CA2222063A1 - Reverse fluorocarbon emulsion compositions for drug delivery - Google Patents

Reverse fluorocarbon emulsion compositions for drug delivery Download PDF

Info

Publication number: CA2222063A1
Authority: CA; Canada
Prior art keywords: emulsion; formulation; fluorocarbon; agents; polar liquid
Prior art date: 1995-06-07
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.): Abandoned

Application number

CA002222063A

Other languages

English (en)

French (fr)

Inventor

Timothy J. Pelura

David H. Klein

Helen M. Ranney

Gina M. Hopper

Thomas E. Tarara

Jeffry G. Weers

Leo A. Trevino

Alexey Kabalnov

Luis A. Dellamary

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Alliance Pharmaceutical Corp

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1995-06-07

Filing date

1996-06-05

Publication date

1996-12-19

1996-06-05 Application filed by Individual filed Critical Individual

1996-12-19 Publication of CA2222063A1 publication Critical patent/CA2222063A1/en

Status Abandoned legal-status Critical Current

Links

239000000839 emulsion Substances 0.000 title claims abstract description 288
239000000203 mixture Substances 0.000 title claims abstract description 107
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 title claims abstract description 70
230000002441 reversible effect Effects 0.000 title claims description 123
238000012377 drug delivery Methods 0.000 title description 5
239000012071 phase Substances 0.000 claims abstract description 110
239000004094 surface-active agent Substances 0.000 claims abstract description 86
239000003814 drug Substances 0.000 claims abstract description 54
230000001225 therapeutic effect Effects 0.000 claims abstract description 44
229940039227 diagnostic agent Drugs 0.000 claims abstract description 29
239000000032 diagnostic agent Substances 0.000 claims abstract description 29
229940124597 therapeutic agent Drugs 0.000 claims abstract description 27
108090000623 proteins and genes Proteins 0.000 claims abstract description 17
239000004530 micro-emulsion Substances 0.000 claims abstract description 16
102000004169 proteins and genes Human genes 0.000 claims abstract description 15
238000009472 formulation Methods 0.000 claims description 73
238000000034 method Methods 0.000 claims description 66
239000007788 liquid Substances 0.000 claims description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 claims description 29
239000007791 liquid phase Substances 0.000 claims description 28
239000001273 butane Substances 0.000 claims description 24
239000000654 additive Substances 0.000 claims description 22
239000003795 chemical substances by application Substances 0.000 claims description 22
230000001804 emulsifying effect Effects 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
150000003904 phospholipids Chemical group 0.000 claims description 18
239000004215 Carbon black (E152) Substances 0.000 claims description 17
150000001298 alcohols Chemical class 0.000 claims description 17
229940067605 phosphatidylethanolamines Drugs 0.000 claims description 17
230000002269 spontaneous effect Effects 0.000 claims description 16
239000003242 anti bacterial agent Substances 0.000 claims description 15
150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 15
229940088710 antibiotic agent Drugs 0.000 claims description 14
239000008344 egg yolk phospholipid Substances 0.000 claims description 14
229940068998 egg yolk phospholipid Drugs 0.000 claims description 14
-1 phosphatidyl ethylene glycols Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
102000004190 Enzymes Human genes 0.000 claims description 13
108090000790 Enzymes Proteins 0.000 claims description 13
229940088598 enzyme Drugs 0.000 claims description 13
239000006185 dispersion Substances 0.000 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 10
239000002246 antineoplastic agent Substances 0.000 claims description 10
229940034982 antineoplastic agent Drugs 0.000 claims description 9
239000002327 cardiovascular agent Substances 0.000 claims description 9
229940125692 cardiovascular agent Drugs 0.000 claims description 9
230000003247 decreasing effect Effects 0.000 claims description 9
150000004665 fatty acids Chemical class 0.000 claims description 9
150000007523 nucleic acids Chemical class 0.000 claims description 9
150000008105 phosphatidylcholines Chemical class 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
229940035674 anesthetics Drugs 0.000 claims description 8
229940121363 anti-inflammatory agent Drugs 0.000 claims description 8
239000002260 anti-inflammatory agent Substances 0.000 claims description 8
230000003110 anti-inflammatory effect Effects 0.000 claims description 8
230000000118 anti-neoplastic effect Effects 0.000 claims description 8
239000003193 general anesthetic agent Substances 0.000 claims description 8
239000012216 imaging agent Substances 0.000 claims description 8
150000008106 phosphatidylserines Chemical class 0.000 claims description 8
230000000241 respiratory effect Effects 0.000 claims description 8
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 claims description 8
239000013603 viral vector Substances 0.000 claims description 8
235000014113 dietary fatty acids Nutrition 0.000 claims description 7
239000000194 fatty acid Substances 0.000 claims description 7
229930195729 fatty acid Natural products 0.000 claims description 7
150000002321 glycerophosphoglycerophosphoglycerols Chemical class 0.000 claims description 7
108020004707 nucleic acids Proteins 0.000 claims description 7
102000039446 nucleic acids Human genes 0.000 claims description 7
150000008103 phosphatidic acids Chemical class 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 6
239000008251 pharmaceutical emulsion Substances 0.000 claims description 6
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 5
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 5
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
229920000570 polyether Polymers 0.000 claims description 5
230000002685 pulmonary effect Effects 0.000 claims description 5
229940031439 squalene Drugs 0.000 claims description 5
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 5
TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical class FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 5
229930182558 Sterol Natural products 0.000 claims description 4
230000000996 additive effect Effects 0.000 claims description 4
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 4
239000000872 buffer Substances 0.000 claims description 4
230000000050 nutritive effect Effects 0.000 claims description 4
239000002357 osmotic agent Substances 0.000 claims description 4
229920001223 polyethylene glycol Polymers 0.000 claims description 4
150000003432 sterols Chemical class 0.000 claims description 4
235000003702 sterols Nutrition 0.000 claims description 4
238000007920 subcutaneous administration Methods 0.000 claims description 4
150000003626 triacylglycerols Chemical class 0.000 claims description 4
125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 3
238000007918 intramuscular administration Methods 0.000 claims description 3
