology (PAT) to monitor the crystal content real-time during prescription preparation process can further realize the control on formulation quality and serve as a core technology to support the patent protection of crystalline forms. In this review, the combined application of crystal analytical techniques and chemometric methods for the quantitative analysis of trace crystals were summarized, aiming to provide guidance for the manufacturing of pharmaceutical preparations and their quality control.

  • Figure  1.   Common solid-state forms and physicochemical properties of drugs, and the characterization techniques as well as chemometrics for the qualitative and quantitative analysis of solid-state drugs

    ASD:Amorphous solid dispersion;SVM: Support vector machine; ANN:Artificial neural network; HCA:Hierarchical cluster analysis; PCA:Principal component analysis;PXRD:Powder X-ray diffraction;IR:Infrared spectroscopy; NIR:Near infrared reflectance spectroscopy;DSC: Differential scanning calorimetry; PLM:Polarized light microscopy

    Figure  2.   Quantitative analysis of niclosamide polymorphs during different preparation processes using Raman, IR and NIR spectroscopy techniques combined with PLS chemometric method [15]

    Figure  3.   (A) Selected Raman spectra showing the recrystallization behavior of amorphous fenofibrate at the temperature ranging from -180 to 80 ℃; (B) Scores plots of fenofibrate from PCA analysis of its Raman spectra [33]

    Figure  4.   Quantitative analysis of crystal and amorphous forms in rivaroxaban ASD system using ATR-FTIR characterization and artificial neural network (ANN) method [21]

    Figure  5.   In-line Raman spectroscopy and chemometrics for monitoring the formation of ibuprofen-nicotinamide cocrystal prepared using hot melt extrusion (HME) technique [49]

    Table  1   Introduction of various quantitative techniques

    Technique
    PXRD IR Raman ss-NMR DSC IMC DVS
    Sample weight/mg 200−400 5−50 2000 500−700 4−10 20−300 5−50
    Probable LOD/LOQ −10% 1%−2% <1% 0.5% ~5% <5% 0.05%
    Internal standard Yes/No No No No No No No
    Calibration required No No No Yes Yes Yes Yes
    Destructive No No No No Yes Yes Yes
    Phase detection Crystalline Crystalline/
    amorphous
    Crystalline/
    amorphous
    Crystalline/
    amorphous
    Crystalline/
    amorphous
    Amorphous Amorphous
    Ability to differentiate surface/bulk amorphicity No No No No No Yes No
    Limitations Existence of preferred orientation Existence of peaks overlapping, interlacing Used as a complementary quantitative technique to IR Long data acquisition time, expensive Vulnerable to sample particle size, etc. Low specificity Vulnerable to excipient interference
    下载: 导出CSV

    Table  2   Chemometrics-assisted determination of API crystal content

    Drug Characterization method Chemometric method Modeling area Observations Ref.
    Azithromycin NIR PLS 1100−2500 cm−1 Various factors (e.g., treatment method, wavelength range and moisture content) were investigated and optimized [27]
    LOD: 0.2%; LOQ: 0.8%
    Entecavir PXRD PLS 14°−34° 2θ An accurate and reliable method was developed for the quantitative determination of entecavir polymorphs in their binary mixtures [3]
    ATR-FTIR 400−2 000 cm−1
    Furosemide Raman PLS 122−3167 cm−1 PLS can be used to quickly and accurately measure the content of various crystal forms of furosemide [28]
    Meloxicam IR PLS 600−4000 cm−1 Smart radial diagrams approach for selecting spectral pre-treatment techniques was presented [5]
    NIR 4000−12500 cm−1
    Raman 1030−1650 cm−1
    Niclosamide IR PLS 1380−1700 cm−1 The combination of three spectral techniques and PLS model was able to predict the polymorphic transformation of drug during the real-time processing like ball milling and wet granulation [15]
    NIR 4545−5000 cm−1
    Raman 1050−1800 cm−1
    Nimodipine ATR-FTIR MCR-ALS 1650−600 cm−1 Method is suitable for the analysis of nimodipine polymorphs and enables study of their possible thermally promoted interconversions [29]
    3600−2500 cm−1
    Paracetamol FT-Raman PLS 0−4000 cm−1 A fast and simple method for the quantitative analysis of form Ⅰ and form Ⅱ of paracetamol was developed [30]
    Piracetam PXRD PLS 8°−35° 2θ NIR combined with PLS had the highest accuracy for the drug detection [31]
    Raman 250−3310 cm−1
    NIR 4000−10000 cm−1
    下载: 导出CSV

