Chinese Journal of Pharmaceuticals

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Synthesis of Regorafenib

ZHENG Deqiang, ZHANG Lijian, LIU Wentao, LI Shuai, REN Wenjie

2016, 47(05): 528. https://doi.org/10.16522/j.cnki.cjph.2016.05.002

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Regorafenib was synthesized from 3-fluoro-4-nitrophenol(2) via reduction nitro group, nucleophilic substitution with N-methyl-4-chloropyridine-2-carboxamide(5), condensation with 4-chloro-3-(trifluoromethyl)phenyl isocyanate(8), and then recrystallization by salt formation and neutralization with an overall yield of 63.8％(based on 2).

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Racemization of the By-product in Resolution of Ramelteon Intermediate

DING Sheng1, WANG Na2, ZHOU Ting3, CHEN Liang3, LIN Kuaile3*

2016, 47(05): 531. https://doi.org/10.16522/j.cnki.cjph.2016.05.003

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The conversion of the by-product in resolution into ramelteon intermediate by racemization was reported. (R)-2-(1,6,7,8-Tetrahydro-2H-indeno[5,4-b]furan-8-yl)acetic acid(7′) in acetic acid, was changed into 2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetic acid by radical reaction in presence of tert-butyl
hydroperoxide and copper nitrate, and the racemic product was obtained by hydrogenation.

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Improvement Synthesis of 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

MAO Baiyang, WANG Minglin, XIA Zhengjun, JI Xiaolong, CHEN Zaixin*

2016, 47(05): 534. https://doi.org/10.16522/j.cnki.cjph.2016.05.004

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1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one, the key intermediate of ramelteon, was synthesized in a total yield of 70％ by hydrogenation of ethyl 3-(2,3-dihydrobenzofuran-5-yl)acrylate with Raney Ni, hydrolysis of ester, tert-butyl substitution, cyclization in the presence of BF3/Et2O and then deprotection.

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Construction of Recombinant Strains for Shikimic Acid Production

LIN Jun, LIU Xianglei, HU Haifeng, ZHOU Bin, ZHU Baoquan*

2016, 47(05): 537. https://doi.org/10.16522/j.cnki.cjph.2016.05.005

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For the accumulation of shikimic acid, the shikimate kinase genes (aroL and aroK) of E. coli were deleted. Then 3-deoxy-D-arabino-heptulosonate-7-phosphate synthetase (aroG gene) and shikimate dehydrogenase (aroEgene) were overexpressed, and the shikimic acid production of the recombinant strain was improved further, which was about 415.4 mg/L, 20 times of that of the parent strain BL21(DE3).

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Fed-batch Fermentation Process of Epidaunorubicin

DING Xiaoyun1,2, ZHENG Linghui1,2, CHEN Zhiwen1, BAI Hua1

2016, 47(05): 543. https://doi.org/10.16522/j.cnki.cjph.2016.05.006

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Epidaunorubicin is the main precursor for the semisynthesis of epirubicin. The fed-batch fermentation process of epidaunorubicin by Streptomyces coeruleorubidus HS14-03549 was studied in a 50 L fermentor to improve its titer. The effects of feeding time and carbon sources on the productivity of epidaunorubicin were mainly investigated. The results showed that the titer of epidaunorubicin was enhanced significantly when maltose or maltodextrin was fed at a rate of 0.5 g·(L·h)-1 as the total sugar concentration in the fermentation broth below 4.0％. The titer of epidaunorubicin reached 203 mg/L when maltose was fed, which was a 50％ increase compared with that under the fermentation process without feeding.

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Separation and Purification of Flavone Diglucuronides from Callicarpa kwangtungensis Chun and Their Anti-inflammatory Activities