238000007912 intraperitoneal administration Methods 0.000 claims description 3
239000002736 nonionic surfactant Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
239000006199 nebulizer Substances 0.000 claims description 2
239000008342 pharmaceutical dispersion Substances 0.000 claims description 2
230000000699 topical effect Effects 0.000 claims description 2
108700005077 Viral Genes Proteins 0.000 claims 6
239000003732 agents acting on the eye Substances 0.000 claims 6
229940125702 ophthalmic agent Drugs 0.000 claims 6
UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims 3
150000001335 aliphatic alkanes Chemical class 0.000 claims 1
235000021281 monounsaturated fatty acids Nutrition 0.000 claims 1
239000008346 aqueous phase Substances 0.000 abstract description 10
239000008177 pharmaceutical agent Substances 0.000 abstract description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 64
MWRBNPKJOOWZPW-CLFAGFIQSA-N dioleoyl phosphatidylethanolamine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-CLFAGFIQSA-N 0.000 description 48
239000003921 oil Substances 0.000 description 48
239000011780 sodium chloride Substances 0.000 description 34
229940079593 drug Drugs 0.000 description 27
239000002245 particle Substances 0.000 description 24
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 20
235000019441 ethanol Nutrition 0.000 description 19
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 18
239000001110 calcium chloride Substances 0.000 description 18
229910001628 calcium chloride Inorganic materials 0.000 description 18
235000011148 calcium chloride Nutrition 0.000 description 18
SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 description 16
150000002632 lipids Chemical group 0.000 description 16
WTWWXOGTJWMJHI-UHFFFAOYSA-N perflubron Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)Br WTWWXOGTJWMJHI-UHFFFAOYSA-N 0.000 description 16
230000000694 effects Effects 0.000 description 15
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 14
238000004945 emulsification Methods 0.000 description 13
230000007423 decrease Effects 0.000 description 12
239000002356 single layer Substances 0.000 description 12
AFSHUZFNMVJNKX-LLWMBOQKSA-N 1,2-dioleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC AFSHUZFNMVJNKX-LLWMBOQKSA-N 0.000 description 11
150000002430 hydrocarbons Chemical class 0.000 description 11
MWRBNPKJOOWZPW-NYVOMTAGSA-N 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine zwitterion Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-NYVOMTAGSA-N 0.000 description 10
235000012000 cholesterol Nutrition 0.000 description 10
238000009826 distribution Methods 0.000 description 10
150000002500 ions Chemical class 0.000 description 10
229960001217 perflubron Drugs 0.000 description 10
239000008215 water for injection Substances 0.000 description 10
238000010790 dilution Methods 0.000 description 9
239000012895 dilution Substances 0.000 description 9
229930195733 hydrocarbon Natural products 0.000 description 9
RDEIXVOBVLKYNT-VQBXQJRRSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;(2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]o Chemical compound OS(O)(=O)=O.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)C(C)N)N)[C@@H](N)C[C@H]1N.O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N RDEIXVOBVLKYNT-VQBXQJRRSA-N 0.000 description 8
230000012010 growth Effects 0.000 description 8
238000003921 particle size analysis Methods 0.000 description 8
238000000527 sonication Methods 0.000 description 8
229930182566 Gentamicin Natural products 0.000 description 7
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
229960002518 gentamicin Drugs 0.000 description 7
239000000523 sample Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
235000013601 eggs Nutrition 0.000 description 6
229960000707 tobramycin Drugs 0.000 description 6
NLVFBUXFDBBNBW-PBSUHMDJSA-S tobramycin(5+) Chemical compound [NH3+][C@@H]1C[C@H](O)[C@@H](C[NH3+])O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H]([NH3+])[C@H](O)[C@@H](CO)O2)O)[C@H]([NH3+])C[C@@H]1[NH3+] NLVFBUXFDBBNBW-PBSUHMDJSA-S 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 5
PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 5
238000004581 coalescence Methods 0.000 description 5
108010067396 dornase alfa Proteins 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 5
229940074096 monoolein Drugs 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
238000012856 packing Methods 0.000 description 5
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 5
229940117972 triolein Drugs 0.000 description 5
238000009423 ventilation Methods 0.000 description 5
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
102000002322 Egg Proteins Human genes 0.000 description 4
108010000912 Egg Proteins Proteins 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
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235000013345 egg yolk Nutrition 0.000 description 4
210000002969 egg yolk Anatomy 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
229940057917 medium chain triglycerides Drugs 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229940107568 pulmozyme Drugs 0.000 description 4
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 3
ZEUUPKVZFKBXPW-TWDWGCDDSA-N (2s,3r,4s,5s,6r)-4-amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid Chemical compound OS(O)(=O)=O.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 ZEUUPKVZFKBXPW-TWDWGCDDSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
239000004098 Tetracycline Substances 0.000 description 3
239000002253 acid Substances 0.000 description 3
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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 description 3
229940126575 aminoglycoside Drugs 0.000 description 3
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238000002296 dynamic light scattering Methods 0.000 description 3
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229910052740 iodine Inorganic materials 0.000 description 3
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239000000463 material Substances 0.000 description 3
238000005259 measurement Methods 0.000 description 3
125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000035515 penetration Effects 0.000 description 3
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235000019364 tetracycline Nutrition 0.000 description 3
150000003522 tetracyclines Chemical class 0.000 description 3
229960004477 tobramycin sulfate Drugs 0.000 description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
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MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
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KFVSLSTULZVNPG-UHFFFAOYSA-N terbutaline sulfate Chemical compound [O-]S([O-])(=O)=O.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1 KFVSLSTULZVNPG-UHFFFAOYSA-N 0.000 description 1
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YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0026—Blood substitute; Oxygen transporting formulations; Plasma extender
- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/113—Multiple emulsions, e.g. oil-in-water-in-oil

