CA2294950C - Levobupivacaine and its use - Google Patents
Levobupivacaine and its use Download PDFInfo
- Publication number
- CA2294950C CA2294950C CA002294950A CA2294950A CA2294950C CA 2294950 C CA2294950 C CA 2294950C CA 002294950 A CA002294950 A CA 002294950A CA 2294950 A CA2294950 A CA 2294950A CA 2294950 C CA2294950 C CA 2294950C
- Authority
- CA
- Canada
- Prior art keywords
- surgery
- levobupivacaine
- block
- sensory
- bupivacaine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- LEBVLXFERQHONN-INIZCTEOSA-N levobupivacaine Chemical compound CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-INIZCTEOSA-N 0.000 title claims abstract description 37
- 229960004288 levobupivacaine Drugs 0.000 title claims abstract description 36
- 238000001356 surgical procedure Methods 0.000 claims abstract description 28
- 230000001953 sensory effect Effects 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- 238000012829 orthopaedic surgery Methods 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 206010019909 Hernia Diseases 0.000 claims description 2
- 238000007486 appendectomy Methods 0.000 claims description 2
- 238000002316 cosmetic surgery Methods 0.000 claims description 2
- 238000002297 emergency surgery Methods 0.000 claims description 2
- 230000008439 repair process Effects 0.000 claims description 2
- 238000007483 tonsillectomy Methods 0.000 claims description 2
- 238000011282 treatment Methods 0.000 claims description 2
- 238000012084 abdominal surgery Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 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 description 23
- 229960003150 bupivacaine Drugs 0.000 description 17
- 229940079593 drug Drugs 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 210000003141 lower extremity Anatomy 0.000 description 10
- ZKMNUMMKYBVTFN-HNNXBMFYSA-N (S)-ropivacaine Chemical class CCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C ZKMNUMMKYBVTFN-HNNXBMFYSA-N 0.000 description 8
- 230000003444 anaesthetic effect Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 210000003169 central nervous system Anatomy 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 229960001549 ropivacaine Drugs 0.000 description 4
- 206010002091 Anaesthesia Diseases 0.000 description 3
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- LEBVLXFERQHONN-MRXNPFEDSA-N dextrobupivacaine Chemical compound CCCCN1CCCC[C@@H]1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-MRXNPFEDSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 210000003414 extremity Anatomy 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 210000001015 abdomen Anatomy 0.000 description 2
- 238000001949 anaesthesia Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 231100000457 cardiotoxic Toxicity 0.000 description 2
- 230000001451 cardiotoxic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000035606 childbirth Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 229960002275 pentobarbital sodium Drugs 0.000 description 2
- 230000002980 postoperative effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000020341 sensory perception of pain Effects 0.000 description 2
- 230000001550 time effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 206010008531 Chills Diseases 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- 206010017577 Gait disturbance Diseases 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 229920000153 Povidone-iodine Polymers 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 210000003489 abdominal muscle Anatomy 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000002692 epidural anesthesia Methods 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 210000003195 fascia Anatomy 0.000 description 1
- PJMPHNIQZUBGLI-UHFFFAOYSA-N fentanyl Chemical compound C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 PJMPHNIQZUBGLI-UHFFFAOYSA-N 0.000 description 1
- 229960002428 fentanyl Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 238000002695 general anesthesia Methods 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 238000002682 general surgery Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 238000009802 hysterectomy Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003601 intercostal effect Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000007971 neurological deficit Effects 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 238000007427 paired t-test Methods 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
- 229960005301 pentazocine Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000010149 post-hoc-test Methods 0.000 description 1