XU Hui, NIU Lixin, LI Li, WU Tong, HU Xiao*

2016, 47(05): 548. https://doi.org/10.16522/j.cnki.cjph.2016.05.007

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Four flavone diglucuronides were separated and purified by means of AB-8 macroporous resin, ODS C18 and Sephadex LH-20 column chromatographies, as well as preparative HPLC, from the 60％ ethanol extract of the aerial parts of Callicarpa kwangtungenses Chun. Their structures were identified on the basis of physicochemical properties and spectrum analyses as acacetin-7-O-[β-D-glucuronopyranosyl(1→2)-O-β-D-glucuronopyranoside] (1), chrysoeriol-
7-O-[β-D-glucuronopyranosyl(1→2)-O-β-D-glucuronopyranoside](2), apigenin-7-O-[β-D-glucuronopyranosyl(1→ 2)-O-β-D-glucuronopyranoside](3), and luteolin-7-O-[β-D-glucuronopyranosyl(1→2)-O-β-D-glucuronopyranoside](4). Compounds 1－4 were isolated from the Callicarpa genus for the first time. Their in vitro anti-inflammatory activities were evaluated through determination of their inhibitory effects against bovine cyclooxygenase(COX)-1 and recombinant human COX-2 according to the measurement of fluorescence intensity. Compounds 2－4 exhibited certain inhibitory effects against COX, and among them compound 4 showed a relative higher activity.

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Preparation and in vitro Assessment of Genistein Solid Dispersions

BIAN Xiaoying1, WANG Zheng2, WANG Wei1, DING Yang1, ZHOU Jianping1*

2016, 47(05): 553. https://doi.org/10.16522/j.cnki.cjph.2016.05.008

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The solid dispersions (SD) of genistein (1) were prepared by spray drying method with polyvinylpyrrolidone (PVP) K30 as carriers and characterized by X-ray powder diffraction (XRPD), differential scanning calorimetry (DSC) and laser diffraction particle size distribution (LD-PSD). The results showed that 1 existed
in the form of amorphous or molecule in the polymeric carriers. The average particle size of the SDs in the drug carrier ratio of 1∶5 was (8.9±1.1)μm. The solubility of 1 in this product was significantly increased and reached 8.37 mg/ml in pH 6.8 buffer, meanwhile the dissolution of 1 was complete within 2 h. In addition, the product was rather stable after storage for 2 months at 25 ℃ and relative humidity of 60％.

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Preparation and in vitro Evaluation of Cationic Mesoporous Silica Nanoparticles Loaded with Puerarin for Oral Administration

ZHANG Kuankuan1, CHEN Danfei2, ZHANG Rongrong2, XIAO Shigeng3, XU Junjun3?

2016, 47(05): 558. https://doi.org/10.16522/j.cnki.cjph.2016.05.009

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The cationic mesoporous silica nanoparticles (CMSN) were synthesized by Stober method. The average particle size and z potential of the prepared CMSN with spherical appearance and obvious mesoporous structure were (98.4±2.8)nm and (13.2±1.8)mV. There was no obvious cytotoxicity in vitro of CMSN in the range of 0—20 μg/ml against Caco-2 cells. By using saturated solution adsorbing method, puerarin (1) was highly encapsulated into CMSN. After repeated adsorption for 7 times, the drug loading of CMSN reached a full load of about 18％. In pH 7.4 phosphate buffer containing 2％ sodium dodecylsulfate, the release data of 1 from the 1-CMSN was well-fitted to the Weibull equation with the correlation coefficient of 0.923 6. In Caco-2 cell monolayers, the apparent permeability coefficients, Papp(A→B) and Papp(B→A), were (23.89±1.22)×10-6 cm/s and (17.03±1.21)×10-6 cm/s. The efflux ratio (ER) of 1-CMSN was 1.403, which was significantly higher than that of the bulk drug (P<0.05).

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Preparation and Targeting Capacity of Lamotrigine-loaded Pluronic Mixed Micelles

MENG Xin1,2,LI Jiajia3,LIU Jiansheng4, WU Yulin 2, SHEN Teng 1*

2016, 47(05): 565. https://doi.org/10.16522/j.cnki.cjph.2016.05.010

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Lamotrigine(1)-loaded polymer micelles, named PF micelles, were prepared by thin-film hydration method with the mixture of Pluronic P123 and F127 (2∶1, w/w) as the carriers. The physicochemical properties of PF micelles were characterized. The results showed that encapsulation efficiency and drug loading of PF micelles were 92.39％ and 4.88％ with the average diameter of 21.32 nm. And the PF micelles were much more kinetically stable in aqueous environment than P123 micelles. Rhodamine 123 (2), a P-glycoprotein substrate, was used to evaluate the effects of PF micelles on cellular uptake of fluorescence by brain capillary endothelial cells (BCECs). The results of confocal laser scanning microscopy showed that 2-loaded PF micelles exhibited a significant increase in cellular uptake in BCECs compared with free 2. These results indicated that 1-loaded PF mixed micelles were promising vehicles for brain targeted delivery, which might have implications in the treatment of intractable epilepsy.

