CA1072446A - Oxygen-transferable fluorocarbon emulsion - Google Patents
Oxygen-transferable fluorocarbon emulsionInfo
- Publication number
- CA1072446A CA1072446A CA256,571A CA256571A CA1072446A CA 1072446 A CA1072446 A CA 1072446A CA 256571 A CA256571 A CA 256571A CA 1072446 A CA1072446 A CA 1072446A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- perfluoro
- carbon atoms
- emulsion
- alkyl
- 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
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 138
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 title abstract description 11
- -1 perfluorocarbon compound Chemical class 0.000 claims description 122
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 239000002245 particle Substances 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 26
- 229930195729 fatty acid Natural products 0.000 claims description 26
- 239000000194 fatty acid Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 22
- 229950011087 perflunafene Drugs 0.000 claims description 22
- UWEYRJFJVCLAGH-IJWZVTFUSA-N perfluorodecalin Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)[C@@]2(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)[C@@]21F UWEYRJFJVCLAGH-IJWZVTFUSA-N 0.000 claims description 22
- 150000003904 phospholipids Chemical class 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 18
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 14
- 210000004369 blood Anatomy 0.000 claims description 14
- 239000008280 blood Substances 0.000 claims description 14
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 14
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 14
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 14
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 14
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 14
- 239000003058 plasma substitute Substances 0.000 claims description 12
- 239000002736 nonionic surfactant Substances 0.000 claims description 9
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 8
- 239000005639 Lauric acid Substances 0.000 claims description 8
- 239000005642 Oleic acid Substances 0.000 claims description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 8
- 235000021313 oleic acid Nutrition 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- LWRNQOBXRHWPGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(C(F)(F)F)(F)C(F)(F)C(F)(F)C(F)(F)C21F LWRNQOBXRHWPGE-UHFFFAOYSA-N 0.000 claims description 7
- 235000021357 Behenic acid Nutrition 0.000 claims description 7
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 7
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 7
- 229920001612 Hydroxyethyl starch Polymers 0.000 claims description 7
- 235000021314 Palmitic acid Nutrition 0.000 claims description 7
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- 239000012736 aqueous medium Substances 0.000 claims description 7
- 235000021342 arachidonic acid Nutrition 0.000 claims description 7
- 229940114079 arachidonic acid Drugs 0.000 claims description 7
- 229940116226 behenic acid Drugs 0.000 claims description 7
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 7
- 229940050526 hydroxyethylstarch Drugs 0.000 claims description 7
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 229960002446 octanoic acid Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 7
- 229920002307 Dextran Polymers 0.000 claims description 6
- 229940096992 potassium oleate Drugs 0.000 claims description 6
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 claims description 6
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 5
- 150000005215 alkyl ethers Chemical class 0.000 claims description 5
- BPKIGYQJPYCAOW-FFJTTWKXSA-I calcium;potassium;disodium;(2s)-2-hydroxypropanoate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].C[C@H](O)C([O-])=O BPKIGYQJPYCAOW-FFJTTWKXSA-I 0.000 claims description 5
- 239000000644 isotonic solution Substances 0.000 claims description 5
- 229950008618 perfluamine Drugs 0.000 claims description 5
