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Levobupivacaine | CAS No: 27262-47-1 | GMP-certified suppliers
A medication that provides local and regional anesthesia for surgery, obstetrics, and postoperative pain management with a prolonged duration and reduced cardiovascular risks.
Therapeutic categories
Primary indications
- For the production of local or regional anesthesia for surgery and obstetrics, and for post-operative pain management
Product Snapshot
- Levobupivacaine is available as an injectable solution formulated for epidural administration
- It is primarily used for local or regional anesthesia in surgical and obstetric procedures, as well as post-operative pain management
- The product is approved in key regulatory markets and also has investigational status in some regions
Clinical Overview
Clinically, levobupivacaine is indicated for the production of local or regional anesthesia in surgical, obstetric, and diagnostic procedures. It is also used for postoperative pain management, including infiltration anesthesia, nerve blocks, ophthalmic anesthesia, as well as epidural and intrathecal administration in adults. Infiltration analgesia applications extend to pediatric populations.
Pharmacodynamically, levobupivacaine exerts its anesthetic effect by blocking nerve impulse generation and conduction. Its mechanism of action involves binding to the intracellular segment of voltage-gated sodium channels in nerve membranes, inhibiting sodium influx. This prevents depolarization and thereby slows nerve conduction velocity. The anesthetic effect correlates inversely with nerve fiber diameter and myelination.
Absorption and distribution depend on the route of administration, with systemic exposure potentially arising from inadvertent intravascular injection or overdose. Levobupivacaine is metabolized hepatically primarily via hepatic cytochrome P450 enzymes (CYP1A2, CYP3A4) and is predominantly eliminated renally in metabolized form. Its pharmacokinetic profile supports a favorable duration of action and reduced cardiovascular toxicity relative to racemic bupivacaine.
Safety considerations emphasize careful dosing and administration technique to minimize systemic toxicity, including central nervous system and cardiovascular effects. Allergic reactions are uncommon but possible. The compound is categorized as a central nervous system depressant with neuraxial and peripheral nervous system activity.
Levobupivacaine hydrochloride is marketed under the trade name Chirocaine by AstraZeneca, among other suppliers. For API sourcing, quality control should rigorously verify enantiomeric purity, conform to pharmacopeial standards, and ensure appropriate impurity profiles to support safety and efficacy in final formulations.
Identification & chemistry
| Generic name | Levobupivacaine |
|---|---|
| Molecule type | Small molecule |
| CAS | 27262-47-1 |
| UNII | A5H73K9U3W |
| DrugBank ID | DB01002 |
Pharmacology
| Summary | Levobupivacaine is a local anesthetic that produces regional anesthesia by blocking voltage-gated sodium channels, specifically targeting the sodium channel protein type 10 subunit alpha. This blockade inhibits nerve impulse generation and conduction by preventing sodium influx and subsequent depolarization. Its pharmacodynamic effect results in reversible loss of nerve signaling, facilitating analgesia during surgical, diagnostic, and obstetrical procedures. |
|---|---|
| Mechanism of action | Local anesthetics such as Levobupivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Specifically, the drug binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. |
| Pharmacodynamics | Levobupivacaine, a local anesthetic agent, is indicated for the production of local or regional anesthesia or analgesia for surgery, for oral surgery procedures, for diagnostic and therapeutic procedures, and for obstetrical procedures. |
Targets
| Target | Organism | Actions |
|---|---|---|
| Sodium channel protein type 10 subunit alpha | Humans | inhibitor |
ADME / PK
| Absorption | The plasma concentration of levobupivacaine following therapeutic administration depends on dose and also on route of administration, because absorption from the site of administration is affected by the vascularity of the tissue. Peak levels in blood were reached approximately 30 minutes after epidural administration, and doses up to 150 mg resulted in mean C<sub>max</sub> levels of up to 1.2 µg/mL. |
|---|---|
| Half-life | 3.3 hours |
| Protein binding | >97% |
| Metabolism | Levobupivacaine is extensively metabolized with no unchanged levobupivacaine detected in urine or feces. In vitro studies using [14 C] levobupivacaine showed that CYP3A4 isoform and CYP1A2 isoform mediate the metabolism of levobupivacaine to desbutyl levobupivacaine and 3-hydroxy levobupivacaine, respectively. In vivo, the 3-hydroxy levobupivacaine appears to undergo further transformation to glucuronide and sulfate conjugates. Metabolic inversion of levobupivacaine to R(+)-bupivacaine was not evident both in vitro and in vivo. |
| Route of elimination | Following intravenous administration, recovery of the radiolabelled dose of levobupivacaine was essentially quantitative with a mean total of about 95% being recovered in urine and feces in 48 hours. Of this 95%, about 71% was in urine while 24% was in feces. |
| Volume of distribution | 66.91 ±18.23 L [after intravenous administration of 40 mg in healthy volunteers] |
| Clearance | 39.06 ±13.29 L/h [after intravenous administration of 40 mg in healthy volunteers] |
Formulation & handling
- Levobupivacaine is a small molecule local anesthetic primarily formulated for epidural injection, not suitable for oral administration.