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Pharmacokinetics and Relative Bioavailability of Sustained-release Granules of Sodium Valproate in Beagle Dogs

KUANG Rongrui1, XIAO Feng1, QIN Yan1, HE Yun2, FAN Xinhua2*

2016, 47(05): 575. https://doi.org/10.16522/j.cnki.cjph.2016.05.012

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The pharmacokinetics and relative bioavailability of sustained-release granules of sodium valproate were evaluated. A two-period crossover study was conducted among six Beagle dogs. Each dog was administered a single oral dose (400 mg) of the test or reference preparation. An LC-MS/MS method was established for the determination of sodium valproate in plasma. The results were calculated by non-compartmental method and the main pharmacokinetic
parameters for the test and reference preparations were as follows: cmax (5.01±1.39) and (5.10±1.42)μg/ml, tmax (3.00± 0.63) and (3.00±0.63)h, AUC0→t (28.83±7.62) and (30.31±6.79)μg·ml-1·h, AUC0→∞ (31.65±10.78) and (33.28± 7.78)μg·ml-1·h, t1/2 (2.87±1.39) and (3.27±0.98)h. The relative bioavailability of the test preparation was (95.5± 13.9)％.

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Pharmacokinetics and Relative Bioavailability of Sustained-release Tablets of Cefaclor in Beagle Dogs

BAO Yingxia, WANG Ting, ZHANG Xiaona, WANG Jiansong, ZHU Shaoxuan

2016, 47(05): 579. https://doi.org/10.16522/j.cnki.cjph.2016.05.013

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An HPLC method was established for the determination of cefaclor in Beagle dog plasma. A single oral dose of the sustained-release tablets of cefaclor (test or reference preparation, 375 mg) were administered to six healthy Beagles dogs in a randomized crossover design, and the pharmacokinetics were investigated. The main pharmacokinetic parameters for the test and reference preparations were as follows: cmax (17.68±1.19) and (18.21± 2.67)μg/ml, tmax (3.83±1.03) and (3.42±0.80)h, AUC0→t (70.40±13.86) and (73.43±20.47)μg·ml-1·h, AUC0→∞ (72.98± 14.93) and (76.99±22.51)μg·ml-1·h, t1/2 (1.51±0.32) and (1.66±0.38)h. The relative bioavailability of the test preparation was (99.59±24.26)％. There was no significant difference between the test and reference preparations in the AUC0→t, cmax and tmax(P>0.5).

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Research of Compound Pseudoephedrine Hydrochloride and Fexofenadine Hydrochloride Sustained-release Capsules. Ⅲ. In vitro and in vivo Evaluation

HUANG Yunran, CHEN Ling, LU Kewei, CHEN Jie, LIANG Chaofeng*

2016, 47(05): 582. https://doi.org/10.16522/j.cnki.cjph.2016.05.014

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The release behaviors of fexofenadine hydrochloride (1) and pseudoephedrine hydrochloride (2) from the self-made title capsules in different media [pH 1.0 hydrochloric acid, pH 4.0 acetate buffer, pH 6.8 phosphate buffer (PBS) and purified water] were investigated with Telfast-D®12H as a reference preparation. According to the calculated similarity factor (f2) values, the release behaviors of 1 and 2 from both preparations were similar in above media. The cumulative amounts of 1 at 0.25 h from both preparations in pH 6.8 PBS and water were more than 85％. The release data of 2 from the self-made capsules were well-fitted to the Higuchi equation (r=0.990). An HPLC-MS/MS method was established for the determination of 1 and 2 in plasma from twenty healthy volunteers after single-dose oral administration of self-made capsules. The main pharmacokinetic parameters were calculated by DAS 2.0 software. The correlations between the absobed fraction and cumulative amounts of 1 and 2 in different media were investigated. The comparison results showed that a good in vitro-in vivo correlation could be obtained with pH 4.0 acetate buffer as the release medium in the in vitro test.