- JAJLKEVKNDUJBG-UHFFFAOYSA-N perfluorotripropylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F JAJLKEVKNDUJBG-UHFFFAOYSA-N 0.000 claims description 5
- 239000008347 soybean phospholipid Substances 0.000 claims description 5
- PSJKAILWKIKKNU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-n-(trifluoromethyl)butan-1-amine Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PSJKAILWKIKKNU-UHFFFAOYSA-N 0.000 claims description 4
- 108010010803 Gelatin Proteins 0.000 claims description 4
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001804 emulsifying effect Effects 0.000 claims description 4
- 229920000159 gelatin Polymers 0.000 claims description 4
- 239000008273 gelatin Substances 0.000 claims description 4
- 235000019322 gelatine Nutrition 0.000 claims description 4
- 235000011852 gelatine desserts Nutrition 0.000 claims description 4
- DNZMDASEFMLYBU-RNBXVSKKSA-N hydroxyethyl starch Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O.OCCOC[C@H]1O[C@H](OCCO)[C@H](OCCO)[C@@H](OCCO)[C@@H]1OCCO DNZMDASEFMLYBU-RNBXVSKKSA-N 0.000 claims description 4
- YDSHWJILVOQURX-UHFFFAOYSA-N 1,2,2,3,3,4,4,5,5,6,6-undecafluoro-n,n-bis(1,1,2,2,2-pentafluoroethyl)cyclohexan-1-amine Chemical compound FC(F)(F)C(F)(F)N(C(F)(F)C(F)(F)F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F YDSHWJILVOQURX-UHFFFAOYSA-N 0.000 claims description 3
- 239000008344 egg yolk phospholipid Substances 0.000 claims description 3
- 229940068998 egg yolk phospholipid Drugs 0.000 claims description 3
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000010008 shearing Methods 0.000 claims description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 6
- 229910052783 alkali metal Inorganic materials 0.000 claims 6
- 235000020778 linoleic acid Nutrition 0.000 claims 6
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 6
- WBQMKAKILKYGRY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,5-undecafluoro-N,N-bis(1,1,2,2,2-pentafluoroethyl)pentan-1-amine Chemical compound FC(F)(F)C(F)(F)N(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F WBQMKAKILKYGRY-UHFFFAOYSA-N 0.000 claims 2
- CJAFXLJLGHAEOC-UHFFFAOYSA-N FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F Chemical compound FC(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CJAFXLJLGHAEOC-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 claims 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 229940045870 sodium palmitate Drugs 0.000 claims 2
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 claims 2
- XDJOUWJLZAWHSI-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluoro-n,n-bis(1,1,2,2,2-pentafluoroethyl)hexan-1-amine Chemical compound FC(F)(F)C(F)(F)N(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XDJOUWJLZAWHSI-UHFFFAOYSA-N 0.000 claims 1
- 235000010469 Glycine max Nutrition 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 239000002473 artificial blood Substances 0.000 abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 239000001301 oxygen Substances 0.000 abstract description 4
- 229920005862 polyol Polymers 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 17
- 229940067631 phospholipid Drugs 0.000 description 13
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 6
- 210000002969 egg yolk Anatomy 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 230000029142 excretion Effects 0.000 description 5
- 239000003978 infusion fluid Substances 0.000 description 5
- 208000032843 Hemorrhage Diseases 0.000 description 4
- 229940119744 dextran 40 Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- CBUDGIQWHQHTHD-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6-nonafluoro-6-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)oxane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C(F)(F)C1(F)F CBUDGIQWHQHTHD-UHFFFAOYSA-N 0.000 description 3
- 108010054147 Hemoglobins Proteins 0.000 description 3
- 102000001554 Hemoglobins Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003633 blood substitute Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 230000002949 hemolytic effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 210000001835 viscera Anatomy 0.000 description 3
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 2
- GDCXYFJTTYCIKU-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6-decafluoro-1-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl)piperidine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F GDCXYFJTTYCIKU-UHFFFAOYSA-N 0.000 description 2
- FCAKFMGNFPPPSH-UHFFFAOYSA-N 2,2,3,3,4,4,5-heptafluoro-5-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl)oxolane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F FCAKFMGNFPPPSH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 238000005534 hematocrit Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 235000015424 sodium Nutrition 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- UVWPNDVAQBNQBG-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-icosafluorononane 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)C(F)(F)F UVWPNDVAQBNQBG-UHFFFAOYSA-N 0.000 description 1
- XZZGMFAUFIVEGL-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)cyclohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F XZZGMFAUFIVEGL-UHFFFAOYSA-N 0.000 description 1
- SXTYPPLQJZRXLD-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluoro-6-(1,1,2,2,3,3,3-heptafluoropropyl)-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F SXTYPPLQJZRXLD-UHFFFAOYSA-N 0.000 description 1
- SIJZIPMRLFRVHV-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5-nonafluoro-5,6,6-tris(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(C(F)(F)F)C(F)(F)F SIJZIPMRLFRVHV-UHFFFAOYSA-N 0.000 description 1
- MQKJLWGJGUUOEJ-UHFFFAOYSA-N 2,2,3,3,4,4,5-heptafluoro-5-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)oxolane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C1(F)F MQKJLWGJGUUOEJ-UHFFFAOYSA-N 0.000 description 1
- WIIMAMOWQWJFEO-UHFFFAOYSA-N 2,2,3,3,5,5,6,6-octafluoro-4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptyl)morpholine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F WIIMAMOWQWJFEO-UHFFFAOYSA-N 0.000 description 1
- DSXQNQQCDMBVOD-UHFFFAOYSA-N FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C(F)(F)C(F)(F)OC(F)(F)C1(F)F DSXQNQQCDMBVOD-UHFFFAOYSA-N 0.000 description 1
- QRGKREXBRIWEMS-UHFFFAOYSA-N FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QRGKREXBRIWEMS-UHFFFAOYSA-N 0.000 description 1
- QFYNLSCJBREZMB-UHFFFAOYSA-N FC(F)(F)C(F)(F)C(F)(F)C1(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F Chemical compound FC(F)(F)C(F)(F)C(F)(F)C1(C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QFYNLSCJBREZMB-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000283907 Tragelaphus oryx Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000013130 cardiovascular surgery Methods 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 108700042971 cyanomethemoglobin Proteins 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000002146 exchange transfusion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 1
- BPHQIXJDBIHMLT-UHFFFAOYSA-N perfluorodecane 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)C(F)(F)C(F)(F)F BPHQIXJDBIHMLT-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 210000003462 vein Anatomy 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
- A61K9/0012—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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65496476A | 1976-02-03 | 1976-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072446A true CA1072446A (en) | 1980-02-26 |
Family
ID=24626936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,571A Expired CA1072446A (en) | 1976-02-03 | 1976-07-08 | Oxygen-transferable fluorocarbon emulsion |
Country Status (22)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4186253A (en) * | 1978-10-10 | 1980-01-29 | The Green Cross Corporation | Perfusate for preserving organ to be transplanted and preserving method |
| JPS55100312A (en) * | 1979-01-25 | 1980-07-31 | Toshiro Wada | Contrast medium for blood vessel |
