JPH0240644B2 - - Google Patents
Info
- Publication number
- JPH0240644B2 JPH0240644B2 JP54054283A JP5428379A JPH0240644B2 JP H0240644 B2 JPH0240644 B2 JP H0240644B2 JP 54054283 A JP54054283 A JP 54054283A JP 5428379 A JP5428379 A JP 5428379A JP H0240644 B2 JPH0240644 B2 JP H0240644B2
- Authority
- JP
- Japan
- Prior art keywords
- liposome
- liposomes
- active substance
- present
- wall
- 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
Links
- 239000002502 liposome Substances 0.000 claims description 107
- 239000013543 active substance Substances 0.000 claims description 46
- 239000012528 membrane Substances 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 25
- 150000003904 phospholipids Chemical class 0.000 claims description 19
- 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 11
- 239000000787 lecithin Substances 0.000 claims description 11
- 229940067606 lecithin Drugs 0.000 claims description 11
- 235000010445 lecithin Nutrition 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 235000014593 oils and fats Nutrition 0.000 claims 1
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 26
- 239000000463 material Substances 0.000 description 22
- 239000002245 particle Substances 0.000 description 17
- 102000004877 Insulin Human genes 0.000 description 13
- 108090001061 Insulin Proteins 0.000 description 13
- 229940125396 insulin Drugs 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 239000008280 blood Substances 0.000 description 11
- 210000004369 blood Anatomy 0.000 description 11
- 238000013268 sustained release Methods 0.000 description 11
- 239000012730 sustained-release form Substances 0.000 description 11
- 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 description 10
- 230000000694 effects Effects 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000002504 physiological saline solution Substances 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 108700012941 GNRH1 Proteins 0.000 description 4
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 238000010254 subcutaneous injection Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 230000000975 bioactive effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 230000002688 persistence Effects 0.000 description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- 239000007929 subcutaneous injection Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 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 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 2
- 239000000275 Adrenocorticotropic Hormone Substances 0.000 description 2
- 101800000414 Corticotropin Proteins 0.000 description 2
- 102400000739 Corticotropin Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007979 citrate buffer Substances 0.000 description 2
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 2
- 229960000258 corticotropin Drugs 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000813 peptide hormone Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 229960001052 streptozocin Drugs 0.000 description 2
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 238000002525 ultrasonication Methods 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- 102000055006 Calcitonin Human genes 0.000 description 1
- 108060001064 Calcitonin Proteins 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 102000009151 Luteinizing Hormone Human genes 0.000 description 1
- 108010073521 Luteinizing Hormone Proteins 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 102400000050 Oxytocin Human genes 0.000 description 1
- 101800000989 Oxytocin Proteins 0.000 description 1
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 1
- 102000002852 Vasopressins Human genes 0.000 description 1
- 108010004977 Vasopressins Proteins 0.000 description 1
- CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 1
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229960004015 calcitonin Drugs 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- RNPXCFINMKSQPQ-UHFFFAOYSA-N dicetyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCC RNPXCFINMKSQPQ-UHFFFAOYSA-N 0.000 description 1
- 229940093541 dicetylphosphate Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 235000011073 invertase Nutrition 0.000 description 1
- 239000001573 invertase Substances 0.000 description 1