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Analysis of Amorphous Rabeprazole Sodium by Raman Spectroscopy

XU Jun, CHANG Liang, CHEN Lei, ZHANG Yueliang, SUN Ningyun*

2016, 47(05): 587. https://doi.org/10.16522/j.cnki.cjph.2016.05.015

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Amorphous rabeprazole sodium was prepared by different deposition methods and characterized by PXRD, IR, DSC and Raman spectroscopy. A specific Raman spectrum of the amorphous rabeprazole sodium was obtained. The Raman spectra of amorphous rabeprazole sodium were determined to verify the stability in the process of oral solid preparations. The results indicated that amorphous rabeprazole sodium in bulk drugs and solid oral preparations
could be easily and quickly identified by Raman analysis. This method was accurate and applicable in the quality control of amorphous rabeprazole sodium in the preparation process.

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Evaluation of Dispersing Performance of Dry Powder Inhalers by Single Frame and Single Exposure Imaging

LIU Yang1, CHEN Lan1*, ZOU Jun1, ZHOU Wu2, FENG Mingliang2

2016, 47(05): 592. https://doi.org/10.16522/j.cnki.cjph.2016.05.016

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In this study, the method of single frame and single exposure imaging (SFSEI) was adopted to measure the particle size distribution and particle velocity of lactose (Respitose® SV003) powders simultaneously. The powders were atomized in two dispersing channels with bending angles of 135 and 90° at the flow rate of 60 L/min. According to the results of Spraytec particle size measurement system and numerical simulation, the reliability of the results measured by SFSEI was preliminary investigated. The results showed that there was a good correlation between the results measured with SFSEI, Spraytec and numerical simulation. It indicated that SFSEI was feasible for evaluation of dispersing performance of inhalation devices.

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Structure Identification of An Unknown Related Substance of Cefotetan Disodium

HUANG Tao, JIN Xin, YU Nana

2016, 47(05): 597. https://doi.org/10.16522/j.cnki.cjph.2016.05.017

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There were 5 related substances found in cefotetan disodium through the stability experiment. Four of them were the same as those reported in the Japanese Pharmacopoeia, while the other one was an unknown impurity. It was obtained through an accelerated experiment and preparative separation, and identified as (6R,7S)-7-[4-(2-amino-1- carboxy-2-oxoethylidene)-1,3-dithietane-2-carboxamido]-7-methoxy-3-[(4-methyl-5-thioxo-4,5-dihydro-

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Separation and Determination of Tofacitinib and Its Optical Isomers by NP-HPLC

PAN Hongjuan1, TANG Chao1, NI Xiang1, HOU Jian2*

2016, 47(05): 600. https://doi.org/10.16522/j.cnki.cjph.2016.05.018

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An NP-HPLC method was established for the chiral separation of tofacitinib and its optical isomers, as well as the determination of the enantiomer and diastereoisomers. A Chiralpak AS-H column was used, with the mobile phase of hexane∶ethanol∶methanol∶2-aminoethanol (70∶20∶10∶0.2) at the detection wavelength of 290 nm. Tofacitinib and its optical isomers could be separated completely. Their were linear for the (3R,4S)- and (3S,4R)- diastereoisomers and (3S,4S)- enantiomer in the ranges of 0.6—12, 0.6—12 and 0.5—10 μg/ml, respectively. The average recoveries of diastereoisomers and enantiomer were 100.8％, 98.8％ and 98.6％, with RSDs of 1.21％, 1.34％ and 1.61％, respectively.

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Determination of Sodium Sulfite in Etimicin Sulfate Injection by Ion Chromatography

HU Mi1, SU Xiaochun2, HE Bing1, CHENG Yan2, SHI Chaoou1*

2016, 47(05): 604. https://doi.org/10.16522/j.cnki.cjph.2016.05.019

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An ion chromatography method was established for the determination of sodium sulfite in etimicin sulfate injection. An IonPac AS17-C type anion analytical column was used, with 10—24 mmol/L potassium hydroxide solution as the eluent, and with the application of a conductivity detector. A ten times volume sodium hypophosphite was added as anti-oxidant of sulfite, and then the solution was adjusted to pH 9.0 with 0.1 mol/L sodium hydroxide solution for the prevention of oxidation. It was directly injected after dilution. It was linear for sodium sulfite in the range of 2— 32 μg/ml, with LOQ of 0.055 μg/ml. The average recoveries were 94.8％—101.6％, with intra- and inter-day RSDs less than 3％.

