AU2013282753B2 - Injectable supersaturated acetaminophen solution for spinal administration - Google Patents
Injectable supersaturated acetaminophen solution for spinal administration Download PDFInfo
- Publication number
- AU2013282753B2 AU2013282753B2 AU2013282753A AU2013282753A AU2013282753B2 AU 2013282753 B2 AU2013282753 B2 AU 2013282753B2 AU 2013282753 A AU2013282753 A AU 2013282753A AU 2013282753 A AU2013282753 A AU 2013282753A AU 2013282753 B2 AU2013282753 B2 AU 2013282753B2
- Authority
- AU
- Australia
- Prior art keywords
- acetaminophen
- solution
- supersaturated
- aqueous solution
- administration
- 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical class CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title claims abstract description 412
- 229960005489 paracetamol Drugs 0.000 claims abstract description 207
- 230000003444 anaesthetic effect Effects 0.000 claims abstract description 57
- 239000007864 aqueous solution Substances 0.000 claims abstract description 34
- 208000002193 Pain Diseases 0.000 claims abstract description 19
- 230000036407 pain Effects 0.000 claims abstract description 17
- 239000000243 solution Substances 0.000 claims description 160
- 230000000202 analgesic effect Effects 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 29
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 229960002023 chloroprocaine Drugs 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 238000007872 degassing Methods 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 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 5
- 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 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 5
- 229960003150 bupivacaine Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229960004194 lidocaine Drugs 0.000 claims description 5
- 229960002409 mepivacaine Drugs 0.000 claims description 5
- INWLQCZOYSRPNW-UHFFFAOYSA-N mepivacaine Chemical compound CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C INWLQCZOYSRPNW-UHFFFAOYSA-N 0.000 claims description 5
- 229960001807 prilocaine Drugs 0.000 claims description 5
- MVFGUOIZUNYYSO-UHFFFAOYSA-N prilocaine Chemical compound CCCNC(C)C(=O)NC1=CC=CC=C1C MVFGUOIZUNYYSO-UHFFFAOYSA-N 0.000 claims description 5
- 229960001549 ropivacaine Drugs 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- QTGIAADRBBLJGA-UHFFFAOYSA-N Articaine Chemical compound CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OC QTGIAADRBBLJGA-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 229960003831 articaine Drugs 0.000 claims description 2
- 229960001747 cinchocaine Drugs 0.000 claims 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 claims description 2
- 229960003976 etidocaine Drugs 0.000 claims description 2
- 229960004288 levobupivacaine Drugs 0.000 claims description 2
- LEBVLXFERQHONN-INIZCTEOSA-N levobupivacaine Chemical compound CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-INIZCTEOSA-N 0.000 claims description 2
- 229960003502 oxybuprocaine Drugs 0.000 claims description 2
- CMHHMUWAYWTMGS-UHFFFAOYSA-N oxybuprocaine Chemical compound CCCCOC1=CC(C(=O)OCCN(CC)CC)=CC=C1N CMHHMUWAYWTMGS-UHFFFAOYSA-N 0.000 claims description 2
- 229960003981 proparacaine Drugs 0.000 claims description 2
- 229960002372 tetracaine Drugs 0.000 claims description 2
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims description 2
- KCLANYCVBBTKTO-UHFFFAOYSA-N Proparacaine Chemical compound CCCOC1=CC=C(C(=O)OCCN(CC)CC)C=C1N KCLANYCVBBTKTO-UHFFFAOYSA-N 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 abstract description 5
- 230000002265 prevention Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 48
- 238000007913 intrathecal administration Methods 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 241000700159 Rattus Species 0.000 description 18
- 206010002091 Anaesthesia Diseases 0.000 description 17
- 230000037005 anaesthesia Effects 0.000 description 17
