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Levobupivacaine hydrochloride, molecular formula C18H29ClN2O, CAS 27262-48-2. It is a white or off-white crystalline powder, odorless and slightly bitter. It is not easily soluble in water and ethanol, but soluble in organic solvents such as chloroform. The solubility is low, the solubility in water is 5mg/mL, and the solubility in ethanol is about 1mg/mL. It is a chiral molecule with two enantiomers, L- and D-. Among them, L- is a left-handed molecule, and D- is a right-handed molecule. Since only the L-enantiomer is pharmacologically active, it usually uses the L-enantiomer as the active ingredient. It is a weakly alkaline substance with an ionization constant (pKa) of about 8.1. According to the principle of left-right symmetry, Levo (left-handed) represents its three-dimensional configuration. It is a local anesthetic with a similar mechanism of action to Lidocaine and Bupivacaine. Its chemical structure determines its characteristics, which is of great significance in pharmacological research, drug development and other fields. This article will describe all the physical properties of product.
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Levobiocaine hydrochloride is an amide local anesthetic with the chemical formula C ₁₈ H ₂₈ ClN ₂ O · HCl and a molecular weight of 342.9 (also known as 324.89, which may vary depending on the presence of crystal water). It has a wide range of clinical applications, and the following is a detailed introduction to its common uses:
Epidural block anesthesia:
It is a commonly used medication for surgical epidural anesthesia. It blocks the generation and transmission of nerve impulses, causing patients to experience temporary and reversible sensory loss in areas related to nerve innervation under conscious conditions, thereby exerting analgesic effects.
When used for nerve block or infiltration anesthesia in adults, the maximum dose at a time is 150mg. In terms of drug concentration preparation, surgical epidural block usually uses a solution of 0.5% to 0.75%, with a dose of 10-20ml, or 50-150mg, which can achieve moderate to complete motor block effect.
When 0.25%~0.5% levobupivacaine hydrochloride is applied for regional blockade, its efficacy is similar to that of bupivacaine at the same concentration; When 0.375%~0.75% epidural block is performed, the onset and duration of sensation and movement block are similar to those of the same concentration of bupivacaine.
Lumbar numbness:
Although the instructions do not explicitly state its use for lumbar anesthesia, clinical anesthesia textbooks indicate that it can be used for lumbar anesthesia. 2-3ml of 0.5% levobupivacaine hcl for lumbar anesthesia is suitable for lower limb, pelvic, and lower abdominal surgeries.
Neuroblock anesthesia:
Widely used in various types of nerve blocks, such as brachial plexus anesthesia, cervical plexus anesthesia, regional anesthesia, etc. It blocks the transmission of nerve impulses, creating an anesthetic effect in the area innervated by the nerves, ensuring the smooth progress of the surgery.
Labor analgesia:
Can be used for pain relief during childbirth, reducing the pain of postpartum women. 0.125%~0.15% levobupivacaine hcl solution is suitable for labor analgesia, with mild blockade of motor nerves and no impact on the delivery process of the mother.
Postoperative analgesia:
Postoperative pain is one of the common symptoms in surgical patients, which can be alleviated by blocking the transmission of nerve impulses. 0.125%~0.15% levobupivacaine hcl solution can also be used for postoperative analgesia to improve patient comfort.
Anesthesia in other medical procedures
Examination and operation anesthesia:
Can be used for anesthesia in various small surgeries, such as endoscopy, biopsy, etc. It uses local infiltration anesthesia or nerve block anesthesia to prevent patients from feeling pain during examination or operation.
topical anesthesia:
Although mainly used for infiltration anesthesia and nerve block anesthesia, it can also be used for surface anesthesia in some cases. For example, in ophthalmic surgery, levobupivacaine hcl can be used by eye drops to induce anesthesia on the surface of the eyeball. However, the more common surface anesthetic is obucaine hydrochloride gel, etc.
Anti inflammatory effect:
It can inhibit the release of inflammatory factors, thereby achieving anti-inflammatory effects. It can be used to alleviate inflammatory reactions caused by surgical trauma, burns, etc., and alleviate patients' inflammatory symptoms. However, this function is not its main use, and it needs to be combined with specific conditions and doctor guidance in clinical applications.
Antiarrhythmic (use with caution):
In theory, levobupivacaine hcl may have a certain anti arrhythmic effect by affecting the electrophysiological activity of myocardial cells.
