CN1248688C - Targeting hydroxycamptothecin bean phospholipid nano freeze-dried powder injection preparation and preparation method thereof - Google Patents
Targeting hydroxycamptothecin bean phospholipid nano freeze-dried powder injection preparation and preparation method thereof Download PDFInfo
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- CN1248688C CN1248688C CN200410013143.2A CN200410013143A CN1248688C CN 1248688 C CN1248688 C CN 1248688C CN 200410013143 A CN200410013143 A CN 200410013143A CN 1248688 C CN1248688 C CN 1248688C
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- CN
- China
- Prior art keywords
- preparation
- targeting
- dried powder
- hydroxy camptothecin
- fabaceous lecithin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- HAWSQZCWOQZXHI-FQEVSTJZSA-N 10-Hydroxycamptothecin Chemical compound C1=C(O)C=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 HAWSQZCWOQZXHI-FQEVSTJZSA-N 0.000 title claims abstract description 40
- 239000000843 powder Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 230000008685 targeting Effects 0.000 title claims abstract description 18
- 238000002347 injection Methods 0.000 title abstract description 16
- 239000007924 injection Substances 0.000 title abstract description 16
- 244000046052 Phaseolus vulgaris Species 0.000 title abstract 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 title abstract 2
- 150000003904 phospholipids Chemical class 0.000 title abstract 2
- 239000007864 aqueous solution Substances 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000243 solution Substances 0.000 claims abstract description 16
- 239000004094 surface-active agent Substances 0.000 claims abstract description 16
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims abstract description 15
- 229920000053 polysorbate 80 Polymers 0.000 claims abstract description 15
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229960000502 poloxamer Drugs 0.000 claims abstract description 11
- 229920001983 poloxamer Polymers 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims abstract description 10
- 235000010355 mannitol Nutrition 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 7
- 229930195725 Mannitol Natural products 0.000 claims abstract description 6
- 239000000594 mannitol Substances 0.000 claims abstract description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 26
- 235000010445 lecithin Nutrition 0.000 claims description 26
- 229940067606 lecithin Drugs 0.000 claims description 26
- 239000000787 lecithin Substances 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 7
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 5
- 238000009834 vaporization Methods 0.000 claims description 5
- 230000008016 vaporization Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 28
- 239000011858 nanopowder Substances 0.000 abstract description 12
- 210000004185 liver Anatomy 0.000 abstract description 9
- 210000000056 organ Anatomy 0.000 abstract description 7
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 238000001704 evaporation Methods 0.000 abstract description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 abstract 2
- 238000004108 freeze drying Methods 0.000 abstract 2
- 239000002131 composite material Substances 0.000 abstract 1
- 238000005538 encapsulation Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229940083466 soybean lecithin Drugs 0.000 abstract 1
- 239000008347 soybean phospholipid Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000003734 kidney Anatomy 0.000 description 6
- 210000000952 spleen Anatomy 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000002440 hepatic effect Effects 0.000 description 5
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 4
- 229960000935 dehydrated alcohol Drugs 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- 229940064457 osmitrol Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000009513 drug distribution Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 description 1
- PAEZRCINULFAGO-OAQYLSRUSA-N (R)-homocamptothecin Chemical compound CC[C@@]1(O)CC(=O)OCC(C2=O)=C1C=C1N2CC2=CC3=CC=CC=C3N=C21 PAEZRCINULFAGO-OAQYLSRUSA-N 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 230000002607 hemopoietic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 229940096998 ursolic acid Drugs 0.000 description 1
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- Medicinal Preparation (AREA)
Abstract
Description
The common flour injection | The nano powder pin |
Parameter | 2.5mg/kg | 5.0mg/kg | 7.5mg/kg | 2.5mg/kg | 5.0mg/kg | 7.5mg/kg |