    Table  3   Chemometrics-assisted monitoring of polymorphic transformations

    Drug Form transformation Characterization method Chemometric method Observations Ref.
    Carbamazepine Anhydrate→Dihydrate ATR-FTIR MCR-ALS The polymorphic transformation rate is delayed by HPC and HPMC [34]
    Cimetidine Monohydrate→Form B →Amorphous ATR-FTIR MCR-ALS The ATR-FTIR/MCR association is a promising and useful technique for monitoring solid-state phase transformations of cimetidine [35]
    Fenofibrate Amorphous→ Form II→Form I→liquid Raman PCA Multiple solid-state forms, including the metastable crystalline form, could be observed [33]
    Indomethacin Amorphous→α Raman PLS Solution-mediated transformation
    The transition of polymorphism slowed down the drug dissolution rate
    [36]
    ε→ζ→η→α ATR-FTIR PCA Three new crystal forms were observed and their transitions process were monitored [37]
    Nitrofurantoin Monohydrate→
    Amorphous→Anhydrate→Melt
    PXRD PCA The critical temperatures (120 ℃,140 ℃,190 ℃) were identified easily using the PCA [38]
    Ranitidine HCl Form I&II→Amorphous;
    Amorphous→Form I&II
    PXRD PLS Forms I and II could be fully amorphized within 30 min.
    After being stored for 14 days under dry conditions (silica gel), amorphous samples recrystallized into form I and II
    [39]
    Theophylline Anhydrate→ Monohydrate NIR PLS Real-time monitoring of crystal form transformation during wet granulation and drying processes [40]
    下载: 导出CSV

    Table  4   Chemometrics-assisted determination of ASD crystallinity

    Drug Characterization method Chemometric method Modeling area Observations Ref.
    Itraconazole Raman PCA 464−1 852 cm−1 The mass ratios of crystal form and amorphous form of API in drug tablets was analyzed and the content of residual crystalline API in ASD was determined [42]
    PLS
    Lopinavir NIR PLS 4100−8000 cm1 Lopinavir ASD was developed to improve dissolution, stability [41]
    The PLS model was validated by external samples
    Metoprolol Raman PLS 50−150 cm−1 A PLS model was developed and validated for drug crystal content monitoring during HME process [43]
    MK-A Raman PLS 490−805 cm−1 A quantitative method was developed using PLS model with ss-NMR as the reference method [44]
    1653−1689 cm−1 LOD: 4.5%
    Piroxicam Raman MCR-ALS 1073−1661 cm−1 Quantitative analysis of piroxicam crystal formed during storage were carried out by Raman combined with MCR-ALS methods [45]
    Rebamipide PXRD PCA 5°−30° 2θ To investigate the effect of polymers and relative humidity on the phase transformation of amorphous rebamipide and its solid dispersion using chemometrics based on multiple datasets [46]
    NIR 900−1700 cm−1
    Rivaroxaban ATR-FTIR ANN, PLS 800−1800 cm−1 ANN showed the superior analysis ability for the detection of drug crystal and amorphous content [21]
    PCR 2800−3500 cm−1
    Tacrolimus PXRD PCA 4°−15.5° 2θ The selected data region showed the maximum differences in the spectra between the amorphous and crystalline tacrolimus [47]
    Ss-NMR PLS 6−60 (×10−6) LOQPXRD: 4%; LOQNMR: 2.5%
    下载: 导出CSV