However, due to its cardiac toxicity (although lower than bupivacaine), it is not recommended for clinical use as an antiarrhythmic drug. In specific situations, such as arrhythmia during local anesthesia, doctors may carefully evaluate the condition before deciding whether to use it.
Anti shock (auxiliary application in specific contexts):
Not a standard treatment drug for shock. But in certain specific situations, such as when shock patients require surgical anesthesia, doctors may carefully use levobupivacaine hydrochloride for anesthesia under close monitoring based on the patient's specific situation and surgical needs.
It is a local anesthetic that can be synthesized by various methods.
This is one of the most commonly used synthetic methods. First, L-phenylacetic acid is obtained by the peroxide method of phenylacetic acid, and then reduced with reducing agents such as potassium sodium, hydrogen or tin hydride. On this basis, HBr, HCl and other reagents are used to carry out alkaline hydrolysis of the reduced compound to obtain L-isobutylamine acetic acid. Finally, L-isobutylamine acetic acid was mixed with the corresponding enantiomer using the rule of racemization and crystallized to obtain the target product.
In this method, 4-amino-2',6'-dimethylacetylacetone (AMDE) and L-isobutylamine need to be condensed first to generate acetylacetone intermediates. Then, use reagents such as HCl to carry out ammonolysis reaction to intermediate product, generate L-berpivacaine. Finally, it was crystallized by adding hydrochloric acid.
In this method, it is first acylated with alkylphenols such as 1-phenylethanol or 2,6-dimethylphenethanol, and then salted with HCl and other reagents to obtain product . Different acylating agents affect the physical properties of the product, such as solubility and the rate of absorption and release.
This route includes the following steps:
(1) First, the corresponding 4-bromo-2′,6′-dimethylacetylacetone and L-isobutylamine were condensed to form four enantiomeric precursors.
(2) Then, the four enantiomers were separated and further purified by crystallization.
(3) For the two enantiomers, the target product, namely product, can be generated through reduction, esterification and condensation reactions.
(4) Finally, the product is purified and separated to obtain high-purity Levobupivacaine hcl.
In conclusion, it can be prepared by a number of different synthetic methods. Among them, the most commonly used synthetic method is through the reduction method of L-phenylacetic acid, the condensation method of reactants and the acylation reaction method of L-isobutylamine. In addition, there are more complex synthetic routes that require more precise chemical experiment operations and crystallization purification processes.
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Chemical Formula |
C18H28N2O |
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Exact Mass |
288 |
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Molecular Weight |
288 |
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m/z |
288 (100.0%), 289 (19.5%), 290 (1.8%) |
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Elemental Analysis |
C, 74.96; H, 9.79; N, 9.71; O, 5.55 |
It is a local anesthetic that was first introduced into clinical use in 1996. Its efficacy is similar to that of bupivacaine, but its analgesic and anesthetic effects are significantly better than the latter. It is also an anesthetic drug with good safety, because this compound can only use its left-handed isomer, while the right-handed isomer is toxic.
The discovery of product dates back to the 1990s, when Pharma-Product Manufacturing Limited (PPM) was conducting a study of oral antimicrobials where they discovered a very unusual deep anesthetic. The company found that a compound extracted from sunflower oil can be used as a raw material to synthesize Levobupivacaine hcl, the left-handed isomer, through a series of chemical reactions.
At the time, PPM didn't know it had created a new anesthetic, so they applied it in experiments evaluating toxicity on guinea pigs. The results showed that product, the levorotatory isomer, had lower toxicity to mice and could produce long-lasting and effective local anesthesia. These findings prompted PPM to begin exploring the new compound in humans to further evaluate its safety and efficacy.
In early clinical trials, it showed similar analgesic and anesthetic effects to bupivacaine, but was safer. The drug's low cardiotoxicity and less impact on the respiratory system and nervous system have been widely used in clinical applications. Since then, it has been recognized as a safe and effective local anesthetic and has become an indispensable anesthetic in the fields of orthopedics, obstetrics, dentistry, and plastic surgery.
Although it has been widely used clinically, the details of its discovery history are still not fully understood. At present, the research on it is limited to its application as a local anesthetic, and no further research on the discovery history of Levobupivacaine hydrochloride has been conducted.
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