AU2014223993B2 - Injectable long-acting local anesthetic semi-solid formulations and its compostions - Google Patents
Injectable long-acting local anesthetic semi-solid formulations and its compostions Download PDFInfo
- Publication number
- AU2014223993B2 AU2014223993B2 AU2014223993A AU2014223993A AU2014223993B2 AU 2014223993 B2 AU2014223993 B2 AU 2014223993B2 AU 2014223993 A AU2014223993 A AU 2014223993A AU 2014223993 A AU2014223993 A AU 2014223993A AU 2014223993 B2 AU2014223993 B2 AU 2014223993B2
- Authority
- AU
- Australia
- Prior art keywords
- semi
- pharmaceutical composition
- solid
- local anesthetic
- triglycerides
- 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.)
- Ceased
Links
- 239000007787 solid Substances 0.000 title claims abstract description 213
- 239000000203 mixture Substances 0.000 title claims abstract description 135
- 239000003589 local anesthetic agent Substances 0.000 title claims abstract description 67
- 238000009472 formulation Methods 0.000 title description 81
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 claims description 89
- 229960003150 bupivacaine Drugs 0.000 claims description 87
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 63
- 150000004665 fatty acids Chemical class 0.000 claims description 43
- 239000008194 pharmaceutical composition Substances 0.000 claims description 43
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 41
- 229930195729 fatty acid Natural products 0.000 claims description 41
- 239000000194 fatty acid Substances 0.000 claims description 41
- 150000002148 esters Chemical class 0.000 claims description 36
- 150000003626 triacylglycerols Chemical class 0.000 claims description 33
- 125000005456 glyceride group Chemical group 0.000 claims description 31
- 208000002193 Pain Diseases 0.000 claims description 22
- 239000007924 injection Substances 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 19
- 230000036407 pain Effects 0.000 claims description 19
- 239000008247 solid mixture Substances 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- -1 diglycerides Chemical class 0.000 claims description 16
- 238000004090 dissolution Methods 0.000 claims description 14
- 230000007423 decrease Effects 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 10
- 238000000338 in vitro Methods 0.000 claims description 10
- 229960004194 lidocaine Drugs 0.000 claims description 10
- 150000003839 salts Chemical group 0.000 claims description 10
- 229960002409 mepivacaine Drugs 0.000 claims description 9
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 9
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000001356 surgical procedure Methods 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 6
- 150000001261 hydroxy acids Chemical class 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
- ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical compound CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 claims description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000005690 diesters Chemical class 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 229960001549 ropivacaine Drugs 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- VTUSIVBDOCDNHS-UHFFFAOYSA-N Etidocaine Chemical compound CCCN(CC)C(CC)C(=O)NC1=C(C)C=CC=C1C VTUSIVBDOCDNHS-UHFFFAOYSA-N 0.000 claims description 3
- 229960003976 etidocaine Drugs 0.000 claims description 3
- 210000005036 nerve Anatomy 0.000 claims description 3
- 231100000862 numbness Toxicity 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000012943 hotmelt Substances 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 230000003381 solubilizing effect Effects 0.000 claims description 2
- 150000005691 triesters Chemical class 0.000 claims description 2
- HDIFHQMREAYYJW-XGXNLDPDSA-N Glyceryl Ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC(O)CO HDIFHQMREAYYJW-XGXNLDPDSA-N 0.000 claims 5
- 229940116338 glyceryl ricinoleate Drugs 0.000 claims 5
- 239000002736 nonionic surfactant Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 239000007928 intraperitoneal injection Substances 0.000 claims 1
- 229940105297 polyglyceryl-2 diisostearate Drugs 0.000 claims 1
- 239000007929 subcutaneous injection Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 abstract description 101
- 229960005015 local anesthetics Drugs 0.000 abstract description 29
- 238000013270 controlled release Methods 0.000 abstract description 12