    Table  5   Chemometrics-assisted determination of cocrystal/coamorphous

    DrugCharacterization methodChemometric methodModeling areaObservationsRef.
    Caffeine:Glutaric
    acid CC (1∶1)
    RamanPLS40−105 cm−1The Raman spectrum was analyzed by PLS to determine the content of CC in the model tablets[51]
    Carbamazepine/Ibuprofen: Nicotinamide CC (1∶1)RamanANN150−2700 cm−1A quantitative method for the determination of CC content was established[25]
    ATR-FTIRPLS900−1700 cm−1ANN has a better fitting superiority than PLS
    2700−4000 cm−1
    Carbamazepine:Nicotinamide CC (1∶1)RamanMCR-ALS285−1708 cm−1The preparation processes of CC were monitored by Raman coupled with MCR-ALS[52]
    PLS
    Carbamazepine:Succinic acid CC (2∶1)RamanPLS200−1800 cm−1LOD: 2.00%; LOQ: 6.06%[53]
    Ibuprofen:Nicotinamide CC (1∶1)RamanPLS100−3425 cm−1In-line Raman in combination with PLS has been proved to be a promising non-invasive technique for real-time monitoring of CC formation during HME[49]
    Indomethacin/Furosemide:Tryptophan CM (1∶1)Ss-NMRPCA0−200(×10-6)Amorphization was observed as reductions in PXRD reflections and was quantified based on normalized PCA scores of the ss-NMR spectra[54]
    Naproxen:
    Indomethacin CM (1∶1)
    PXRDPLS5°−35° 2θPXRD combined with PLS enables simultaneous determination of up to four solid state fractions[19]
    Olanzapine:
    Saccharin CM (1∶1)
    PXRDRIR20.7°−21.2° 2θA model was developed to predict the fraction of amorphous and olanzapine CM present in samples of tablets immediately after tableting[50]
    NIRPLS6094−5577 cm−1LODNIR: 0.2%; LOQNIR: 0.6%
    IR1500−1620 cm−1
    下载: 导出CSV

    Table  6   Chemometrics-assisted determination of active pharmaceutical ingredients(APIs) in preparations

    DrugCharacterization methodChemometric methodModeling areaObservationsRef.
    Canagliflozin
    (Tablet)
    PXRD
    NIR
    ATR-FTIR
    Raman
    PLS2°−35° 2θ

    6850−7 100 cm−1
    400−4 000 cm−1
    100−3 200 cm−1
    NIR was the best method in accuracy, repeatability and stability, followed by Raman, ATR-FTIR and PXRD methods
    LODNIR: 0.01%; LOQNIR: 0.05%
    [55]
    Carbamazepine
    (Tablet)
    NIRPCR860−1680 nm
    1245−1285 nm
    The double-sided data set is more robust than the single-sided data set[56]
    Griseofulvin
    (Tablet)
    RamanPLS940−1750 cm−1The PLS models based on the FT-Raman and low-frequency Raman data are suitable for quality control purposes
    LOD: 0.58%; LOQ: 1.77%
    [57]
    Indomethacin
    (Tablet)
    RamanPLS1520−1730 cm−1The method is suited for precise quantification of microanalysis of drug substances and drug products, particularly at the surface and interior of the tablet
    LOD: 0.2%
    [58]
    Irbesartan
    (Tablet)
    NIRPLS4385−4410 cm−1The content of trace amount of irbesartan form B in Avalide@ tablets was successfully quantified, and the accuracy was verified by ss-NMR
    LOD: 1.3%; LOQ: 3.9%
    [59]
    Valsartan
    (Tablet)
    RamanPLS110−1100 cm−1An analytical method was developed to simultaneously quantify crystalline and amorphous valsartan by Raman in the presence of excipients[60]
    下载: 导出CSV
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  • 收稿日期:  2023-08-13
  • 刊出日期:  2024-04-24

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