2180-92-9 Usage
Chemical Description
Bupivacaine is a local anesthetic that is often used in epidural anesthesia.
Description
Bupivacaine is a local anesthetic medication that was synthesized in 1957 alongside mepivacaine. It is characterized by its increased lipophilicity, potency, and long-lasting action compared to mepivacaine. Bupivacaine is highly bound to plasma proteins (95%), which can lead to rapid increases in plasma levels and potential cardiotoxicity if all protein binding sites are occupied. The cardiotoxicity of bupivacaine is more prominent with the "R" isomer, leading to the development of the "S" stereoisomer, levobupivacaine.
Uses
Used in Anesthetic Applications:
Bupivacaine is used as a local anesthetic for various medical procedures, including infiltration, spinal, and epidural anesthesia. It is particularly effective in blocking nerve transmission and is known for its long-lasting action.
Used in Surgical Interventions:
In the medical field, bupivacaine is used for surgical interventions in urology and lower thoracic surgery, providing anesthesia for durations ranging from 3 to 5 hours. It is also used in abdominal surgeries lasting approximately 45 to 60 minutes.
Used in Nerve Blockade Procedures:
Bupivacaine is utilized to block the trifacial nerve, the sacral and brachial plexuses, and is applied in resetting dislocations. It is also used in epidural anesthesia and during Cesarean sections to provide pain relief and ensure a smooth surgical process.
Therapeutic Function
Local anesthetic
Mechanism of action
Bupivacaine is a local anaesthetic containing a chiral centre and adopts dextro and laevo forms. The enantiopure l form is less cardio- and neurotoxic and has an equivalent potency to the racemic mixture; therefore levobupivacaine is often preferred to reduce the potential for toxicity. Stereoselectivity describes the differences in response at a given receptor for the different enantiomers (such as the response discussed for S(+) ketamine). The opioid and NMDA receptors also exhibit stereoselectivity.
Pharmacology
Bupivacaine is a chiral compound used clinically for 50 years, with a slower
onset, greater potency and longer duration of action than lidocaine. Initial
benefits of bupivacaine were sensory–motor separation and minimal
tachyphylaxis, unlike repeated doses of lidocaine. However, it has greater
potential for cardiac toxicity, related to its avid binding to and slow
dissociation from cardiac N a+ channels. Inadvertent intravenous
administration may result in systemic toxicity (see later), and it is
contraindicated for intravenous regional anaesthesia.Bupivacaine is commonly used for epidural administration in obstetrics and
postoperative pain management. A hyperbaric preparation containing
80 mg ml-1 glucose is available for spinal anaesthesia.
Side effects
Common side effects of bupivacaine include:weakness, long-lasting numbness or tingling;feeling restless or drowsy;tremors;headache, blurred vision;fast or slow heartbeats;breathing problems;chills or shivering;back pain; nausea, vomiting.
Synthesis
Bupivacaine, N-2,6-(dimethyl)1-butyl-2-piperidincarboxamide (2.2.7), is chemically similar to mepivacaine and only differs in the replacement of the N-methyl substituent on the piperidine ring with an N-butyl substituent. There are also two suggested methods of synthesis. The first comes from α-picolin-2,6-xylidide (2.2.4). The alkylation of the last with butyl bromide gives the corresponding pyridine salt (2.2.6). Finally, it is reduced by hydrogen using platinum oxide as a catalyst into a piperidine derivative—bupivacaine.
The other method results directly from the piperidine-2-carboxylic acid chloride, which is reacted with 2,6-dimethylaniline. The resulting amide (2.2.8) is further alkylated with butyl bromide to bupivacaine [17–19].
Check Digit Verification of cas no
The CAS Registry Mumber 2180-92-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,8 and 0 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 2180-92:
(6*2)+(5*1)+(4*8)+(3*0)+(2*9)+(1*2)=69
69 % 10 = 9
So 2180-92-9 is a valid CAS Registry Number.
InChI:InChI=1/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)
2180-92-9Relevant articles and documents
HYDROPHOBIC ACID ADDITION SALTS AND PHARMACEUTICAL FORMULATIONS THEREOF
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Page/Page column 86, (2019/05/22)
The invention provides hydrohphobic drug salts and pharmaceutical compositions comprising such salts. The invention fourther provides compositions for delivering poorly soluble drugs, including hydrophobic drug salts.
Preparation method of levobupivacaine hydrochloride
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, (2017/07/19)
The invention belongs to the technical field of chemical synthesis and in particular relates to a preparation method of levobupivacaine hydrochloride. The preparation method takes racemic or S-configuration 2-piperidinecarboxylic acid as a starting raw material and comprises the following steps: taking the starting raw material and n-butylaldehyde to react and carrying out borohydride reduction reaction to obtain 1-butylpiperidine-2-carboxylic acid; taking the 1-butylpiperidine-2-carboxylic acid and 2,6-dimethylaniline to be subjected to condensation reaction, so as to generate bupivacaine or levobupivacaine; carrying out subsequent treatment to obtain a final product levobupivacaine hydrochloride. Compared with an existing synthesis route, the preparation method has the advantages of short synthesis route, simple method, convenience for operation, low cost and easiness for industrial production; reaction conditions of each step are relatively moderate, a process is stable, a strong-corrosion chlorination reagent is not used, the pollution to environment is reduced and the like.
DERMAL COMPOSITIONS OF SUBSTITUTED AMIDES AND THE USE THEREOF AS MEDICATION FOR PAIN AND PRURITUS
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Page/Page column 30-31, (2008/12/07)
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