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Determination of Related Substances in O-Desmethylvenlafaxine by HPLC

SHANG Weiding1, SHI Xiaowei1, MA Liang1, XUE Na2, ZHANG Kai1*

2016, 47(05): 607. https://doi.org/10.16522/j.cnki.cjph.2016.05.020

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An HPLC method was established for the determination of the related substances in O-desmethylvenlafaxine. A C8 column was used with the mobile phase of 25 mmol/L ammonium dihydrogen phosphate solution (containing 5 mmol/L sodium 1-heptane sulphonate, adjusted to pH 3.0 with phosphoric acid)∶acetonitrile (75∶25) at the detection wavelength of 224 nm. It was linear for O-desmethylvenlafaxine and its three related substances in the range of 0.5—2.0 μg/ml. Their limits of detection were 0.14, 0.20, 0.20 and 0.10 μg/ml, respectively. The key impurities and degradation products generated in stress experiments could be separated effectively from O-desmethylvenlafaxine.

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Quantitation of the Bacterial Endotoxin in Oleic Acid

WAN Liqing, GU Shuyi, TANG Liming*

2016, 47(05): 611. https://doi.org/10.16522/j.cnki.cjph.2016.05.021

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The homologous system method was applied for the establishment of a quantification method for the bacterial endotoxin (1) in oleic acid. The standard solutions of 1 were prepared with water (for the test of 1) and different concentrations of oleic acid (0.05 and 0.1 mg/ml) as the solvents for the reliability validation of the standard curves in the kinetic-turibidimetric assay. The results showed that the correlation coefficients for the standard curves in different systems were all greater than 0.98. The concentrations of the negative controls were lower than the lowest value in the corresponding standard curves. The recoveries in oleic acid were calculated respectively in the above systems. As a result, it would interfere the quantification of 1 in oleic acid when water (for the test of 1) was used as the solvent to prepare the standard solutions. However, it had no disturbance when oleic acid was used as the solvent, and the method reproducibility was good. The quantification results for three batches of samples determined by this method complied with the requirements.

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Determination of Octylphenol from Octyl-phenolic Curing Resin in Rubber Stoppers for Pharmaceutical Use

LI Ligen, WU Ying, ZHANG Yilan*

2016, 47(05): 614. https://doi.org/10.16522/j.cnki.cjph.2016.05.022

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An HPLC method was established for the determination of octylphenol, which was the residual monomer of octyl-phenolic curing resin, a vulcanizing agent, in rubber stoppers for pharmaceutical use. The extracted amount of octylphenol in different extractants, as well as the migration of octylphenol to the extractants were investigated. An Agilent C18 column was used, with the mobile phase of 75％ methanol, at the detection wavelength of 280 nm. It was linear in the concentration range of 0.35—104 μg/ml. The average recoveries were all in a range of 90％—105％ (RSD<5.0％) in pH 3.0, pH 7.0, pH 11.0 phosphate buffer solutions and 10％, 50％, 100％ ethanol.

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HPLC Determination of Irganox 1310 in Sodium Chloride Injection in Three-layer Co-extrusion Bags

ZHOU Yaju, ZHANG Fangfang

2016, 47(05): 618. https://doi.org/10.16522/j.cnki.cjph.2016.05.023

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An HPLC method was established for the determination of 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid (Irganox 1310) in sodium chloride injection packaged in three-layer co-extrusion bags. The study was carried out with Eclipse C18 column and acetonitrile (containing 0.1％ acetic acid)∶0.1％ acetic acid (60∶40) as mobile phase. The detection wavelength was 210 nm. The results showed that it was linear for Irganox 1310 in the range of 0.4—100 μg/ml. The recoveries were 94％—106％ with RSDs less than 4％.