- 229960001621 povidone-iodine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 229960004134 propofol Drugs 0.000 description 1
- 210000001139 rectus abdominis Anatomy 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000037152 sensory function Effects 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003894 surgical glue Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 210000001364 upper extremity Anatomy 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
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9715322.5 | 1997-07-21 | ||
| GB9715322A GB9715322D0 (en) | 1997-07-21 | 1997-07-21 | Levobupivacaine and its use |
| GBGB9722023.0A GB9722023D0 (en) | 1997-10-17 | 1997-10-17 | Levobupivacaine and its use |
| GB9722023.0 | 1997-10-17 | ||
| PCT/GB1998/002169 WO1999004771A2 (en) | 1997-07-21 | 1998-07-21 | Use of levobupivacaine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2294950A1 CA2294950A1 (en) | 1999-02-04 |
| CA2294950C true CA2294950C (en) | 2009-04-07 |
Family
ID=26311915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002294950A Expired - Lifetime CA2294950C (en) | 1997-07-21 | 1998-07-21 | Levobupivacaine and its use |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5945435A (https=) |
| EP (1) | EP0998286A2 (https=) |
| JP (1) | JP2001510794A (https=) |
| AU (1) | AU742488B2 (https=) |
| BR (1) | BR9802536A (https=) |
| CA (1) | CA2294950C (https=) |
| WO (1) | WO1999004771A2 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU752802C (en) | 1997-11-14 | 2006-04-13 | Pacira Pharmaceuticals, Inc. | Production of multivesicular liposomes |
| IL140899A0 (en) | 1998-07-17 | 2002-02-10 | Skyepharma Inc | Lipid/polymer containing pharmaceutical compositions and processes for the preparation thereof |
| US6520949B2 (en) * | 2001-04-02 | 2003-02-18 | Martin St. Germain | Method and apparatus for administering fluid to animals subcutaneously |
| AU2002322024B2 (en) * | 2001-05-31 | 2008-05-08 | Pacira Pharmaceuticals, Inc. | Encapsulation of nanosuspensions in liposomes and microspheres |
| US11033495B1 (en) | 2021-01-22 | 2021-06-15 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US12151024B2 (en) | 2021-01-22 | 2024-11-26 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US11357727B1 (en) | 2021-01-22 | 2022-06-14 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US11278494B1 (en) | 2021-01-22 | 2022-03-22 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| EP4415713A4 (en) | 2021-10-14 | 2025-08-06 | Pacira Pharmaceuticals Inc | MULTIVESICULAR LIPOSOME FORMULATIONS OF BUPIVACAINE AND THEIR USES |
| CN119677554A (zh) | 2022-05-05 | 2025-03-21 | 普络夫有限责任公司 | 麻醉神经阻滞和方法 |
| US12070454B1 (en) | 2022-05-05 | 2024-08-27 | Pfof Llc | Anesthetic nerve block and method |
| US12251472B1 (en) | 2024-05-20 | 2025-03-18 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US12156940B1 (en) | 2024-05-20 | 2024-12-03 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
| US12280149B1 (en) | 2024-05-20 | 2025-04-22 | Pacira Pharmaceuticals, Inc. | Manufacturing of bupivacaine multivesicular liposomes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| SE9302218D0 (sv) * | 1993-06-28 | 1993-06-28 | Ab Astra | New use |
| EP0727210B1 (en) * | 1993-10-13 | 2001-12-19 | Darwin Discovery Limited | Analgesic agent and its use |
| AU704806B2 (en) * | 1995-04-13 | 1999-05-06 | Darwin Discovery Limited | Levobupivacaine and its use as an anaesthetic in pregnant women |
| GB9704352D0 (en) * | 1997-03-03 | 1997-04-23 | Chiroscience Ltd | Levobupivacaine and its use |
-
1998
- 1998-07-21 WO PCT/GB1998/002169 patent/WO1999004771A2/en not_active Ceased
- 1998-07-21 US US09/119,910 patent/US5945435A/en not_active Expired - Lifetime
- 1998-07-21 AU AU84527/98A patent/AU742488B2/en not_active Expired
- 1998-07-21 EP EP98935175A patent/EP0998286A2/en not_active Withdrawn
- 1998-07-21 JP JP2000503830A patent/JP2001510794A/ja active Pending
- 1998-07-21 BR BR9802536A patent/BR9802536A/pt not_active Application Discontinuation
- 1998-07-21 CA CA002294950A patent/CA2294950C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999004771A3 (en) | 1999-04-08 |
| CA2294950A1 (en) | 1999-02-04 |
| AU742488B2 (en) | 2002-01-03 |
| JP2001510794A (ja) | 2001-08-07 |
| EP0998286A2 (en) | 2000-05-10 |
| BR9802536A (pt) | 1999-07-20 |
| WO1999004771A2 (en) | 1999-02-04 |
| AU8452798A (en) | 1999-02-16 |
| US5945435A (en) | 1999-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20180723 |