- 238000001949 anaesthesia Methods 0.000 description 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 208000004550 Postoperative Pain Diseases 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 206010061218 Inflammation Diseases 0.000 description 10
- 208000000114 Pain Threshold Diseases 0.000 description 10
- 230000004054 inflammatory process Effects 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- 229960005015 local anesthetics Drugs 0.000 description 10
- 230000037040 pain threshold Effects 0.000 description 10
- 238000004659 sterilization and disinfection Methods 0.000 description 9
- 230000000638 stimulation Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000011477 surgical intervention Methods 0.000 description 8
- 206010065390 Inflammatory pain Diseases 0.000 description 7
- 238000001356 surgical procedure Methods 0.000 description 7
- 230000008901 benefit Effects 0.000 description 6
- 239000000679 carrageenan Substances 0.000 description 6
- 229940113118 carrageenan Drugs 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 5
- 229940124326 anaesthetic agent Drugs 0.000 description 5
- 239000006172 buffering agent Substances 0.000 description 5
- 238000011260 co-administration Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000902 placebo Substances 0.000 description 5
- 229940068196 placebo Drugs 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 210000000278 spinal cord Anatomy 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 208000004454 Hyperalgesia Diseases 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000001802 infusion Methods 0.000 description 4
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 4
- 235000019799 monosodium phosphate Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- 239000008223 sterile water Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000008215 water for injection Substances 0.000 description 4
- 208000035154 Hyperesthesia Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- 230000003542 behavioural effect Effects 0.000 description 3
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 210000003141 lower extremity Anatomy 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000003574 anti-allodynic effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 238000007486 appendectomy Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000008366 buffered solution Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000004941 influx Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 238000012829 orthopaedic surgery Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000004797 therapeutic response Effects 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- SXLHPBDGZHWKSX-UHFFFAOYSA-N 1-(5-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(N)=CC=C1O SXLHPBDGZHWKSX-UHFFFAOYSA-N 0.000 description 1
- BFUUJUGQJUTPAF-UHFFFAOYSA-N 2-(3-amino-4-propoxybenzoyl)oxyethyl-diethylazanium;chloride Chemical compound [Cl-].CCCOC1=CC=C(C(=O)OCC[NH+](CC)CC)C=C1N BFUUJUGQJUTPAF-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 241001269524 Dura Species 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 229940086138 acetaminophen 80 mg Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 230000000307 algesic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000003070 anti-hyperalgesia Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- -1 citric acid Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 210000001951 dura mater Anatomy 0.000 description 1
- 230000007159 enucleation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 208000022084 motor paralysis Diseases 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000008062 neuronal firing Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 229940124636 opioid drug Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 210000003446 pia mater Anatomy 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 210000002330 subarachnoid space Anatomy 0.000 description 1
