- 関
- levobupivacaine
WordNet
- a complex consisting of an organic base in association with hydrogen chloride
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/12/09 00:38:37」(JST)
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Levobupivacaine
|
| Clinical data |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy
category |
|
Routes of
administration |
Parenteral |
| ATC code |
N01BB10 (WHO) |
| Legal status |
| Legal status |
- AU: S4 (Prescription only)
|
| Pharmacokinetic data |
| Bioavailability |
n/a |
| Metabolism |
Hepatic |
| Biological half-life |
2–2.6 hours |
| Excretion |
Renal 70%, faecal 24% |
| Identifiers |
IUPAC name
- (S)-1-butyl-N-(2,6-dimethylphenyl)
piperidine-2-carboxamide
|
| CAS Number |
27262-47-1 Y |
| PubChem (CID) |
92253 |
| IUPHAR/BPS |
7211 |
| DrugBank |
DB01002 Y |
| ChemSpider |
83289 Y |
| UNII |
A5H73K9U3W Y |
| ChEBI |
CHEBI:6149 Y |
| ChEMBL |
CHEMBL1201193 N |
| Chemical and physical data |
| Formula |
C18H28N2O |
| Molar mass |
288.43 g/mol |
| 3D model (Jmol) |
Interactive image |
SMILES
-
O=C([C@H]1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
|
InChI
-
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1 Y
-
Key:LEBVLXFERQHONN-INIZCTEOSA-N Y
|
| NY (what is this?) (verify) |
Levobupivacaine (rINN) is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine.[1]
Levobupivacaine hydrochloride is commonly marketed by AbbVie under the trade name Chirocaine.[2]
Contents
- 1 Clinical use
- 1.1 Indications
- 1.2 Contraindications
- 1.3 Adverse effects
- 2 References
Clinical use
Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 percent less potent (by molarity) than racemic bupivacaine and has a longer motor block onset time.[3]
Indications
Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children.
Contraindications
Levobupivacaine is contraindicated for IV regional anaesthesia (IVRA).
Adverse effects
Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur.
Systemic exposure to excessive quantities of bupivacaine mainly result in central nervous system (CNS) and cardiovascular effects – CNS effects usually occur at lower blood plasma concentrations and additional cardiovascular effects present at higher concentrations, though cardiovascular collapse may also occur with low concentrations. CNS effects may include CNS excitation (nervousness, tingling around the mouth, tinnitus, tremor, dizziness, blurred vision, seizures) followed by depression (drowsiness, loss of consciousness, respiratory depression and apnea). Cardiovascular effects include hypotension, bradycardia, arrhythmias, and/or cardiac arrest – some of which may be due to hypoxemia secondary to respiratory depression.[2]
References
- ^ Burlacu CL, Buggy DJ (April 2008). "Update on local anesthetics: focus on levobupivacaine". Ther Clin Risk Manag. 4 (2): 381–92. PMC 2504073. PMID 18728849.
- ^ a b Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
- ^ Gulec D (Apr 2014). "Intrathecal bupivacaine or levobupivacaine: which should be used for elderly patients?.". J Int Med Res. 42 (2): 376–385. doi:10.1177/0300060513496737. PMID 24595149.
|
Local anesthetics (primarily sodium channel blockers) (N01B)
|
|
| Esters by acid |
|
Aminobenzoic
|
- Benzocaine
- Butacaine
- Butamben
- Chloroprocaine
- Dimethocaine
- Lucaine
- Meprylcaine
- Metabutethamine
- Metabutoxycaine
- Nitracaine
- Orthocaine
- Propoxycaine
- Procaine (Novocaine)
- Proxymetacaine
- Risocaine
- Tetracaine
|
|
|
Benzoic
|
- Amylocaine
- Cocaine
- Cyclomethycaine
- α-Eucaine
- β-Eucaine
- Hexylcaine
- Isobucaine
- Piperocaine
|
|
|
ArCO2- (not para-amino or Ph)
|
- Amoproxan (3,4,5-Trimethoxybenzoyl)
- 3-(p-Fluorobenzoyloxy)tropane
|
|
|
| Amides |
- Articaine
- Bupivacaine# / Levobupivacaine / Ropivacaine
- Butanilicaine
- Carticaine
- Dibucaine
- Etidocaine
- Lidocaine#
- Mepivacaine
- Prilocaine
- Trimecaine
|
|
| Combinations |
- Lidocaine / prilocaine
- Anesthetic / vasoconstrictor
- TAC
- Iontocaine
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
UpToDate Contents
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English Journal
- Patient-controlled bolus femoral nerve block after knee arthroplasty: quadriceps recovery, analgesia, local anesthetic consumption.
