CN103127098B - Anti-cancer pharmaceutical composition containing clavulanic acid or salts thereof and pharmaceutical application - Google Patents
Anti-cancer pharmaceutical composition containing clavulanic acid or salts thereof and pharmaceutical application Download PDFInfo
- Publication number
- CN103127098B CN103127098B CN201310094091.5A CN201310094091A CN103127098B CN 103127098 B CN103127098 B CN 103127098B CN 201310094091 A CN201310094091 A CN 201310094091A CN 103127098 B CN103127098 B CN 103127098B
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- CN
- China
- Prior art keywords
- clavulanic acid
- salt
- pharmaceutical composition
- oxaliplatin
- cancer
- 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.)
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- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title claims abstract description 50
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 229960003324 clavulanic acid Drugs 0.000 title claims abstract description 45
- 150000003839 salts Chemical class 0.000 title claims abstract description 32
- 230000001093 anti-cancer Effects 0.000 title claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 17
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims abstract description 27
- 229960001756 oxaliplatin Drugs 0.000 claims abstract description 22
- 239000003814 drug Substances 0.000 claims abstract description 16
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 13
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 claims description 10
- 229940038649 clavulanate potassium Drugs 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000004480 active ingredient Substances 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 description 27
- 210000004027 cell Anatomy 0.000 description 13
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 11
- 230000002401 inhibitory effect Effects 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 201000005202 lung cancer Diseases 0.000 description 7
- 208000020816 lung neoplasm Diseases 0.000 description 7
- 241000699660 Mus musculus Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011580 nude mouse model Methods 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 208000000649 small cell carcinoma Diseases 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 230000002980 postoperative effect Effects 0.000 description 3
- 238000001959 radiotherapy Methods 0.000 description 3
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229960003668 docetaxel Drugs 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- 239000011812 mixed powder Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 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 1
- 241000304886 Bacilli Species 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 108090000204 Dipeptidase 1 Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 208000005016 Intestinal Neoplasms Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241001655322 Streptomycetales Species 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
- 229960003022 amoxicillin Drugs 0.000 description 1
- 229940038195 amoxicillin / clavulanate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 239000003781 beta lactamase inhibitor Substances 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000011254 conventional chemotherapy Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 230000003284 homeostatic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 201000002313 intestinal cancer Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 208000003849 large cell carcinoma Diseases 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000011248 postoperative chemotherapy Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011127 radiochemotherapy Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000007761 synergistic anti-cancer Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Group | Tumor weight/mg | Average tumour inhibiting rate/% |
Model control group | 369.8±48.1 | |
Oxaliplatin group | 201.6±53.8 ** | 45.5 |
Clavulanic acid group | 292.5±31.2 * | 20.9 |
Connection and medication A group | 152.7±49.0 **$$ | 58.7 |
Connection and medication B group | 106.3±30.3 **¥¥$$ | 71.3 |
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310094091.5A CN103127098B (en) | 2013-03-22 | 2013-03-22 | Anti-cancer pharmaceutical composition containing clavulanic acid or salts thereof and pharmaceutical application |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310094091.5A CN103127098B (en) | 2013-03-22 | 2013-03-22 | Anti-cancer pharmaceutical composition containing clavulanic acid or salts thereof and pharmaceutical application |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103127098A CN103127098A (en) | 2013-06-05 |
CN103127098B true CN103127098B (en) | 2014-05-14 |
Family
ID=48487972
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201310094091.5A Active CN103127098B (en) | 2013-03-22 | 2013-03-22 | Anti-cancer pharmaceutical composition containing clavulanic acid or salts thereof and pharmaceutical application |
Country Status (1)
Country | Link |
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CN (1) | CN103127098B (en) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2546195A1 (en) * | 2003-11-21 | 2005-06-02 | Pfizer Products Inc. | The use of anti biotics as vaccine adjuvants |
-
2013
- 2013-03-22 CN CN201310094091.5A patent/CN103127098B/en active Active
Also Published As
Publication number | Publication date |
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CN103127098A (en) | 2013-06-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CB03 | Change of inventor or designer information |
Inventor after: Ying Shuhuan Inventor after: Pi Hongjun Inventor before: Yu Fazhou |
|
CB03 | Change of inventor or designer information | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170417 Address after: 202153 Shanghai free trade zone GuoShouJing Road No. 351 Building No. 2 room A679-04 Patentee after: SHANGHAI BOCIMED PHARMACEUTICAL Co.,Ltd. Address before: 235000 Anhui Province Economic Development Zone Huaibei City Duji District Tengfei Road No. 7 Patentee before: Yu Fazhou |
|
TR01 | Transfer of patent right | ||
CP03 | Change of name, title or address |
Address after: 201203 Building 1, Lane 647, Songtao Road, Zhangjiang High Tech Park, Pudong New Area, Shanghai Patentee after: Shanghai Yunshengyan neoplasm Technology Co.,Ltd. Country or region after: China Address before: Room A679-04, Building 2, No. 351 Guoshoujing Road, Shanghai Pilot Free Trade Zone, 202153 Patentee before: SHANGHAI BOCIMED PHARMACEUTICAL Co.,Ltd. Country or region before: China |
|
TR01 | Transfer of patent right |
Effective date of registration: 20240930 Address after: Room 510, Building 1, No. 111 Hongxing Road, Xiaoshan Economic and Technological Development Zone, Hangzhou City, Zhejiang Province 311217 Patentee after: Zhejiang Medideep Biopharmaceutical Co.,Ltd. Country or region after: China Address before: 201203 Building 1, Lane 647, Songtao Road, Zhangjiang High Tech Park, Pudong New Area, Shanghai Patentee before: Shanghai Yunshengyan neoplasm Technology Co.,Ltd. Country or region before: China |