CN1965805A - Coenzyme Q10Submicron emulsion injection and preparation method thereof - Google Patents
Coenzyme Q10Submicron emulsion injection and preparation method thereof Download PDFInfo
- Publication number
- CN1965805A CN1965805A CN 200510047715 CN200510047715A CN1965805A CN 1965805 A CN1965805 A CN 1965805A CN 200510047715 CN200510047715 CN 200510047715 CN 200510047715 A CN200510047715 A CN 200510047715A CN 1965805 A CN1965805 A CN 1965805A
- Authority
- CN
- China
- Prior art keywords
- injection
- ubiquinone
- water
- lecithin
- sub
- 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.)
- Granted
Links
- 238000002347 injection Methods 0.000 title claims abstract description 70
- 239000007924 injection Substances 0.000 title claims abstract description 70
- 239000000839 emulsion Substances 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000005515 coenzyme Substances 0.000 title abstract description 5
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims abstract description 109
- 235000017471 coenzyme Q10 Nutrition 0.000 claims abstract description 99
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 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 abstract description 30
- 235000010445 lecithin Nutrition 0.000 claims abstract description 30
- 239000000787 lecithin Substances 0.000 claims abstract description 30
- 229940067606 lecithin Drugs 0.000 claims abstract description 30
- 239000008215 water for injection Substances 0.000 claims abstract description 28
- 239000003549 soybean oil Substances 0.000 claims abstract description 25
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 16
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000005642 Oleic acid Substances 0.000 claims abstract description 16
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 16
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 239000003921 oil Substances 0.000 claims abstract description 10
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 96
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 claims description 95
- 229940035936 ubiquinone Drugs 0.000 claims description 94
- 239000004530 micro-emulsion Substances 0.000 claims description 36
- 235000012424 soybean oil Nutrition 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 230000001954 sterilising effect Effects 0.000 claims description 15
- 210000003022 colostrum Anatomy 0.000 claims description 13
- 235000021277 colostrum Nutrition 0.000 claims description 13
- 238000004659 sterilization and disinfection Methods 0.000 claims description 13
- 238000000265 homogenisation Methods 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 9
- 235000019198 oils Nutrition 0.000 claims description 9
- 230000004087 circulation Effects 0.000 claims description 8
- 239000012982 microporous membrane Substances 0.000 claims description 6
- 238000012856 packing Methods 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 239000008158 vegetable oil Substances 0.000 claims description 5
- 102000002322 Egg Proteins Human genes 0.000 claims description 4
- 108010000912 Egg Proteins Proteins 0.000 claims description 4
- 241000287828 Gallus gallus Species 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 230000010355 oscillation Effects 0.000 claims description 4
- 210000004681 ovum Anatomy 0.000 claims description 4
- 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 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 229940083466 soybean lecithin Drugs 0.000 claims description 3
- 238000007731 hot pressing Methods 0.000 claims description 2
- 238000011085 pressure filtration Methods 0.000 claims description 2
- 150000003669 ubiquinones Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 206010018910 Haemolysis Diseases 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 230000008588 hemolysis Effects 0.000 abstract description 4
- 230000007794 irritation Effects 0.000 abstract description 3
- 239000004005 microsphere Substances 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 230000000857 drug effect Effects 0.000 abstract description 2
- 208000006454 hepatitis Diseases 0.000 abstract description 2
- 231100000283 hepatitis Toxicity 0.000 abstract description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 abstract 1
- 230000036783 anaphylactic response Effects 0.000 abstract 1
- 208000003455 anaphylaxis Diseases 0.000 abstract 1
- 230000004530 effect on cardiovascular disease Effects 0.000 abstract 1
- 230000036039 immunity Effects 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 230000008685 targeting Effects 0.000 abstract 1
- 239000002245 particle Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 7
- 210000002969 egg yolk Anatomy 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000000481 breast Anatomy 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004204 blood vessel Anatomy 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 208000033065 inborn errors of immunity Diseases 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 208000028529 primary immunodeficiency disease Diseases 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