- 239000011159 matrix material Substances 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000006104 solid solution Substances 0.000 abstract description 4
- 239000003981 vehicle Substances 0.000 description 88
- 229940079593 drug Drugs 0.000 description 61
- 239000003814 drug Substances 0.000 description 61
- 239000007788 liquid Substances 0.000 description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000013543 active substance Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 22
- 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 description 15
- 101710145576 Prostaglandin-H2 D-isomerase Proteins 0.000 description 15
- 241000700159 Rattus Species 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 230000008018 melting Effects 0.000 description 13
- 230000036961 partial effect Effects 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 238000012377 drug delivery Methods 0.000 description 10
- 210000002683 foot Anatomy 0.000 description 10
- 239000000499 gel Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 9
- 239000002953 phosphate buffered saline Substances 0.000 description 9
- 210000003497 sciatic nerve Anatomy 0.000 description 9
- 229940126534 drug product Drugs 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000009974 thixotropic effect Effects 0.000 description 8
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 206010061218 Inflammation Diseases 0.000 description 6
- 208000004550 Postoperative Pain Diseases 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000003628 erosive effect Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
- 230000017074 necrotic cell death Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000029663 wound healing Effects 0.000 description 6
- 206010028851 Necrosis Diseases 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 231100000989 no adverse effect Toxicity 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 230000001953 sensory effect Effects 0.000 description 5
- 238000010008 shearing Methods 0.000 description 5
- 230000036269 ulceration Effects 0.000 description 5
- 229920001710 Polyorthoester Polymers 0.000 description 4
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000004005 microsphere Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 206010052428 Wound Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000036760 body temperature Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940105990 diglycerin Drugs 0.000 description 3
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 150000004667 medium chain fatty acids Chemical class 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000006174 pH buffer Substances 0.000 description 3
- 239000002745 poly(ortho ester) Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
- 229960002372 tetracaine Drugs 0.000 description 3
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- VLHZUYUOEGBBJB-UHFFFAOYSA-N 18-hydroxyoctadecanoic acid Chemical compound OCCCCCCCCCCCCCCCCCC(O)=O VLHZUYUOEGBBJB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 206010012335 Dependence Diseases 0.000 description 2
- 102000002265 Human Growth Hormone Human genes 0.000 description 2
- 108010000521 Human Growth Hormone Proteins 0.000 description 2
- 239000000854 Human Growth Hormone Substances 0.000 description 2
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 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 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 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 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960001747 cinchocaine Drugs 0.000 description 2
- PUFQVTATUTYEAL-UHFFFAOYSA-N cinchocaine Chemical compound C1=CC=CC2=NC(OCCCC)=CC(C(=O)NCCN(CC)CC)=C21 PUFQVTATUTYEAL-UHFFFAOYSA-N 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 238000002224 dissection Methods 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 210000005069 ears Anatomy 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229960002725 isoflurane Drugs 0.000 description 2
- 125000000400 lauroyl 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])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 230000007830 nerve conduction Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000012056 semi-solid material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 210000003371 toe Anatomy 0.000 description 2
- 210000000689 upper leg Anatomy 0.000 description 2