- Sakai N1, Nakatsuka M2, Tomita T3.
- Acta anaesthesiologica Scandinavica.Acta Anaesthesiol Scand.2016 Nov;60(10):1461-1469. doi: 10.1111/aas.12778. Epub 2016 Aug 23.
- BACKGROUND: Continuous femoral nerve block (cFNB) induces quadriceps muscle weakness, but patient-controlled femoral nerve block (PCFNB) can provide analgesia with lower consumption of local anesthetics compared to cFNB. We hypothesized that cFNB followed by PCFNB leads to accelerated recovery of qu
- PMID 27553442
- The effect of serratus plane block performed under direct vision on postoperative pain in breast surgery.
- Hards M1, Harada A2, Neville I2, Harwell S2, Babar M2, Ravalia A2, Davies G2.
- Journal of clinical anesthesia.J Clin Anesth.2016 Nov;34:427-31. doi: 10.1016/j.jclinane.2016.05.029. Epub 2016 Jun 16.
- STUDY OBJECTIVES: To determine the effectiveness of serratus plane block performed under direct vision on postoperative pain after mastectomy.DESIGN: We performed a retrospective study of elective breast surgery patients undergoing mastectomy over 6 months. We collected data on the outcomes for the
- PMID 27687427
- Ultrasound-guided transversalis fascia plane block versus anterior transversus abdominis plane block in outpatient inguinal hernia repair.
- López-González JM1, López-Álvarez S2, Jiménez Gómez BM3, Areán González I4, Illodo Miramontes G4, Padín Barreiro L4.
- Revista espanola de anestesiologia y reanimacion.Rev Esp Anestesiol Reanim.2016 Nov;63(9):498-504. doi: 10.1016/j.redar.2016.02.005. Epub 2016 Apr 8.
- INTRODUCTION: The aim of the study was to assess the effectiveness of ultrasound-guided transversalis fascia plane block (TFP) compared to anterior transversus abdominis plane block (TAP-A) for post-operative analgesia in outpatient unilateral inguinal hernia repair.MATERIALS AND METHODS: Retrospect
- PMID 27067036
Japanese Journal
- 長時間作用性局所麻酔薬 塩酸レボブピバカイン(注射剤ポプスカイン^【○!R】)の薬理学的特徴および臨床試験成績
- 田矢 廣司,清水 聡
- 日本薬理学雑誌 133(3), 159-167, 2009-03-01
- レボブピバカインは，英国のChiroscience社（現UCB社）が開発した長時間作用性の局所麻酔薬であり，ブピバカイン（ラセミ体）のS（-）異性体である．摘出ラット脊髄後根神経細胞外電位に対する抑制作用を指標にレボブピバカインの作用を検討した結果，ブピバカインあるいはR（+）異性体（R-ブピバカイン）と同等であり，ロピバカインに比べ約3倍強かった．さらに，ラットを用いた硬膜外投与および脊髄くも膜 …
- NAID 10025740271
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- 英
- levobupivacaine
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- 塩酸レボブピバカイン levobupivacaine hydrochloride
- 商
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- 局所麻酔薬
局所麻酔薬;アミド型
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- 英
- levobupivacaine hydrochloride
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- レボブピバカイン
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塩酸塩、ハイドロクロライド