Levobupivacaine
Chirocaine
Amide local anesthetic (long-acting)
The S(−)-enantiomer of bupivacaine → similar block with LESS cardiotoxicity + CNS toxicity than racemic bupivacaine.
Indications
- •Epidural
- •Peripheral nerve block
- •Infiltration
- •Postop analgesia
Dosing
| Context | Adult | Pediatric |
|---|---|---|
| Epidural (surgical) | 0.5–0.75% 10–20 mL | — |
| Nerve block | 0.25–0.5% | — |
Maximum dose
2 mg/kg plain (absolute max 150 mg)
Max-dose calculator
single-injection infiltration / blockPlain
140 mg
| Concentration | Max volume (plain) |
|---|---|
| 0.25% (2.5 mg/mL) | 56 mL |
| 0.5% (5 mg/mL) | 28 mL |
| 0.75% (7.5 mg/mL) | 18.7 mL |
Less cardiotoxic S-enantiomer of bupivacaine; still respect LAST. Education only — confirm against the package insert. Max doses are not additive across agents; account for total LA when mixing.
Pharmacokinetics
Onset + duration similar to bupivacaine (long, 4–8 h). Amide hepatic metabolism.
Side effects
- !LAST (less cardiotoxic than bupivacaine)
- !Motor block
Contraindications
- ×Amide allergy (rare)
- ×IV regional (Bier) — cardiotoxic LA contraindicated
Clinical pearls
- ★Chosen when bupivacaine-level duration is wanted with a wider cardiac safety margin.
- ★Still a long-acting LA — treat LAST with lipid emulsion; never for Bier blocks.
Other drugs in Local Anesthetics
- Lidocaine
Blocks voltage-gated Na⁺ channels in nerves (LA) and cardiac myocytes (antiarrhythmic).
- Bupivacaine
Voltage-gated Na⁺ channel blocker. Higher protein binding and lipid solubility than lidocaine → longer duration but greater cardiotoxicity.
- Ropivacaine
S-enantiomer of propivacaine. Less lipid-soluble than bupivacaine → less cardiotoxicity but slightly less potency.
- Tetracaine
Blocks voltage-gated Na⁺ channels. Long-acting ester, metabolized by plasma cholinesterase. High potency + toxicity.
- Chloroprocaine
Na⁺-channel blocker. Extremely rapid plasma-cholinesterase metabolism (half-life seconds) → lowest systemic toxicity of the LAs, ideal for OB epidural top-up.
- Procaine
Na⁺-channel blocker; prototype ester LA. Plasma-cholinesterase metabolized to PABA.
- Prilocaine
Na⁺-channel blocker. Metabolized to o-toluidine → oxidizes hemoglobin → methemoglobinemia at high doses.
- Articaine
Amide LA that uniquely also has a thiophene ester group → partial plasma-esterase metabolism → shorter systemic half-life. Excellent bone/tissue penetration in dentistry.
Browse all classes: /reference/drugs
Suggested reading
- •Stoelting & Hines, Pharmacology & Physiology in Anesthetic Practice, 6e
- •FDA package insert
- •ASRA LAST checklist, 2020