C max(g/ml)A (g/ml) a (l/min)0.58±0.22 β (l/min)V (c)(l/kg)T 1/2a T 1/2β AUC (min.ug/ml)CL (s)/(kg.min)K10 (l/min)K21 (l/min)K12 (l/min)K13 (l/min)K31 (l/min) | 10.53±5.29 10.28±2.74 0.152±0.048 1.40±0.47 0.021±0.006 0.239±0.054 4.823±1.315 33.874±8.262 100.06±34.54 0.027±0.010 0.112±0.019 0.030±0.013 0.032±0.022 | 17.47±3.00 16.11±3.64 0.089±0.010 2.73±2.90 0.022±0.006 0.295±0.061 7.886±0.959 32.386±10.299 241.69±29.72 0.021±0.002 0.072±0.009 0.028±0.008 0.012±0.002 | 16.94±5.36 9.72±2.88 0.078±0.024 0.31±0.16 0.025±0.014 0.613±0.098 9.704±3.666 39.512±30.359 222.87±9.67 0.034±0.002 0.056±0.011 0.036±0.026 0.010±0.006 | 3.27±1.40 1.43±0.75 0.095±0.045 0.75±0.38 0.013±0.007 0.437±0.434 8.536±4.073 66.421±37.874 50.65±12.47 0.052±0.014 0.205±0.162 0.185±0.033 0.226±0.199 0.111±0.084 0.022±0.011 | 5.76±0.63 3.59±5.05 0.112±0.143 0.67±0.21 0.018±0.007 0.513±0.105 17.578±14.564 43.114±21.133 81.93±12.31 0.062±0.009 0.122±0.016 0.415±0.607 0.089±0.082 0.049±0.060 0.028±0.018 | 5.62±0.77 1.78±0.85 B(ug/ml) 0.054±0.009 0.013±0.005 0.785±0.141 12.960±1.892 57.390±17.254 106.91±9.52 0.071±0.006 0.091±0.014 0.138±0.070 0.164±0.140 0.041±0.009 0.022±0.007 |
Group | Tissue | Time minute | Average content (ng/ml) | Standard deviation | 95%Cl for Mean | Minima | Maximum | |
Low combination rate | High-bonding-ratio | |||||||
Common | Liver | 15 60 120 | 1693.41 2282.97 2985.07 | 1368.93 2048.06 5077.01 | 427.36 -260.04 1710.38 | 2959.47 4825.98 7680.53 | 316.08 332.71 117.11 | 3557.47 5626.78 14119.44 |
Lung | 15 | 143.55 | 58.93 | 89.05 | 198.05 | 85.58 | 222.59 |
The powder pin | 60 120 | 124.96 189.66 | 57.07 119.04 | 72.17 79.56 | 177.74 299.76 | 86.89 87.30 | 229.23 351.3 | |
Stomach | 15 60 120 | 284.47 373.79 1591.48 | 199.27 474.62 2114.63 | 37.04 -65.16 -627.69 | 531.9 812.73 3810.65 | 57.98 32.66 133.44 | 604.75 1219.91 5209.35 | |
Kidney | 15 60 120 | 871.22 134.21 860.55 | 801.12 83.29 1111.79 | 130.31 57.18 -167.69 | 1612.13 211.25 1888.78 | 206.12 64.47 81.84 | 2088.05 272.58 2935.98 | |
Intestinal | 15 60 120 | 871.22 134.21 860.55 | 801.12 83.29 1111.79 | 130.31 57.18 -167.69 | 1612.13 211.25 1888.78 | 206.12 64.47 81.84 | 2088.05 272.58 2935.98 | |
Spleen | 15 60 120 | 85.61 71.96 130.31 | 6.79 6.55 100 | 77.18 65.90 36.99 | 94.05 78.01 223.64 | 78.59 64.46 70.39 | 96.97 93.71 347.38 | |
15 60 120 | <100.00 <100.00 <100.00 | |||||||
Sodium rice flour pin | Liver | 15 60 120 | 63775.03 52600.94 43739.0 | 25166.71 22858.48 27341.46 | 32526.44 24218.38 9790.12 | 95023.63 80983.50 77687.93 | 41360.59 29074.37 4938.02 | 106149.8 89316.77 72056.25 |
Lung | 15 60 120 | 624.25 239.04 88.82 | 307.42 81.09 6.18 | 339.94 164.05 83.10 | 908.57 314.04 94.54 | 183.76 156.66 82.18 | 1140.67 405.78 101.86 | |
Stomach | 15 60 120 | 1539.01 145.37 248.42 | 1325.60 75.95 329.92 | -106.94 65.67 -97.80 | 3184.96 225.08 594.65 | 507.03 33.60 50.40 | 3819.35 227.17 909.62 | |
Kidney | 15 60 120 | 14682.41 1438.77 756.98 | 9095.38 1231.14 741.02 | 6270.59 300.16 71.64 | 23094.24 2577.38 1442.31 | 3407.98 405.44 125.70 | 28338.69 3470.75 2271.75 | |
Intestinal | 15 60 120 | 611.85 1288.26 1344.01 | 2528.33 588.53 974.10 | 1273.54 557.51 443.12 | 5950.17 2019.02 2244.90 | 658.62 689.34 471.09 | 7050.39 2116.30 3395.96 | |
Spleen | 15 | 11278.13 | 8221.27 | 3674.72 | 18881.54 | 3309.36 | 22883.63 |
60 120 | 1466.09 1232.20 | 660.07 987.21 | 855.63 319.19 | 2076.56 2145.23 | 414.38 171.20 | 2544.69 2673.95 | ||
The heart | 15 60 120 | 386.44 <100.00 <100.00 | 157.23 | 136.26 | 636.62 | 249.62 | 612.89 |
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN200410013143.2A CN1248688C (en) | 2004-05-13 | 2004-05-13 | Targeting hydroxycamptothecin bean phospholipid nano freeze-dried powder injection preparation and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200410013143.2A CN1248688C (en) | 2004-05-13 | 2004-05-13 | Targeting hydroxycamptothecin bean phospholipid nano freeze-dried powder injection preparation and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
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CN1568994A CN1568994A (en) | 2005-01-26 |
CN1248688C true CN1248688C (en) | 2006-04-05 |
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CN200410013143.2A Expired - Lifetime CN1248688C (en) | 2004-05-13 | 2004-05-13 | Targeting hydroxycamptothecin bean phospholipid nano freeze-dried powder injection preparation and preparation method thereof |
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CN (1) | CN1248688C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101167718B (en) * | 2007-10-19 | 2010-07-14 | 浙江大学 | Rebescensine A powder injection and preparing process thereof |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101028251B (en) * | 2007-02-14 | 2010-05-19 | 四川大学 | Camptothecine derivative phosphatide composite liposome nano-preparation and its making method |
CN101461787B (en) * | 2008-05-07 | 2011-04-06 | 郑州大学 | Preparation method of hydroxycamptothecin nano crystal lyophilized powder for injection preparation |
-
2004
- 2004-05-13 CN CN200410013143.2A patent/CN1248688C/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101167718B (en) * | 2007-10-19 | 2010-07-14 | 浙江大学 | Rebescensine A powder injection and preparing process thereof |
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CN1568994A (en) | 2005-01-26 |
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Granted publication date: 20060405 |