- 235000013311 vegetables Nutrition 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
- WECGLUPZRHILCT-GSNKCQISSA-N 1-linoleoyl-sn-glycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)CO WECGLUPZRHILCT-GSNKCQISSA-N 0.000 description 1
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 1
- JBSOOFITVPOOSY-KTKRTIGZSA-N 2-hydroxyoleic acid Chemical compound CCCCCCCC\C=C/CCCCCCC(O)C(O)=O JBSOOFITVPOOSY-KTKRTIGZSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- QTGIAADRBBLJGA-UHFFFAOYSA-N Articaine Chemical compound CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OC QTGIAADRBBLJGA-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- YZDBUGSKTDAWFD-UHFFFAOYSA-N OC(C(=O)OCC(O)CO)CCCCCCC=C/CCCCCCCC Chemical compound OC(C(=O)OCC(O)CO)CCCCCCC=C/CCCCCCCC YZDBUGSKTDAWFD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101150034459 Parpbp gene Proteins 0.000 description 1
- 239000004107 Penicillin G sodium Substances 0.000 description 1
- YQKAVWCGQQXBGW-UHFFFAOYSA-N Piperocaine Chemical compound CC1CCCCN1CCCOC(=O)C1=CC=CC=C1 YQKAVWCGQQXBGW-UHFFFAOYSA-N 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920002675 Polyoxyl Polymers 0.000 description 1
- KCLANYCVBBTKTO-UHFFFAOYSA-N Proparacaine Chemical compound CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N KCLANYCVBBTKTO-UHFFFAOYSA-N 0.000 description 1
- CAJIGINSTLKQMM-UHFFFAOYSA-N Propoxycaine Chemical compound CCCOC1=CC(N)=CC=C1C(=O)OCCN(CC)CC CAJIGINSTLKQMM-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000002847 Surgical Wound Diseases 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 229940052294 amide local anesthetics Drugs 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000012984 antibiotic solution Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229960003831 articaine Drugs 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- NGPTYCZGBCGWBE-UHFFFAOYSA-N decanoic acid hexadecanoic acid octadecanoic acid octanoic acid propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O NGPTYCZGBCGWBE-UHFFFAOYSA-N 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229940042577 exparel Drugs 0.000 description 1
- 210000003195 fascia Anatomy 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 229940074047 glyceryl cocoate Drugs 0.000 description 1
- 229940074046 glyceryl laurate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940074050 glyceryl myristate Drugs 0.000 description 1
- 229940096898 glyceryl palmitate Drugs 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 235000019866 hydrogenated palm kernel oil Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000008384 ileus Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000005022 impaired gait Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229960004288 levobupivacaine Drugs 0.000 description 1
- LEBVLXFERQHONN-INIZCTEOSA-N levobupivacaine Chemical compound CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-INIZCTEOSA-N 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 229940106885 marcaine Drugs 0.000 description 1
- 231100000647 material safety data sheet Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940063149 nutropin Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 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 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940124583 pain medication Drugs 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 150000002942 palmitic acid derivatives Chemical class 0.000 description 1
- 235000019369 penicillin G sodium Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229960001045 piperocaine Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229960003981 proparacaine Drugs 0.000 description 1
- 229950003255 propoxycaine Drugs 0.000 description 1
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000004666 short chain fatty acids Chemical class 0.000 description 1
- 238000012154 short term therapy Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960004532 somatropin Drugs 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000013269 sustained drug release Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- GOZBHBFUQHMKQB-UHFFFAOYSA-N trimecaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=C(C)C=C1C GOZBHBFUQHMKQB-UHFFFAOYSA-N 0.000 description 1
- 229950002569 trimecaine Drugs 0.000 description 1