- Due to its lipophilic nature (LogP 4.52) and low water solubility, formulation strategies must ensure adequate solubilization for injectable solutions.
- Stability considerations include protection from light and temperature control during storage to maintain potency in injectable formats.
Regulatory status
| Lifecycle | The active pharmaceutical ingredient's primary patent in the United States expired on October 13, 2014, allowing for generic competition. The product is currently marketed in mature pharmaceutical markets. |
|---|
Supply Chain
| Supply chain summary | Levobupivacaine manufacturing is primarily associated with a limited number of originator companies, including Purdue Pharma LP. Its branded products have a global presence, notably in the US and EU markets. The patent listed, granted in 2014, may suggest that generic competition is either emerging or anticipated as patent protections approach expiration. |
|---|
Safety
| Toxicity | LD50: 5.1mg/kg in rabbit, intravenous; 18mg/kg in rabbit, oral; 207mg/kg in rabbit, parenteral; 63mg/kg in rat, subcutaneous (Archives Internationales de Pharmacodynamie et de Therapie. Vol. 200, Pg. 359, 1972.) Levobupivacaine appears to cause less myocardial depression than both bupivacaine and ropivacaine, despite being in higher concentrations. |
|---|
- Handle with caution due to low LD50 values indicating high acute toxicity via multiple administration routes
- Avoid exposure routes that may lead to systemic absorption, given potential for myocardial depression at elevated concentrations
- Employ appropriate containment and personal protective equipment to minimize risk during manufacturing and processing
Levobupivacaine is a type of Local anesthetics
Local anesthetics are a category of pharmaceutical Active Pharmaceutical Ingredients (APIs) commonly used to numb a specific area of the body during medical procedures or surgeries. They work by blocking the transmission of nerve signals, preventing the sensation of pain in the targeted region. Local anesthetics are vital for various medical applications, including dental procedures, minor surgeries, and childbirth.
The main mechanism of action for local anesthetics involves the reversible inhibition of sodium channels, which are responsible for the conduction of nerve impulses. By binding to these channels, local anesthetics prevent the influx of sodium ions, which blocks the generation and propagation of nerve signals. This results in temporary loss of sensation in the area where the medication is administered.
Local anesthetics can be categorized into two main types: esters and amides. Esters, such as procaine and benzocaine, are metabolized by plasma esterases, while amides, including lidocaine and bupivacaine, undergo hepatic metabolism. The choice of local anesthetic depends on factors such as the duration of action required, the specific procedure being performed, and the patient's medical history.
It is important to note that local anesthetics should be administered with caution, as they can have potential side effects, including allergic reactions, systemic toxicity, and nerve damage if used improperly. Therefore, proper dosage and administration techniques must be followed to ensure patient safety.
In summary, local anesthetics are essential pharmaceutical APIs used to temporarily block nerve signals, providing localized pain relief during medical procedures. Understanding the different types and their mechanisms of action allows healthcare professionals to select the most appropriate local anesthetic for each patient and procedure, ensuring optimal outcomes and patient comfort.
Levobupivacaine API manufacturers & distributors
Compare qualified Levobupivacaine API suppliers worldwide. We currently have 6 companies offering Levobupivacaine API, with manufacturing taking place in 2 different countries. Use the table below to review supplier type, countries of origin, certifications, product portfolio and GMP audit availability.
| Supplier | Type | Country | Product origin | Certifications | Portfolio |
|---|---|---|---|---|---|
| Gonane Pharma | Producer | India | India | BSE/TSE, CoA, GMP, MSDS | 166 products |
| Pioneer AGRO Ind. | Producer | India | India | CoA, GMP, WC | 12 products |
| Senova Technology Co., Lt... | Producer | China | China | CoA, ISO9001, USDMF | 157 products |
| Shandong Chenghui Shuangd... | Producer | China | China | CoA, ISO9001 | 98 products |
| Sichuan Benepure | Producer | China | China | CoA | 23 products |
| Zhuhai Rundu | Producer | China | China | CoA, WC | 11 products |
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