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Dispersion Chemistry (AREA)
Hematology (AREA)
Dermatology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Medicinal Preparation (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA002222063A 1995-06-07 1996-06-05 Reverse fluorocarbon emulsion compositions for drug delivery Abandoned CA2222063A1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US48761295A	1995-06-07	1995-06-07
US08/487,612		1995-06-07

Publications (1)

Publication Number	Publication Date
CA2222063A1 true CA2222063A1 (en)	1996-12-19

Family

ID=23936452

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002222063A Abandoned CA2222063A1 (en)	1995-06-07	1996-06-05	Reverse fluorocarbon emulsion compositions for drug delivery

Country Status (11)

Country	Link
EP (1)	EP0833608A2 (no)
JP (1)	JPH11508237A (no)
KR (1)	KR19990022354A (no)
CN (1)	CN1195981A (no)
AU (1)	AU704918B2 (no)
CA (1)	CA2222063A1 (no)
HU (1)	HUP9900879A2 (no)
IL (1)	IL122249A0 (no)
NO (1)	NO975321L (no)
PL (1)	PL323931A1 (no)
WO (1)	WO1996040057A2 (no)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9781250B2 (en) *	2015-05-31	2017-10-03	Emma Michaela Siritzky	Methods, devices and systems supporting driving without distraction

