RU2419421C2 - Инъецируемая жидкая композиция парацетамола - Google Patents
Инъецируемая жидкая композиция парацетамола Download PDFInfo
- Publication number
- RU2419421C2 RU2419421C2 RU2009105480/15A RU2009105480A RU2419421C2 RU 2419421 C2 RU2419421 C2 RU 2419421C2 RU 2009105480/15 A RU2009105480/15 A RU 2009105480/15A RU 2009105480 A RU2009105480 A RU 2009105480A RU 2419421 C2 RU2419421 C2 RU 2419421C2
- Authority
- RU
- Russia
- Prior art keywords
- paracetamol
- solution
- solutions
- aqueous solution
- color
- Prior art date
Links
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 229960005489 paracetamol Drugs 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title description 16
- 239000007788 liquid Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 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 abstract description 9
- 239000008103 glucose Substances 0.000 claims abstract description 9
- 230000010412 perfusion Effects 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 69
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 239000000872 buffer Substances 0.000 claims description 4
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 3
- 150000004701 malic acid derivatives Chemical class 0.000 claims description 3
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 150000003893 lactate salts Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- WXKPPMQZRGORPB-UHFFFAOYSA-M sodium;2-hydroxypropane-1,2,3-tricarboxylic acid;acetate Chemical group [Na+].CC([O-])=O.OC(=O)CC(O)(C(O)=O)CC(O)=O WXKPPMQZRGORPB-UHFFFAOYSA-M 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 22
- 230000000694 effects Effects 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract 1
- 230000003019 stabilising effect Effects 0.000 abstract 1
- 239000012535 impurity Substances 0.000 description 25
- 239000003963 antioxidant agent Substances 0.000 description 18
- 235000006708 antioxidants Nutrition 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 14
- 230000003078 antioxidant effect Effects 0.000 description 11
- 229920003023 plastic Polymers 0.000 description 11
- 239000004033 plastic Substances 0.000 description 11
- -1 polypropylene Polymers 0.000 description 8
- 239000004800 polyvinyl chloride Substances 0.000 description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 229940031826 phenolate Drugs 0.000 description 5
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- 229940050410 gluconate Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000006196 deacetylation Effects 0.000 description 3
- 238000003381 deacetylation reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000004061 benzoquinone imines Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 229940097042 glucuronate Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229940102223 injectable solution Drugs 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- 229940099584 lactobionate Drugs 0.000 description 2
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 150000004707 phenolate Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- XCPFSALHURPPJE-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XCPFSALHURPPJE-UHFFFAOYSA-N 0.000 description 1
- WELKBINNNXKQQS-UHFFFAOYSA-N 1,4-benzoquinone imine Chemical compound N=C1C=CC(=O)C=C1 WELKBINNNXKQQS-UHFFFAOYSA-N 0.000 description 1
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 1
- BBACMRQZSJPPMD-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[3-[(3-tert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethyl-5-[(3,3,5-tritert-butyl-4-hydroxycyclohexa-1,5-dien-1-yl)methyl]phenyl]methyl]phenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=CC=2)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)(C(C)(C)C)C(O)C(C(C)(C)C)=C1 BBACMRQZSJPPMD-UHFFFAOYSA-N 0.000 description 1
- JOWXNCPELQZFHF-UHFFFAOYSA-N 2-[3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoyloxy]ethyl 3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoate Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(CC(=O)OCCOC(=O)CC(C)(C=2C=C(C(O)=CC=2)C(C)(C)C)C=2C=C(C(O)=CC=2)C(C)(C)C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 JOWXNCPELQZFHF-UHFFFAOYSA-N 0.000 description 1
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- KJFSPOVZVRDQAX-UHFFFAOYSA-N 5-iminocyclohex-2-ene-1,4-dione Chemical class N=C1CC(=O)C=CC1=O KJFSPOVZVRDQAX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000021550 forms of sugar Nutrition 0.000 description 1