| EP0077114B1 (en) * | 1981-09-08 | 1987-12-02 | Green Cross Corporation | Perfluorochemicals, process for preparing the same and their use as blood substitutes |
| US4423077A (en) * | 1982-07-27 | 1983-12-27 | The University Of Pennsylvania | Perfluorochemical emulsion artificial blood |
| JPS5946218A (ja) * | 1982-09-09 | 1984-03-15 | Green Cross Corp:The | フルオロカ−ボン乳化製剤 |
| JPS59175421A (ja) * | 1983-03-24 | 1984-10-04 | Tetsuzou Agishi | 血液浄化剤 |
| WO1993002653A1 (en) * | 1991-08-08 | 1993-02-18 | Segel Leigh D | Fluorocarbon blood substitute |
| US5502094A (en) * | 1994-05-20 | 1996-03-26 | Minnesota Mining And Manufacturing Company | Physiologically acceptable emulsions containing perfluorocarbon ether hydrides and methods for use |
| US5658962A (en) * | 1994-05-20 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| WO1997025978A1 (fr) * | 1996-01-15 | 1997-07-24 | BELOYARTSEV, Arkady Felixovich | Procede de production d'emulsions perfluorocarbonees a des fins medicales |
| CN1068778C (zh) * | 1998-05-15 | 2001-07-25 | 赵超英 | 救治用的药物组合物及其制备方法 |
| US7357937B2 (en) | 2002-09-24 | 2008-04-15 | Therox, Inc. | Perfluorocarbon emulsions with non-fluorinated surfactants |
| RU2259819C1 (ru) | 2004-03-01 | 2005-09-10 | Кузнецова Ирина Николаевна | Эмульсия перфторорганических соединений медицинского назначения и способ её получения |
| WO2007105978A1 (fr) | 2006-03-14 | 2007-09-20 | Sergey Ivanovich Vorobyev | Émulsion perfluorocarbonée de transfert de gaz destinée à une utilisation médicale et biologique : composition, procédé de production et agent curatif (variantes) |
| US8063020B2 (en) * | 2007-12-22 | 2011-11-22 | Simpkins Cuthbert O | Resuscitation fluid |
| GB2467353B (en) | 2009-01-30 | 2011-07-20 | Steven Skill | Apparatus for treatment of fluid streams and method of conducting the same |
| ES2541226B2 (es) * | 2014-01-15 | 2016-02-12 | MONDRAGÓN GOI ESKOLA POLITEKNIKOA J. Mª. ARIZMENDIARRIETA, S.C | Fantoma de sangre |
| RU2745290C2 (ru) * | 2019-04-12 | 2021-03-23 | Ирина Николаевна Кузнецова | Эмульсия перфторуглеродных соединений медико-биологического назначения и способ её получения |
| WO2024046999A1 (de) * | 2022-08-31 | 2024-03-07 | Johann Wolfgang Goethe-Universität Frankfurt am Main | Lecithin-modifizierte nanoskalierte sauerstoffträger (lenox) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH604490A5 (enrdf_load_stackoverflow) * | 1970-09-05 | 1978-09-15 | Green Cross Corp | |
| JPS5331209B2 (enrdf_load_stackoverflow) * | 1973-10-05 | 1978-09-01 |
-
1976
- 1976-07-01 JP JP51078127A patent/JPS5835485B2/ja not_active Expired
- 1976-07-02 GB GB27739/76A patent/GB1549038A/en not_active Expired
- 1976-07-06 SE SE7607727A patent/SE442706B/xx not_active IP Right Cessation
- 1976-07-07 AT AT496676A patent/AT355214B/de not_active IP Right Cessation
- 1976-07-07 NL NLAANVRAGE7607514,A patent/NL171533C/xx not_active IP Right Cessation
- 1976-07-07 DK DK307276A patent/DK152256C/da not_active IP Right Cessation
- 1976-07-07 CH CH869676A patent/CH633674A5/de not_active IP Right Cessation
- 1976-07-07 ES ES449635A patent/ES449635A1/es not_active Expired
- 1976-07-07 DE DE2630586A patent/DE2630586C2/de not_active Expired
- 1976-07-08 CA CA256,571A patent/CA1072446A/en not_active Expired
- 1976-07-08 FR FR7620907A patent/FR2361867A1/fr active Granted
-
1977
- 1977-01-17 ZA ZA770229A patent/ZA77229B/xx unknown
- 1977-01-17 NZ NZ183096A patent/NZ183096A/xx unknown
- 1977-01-21 MX MX775377U patent/MX4136E/es unknown
- 1977-01-25 IL IL51325A patent/IL51325A/xx unknown
- 1977-01-31 AR AR266381A patent/AR218864A1/es active
- 1977-02-01 FI FI770354A patent/FI58071C/fi not_active IP Right Cessation
- 1977-02-01 NO NO770324A patent/NO145370C/no unknown
- 1977-02-02 SU SU772447657A patent/SU797546A3/ru active
- 1977-02-02 BE BE174577A patent/BE850992A/xx not_active IP Right Cessation
- 1977-02-03 DD DD7700197227A patent/DD132231A5/xx unknown
- 1977-02-03 LU LU76698A patent/LU76698A1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |