CN101267806A - 缓释的抗感染药 - Google Patents
缓释的抗感染药 Download PDFInfo
- Publication number
- CN101267806A CN101267806A CNA200680034397XA CN200680034397A CN101267806A CN 101267806 A CN101267806 A CN 101267806A CN A200680034397X A CNA200680034397X A CN A200680034397XA CN 200680034397 A CN200680034397 A CN 200680034397A CN 101267806 A CN101267806 A CN 101267806A
- Authority
- CN
- China
- Prior art keywords
- lipid
- infectives
- preparation
- amikacin
- liposome
- 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
- 238000013268 sustained release Methods 0.000 title description 2
- 239000012730 sustained-release form Substances 0.000 title description 2
- 150000002632 lipids Chemical class 0.000 claims abstract description 390
- 230000002924 anti-infective effect Effects 0.000 claims abstract description 279
- 238000000034 method Methods 0.000 claims abstract description 159
- 230000002685 pulmonary effect Effects 0.000 claims abstract description 55
- 208000015181 infectious disease Diseases 0.000 claims abstract description 35
- 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 22
- 229960005475 antiinfective agent Drugs 0.000 claims description 262
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 240
- 239000000203 mixture Substances 0.000 claims description 237
- 229960004821 amikacin Drugs 0.000 claims description 232
- 239000002502 liposome Substances 0.000 claims description 215
- 238000002360 preparation method Methods 0.000 claims description 184
- 238000009472 formulation Methods 0.000 claims description 115
- 239000000243 solution Substances 0.000 claims description 102
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 90
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims description 53
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- 238000002347 injection Methods 0.000 claims description 39
- 239000007924 injection Substances 0.000 claims description 39
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 39
- 229960000707 tobramycin Drugs 0.000 claims description 37
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- 150000003904 phospholipids Chemical class 0.000 claims description 25
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 12
- 230000007935 neutral effect Effects 0.000 claims description 12
- 150000003952 β-lactams Chemical class 0.000 claims description 11
- BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 claims description 10
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- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 claims description 10
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- 239000003429 antifungal agent Substances 0.000 claims description 7
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 claims description 7
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 7
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- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 7
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- MBRHNTMUYWQHMR-UHFFFAOYSA-N 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one Chemical compound NCCO.ON1C(=O)C=C(C)C=C1C1CCCCC1 MBRHNTMUYWQHMR-UHFFFAOYSA-N 0.000 claims description 6
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- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 claims description 6
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 6
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- 229960003071 bacitracin Drugs 0.000 claims description 6
- 229930184125 bacitracin Natural products 0.000 claims description 6
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 claims description 6
- SWLMUYACZKCSHZ-UHFFFAOYSA-N butoconazole Chemical compound C1=CC(Cl)=CC=C1CCC(SC=1C(=CC=CC=1Cl)Cl)CN1C=NC=C1 SWLMUYACZKCSHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960005074 butoconazole Drugs 0.000 claims description 6
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 6
- 229960003749 ciclopirox Drugs 0.000 claims description 6
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 claims description 6
- 229960004375 ciclopirox olamine Drugs 0.000 claims description 6
- 229960004413 flucytosine Drugs 0.000 claims description 6