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Discussion on the Quality Standard of Compressed Air for Pharmaceutical Industry and Its Preparation System

WANG Lijiang

2016, 47(05): 621. https://doi.org/10.16522/j.cnki.cjph.2016.05.024

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With the development of pharmaceutical technology, clean compressed air as a process gas source is used more and more widely in the field of pharmaceutical industry. Clean compressed air has become an important influence factor for quality of pharmaceutical products because it contact directly with raw materials and packaging materials. However, there is no legal standards of compressed air for pharmaceutical use in domestic and foreign countries. As a result, the quality of pharmaceutical products are seriously affected due to the difference of enterprise standards and preparation methods. So, the quality standard and preparation system of clean compressed air are discussed in this paper. Several indexes (such as suspended particles, pressure dew point, oleaginousness and microbial limit) affected the grade of cleanliness of compressed air are introduced. The standard and the corresponding preparation technology for the clean compressed air are also recommended.

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Applications of Eudragit to Oral Solid Preparations

LI Yang, LI Jin, TAO Tao*

2016, 47(05): 629. https://doi.org/10.16522/j.cnki.cjph.2016.05.025

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On the basis of a literature survey, this paper summarizes the characteristics and applications to oral solid preparations of Eudragit, a series of commonly used pharmaceutical excipients. The film forming process of Eudragit depends on its minimum film forming temperature (MFT) and glass transition temperature (Tg). Eudragit polymers can be divided into pH- and osmotic-dependent acrylic resins. pH-Dependent acrylic resins can be dissolved in different
pH media and with popular applications to the site-specific delivery systems. For example, the Eudragit series E are commonly used in solubilization, taste-masking, moisture-protection. Osmotic-dependent resins can be used as sustainedrelease materials. Moreover, several application technologies, such as EudrapulseTM, EudramodeTM and EudracolTM, based on the combination of insoluble Eudragit and other materials, are developed to regulate the drug release rate. In addition, the applications of Eudragit to novel pharmaceutical technologies (3D printing and electrostatic spinning) are briefly introduced.

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Progress of Quality Evaluation of Self-microemulsifying Drug Delivery System

ZHANG Xifeng, MA Jinlong*, SHI Jiajun, NI Rui, XU Yi

2016, 47(05): 637. https://doi.org/10.16522/j.cnki.cjph.2016.05.026

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Self-microemulsifying drug delivery system (SMEDDS) can spontaneously emulsify to form microemulsion with uniform particle size in the gastrointestinal environment after oral administration. SMEDDS is an approach to enhance solubility and bioavailability of poorly soluble drugs. Therefore, the quality evaluation of SMEDDS has received more attention. The evaluation items reflecting structure, stability and in vitro release of SMEDDS and their determination methods are reviewed in this paper. In addition, solid self-microemulsifying drug delivery system (S-SMEDDS) prepared with the combination of SMEDDS and solid dispersion, adsorption or extrusion-spheronization as well as the quality evaluation are briefly introduced.

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Progress of Applications of New Materials to Pulsatile Drug Delivery System

WANG Jiemin, WANG Xiongfei, WANG Jing, FANG Yu, CAO Deying*

2016, 47(05): 643. https://doi.org/10.16522/j.cnki.cjph.2016.05.027

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Drug release profiles of pulsatile drug delivery system (PDDS) can be characterized by a time period of no release (lag time) followed by a rapid or sustained- and controlled-release. Through utilizing triggering signals of external stimulations or formulation itself, the lag time is controlled. Nowadays, the researches on the systems with a triggered release induced by external stimuli are increasing. On the basis of the relevant literatures of recent years, the progress of applications of new materials (such as enzyme-, pH- and temperature-sensitive as well as dual sensitive materials) to oral preparations, films, hydrogels and injections with pulsatile release profiles is reviewed in this paper.

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Program of National Standard Nucleotide Sequence Database Used in Quality Control of Pharmaceutical Products by Molecular Biology Technology

HONG Xiaoxu1, FENG Zhen2, XU Huayu1, YANG Meicheng2

2016, 47(05): 651. https://doi.org/10.16522/j.cnki.cjph.2016.05.029

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Comparative Study of Innovation Medicine Appraisal Mechanism between China and America

GU Hongzheng, ZHU Jianying, ZHOU Bin*

2016, 47(05): 656. https://doi.org/10.16522/j.cnki.cjph.2016.05.030

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