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WO1999021541A2 (en) *	1997-10-24	1999-05-06	Alliance Pharmaceutical Corp.	Amelioration of ischemic damage using synthetic oxygen carriers
WO1999024016A1 (en) *	1997-11-10	1999-05-20	Sonus Pharmaceuticals, Inc.	Emulsions for aerosolization and drug delivery
US6127430A (en) *	1998-12-16	2000-10-03	3M Innovative Properties Company	Microemulsions containing water and hydrofluroethers
US6159917A (en) *	1998-12-16	2000-12-12	3M Innovative Properties Company	Dry cleaning compositions containing hydrofluoroether
US6312665B1 (en) *	1998-12-21	2001-11-06	Generex Pharmaceuticals Incorporated	Aerosol formulations for buccal and pulmonary application
US7087215B2 (en)	1998-12-21	2006-08-08	Generex Pharmaceuticals Incorporated	Methods of administering and enhancing absorption of pharmaceutical agents
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1996
- 1996-06-05 WO PCT/US1996/009064 patent/WO1996040057A2/en not_active Application Discontinuation
- 1996-06-05 CN CN96195973A patent/CN1195981A/zh active Pending
- 1996-06-05 KR KR1019970708834A patent/KR19990022354A/ko not_active Application Discontinuation
- 1996-06-05 PL PL96323931A patent/PL323931A1/xx unknown
- 1996-06-05 IL IL12224996A patent/IL122249A0/xx unknown
- 1996-06-05 EP EP96919114A patent/EP0833608A2/en not_active Ceased
- 1996-06-05 CA CA002222063A patent/CA2222063A1/en not_active Abandoned
- 1996-06-05 AU AU61537/96A patent/AU704918B2/en not_active Ceased
- 1996-06-05 JP JP9501474A patent/JPH11508237A/ja active Pending
- 1996-06-05 HU HU9900879A patent/HUP9900879A2/hu unknown
1997
- 1997-11-19 NO NO975321A patent/NO975321L/no not_active Application Discontinuation

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Also Published As

Publication number	Publication date
AU704918B2 (en)	1999-05-06
HU9900879D0 (en)	1999-05-28
KR19990022354A (ko)	1999-03-25
JPH11508237A (ja)	1999-07-21
MX9709561A (es)	1998-10-31
PL323931A1 (en)	1998-04-27
HUP9900879A2 (hu)	1999-08-30
NO975321L (no)	1998-01-27
CN1195981A (zh)	1998-10-14
EP0833608A2 (en)	1998-04-08
NO975321D0 (no)	1997-11-19
IL122249A0 (en)	1998-04-05
AU6153796A (en)	1996-12-30
WO1996040057A3 (en)	1997-02-20
WO1996040057A2 (en)	1996-12-19

Publication	Publication Date	Title
AU704918B2 (en)	1999-05-06	Reverse fluorocarbon emulsion compositions for drug delivery
US5980936A (en)	1999-11-09	Multiple emulsions comprising a hydrophobic continuous phase
KR100454377B1 (ko)	2005-08-04	약제전달을위한연속플루오로화합물미립분산액
US5733526A (en)	1998-03-31	Hydrocarbon oil/fluorochemical preparations and methods of use
Hippalgaonkar et al.	2010	Injectable lipid emulsions—advancements, opportunities and challenges
US5904933A (en)	1999-05-18	Stable reverse and multiple fluorocarbon emulsions
US20180000828A1 (en)	2018-01-04	Emulsion formulations of aprepitant
WO1998005301A1 (en)	1998-02-12	Multiple emulsions comprising a hydrophobic continuous phase
JPH08511245A (ja)	1996-11-26	薬剤搬送ビヒクルとしての固体脂肪ナノエマルジョン体
WO1997030695A1 (en)	1997-08-28	Drug delivery compositions suitable for intravenous injection
US9700866B2 (en)	2017-07-11	Surfactant systems for delivery of organic compounds
CA2151491A1 (en)	1994-07-07	Fluorocarbon emulsions
AU717321B2 (en)	2000-03-23	Reverse gels comprising a continuous fluorinated phase
WO1991007973A1 (fr)	1991-06-13	Emulsion grasse
MXPA97009561A (es)	1999-01-11	Composiciones de la emulsion de huorocarbobo inverso (privado) para el suministro de medicamento
JP2001515503A (ja)	2001-09-18	軟質粒子、非イオン性界面活性剤および非イオン性曇点調節剤を含む組成物
Rosoff	2020	Specialized Pharmaceutical Emulsions
JPH11279082A (ja)	1999-10-12	注射用脂肪乳剤
TOULIYAT et al.	2003	Development of a Depofoam technology for the sustained delivery of desferrioxamine mesylate
JPH04356417A (ja)	1992-12-10	静脈注射用脂肪乳剤
MXPA97009690A (en)	1998-10-15	Continuous microdispersions of fluorochemicals for the supply of agents farmaceuti
Apte	1993	Preparation and characterization of a 40 percent V/V parenteral perfluorocarbon emulsion
AU6651100A (en)	2000-12-14	Continuous fluorochemical microdispersions for the delivery of pharmaceutical agents

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2002-06-05	FZDE	Discontinued

CA2222063A1 - Reverse fluorocarbon emulsion compositions for drug delivery - Google Patents

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