- 238000000464 low-speed centrifugation Methods 0.000 description 1
- 229940040129 luteinizing hormone Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
- 229960001723 oxytocin Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- -1 sterol lipids Chemical class 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5428379A JPS55153713A (en) | 1979-05-02 | 1979-05-02 | Pharmaceutical preparation of ribosome containing active substance |
| CA000351077A CA1143656A (en) | 1979-05-02 | 1980-05-01 | Liposome including active substance |
| DE19803016976 DE3016976A1 (de) | 1979-05-02 | 1980-05-02 | Liposom mit einem gehalt an einer aktiven substanz und verfahren zu dessen herstellung |
| GB8014793A GB2050287B (en) | 1979-05-02 | 1980-05-02 | Liposomes containing physiologically active substances |
| FR8009985A FR2455458A1 (fr) | 1979-05-02 | 1980-05-05 | Liposomes contenant une substance active, notamment un principe actif de medicament |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5428379A JPS55153713A (en) | 1979-05-02 | 1979-05-02 | Pharmaceutical preparation of ribosome containing active substance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55153713A JPS55153713A (en) | 1980-11-29 |
| JPH0240644B2 true JPH0240644B2 (US06272168-20010807-M00014.png) | 1990-09-12 |
Family
ID=12966226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5428379A Granted JPS55153713A (en) | 1979-05-02 | 1979-05-02 | Pharmaceutical preparation of ribosome containing active substance |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0657741U (ja) * | 1993-01-22 | 1994-08-12 | 株式会社村上開明堂 | 監視機能付きミラー装置 |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4692433A (en) * | 1983-10-12 | 1987-09-08 | The Regents Of The University Of California | Method and composition for regulating serum calcium levels of mammals |
| WO1995013796A1 (en) * | 1993-11-16 | 1995-05-26 | Depotech Corporation | Vesicles with controlled release of actives |
| JPS60152410A (ja) * | 1984-01-23 | 1985-08-10 | Pola Chem Ind Inc | 皮膚外用剤 |
| CH668554A5 (de) * | 1984-04-09 | 1989-01-13 | Sandoz Ag | Liposomen welche polypeptide mit interleukin-2-aktivitaet enthalten sowie verfahren zu ihrer herstellung. |
| JPS61100518A (ja) * | 1984-10-22 | 1986-05-19 | Ono Pharmaceut Co Ltd | ジミリストイルホスフアチジルコリンを主成分とする凍結乾燥されたリポゾ−ム製剤 |
| GB8428222D0 (en) * | 1984-11-08 | 1984-12-19 | Bentall R H C | Quantifying interaction of induced currents |
| US5023087A (en) * | 1986-02-10 | 1991-06-11 | Liposome Technology, Inc. | Efficient method for preparation of prolonged release liposome-based drug delivery system |
| US4849227A (en) * | 1986-03-21 | 1989-07-18 | Eurasiam Laboratories, Inc. | Pharmaceutical compositions |
| ES2068197T3 (es) * | 1987-01-27 | 1995-04-16 | Vestar Inc | Vehiculo de liberacion a base de fosfolipidos para ingredientes activos insolubles en agua. |
| US5723147A (en) * | 1987-02-23 | 1998-03-03 | Depotech Corporation | Multivesicular liposomes having a biologically active substance encapsulated therein in the presence of a hydrochloride |
| US5811119A (en) * | 1987-05-19 | 1998-09-22 | Board Of Regents, The University Of Texas | Formulation and use of carotenoids in treatment of cancer |
| WO1988009170A1 (en) * | 1987-05-22 | 1988-12-01 | The Liposome Company, Inc. | Prostaglandin-lipid formulations |
| US5262168A (en) * | 1987-05-22 | 1993-11-16 | The Liposome Company, Inc. | Prostaglandin-lipid formulations |
| US5811118A (en) * | 1987-05-22 | 1998-09-22 | The Liposome Company, Inc. | Methods of treatment using unilamellar liposomal arachidonic acid metabolite formulations |
| US5925375A (en) * | 1987-05-22 | 1999-07-20 | The Liposome Company, Inc. | Therapeutic use of multilamellar liposomal prostaglandin formulations |
| SE457933B (sv) * | 1987-07-06 | 1989-02-13 | Larsson Kare | Farmaceutisk komposition innefattande en vattendispergerad blandning av lipider, monoglycerider och fosfatidylkolin samt dess anvaendning foer framstaellning av en gastronintestinalt verksam kompostion |
| US5807572A (en) * | 1988-02-18 | 1998-09-15 | Depotech Corporation | Multivesicular liposomes having a biologically active substance encapsulated therein in the presence of a hydrochloride |
| US5422120A (en) * | 1988-05-30 | 1995-06-06 | Depotech Corporation | Heterovesicular liposomes |
| GB8822857D0 (en) * | 1988-09-29 | 1988-11-02 | Patralan Ltd | Pharmaceutical formulations |
| FR2649610B1 (fr) * | 1989-07-13 | 1994-06-03 | Dior Christian Parfums | Composition cosmetique ou pharmaceutique et notamment dermatologique contenant de l'ampc ou ses derives en liposomes |
| DE4005711C1 (US06272168-20010807-M00014.png) * | 1990-02-23 | 1991-06-13 | A. Nattermann & Cie Gmbh, 5000 Koeln, De | |
| DE4108902A1 (de) * | 1990-08-06 | 1992-02-13 | Nattermann A & Cie | Wasserhaltiges liposomensystem |
| US5556637A (en) * | 1990-08-06 | 1996-09-17 | A. Nattermann & Cie. Gmbh | Water containing liposome system |
| US6165500A (en) * | 1990-08-24 | 2000-12-26 | Idea Ag | Preparation for the application of agents in mini-droplets |
| DE4107152C2 (de) * | 1991-03-06 | 1994-03-24 | Gregor Cevc | Präparate zur nichtinvasiven Verabreichung von Antidiabetica |
| DE4107153A1 (de) * | 1991-03-06 | 1992-09-10 | Gregor Cevc | Praeparat zur wirkstoffapplikation in kleinsttroepfchenform |
| FR2685868B1 (fr) * | 1992-01-03 | 1995-06-23 | Corbiere Jerome | Nouvelles preparations pharmaceutiques a base de peptides pour la voie generale. |
| WO1995001163A1 (fr) * | 1992-01-03 | 1995-01-12 | Corbiere Jerome | Nouvelles preparations pharmaceutiques a base de peptides pour la voie generale |
| DE69322252T2 (de) * | 1992-01-16 | 1999-08-12 | Univ Texas | Formulierung und verwendung von carotenoiden in der krebsbehandlung |
| IL101241A (en) * | 1992-03-16 | 1997-11-20 | Yissum Res Dev Co | Pharmaceutical or cosmetic composition comprising stabilized oil-in-water type emulsion as carrier |
| US5989587A (en) * | 1992-10-23 | 1999-11-23 | National Research Council Of Canada | Formation of stable liposomes from lipid extracts of archaeobacteria (archaeu) |
| US5455044A (en) * | 1993-05-14 | 1995-10-03 | Depotech Corporation | Method for treating neurological disorders |
| US5853755A (en) * | 1993-07-28 | 1998-12-29 | Pharmaderm Laboratories Ltd. | Biphasic multilamellar lipid vesicles |
| IL107471A (en) * | 1993-11-02 | 1997-09-30 | Yissum Res Dev Co | Pharmaceutical preparation comprising a self- emulsifying formulation and process for its production |
| US5840328A (en) * | 1994-01-11 | 1998-11-24 | The Liposome Company, Inc. | Treatment using arachidonic acid metabolite and particulate formulations |
| AU3361595A (en) * | 1994-08-08 | 1996-03-07 | Argus Pharmaceuticals, Inc. | Formulation and use of carotenoids in treatment of cancer |
| US5993850A (en) * | 1994-09-13 | 1999-11-30 | Skyepharma Inc. | Preparation of multivesicular liposomes for controlled release of encapsulated biologically active substances |
| AU692255B2 (en) * | 1995-04-24 | 1998-06-04 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Self-emulsifiable formulation producing an oil-in-water emulsion |
| US5931809A (en) * | 1995-07-14 | 1999-08-03 | Depotech Corporation | Epidural administration of therapeutic compounds with sustained rate of release |
| IL117773A (en) * | 1996-04-02 | 2000-10-31 | Pharmos Ltd | Solid lipid compositions of coenzyme Q10 for enhanced oral bioavailability |
| US5997899A (en) * | 1996-10-01 | 1999-12-07 | Skyepharma Inc. | Method for producing liposomes with increased percent of compound encapsulated |
| CA2296056A1 (en) * | 1997-07-10 | 1999-01-21 | Keith Baker | Methods for universally distributing therapeutic agents to the brain |
| US6306432B1 (en) | 1997-09-08 | 2001-10-23 | Chiron Corporation | High and low load formulations of IGF-I in multivesicular liposomes |
| ATE535232T1 (de) | 1997-09-18 | 2011-12-15 | Pacira Pharmaceuticals Inc | Retardierte freisetzung liposomaler anesthetischer zusammensetzungen |
| US20020039596A1 (en) | 1997-11-14 | 2002-04-04 | Hartoun Hartounian | Production of multivesicular liposomes |
| JP2002533379A (ja) | 1998-12-23 | 2002-10-08 | イデア アクチェンゲゼルシャフト | 生体内における局所的に非侵襲性である用途のための改善された製剤 |
| EP1031346B1 (en) | 1999-01-27 | 2002-05-02 | Idea Ag | Noninvasive vaccination through the skin |
| EP1031347B1 (en) | 1999-01-27 | 2002-04-17 | Idea Ag | Transnasal transport/immunisation with highly adaptable carriers |
| MXPA02000053A (es) | 1999-07-05 | 2003-07-21 | Idea Ag | Un metodo para mejorar el tratamiento a traves de barreras adaptables semipermeables. |