- DUXYWXYOBMKGIN-UHFFFAOYSA-N trimyristin Chemical compound CCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCC DUXYWXYOBMKGIN-UHFFFAOYSA-N 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 150000004669 very long chain fatty acids Chemical class 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Anesthesiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pain & Pain Management (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361771011P | 2013-02-28 | 2013-02-28 | |
| US61/771,011 | 2013-02-28 | ||
| PCT/US2014/019704 WO2014134586A2 (en) | 2013-02-28 | 2014-02-28 | Injectable long-acting local anesthetic semi-solid formulations and its compostions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2014223993A1 AU2014223993A1 (en) | 2015-10-15 |
| AU2014223993B2 true AU2014223993B2 (en) | 2016-09-08 |
Family
ID=50288331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2014223993A Ceased AU2014223993B2 (en) | 2013-02-28 | 2014-02-28 | Injectable long-acting local anesthetic semi-solid formulations and its compostions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10500281B2 (https=) |
| EP (1) | EP2961380B1 (https=) |
| JP (1) | JP6363115B2 (https=) |
| KR (1) | KR101768843B1 (https=) |
| CN (1) | CN105120839B (https=) |
| AU (1) | AU2014223993B2 (https=) |
| CA (1) | CA2903020C (https=) |
| WO (1) | WO2014134586A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6363115B2 (ja) | 2013-02-28 | 2018-07-25 | ミラ ファーマ コーポレイション | 注射可能局所麻酔半固体製剤およびその組成物 |
| US9849180B2 (en) * | 2014-09-15 | 2017-12-26 | Hui Rong Shen | Long-acting semi-solid lipid formulations |
| US10220093B2 (en) | 2013-02-28 | 2019-03-05 | Mira Pharma Corporation | Long-acting semi-solid lipid formulations |
| JP7145363B2 (ja) * | 2015-11-23 | 2022-10-03 | グレイス セラピューティクス インコーポレイテッド | 局所皮膜形成スプレー |
| EP3452119A1 (en) * | 2016-05-02 | 2019-03-13 | The General Hospital Corporation | Implant surfaces for pain control |
| KR102442753B1 (ko) * | 2016-12-26 | 2022-09-16 | 셀릭스 바이오 프라이빗 리미티드 | 만성 통증 치료를 위한 화합물 |
| US10561606B2 (en) | 2017-12-06 | 2020-02-18 | Mira Pharma Corporation | Injectable long-acting local anesthetic semi-solid gel formulations |
| US11426418B2 (en) | 2017-12-06 | 2022-08-30 | Mira Pharma Corporation | Injectable long-acting semi-solid gel formulations |
| EP3720420B1 (en) * | 2017-12-06 | 2025-08-27 | HuZhou Hui Zhong Ji Shi Biotechnology Co., Ltd. | Injectable long-acting local anesthetic semi-solid gel formulations |
| EP3846852A4 (en) | 2018-09-07 | 2022-06-15 | R.P. Scherer Technologies, LLC | Solid or semisolid lipid based dosage form stabilization through curing and addition of low hlb surfactant(s) |
| CN113262302B (zh) * | 2020-02-17 | 2022-12-09 | 湖州惠中济世生物科技有限公司 | 可注射长效半固体凝胶制剂 |
| EP4284272A4 (en) * | 2021-01-29 | 2024-12-25 | Insitu Biologics, Inc. | COMPOSITIONS AND METHODS OF SUSTAINED TREATMENT OF PAIN |
| WO2022175974A1 (en) * | 2021-02-18 | 2022-08-25 | Navin Saxena Research And Technology Private Limited | Non-aqueous injectable composition for sustained release of buprenorphine and use thereof |
| JP7802471B2 (ja) * | 2021-08-17 | 2026-01-20 | 株式会社カネカ | 貼付剤、貼付剤の製造方法、加水分解抑制剤、及び加水分解抑制方法 |
| WO2026040167A1 (zh) * | 2024-08-20 | 2026-02-26 | 南光化学制药股份有限公司 | 医药组成物及其粒剂与针剂 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007066148A1 (en) * | 2005-12-07 | 2007-06-14 | Pharmakodex Ltd | Transdermal administration of active agents , in particular diclofenac |
| WO2010142457A1 (en) * | 2009-06-11 | 2010-12-16 | Photocure Asa | Semi-solid compositions and pharmaceutical products |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4775659A (en) * | 1985-08-19 | 1988-10-04 | Eli Lilly And Company | Injectable semi-solid formulations |
| SE9200952D0 (sv) * | 1992-03-27 | 1992-03-27 | Kabi Pharmacia Ab | Pharmaceutical carrier system containing defined lipids |
| US5700485A (en) | 1992-09-10 | 1997-12-23 | Children's Medical Center Corporation | Prolonged nerve blockade by the combination of local anesthetic and glucocorticoid |
| JPH08143449A (ja) * | 1994-11-17 | 1996-06-04 | Lederle Japan Ltd | 徐放性局所麻酔用注射剤 |
| US6413536B1 (en) | 1995-06-07 | 2002-07-02 | Southern Biosystems, Inc. | High viscosity liquid controlled delivery system and medical or surgical device |
| NZ311474A (en) | 1995-06-09 | 1997-09-22 | Euro Celtique Sa | Formulations for providing prolonged local anesthesia |
| GB9610862D0 (en) * | 1996-05-23 | 1996-07-31 | Evans Brian K | Pharmaceutical products |