- 235000012209 glucono delta-lactone Nutrition 0.000 description 1
- 229960003681 gluconolactone Drugs 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 230000003082 hepatotoxic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000009916 joint effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000003186 pharmaceutical solution Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BVXCVHRMIDFOLY-UHFFFAOYSA-N phenylphosphinous acid Chemical group OPC1=CC=CC=C1 BVXCVHRMIDFOLY-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
-
- 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
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/ES2006/070108 WO2008009756A1 (es) | 2006-07-18 | 2006-07-18 | Formulación líquida inyectable de paracetamol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009105480A RU2009105480A (ru) | 2010-08-27 |
| RU2419421C2 true RU2419421C2 (ru) | 2011-05-27 |
Family
ID=38474429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009105480/15A RU2419421C2 (ru) | 2006-07-18 | 2006-07-18 | Инъецируемая жидкая композиция парацетамола |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US9943479B2 (enExample) |
| EP (2) | EP1889607B1 (enExample) |
| JP (1) | JP4929352B2 (enExample) |
| AT (1) | ATE432690T1 (enExample) |
| AU (2) | AU2006346318B2 (enExample) |
| CA (1) | CA2628806C (enExample) |
| CY (1) | CY1110480T1 (enExample) |
| DE (1) | DE602007001215D1 (enExample) |
| DK (1) | DK1889607T3 (enExample) |
| ES (1) | ES2327286T3 (enExample) |
| HR (1) | HRP20090350T1 (enExample) |
| MA (1) | MA31346B1 (enExample) |
| PL (1) | PL1889607T3 (enExample) |
| PT (1) | PT1889607E (enExample) |
| RU (1) | RU2419421C2 (enExample) |
| SI (1) | SI1889607T1 (enExample) |
| WO (1) | WO2008009756A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2926992B1 (fr) * | 2008-02-06 | 2011-01-14 | Moly Pharma | Formulation d'une solution de paracetamol injectable,procede de preparation et de conditionnement d'une telle solution et dispositif de conditionnement d'une telle solution |
| EP2243477A1 (de) | 2009-04-22 | 2010-10-27 | Fresenius Kabi Deutschland GmbH | Paracetamol zur parenteralen Verabreichung |
| US8404748B2 (en) | 2009-08-13 | 2013-03-26 | Neogen N.V. | Storage-stable formulation of paracetamol in aqueous solution |
| DK2525796T3 (en) * | 2010-01-21 | 2016-07-04 | Aprea Ab | An aqueous solution comprising 3-quinuclidinoner for the treatment of hyperproliferative disease, autoimmune disease and heart disease |
| EP2377516B1 (en) | 2010-04-14 | 2012-06-20 | B. Braun Melsungen AG | Acetaminophen composition |
| ES2414557B1 (es) | 2012-01-16 | 2014-06-10 | Novocat Farma, S.A. | Composición acuosa de paracetamol para inyección |
| ITMI20121154A1 (it) * | 2012-06-29 | 2013-12-30 | Sint Sa | Soluzione iniettabile di acetaminofene per la somministrazione spinale |
| ZA201300398B (en) * | 2012-11-27 | 2013-09-25 | Genfarma Laboratories S L | Injectable liquid formulation of the combination of tramadol and paracetamol |
| US20140303254A1 (en) * | 2013-04-08 | 2014-10-09 | InnoPharma Licensing LLC | Process Of Manufacturing A Stable, Ready To Use Infusion Bag For An Oxidation Sensitive Formulation |
| BR102014005885B1 (pt) * | 2014-03-13 | 2021-04-13 | Biotec Biológica Indústria Farmacêutica Ltda E.P.P | Formulação farmacêutica líquida injetável estável de paracetamol em bolsa plástica pronta para uso |
| WO2016013049A1 (en) * | 2014-07-25 | 2016-01-28 | Terumo Kabushiki Kaisha | Packaged acetaminophen injection solution preparation |
| PL3411004T3 (pl) * | 2016-02-05 | 2021-10-18 | Innopharma, Inc. | Sposób wytwarzania trwałego gotowego do użycia worka infuzyjnego z preparatem wrażliwym na utlenianie |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2751875A1 (fr) * | 1996-08-05 | 1998-02-06 | Scr Newpharm | Nouvelles formulations liquides stables a base de paracetamol et leur mode de preparation |
| EP0916347A1 (en) * | 1997-11-18 | 1999-05-19 | Uni-Pharma Kleon Tsetis A.B.E.E., Farmakeftika Ergastiria | Pharmaceutical injectable solutions containing paracetamol and combinations of paracetamol with other active substances |
| WO2003033026A1 (en) * | 2001-10-16 | 2003-04-24 | Bioren S.A. | Ready-to-use paracetamol injection solutions containing propylene glycol as the only cosolvent |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440815A (en) | 1981-06-29 | 1984-04-03 | Abbott Laboratories | Clear, autoclavable plastic formulation for medical liquid containers |