| US20030068361A1 (en) * | 2001-10-09 | 2003-04-10 | Rimona Margalit | Liposome-encapsulated insulin formulations |
| US7473432B2 (en) | 2002-10-11 | 2009-01-06 | Idea Ag | NSAID formulations, based on highly adaptable aggregates, for improved transport through barriers and topical drug delivery |
| WO2005053643A1 (ja) * | 2003-12-01 | 2005-06-16 | Mitsubishi Pharma Corporation | リポソーム |
| KR20130028967A (ko) * | 2010-06-23 | 2013-03-20 | 브라잇사이드 이노베이션스 인크. | 레시틴 캐리어 베시클 및 이의 제조 방법 |
| CN104394850A (zh) * | 2012-02-16 | 2015-03-04 | 布莱特赛德创新有限公司 | 膳食和营养组合物及应用的方法 |
| JP6661319B2 (ja) * | 2015-09-28 | 2020-03-11 | 小林製薬株式会社 | リポソーム |
| TWI658840B (zh) * | 2017-05-23 | 2019-05-11 | 大江生醫股份有限公司 | 乳化微脂粒組成物及其製備方法 |
| US11033495B1 (en) | 2021-01-22 | 2021-06-15 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US11357727B1 (en) | 2021-01-22 | 2022-06-14 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US11278494B1 (en) | 2021-01-22 | 2022-03-22 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49118826A (US06272168-20010807-M00014.png) * | 1971-10-12 | 1974-11-13 | ||
| JPS5186117A (en) * | 1975-01-27 | 1976-07-28 | Tanabe Seiyaku Co | Johoseibiryushiseizainoseiho |
| JPS5513260A (en) * | 1978-04-14 | 1980-01-30 | Little Inc A | Xenobiotics transfer vehicles*their production and use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3060030A (en) * | 1960-04-04 | 1962-10-23 | Carl F Obenauf | Lecithinated product |
| JPS5126213A (ja) * | 1974-08-21 | 1976-03-04 | Tanabe Seiyaku Co | Johoseibiryushiseizaino seiho |
| GB1575343A (en) * | 1977-05-10 | 1980-09-17 | Ici Ltd | Method for preparing liposome compositions containing biologically active compounds |
-
1979
- 1979-05-02 JP JP5428379A patent/JPS55153713A/ja active Granted
-
1980
- 1980-05-01 CA CA000351077A patent/CA1143656A/en not_active Expired
- 1980-05-02 GB GB8014793A patent/GB2050287B/en not_active Expired
- 1980-05-02 DE DE19803016976 patent/DE3016976A1/de not_active Ceased
- 1980-05-05 FR FR8009985A patent/FR2455458A1/fr active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49118826A (US06272168-20010807-M00014.png) * | 1971-10-12 | 1974-11-13 | ||
| JPS5186117A (en) * | 1975-01-27 | 1976-07-28 | Tanabe Seiyaku Co | Johoseibiryushiseizainoseiho |
| JPS5513260A (en) * | 1978-04-14 | 1980-01-30 | Little Inc A | Xenobiotics transfer vehicles*their production and use |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0657741U (ja) * | 1993-01-22 | 1994-08-12 | 株式会社村上開明堂 | 監視機能付きミラー装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2455458B1 (US06272168-20010807-M00014.png) | 1983-04-15 |
| GB2050287B (en) | 1983-04-20 |
| CA1143656A (en) | 1983-03-29 |
| FR2455458A1 (fr) | 1980-11-28 |
| GB2050287A (en) | 1981-01-07 |
| JPS55153713A (en) | 1980-11-29 |
| DE3016976A1 (de) | 1980-11-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0240644B2 (US06272168-20010807-M00014.png) | ||
| CA2845784C (en) | Sustained-release lipid pre-concentrate of pharmacologically active substance and pharmaceutical composition comprising the same | |
| US5662931A (en) | Process for preparing liposome composition | |
| EP0755270B1 (en) | Microcapsules, method of making and their use | |
| KR910004580B1 (ko) | 의약용 소입자 에어로졸 리포좀 및 의약용 리포좀-약제 조합물 | |
| CN102274183B (zh) | 一种多囊脂质体制备方法和应用 | |
| RU2493874C2 (ru) | Транслегочная липосома для регулирования доставки лекарственного средства | |
| JPH0665650B2 (ja) | インタ−リユ−キン療法に関する改良 | |
| JPS6354684B2 (US06272168-20010807-M00014.png) | ||
| CN107427482A (zh) | 凝血酸的多囊脂质体制剂 | |
| WO2010083778A1 (zh) | 注射用肺靶向脂质体药物组合物 | |
| DK165220B (da) | Liposomsammensaetninger indeholdende syntetiske phospholipider og et farmaceutisk aktivt stof samt deres fremstilling og phospholipidblanding til fremstilling af sammensaetningerne | |
| JPH0751496B2 (ja) | リポソ−ムの製造法 | |
| Weiner | Liposomes as carriers for polypeptides | |
| JPH0768130B2 (ja) | 微粒子化薬剤 | |
| JPH0395118A (ja) | プロスタグランジン含有脂肪小体製剤 | |
| WO2017114186A1 (zh) | 特利加压素脂质体及其制备方法 | |
| AU583272B2 (en) | Coacervate system synthetic whole blood substitute | |
| JPS59222410A (ja) | 薬物保持リポソ−ム製剤 | |
| JP4444385B2 (ja) | リポソーム用時調製用キット | |
| JPH0741432A (ja) | 新規な徐放性医薬品組成物 | |
| JPWO2003015753A1 (ja) | リポソーム製剤 | |
| CN112773776B (zh) | 一种载药纳米粒体系 | |
| JPH04356421A (ja) | プロスタグランジン類含有脂肪小体組成物 | |
| WO2024056062A1 (zh) | 一种甾体类激素磷脂组合物及其制备方法 |