| EP2198854B1 (en) | 1997-09-18 | 2011-11-30 | Pacira Pharmaceuticals, Inc. | Sustained-release liposomal anesthetic compositions |
| AU781682B2 (en) * | 2000-03-20 | 2005-06-09 | Zoetis Services Llc | Sustained-release compositions for parenteral administration |
| US6613355B2 (en) | 2000-05-11 | 2003-09-02 | A.P. Pharma, Inc. | Semi-solid delivery vehicle and pharmaceutical compositions |
| GB0015617D0 (en) * | 2000-06-26 | 2000-08-16 | Vectura Ltd | Improved preparations for dermal delivery of active substances |
| DE10033059A1 (de) * | 2000-07-07 | 2002-01-31 | Wacker Chemie Gmbh | Komplexe aus gamma-Cyclodextrin und Benzocain, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10041478A1 (de) * | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| US20040001889A1 (en) * | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
| US20070184089A1 (en) * | 2002-07-15 | 2007-08-09 | Alcon, Inc. | Non-Polymeric Lipophilic Pharmaceutical Implant Compositions for Intraocular Use |
| US8221778B2 (en) | 2005-01-12 | 2012-07-17 | The Trustees Of The University Of Pennsylvania | Drug-containing implants and methods of use thereof |
| US7666914B2 (en) | 2004-06-03 | 2010-02-23 | Richlin David M | Topical preparation and method for transdermal delivery and localization of therapeutic agents |
| EP3085363B1 (en) * | 2007-03-28 | 2019-03-20 | Innocoll Pharmaceuticals Limited | A drug delivery device for providing local analgesia, local anesthesia or nerve blockade |
| CN102933200B (zh) | 2009-12-18 | 2015-11-25 | 莱迪杜德制药公司 | 包含磷脂的单相凝胶组合物 |
| MX2012011261A (es) | 2010-04-01 | 2012-12-05 | Pharmanest Ab | Composiciones bioadhesivas de anestesicos locales. |
| EP2552408A2 (en) * | 2010-04-01 | 2013-02-06 | Pharmanest AB | Water-free pharmaceutical compositions suitable for local anaesthetics |
| WO2011121074A1 (en) * | 2010-04-01 | 2011-10-06 | Pharmanest Ab | Thermogelling anaesthetic compositions |
| JP6363115B2 (ja) | 2013-02-28 | 2018-07-25 | ミラ ファーマ コーポレイション | 注射可能局所麻酔半固体製剤およびその組成物 |
| CA2946281C (en) | 2014-04-21 | 2022-12-13 | Heron Therapeutics, Inc. | Long-acting polymeric delivery systems |
-
2014
- 2014-02-28 JP JP2015560385A patent/JP6363115B2/ja not_active Expired - Fee Related
- 2014-02-28 CN CN201480011256.0A patent/CN105120839B/zh active Active
- 2014-02-28 AU AU2014223993A patent/AU2014223993B2/en not_active Ceased
- 2014-02-28 WO PCT/US2014/019704 patent/WO2014134586A2/en not_active Ceased
- 2014-02-28 EP EP14710751.0A patent/EP2961380B1/en active Active
- 2014-02-28 CA CA2903020A patent/CA2903020C/en not_active Expired - Fee Related
- 2014-02-28 KR KR1020157026862A patent/KR101768843B1/ko not_active Expired - Fee Related
-
2015
- 2015-08-28 US US14/839,352 patent/US10500281B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007066148A1 (en) * | 2005-12-07 | 2007-06-14 | Pharmakodex Ltd | Transdermal administration of active agents , in particular diclofenac |
| WO2010142457A1 (en) * | 2009-06-11 | 2010-12-16 | Photocure Asa | Semi-solid compositions and pharmaceutical products |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105120839A (zh) | 2015-12-02 |
| CN105120839B (zh) | 2020-07-28 |
| KR101768843B1 (ko) | 2017-08-17 |
| JP2016510041A (ja) | 2016-04-04 |
| CA2903020A1 (en) | 2014-09-04 |
| CA2903020C (en) | 2019-06-18 |
| EP2961380A2 (en) | 2016-01-06 |
| AU2014223993A1 (en) | 2015-10-15 |
| EP2961380B1 (en) | 2020-04-08 |
| US20150366967A1 (en) | 2015-12-24 |
| KR20150126375A (ko) | 2015-11-11 |
| WO2014134586A2 (en) | 2014-09-04 |
| US10500281B2 (en) | 2019-12-10 |
| JP6363115B2 (ja) | 2018-07-25 |
| WO2014134586A3 (en) | 2014-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2014223993B2 (en) | Injectable long-acting local anesthetic semi-solid formulations and its compostions | |
| JP7181248B2 (ja) | 長期作用性ポリマー送達系 | |
| US10561606B2 (en) | Injectable long-acting local anesthetic semi-solid gel formulations | |
| US10220093B2 (en) | Long-acting semi-solid lipid formulations | |
| US11426418B2 (en) | Injectable long-acting semi-solid gel formulations | |
| CN113262302B (zh) | 可注射长效半固体凝胶制剂 | |
| EP3720420B1 (en) | Injectable long-acting local anesthetic semi-solid gel formulations | |
| CN116669717A (zh) | 长效原位成型/胶凝组合物 | |
| JP7767636B2 (ja) | 疼痛治療用医薬組成物 | |
| US9849180B2 (en) | Long-acting semi-solid lipid formulations | |
| WO2025015222A2 (en) | Pharmaceutical compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |