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Bupivacaine

Bupivacaine structure

CAS No:
2180-92-9
Formula:
C18H28N2O
Chemical Name:
Bupivacaine
Synonyms:
MARCAINE;BUPIVACAINE;BUPIVACAINE BASE;2',6'-Pipecoloxylidide, 1-butyl-;6’-pipecoloxylidide,1-butyl-2;Anekain;Carbostesin;DL-Bupivacaine
Categories:
Active Pharmaceutical Ingredients > Anesthetic Agents

Description

Solid

ChEBI: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide is a piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline. It is a piperidinecarboxamide, an aromatic amide and a tertiary amino compound. It is a conjugate base of a 1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium.

Bupivacaine was synthesized simultaneously with mepivacainein 1957 but was at first overlooked because of the increasedtoxicity compared with mepivacaine. When themethyl on the cyclic amine of mepivacaine is exchanged fora butyl group the lipophilicity, potency and the duration ofaction all increase. Literature reports of cardiovascular toxicity,including severe hypotension and bradycardia, areabundant in the literature.91 Bupivacaine is highly bound toplasma proteins (95%), and thus the free concentration mayremain low until all of the protein binding sites are occupied.After that point, the plasma levels of bupivacaine rise rapidlyand patients may progress to overt cardiac toxicity withoutever showing signs of CNS toxicity. The cardiotoxicity ofbupivacaine is a result of its affinity to cardiac tissues and itsability to depress electrical conduction and predispose theheart to reentry types of arrhythmias. The cardiotoxicity ofbupivacaine was found to be significantly more prominentwith the “R” isomer, or the racemic mixture, thus the “S”stereoisomer is now on the market as levobupivacaine.

Bupivacaine Basic Attributes

Molecular Weight：

288.43

Exact Mass：

288.43

EC Number：

218-553-3

Characteristics

PSA：

32.3

XLogP3：

3.6

Appearance：

Solid

Density：

1.0238 (rough estimate)

Melting Point：

107.5-108°

Boiling Point：

430.65°C (rough estimate)

Flash Point：

209.9±28.7 °C

Refractive Index：

1.5700 (estimate)

Water Solubility：

101.5mg/L(25 ºC)

Storage Conditions：

Bupivacaine hydrochloride solutions should be stored between 15-30 deg C and freezing should be avoided; solutions containing epinephrine should be protected from light.

Vapor Pressure：

1.31X10-7 mm Hg at 25 deg C (est)

Toxicity：

Highly toxic

Flammability characteristics：

Thermal decomposition to emit toxic nitrogen oxide fumes

PKA：

8.09; also reported as 8.17(at 25℃)

Safety Information

Transport codes：

2811

hazard class code：

T+

safety instructions：

22-26-36/37/39-45

Marks：

T+

Storage features：

Treasury is ventilated, low temperature and dry; stored separately from food materials

Precautionary statement(s)：

P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501

Hazard Statements：

26/27/28-38-41

RIDADR：

2811

Bupivacaine Use and Manufacturing

This product is a safe and effective local anesthetic, which is produced in Japan, the United Kingdom, the United States, and Germany. The LD50 of bupivacaine hydrochloride in mice (subcutaneous administration) was 82±6mg/kg. The spasticity (CD50) caused by continuous intravenous administration of home-free vaccine was 0.18±0.02mg/kg/min.

Anesthetic (local).

Like lidocaine and mepivacaine, bupivacaine is used in infiltration, spinal, and epidural anesthesia in blocking nerve transmission. Its most distinctive property is its long-lasting action. It is used for surgical intervention in urology and in lower thoracic surgery from 3 to 5 h in length, and in abdominal surgery lasting from 45 to 60 min. It is used to block the trifacial nerve, the sacral and brachial plexuses, in resetting dislocations, in epidural anesthesia, and during Cesarian sections.

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