- 210000000701 subdural space Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229910021643 water for pharmaceutical use Inorganic materials 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
- 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
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- 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
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0085—Brain, e.g. brain implants; Spinal cord
-
- 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
- A61P23/00—Anaesthetics
- A61P23/02—Local anaesthetics
-
- 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]
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2012A001154 | 2012-06-29 | ||
| IT001154A ITMI20121154A1 (it) | 2012-06-29 | 2012-06-29 | Soluzione iniettabile di acetaminofene per la somministrazione spinale |
| PCT/IB2013/055277 WO2014002042A1 (en) | 2012-06-29 | 2013-06-27 | Injectable supersaturated acetaminophen solution for spinal administration |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013282753A1 AU2013282753A1 (en) | 2015-02-05 |
| AU2013282753B2 true AU2013282753B2 (en) | 2017-03-02 |
Family
ID=46690603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013282753A Ceased AU2013282753B2 (en) | 2012-06-29 | 2013-06-27 | Injectable supersaturated acetaminophen solution for spinal administration |
Country Status (44)
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1752139A1 (de) * | 2005-08-05 | 2007-02-14 | TheraSelect GmbH | Stabile, flüssige Formulierung von Paracetamol |
| US20090143474A1 (en) * | 2007-11-13 | 2009-06-04 | Cadence Pharmaceuticals, Inc. | Reduced dose intravenous acetaminophen |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0162115B1 (ko) * | 1993-04-14 | 1998-11-16 | 노자키 지로 | 용존산소 감소장치 |
| US6171298B1 (en) * | 1996-05-03 | 2001-01-09 | Situs Corporation | Intravesical infuser |
| FR2751875B1 (fr) | 1996-08-05 | 1998-12-24 | Scr Newpharm | Nouvelles formulations liquides stables a base de paracetamol et leur mode de preparation |
| 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 |
| WO2003051398A1 (en) * | 2001-12-18 | 2003-06-26 | Uni-Pharma Kleon Tsetis Pharmaceutical Laboratories S.A. | Parenteral composition of paracetamol |
| FR2851164B1 (fr) | 2003-02-14 | 2005-04-22 | Xuan Tho Nguyen | Formulation liquide injectable de paracetamol |
| AU2006346318B2 (en) * | 2006-07-18 | 2011-02-10 | Genfarma Laboratorio S.L. | Injectable liquid paracetamol formulation |
| CN101015542A (zh) * | 2007-02-13 | 2007-08-15 | 天津生机集团有限公司 | 家畜用复方对乙酰氨基酚注射液及其制备方法 |
| MD3528G2 (ro) * | 2007-09-28 | 2008-11-30 | Сергей ШАНДРУ | Metodă de anestezie spinală continuă la pacienţii în etate |
| WO2009098716A2 (en) | 2008-01-17 | 2009-08-13 | Aptuit Laurus Private Limited | Stable pharmaceutical aqueous compositions |
| WO2009143558A1 (en) * | 2008-05-26 | 2009-12-03 | Silphion Pty Limited | Injectable formulations |
| EP2243477A1 (de) | 2009-04-22 | 2010-10-27 | Fresenius Kabi Deutschland GmbH | Paracetamol zur parenteralen Verabreichung |
| JP2013006770A (ja) * | 2009-10-09 | 2013-01-10 | Ssp Co Ltd | アセトアミノフェン含有経口液剤 |
| PH12012502444A1 (en) * | 2010-06-30 | 2013-02-11 | Troikaa Pharmaceuticals Ltd | Pharmaceutical compositions comprising paracetamol and process for preparing the same |
-
2012
- 2012-06-29 IT IT001154A patent/ITMI20121154A1/it unknown
-
2013
- 2013-06-27 KR KR1020147036909A patent/KR102118227B1/ko not_active Expired - Fee Related
- 2013-06-27 WO PCT/IB2013/055277 patent/WO2014002042A1/en not_active Ceased
- 2013-06-27 MA MA37811A patent/MA37811B1/fr unknown
- 2013-06-27 EA EA201500065A patent/EA028909B1/ru unknown
- 2013-06-27 AP AP2014008152A patent/AP2014008152A0/xx unknown
- 2013-06-27 JP JP2015519450A patent/JP5876620B2/ja not_active Expired - Fee Related
- 2013-06-27 MY MYPI2014703994A patent/MY169251A/en unknown
- 2013-06-27 MX MX2014015402A patent/MX369264B/es active IP Right Grant
