A sodium channel blocker and local anesthetic
Related Products
Isomer(s)
16618Bupivacaine
Labeled Version(s)
38904Levobupivacaine-d9 (hydrochloride)
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Levobupivacaine (hydrochloride)

Item No. 31596

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-butyl-N-(2,6-dimethylphenyl)-(2S)-2-piperidinecarboxamide, monohydrochloride
CAS Number
27262-48-2
Synonyms
  • (S)-(–)-Bupivacaine
Molecular Formula
C18H28N2O • HCl
Formula Weight
324.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1 mg/mlDMSO: 1 mg/mlDMSO:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
CC(C=CC=C1C)=C1NC([C@H]2N(CCCC2)CCCC)=O.Cl
InChi Code
InChI=1S/C18H28N2O.ClH/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);1H/t16-;/m0./s1
InChi Key
SIEYLFHKZGLBNX-NTISSMGPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    100 mg

    $90

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    250 mg

    $165

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    500 mg

    $306

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    1 g

    $523

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    Product Description

    Levobupivacaine is a sodium channel blocker and local anesthetic, as well as the levorotary stereoisomer of bupivacaine (Item No. 16618).1,2,3 It inhibits cardiac sodium channel currents (INa) by 57.8% in isolated guinea pig ventricular myocytes when used at a concentration of 10 μM.1 Levobupivacaine (10 μM) reduces the maximal rate of depolarization (Vmax) and action potential duration to 76.7 and 83.4% of controls, respectively, in isolated guinea pig papillary muscle.2 It induces a complete block of proprioception, motor function, and nociception in the hindleg of rats when administered at a dose of 7.7 mM by percutaneous injection into the sciatic nerve.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Valenzuela, C., Snyders, D.J., Bennett, P.B., et al. Stereoselective block of cardiac sodium channels by bupivacaine in guinea pig ventricular myocytes. Circulation 92(10), 3014-3024 (1995).

    2. Vanhoutte, F., Vereecke, J., Verbeke, N., et al. Stereoselective effects of the enantiomers of bupivacaine on the electrophysiological properties of the guinea-pig papillary muscle. Br. J. Pharmacol. 103(1), 1275-1281 (1991).

    3. Sinnott, C.J., and Strichartz, G.R. Levobupivacaine versus ropivacaine for sciatic nerve block in the rat. Reg. Anesth. Pain Med. 28(4), 294-303 (2003).