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims description 6
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 6
- 229960002867 griseofulvin Drugs 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- 229960003350 isoniazid Drugs 0.000 claims description 6
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 6
- 229960005287 lincomycin Drugs 0.000 claims description 6
- 150000004291 polyenes Chemical class 0.000 claims description 6
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims description 6
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims description 6
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- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 6
- VCOPTHOUUNAYKQ-WBTCAYNUSA-N (3s)-3,6-diamino-n-[[(2s,5s,8e,11s,15s)-15-amino-11-[(6r)-2-amino-1,4,5,6-tetrahydropyrimidin-6-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;(3s)-3,6-diamino-n-[[(2s,5s,8 Chemical compound N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1.N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1 VCOPTHOUUNAYKQ-WBTCAYNUSA-N 0.000 claims description 5
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- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 claims description 5
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Abstract
Description
批次 | 温度℃L/AMK/W | AMK原药mg/mL | 总AMKmg/mL | AMK单体% | 脂质mg/mL | L/D | VOL尺寸nm | SD尺寸% |
689101112131415161718 | 40/40/3050/RT/3050/RT/3050/RT/3050/RT/3050/RT/3050/RT/3050/RT/3050/RT/3030/30/3030/30/3030/30/30 | 505050504040304040404040 | 36.148.541.653.120.781.068.679.671.361.973.874.4 | 2.79.65.110.24.81.91.71.62.06.12.42.3 | 61.849.343.234.446.949.462.547.842.351.557.254.0 | 1.711.021.040.652.270.610.910.600.590.830.770.73 | 392332359350407341311346353369362549 | 43.432.034.428.635.933.022.437.233.428.432.661.7 |
批次 | AMK原药mg/mL | 总AMKmg/mL | AMK单体% | 脂质mg/mL | L/D | VOL尺寸nm | AMK回收率% |
10 | 50 | 53.1 | 10.2 | 34.4 | 0.65 | 350 | 37.0 |
12 | 40 | 81.0 | 1.9 | 49.4 | 0.61 | 341 | 51.2 |
13 | 30 | 68.6 | 1.7 | 62.5 | 0.91 | 311 | 45.7 |
14 | 40 | 79.6 | 1.6 | 47.8 | 0.60 | 346 | 52.0 |
时间(小时数) | BAL中的阿米卡星(μg/mL) | BAL中的阿米卡星(μg/mL) | MIC(μg/mL) |
2 | 160 | 119 | 1.9 |
24 | 73 | 32 | 4.0 |
制剂 | 生物试验(毫克/mL) | 临床试验(毫克/mL) |
Lip-An-14(1mg/大鼠) | 9.5 | 9.1 |
Lip-An-15(1mg/大鼠) | 21.5 | 18.4 |
阿米卡星单体(10mg/大鼠) | nd | 2.0 |
妥布霉素单体(10mg/大鼠) | nd | 1.4 |
Claims (92)
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CN201310149581.0A CN103263387B (zh) | 2005-07-19 | 2006-07-19 | 缓释的抗感染药 |
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US11/185,448 | 2005-07-19 | ||
US11/185,448 US7718189B2 (en) | 2002-10-29 | 2005-07-19 | Sustained release of antiinfectives |
PCT/US2006/027859 WO2007011940A2 (en) | 2005-07-19 | 2006-07-19 | Sustained release of antiinfectives |
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US (7) | US7718189B2 (zh) |
EP (2) | EP1909759B2 (zh) |
JP (6) | JP5415759B2 (zh) |
KR (2) | KR101437338B1 (zh) |
CN (2) | CN103263387B (zh) |
AU (1) | AU2006270008B2 (zh) |
BR (1) | BRPI0613865A2 (zh) |
CA (2) | CA2614764C (zh) |
CR (1) | CR9736A (zh) |
CY (1) | CY1114685T1 (zh) |
DK (1) | DK1909759T3 (zh) |
EC (1) | ECSP088175A (zh) |
ES (1) | ES2437866T5 (zh) |
HK (1) | HK1124770A1 (zh) |
HN (1) | HN2008000084A (zh) |
IL (3) | IL188406A0 (zh) |
ME (1) | ME00597B (zh) |
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NZ (1) | NZ565300A (zh) |
PL (1) | PL1909759T3 (zh) |
PT (1) | PT1909759E (zh) |
RS (1) | RS20080019A (zh) |
RU (1) | RU2438655C2 (zh) |
SI (1) | SI1909759T1 (zh) |
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CN104873463A (zh) * | 2015-03-06 | 2015-09-02 | 朱孝云 | 用于治疗肺部感染的1-N-乙基庆大霉素Cla或其衍生物新制剂 |
CN107920994A (zh) * | 2015-06-23 | 2018-04-17 | 板层小体生物医学有限公司 | 用于治疗目的的板层小体的组合物和方法 |
CN107823695A (zh) * | 2017-09-19 | 2018-03-23 | 华东理工大学 | 一种智能型抗菌敷料及其制备方法 |
CN107823695B (zh) * | 2017-09-19 | 2022-03-15 | 华东理工大学 | 一种智能型抗菌敷料及其制备方法 |
CN112584821A (zh) * | 2018-05-02 | 2021-03-30 | 英斯梅德股份有限公司 | 脂质体药物配制品的制造方法 |
CN109330992A (zh) * | 2018-12-07 | 2019-02-15 | 中国医科大学 | 一种聚多巴胺修饰纳米结构脂质载体及其在皮内递药中的应用 |
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