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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/04/20 21:37:44」(JST)
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Levobupivacaine
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| Systematic (IUPAC) name |
|
(S)-1-butyl-N-(2,6-dimethylphenyl)
piperidine-2-carboxamide
|
| Clinical data |
| AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy
category |
|
Routes of
administration |
Parenteral |
| 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 |
| CAS Number |
27262-47-1 Y |
| ATC code |
N01BB10 (WHO) |
| PubChem |
CID 92253 |
| IUPHAR/BPS |
7211 |
| DrugBank |
DB01002 Y |
| ChemSpider |
83289 Y |
| UNII |
A5H73K9U3W Y |
| ChEBI |
CHEBI:6149 Y |
| ChEMBL |
CHEMBL1201193 N |
| Chemical data |
| Formula |
C18H28N2O |
| Molar mass |
288.43 g/mol |
SMILES
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O=C([C@H]1N(CCCC1)CCCC)NC2=C(C)C=CC=C2C
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InChI
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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
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| 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 Abbott 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.
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Local anesthetics (primarily sodium channel blockers) (N01B)
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| Esters by acid |
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Aminobenzoic
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- Benzocaine
- Butacaine
- Butamben
- Chloroprocaine
- Dimethocaine
- Lucaine
- Meprylcaine
- Metabutethamine
- Metabutoxycaine
- Orthocaine
- Propoxycaine
- Procaine (Novocaine)
- Proxymetacaine
- Risocaine
- Tetracaine
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|
|
Benzoic
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- Amylocaine
- Cocaine
- Cyclomethycaine
- α-Eucaine
- β-Eucaine
- Hexylcaine
- Isobucaine
- Piperocaine
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|
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ArCO2- (not para-amino or Ph)
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- Amoproxan (3,4,5-Trimethoxybenzoyl)
- 3-(p-Fluorobenzoyloxy)tropane
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|
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| Amides |
- Articaine
- Bupivacaine # / Levobupivacaine / Ropivacaine
- Butanilicaine
- Carticaine
- Dibucaine
- Etidocaine
- Lidocaine #
- Mepivacaine
- Prilocaine
- Trimecaine
|
|
| Combinations |
- Lidocaine / prilocaine
- Anesthetic / vasoconstrictor
- Iontocaine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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|
UpToDate Contents
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English Journal
- Beneficial effects of levobupivacaine regional anaesthesia on postoperative opioid induced hyperalgesia in diabetic mice.
- Gomez-Brouchet A1, Blaes N2, Mouledous L3, Fourcade O4, Tack I5, Francès B6, Girolami JP7, Minville V8,9.
- Journal of translational medicine.J Transl Med.2015 Jul 2;13(1):208. doi: 10.1186/s12967-015-0575-0.
- BACKGROUND: Diabetic neuropathy is one of the most common complications of diabetes and causes various problems in daily life. The aim of this study was to assess the effect of regional anaesthesia on post surgery opioid induced hyperalgesia in diabetic and non-diabetic mice.METHODS: Diabetic and no
- PMID 26136113
- Plasma concentrations of levobupivacaine associated with two different intermittent wound infusion regimens following surgical ductus ligation in preterm infants.
- Anell-Olofsson M1, Lönnqvist PA2, Bitkover C3, Lundeberg S2, Larsson BA2, Eksborg S1, Bartocci M1.
- Paediatric anaesthesia.Paediatr Anaesth.2015 Jul;25(7):711-8. doi: 10.1111/pan.12634. Epub 2015 Mar 10.
- BACKGROUND: Administration of local anesthetics by a surgically placed wound catheter has recently been shown to reduce the need for postoperative morphine administration in extremely preterm infants undergoing ductus ligation. The primary aim of this randomized safety study was to define the plasma
- PMID 25752903
- Electrophysiological, hemodynamic and mitochondrial alterations induced by levobupivacaine during myocardial ischemia in a pig model. Protection by lipid emulsions?
- Mamou Z1, Descotes J1, Chevalier P1, Bui-Xuan B1, Romestaing C2,3, Timour Q1.
- Fundamental & clinical pharmacology.Fundam Clin Pharmacol.2015 Jun 27. doi: 10.1111/fcp.12131. [Epub ahead of print]
- Accidental intravascular or high-dose injection of local anesthetics (LA) can result in serious, potentially life-threatening complications. Indeed, adequate supportive measures and the administration of lipid emulsions are required in such complications. The study's objectives were threefold: (i) e
- PMID 26118736
Japanese Journal
- 臨床経験 鼠径ヘルニア根治術における0.25%と0.5%レボブピバカインを用いた創部散布法での術後鎮痛の比較
- 臨床経験 超音波ガイド下斜角筋間腕神経叢ブロック : 0.5%レボブピバカイン6mlは呼吸機能の低下と横隔膜奇異性運動の発生を減少させる
- 腕神経叢ブロック—局所麻酔薬の薬物動態と全身毒性，およびその治療法—
Related Links
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- levobupivacaine [le″vo-bu-piv´ah-kān] a local anesthetic used as the hydrochloride salt for local infiltration anesthesia, peripheral nerve block, and epidural anesthesia during surgical procedures and for postoperative pain management.
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