- 2013-06-27 GE GEAP201313679A patent/GEP201706689B/en unknown
- 2013-06-27 NZ NZ703829A patent/NZ703829A/en not_active IP Right Cessation
- 2013-06-27 MD MDA20140138A patent/MD4537C1/ro not_active IP Right Cessation
- 2013-06-27 PE PE2014002536A patent/PE20150331A1/es active IP Right Grant
- 2013-06-27 HR HRP20160706TT patent/HRP20160706T1/hr unknown
- 2013-06-27 ES ES13765450.5T patent/ES2578012T3/es active Active
- 2013-06-27 UA UAA201413899A patent/UA117101C2/uk unknown
- 2013-06-27 SG SG11201408479WA patent/SG11201408479WA/en unknown
- 2013-06-27 PL PL13765450.5T patent/PL2874602T3/pl unknown
- 2013-06-27 RS RS20160435A patent/RS54844B1/sr unknown
- 2013-06-27 HU HUE13765450A patent/HUE029431T2/en unknown
- 2013-06-27 DK DK13765450.5T patent/DK2874602T3/en active
- 2013-06-27 CN CN201380034500.0A patent/CN104487051B/zh not_active Expired - Fee Related
- 2013-06-27 PT PT137654505T patent/PT2874602T/pt unknown
- 2013-06-27 EP EP13765450.5A patent/EP2874602B1/en active Active
- 2013-06-27 CA CA2876801A patent/CA2876801C/en active Active
- 2013-06-27 SI SI201330208A patent/SI2874602T1/sl unknown
- 2013-06-27 ME MEP-2016-118A patent/ME02431B/me unknown
- 2013-06-27 AU AU2013282753A patent/AU2013282753B2/en not_active Ceased
- 2013-06-27 US US14/411,532 patent/US11344517B2/en active Active
- 2013-06-27 SG SG10201704482YA patent/SG10201704482YA/en unknown
- 2013-06-27 BR BR112014032818-8A patent/BR112014032818B1/pt not_active IP Right Cessation
- 2013-06-28 AR ARP130102331 patent/AR091633A1/es unknown
-
2014
- 2014-12-18 TN TN2014000526A patent/TN2014000526A1/fr unknown
- 2014-12-18 NI NI201400147A patent/NI201400147A/es unknown
- 2014-12-22 ZA ZA2014/09478A patent/ZA201409478B/en unknown
- 2014-12-23 IL IL236423A patent/IL236423A/en active IP Right Grant
- 2014-12-26 CL CL2014003536A patent/CL2014003536A1/es unknown
- 2014-12-26 CU CUP2014000150A patent/CU20140150A7/es unknown
- 2014-12-29 DO DO2014000302A patent/DOP2014000302A/es unknown
-
2015
- 2015-01-08 EC ECIEPI2015500A patent/ECSP15000500A/es unknown
- 2015-01-27 CR CR20150036A patent/CR20150036A/es unknown
- 2015-01-27 PH PH12015500178A patent/PH12015500178B1/en unknown
- 2015-01-27 CO CO15015754A patent/CO7240357A2/es unknown
-
2016
- 2016-01-19 US US15/001,064 patent/US20160128955A1/en not_active Abandoned
- 2016-06-28 CY CY20161100584T patent/CY1117691T1/el unknown
- 2016-07-26 SM SM201600248T patent/SMT201600248B/it unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1752139A1 (de) * | 2005-08-05 | 2007-02-14 | TheraSelect GmbH | Stabile, flüssige Formulierung von Paracetamol |
| US20090143474A1 (en) * | 2007-11-13 | 2009-06-04 | Cadence Pharmaceuticals, Inc. | Reduced dose intravenous acetaminophen |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6898980B2 (ja) | 延長された持続時間の局所麻酔薬製剤 | |
| RU2095060C1 (ru) | Композиция, обладающая аналгетической или противовоспалительной активностью, способ аналгезии или лечения аллергических заболеваний | |
| JPH064534B2 (ja) | 長期間の疼痛緩和をもたらす配合剤 | |
| Grover et al. | An approach towards painless administration of local anaesthetic agents in pediatric dentistry: In vivo study | |
| AU2013282753B2 (en) | Injectable supersaturated acetaminophen solution for spinal administration | |
| US11672863B2 (en) | Enhanced solubility drug-containing formulations | |
| US20100190860A1 (en) | Methods for selectively enhancing antinociceptive potency of local anesthetics | |
| KR102162587B1 (ko) | 경막 내 반복 투여를 위한 클로로프로카인계 제약 조성물 | |
| Johnson | Treatment of acute pain in cats | |
| OA17190A (en) | Injectable supersaturated acetaminophen solution for spinal administration. | |
| WO2025212904A1 (en) | Pharmaceutical oil-in-water emulsion for treating pain | |
| EA044480B1 (ru) | Фармацевтическая композиция для лечения послеоперационной боли и способ приготовления такой композиции | |
| Khandagale et al. | A REVIEW ON LOCAL ANESTHETIC SUSTAINED-RELEASE PAIN MANAGEMENT |
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 |