- 101100007300 Caenorhabditis elegans coq-2 gene Proteins 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000020603 homogenised milk Nutrition 0.000 description 1
- 210000004276 hyalin Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000008811 mitochondrial respiratory chain Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 208000001297 phlebitis Diseases 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229960004747 ubidecarenone Drugs 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940045042 ubiquinone q2 Drugs 0.000 description 1
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
5 10 | The yellow clear liquid of yellow clear liquid | - - | 86 78 |
Lot number | Time (min) | |||||
0 | 30 | 60 | 120 | 240 | 480 |
1 2 3 | 0 0 0 | 24.99 24.95 25.00 | 34.22 38.58 33.59 | 58.38 60.07 56.79 | 85.47 88.90 80.63 | 97.99 96.75 92.95 |
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100477153A CN100525753C (en) | 2005-11-15 | 2005-11-15 | Coenzyme Q10Submicron emulsion injection and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100477153A CN100525753C (en) | 2005-11-15 | 2005-11-15 | Coenzyme Q10Submicron emulsion injection and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1965805A true CN1965805A (en) | 2007-05-23 |
CN100525753C CN100525753C (en) | 2009-08-12 |
Family
ID=38074898
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2005100477153A Active CN100525753C (en) | 2005-11-15 | 2005-11-15 | Coenzyme Q10Submicron emulsion injection and preparation method thereof |
Country Status (1)
Country | Link |
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CN (1) | CN100525753C (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101381747B (en) * | 2008-10-28 | 2012-07-04 | 中国人民解放军军事医学科学院野战输血研究所 | Method for extracting coenzyme Q10 from microorganism |
CN101721373B (en) * | 2009-11-12 | 2012-09-05 | 王明 | Solid cefdinir sub-microemulsion and application thereof |
CN114588109A (en) * | 2020-12-07 | 2022-06-07 | 沈阳药科大学 | Coenzyme Q10Emulsion, preparation method and application thereof |
WO2022192633A1 (en) * | 2021-03-11 | 2022-09-15 | The Trustees Of Columbia University In The City Of New York | A pharmaceutical composition comprising ubiquinone-5 and method of use thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19859045A1 (en) * | 1998-12-21 | 2000-06-29 | Fresenius Pharma Austria Gmbh | Oil-in-water emulsion with protective effect against peroxidation damage to human organs, their production and use |
JP3742602B2 (en) * | 2001-05-09 | 2006-02-08 | 株式会社カネカ | Stable solution of reduced coenzyme Q |
CN100335045C (en) * | 2001-07-17 | 2007-09-05 | 出光兴产株式会社 | Preventive agent for ascites in poultry |
CN1520805A (en) * | 2003-01-30 | 2004-08-18 | 日清药业股份有限公司 | Ubiquinone containing composition |
CN1270702C (en) * | 2004-03-10 | 2006-08-23 | 刘红 | Intravenous injection liquid of coenzyme Q10, and its prepn. method |
-
2005
- 2005-11-15 CN CNB2005100477153A patent/CN100525753C/en active Active
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101381747B (en) * | 2008-10-28 | 2012-07-04 | 中国人民解放军军事医学科学院野战输血研究所 | Method for extracting coenzyme Q10 from microorganism |
CN101721373B (en) * | 2009-11-12 | 2012-09-05 | 王明 | Solid cefdinir sub-microemulsion and application thereof |
CN114588109A (en) * | 2020-12-07 | 2022-06-07 | 沈阳药科大学 | Coenzyme Q10Emulsion, preparation method and application thereof |
CN114588109B (en) * | 2020-12-07 | 2023-09-12 | 沈阳药科大学 | Coenzyme Q 10 Emulsion, preparation method and application thereof |
WO2022192633A1 (en) * | 2021-03-11 | 2022-09-15 | The Trustees Of Columbia University In The City Of New York | A pharmaceutical composition comprising ubiquinone-5 and method of use thereof |
Also Published As
Publication number | Publication date |
---|---|
CN100525753C (en) | 2009-08-12 |
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Effective date of registration: 20100716 Address after: 117000 bio pharmaceutical industry park, economic development zone, Benxi, Liaoning Patentee after: LIAONING WANJIA MEDICAL TECHNOLOGY Co.,Ltd. Address before: Fengle Shenhe District of Shenyang city in Liaoning province 110015 Street No. 88 Patentee before: Shenyang Wanjia Institute of Biotechnology Co.,Ltd. Effective date of registration: 20100716 Address after: Fengle Shenhe District of Shenyang city in Liaoning province 110015 Street No. 88 Patentee after: Shenyang Wanjia Institute of Biotechnology Co.,Ltd. Address before: 110015 Liaoning Province in Dongling District of Shenyang City fengle Street No. 88 Patentee before: Dong Yingjie |
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Effective date of registration: 20190731 Address after: Fengle Shenhe District of Shenyang city in Liaoning province 110015 Street No. 88 Co-patentee after: Suqian Medical Technology Co.,Ltd. Patentee after: LIAONING WANJIA MEDICAL TECHNOLOGY Co.,Ltd. Address before: 117000 bio pharmaceutical industry park, economic development zone, Benxi, Liaoning Patentee before: LIAONING WANJIA MEDICAL TECHNOLOGY Co.,Ltd. |