| KR100226191B1 (ko) | 1997-04-03 | 1999-10-15 | 구광시 | 음료용 플라스틱 병 |
| JP3674685B2 (ja) * | 1997-10-23 | 2005-07-20 | 森永乳業株式会社 | 液体の連続式加熱殺菌方法及び装置 |
| IT1301976B1 (it) | 1998-07-31 | 2000-07-20 | Angelini Ricerche Spa | Composizione farmaceutica iniettabile a base di paracetamolo |
| FR2809619B1 (fr) * | 2000-06-06 | 2004-09-24 | Pharmatop | Nouvelles formulations aqueuses de principes actifs sensibles a l'oxydation et leur procede d'obtention |
| DE10112325A1 (de) | 2001-03-13 | 2002-10-02 | Fresenius Kabi De Gmbh | Lagerstabile Fertiginfusionslösungen des Paracetamols |
| HUP0402549A3 (en) | 2001-12-18 | 2006-01-30 | Tseti Ioulia | Parenteral composition of paracetamol |
| EP1508566B1 (en) | 2002-05-27 | 2007-07-18 | Kyorin Pharmaceutical Co., Ltd. | (2s)-2-ethylphenylpropionic acid derivative |
| WO2004004705A2 (en) * | 2002-07-03 | 2004-01-15 | Shannon Biotechnology Ltd | Pharmaceutical formulations for preparing drink products |
| FR2851164B1 (fr) | 2003-02-14 | 2005-04-22 | Xuan Tho Nguyen | Formulation liquide injectable de paracetamol |
| FR2862872A1 (fr) | 2003-12-02 | 2005-06-03 | Palbian Snc | Composition a l'etat aqueux pour l'application perfusable d'un principe actif, notamment pharmacologique tel que le paracetamol. |
| US20060292225A1 (en) | 2005-06-24 | 2006-12-28 | Felix Arthur M | Water soluble analgesic formulations and methods for production |
-
2006
- 2006-07-18 JP JP2009519998A patent/JP4929352B2/ja active Active
- 2006-07-18 WO PCT/ES2006/070108 patent/WO2008009756A1/es not_active Ceased
- 2006-07-18 CA CA2628806A patent/CA2628806C/en active Active
- 2006-07-18 RU RU2009105480/15A patent/RU2419421C2/ru not_active IP Right Cessation
- 2006-07-18 AU AU2006346318A patent/AU2006346318B2/en active Active
- 2006-07-18 US US12/084,541 patent/US9943479B2/en active Active
-
2007
- 2007-07-12 EP EP07112327A patent/EP1889607B1/en active Active
- 2007-07-12 PT PT07112327T patent/PT1889607E/pt unknown
- 2007-07-12 AT AT07112327T patent/ATE432690T1/de active
- 2007-07-12 DE DE602007001215T patent/DE602007001215D1/de active Active
- 2007-07-12 ES ES07112327T patent/ES2327286T3/es active Active
- 2007-07-12 PL PL07112327T patent/PL1889607T3/pl unknown
- 2007-07-12 EP EP09161268A patent/EP2100596A3/en not_active Withdrawn
- 2007-07-12 DK DK07112327T patent/DK1889607T3/da active
- 2007-07-12 SI SI200730058T patent/SI1889607T1/sl unknown
-
2008
- 2008-11-07 MA MA31365A patent/MA31346B1/fr unknown
-
2009
- 2009-06-16 HR HR20090350T patent/HRP20090350T1/xx unknown
- 2009-07-23 CY CY20091100789T patent/CY1110480T1/el unknown
-
2011
- 2011-03-21 AU AU2011201253A patent/AU2011201253B2/en active Active
-
2016
- 2016-03-21 US US15/076,072 patent/US9943492B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2751875A1 (fr) * | 1996-08-05 | 1998-02-06 | Scr Newpharm | Nouvelles formulations liquides stables a base de paracetamol et leur mode de preparation |
| EP0916347A1 (en) * | 1997-11-18 | 1999-05-19 | Uni-Pharma Kleon Tsetis A.B.E.E., Farmakeftika Ergastiria | Pharmaceutical injectable solutions containing paracetamol and combinations of paracetamol with other active substances |
| WO2003033026A1 (en) * | 2001-10-16 | 2003-04-24 | Bioren S.A. | Ready-to-use paracetamol injection solutions containing propylene glycol as the only cosolvent |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2009105480A (ru) | 2010-08-27 |
| CA2628806A1 (en) | 2008-01-24 |
| ATE432690T1 (de) | 2009-06-15 |
| US9943492B2 (en) | 2018-04-17 |
| AU2006346318B2 (en) | 2011-02-10 |
| SI1889607T1 (sl) | 2009-10-31 |
| AU2006346318A1 (en) | 2008-01-24 |
| CA2628806C (en) | 2012-08-21 |
| US20090215903A1 (en) | 2009-08-27 |
| PL1889607T3 (pl) | 2009-10-30 |
| PT1889607E (pt) | 2009-07-20 |
| EP2100596A3 (en) | 2010-04-28 |
| CY1110480T1 (el) | 2015-04-29 |
| JP4929352B2 (ja) | 2012-05-09 |
| WO2008009756A1 (es) | 2008-01-24 |
| EP2100596A2 (en) | 2009-09-16 |
| DK1889607T3 (da) | 2009-07-27 |
| JP2009543851A (ja) | 2009-12-10 |
| US20160199325A1 (en) | 2016-07-14 |
| MA31346B1 (fr) | 2010-05-03 |
| AU2011201253B2 (en) | 2012-03-29 |
| US9943479B2 (en) | 2018-04-17 |
| DE602007001215D1 (de) | 2009-07-16 |
| ES2327286T3 (es) | 2009-10-27 |
| EP1889607B1 (en) | 2009-06-03 |
| HRP20090350T1 (en) | 2009-08-31 |
| AU2011201253A1 (en) | 2011-04-07 |
| EP1889607A1 (en) | 2008-02-20 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130719 |