What Is Bupivacaine?
Bupivacaine, whose chemical name is 1-n-butyl-2- (2,6-dimethylcarbamoyl) piperidine, is commonly used as its hydrochloride salt. It is a white crystalline powder, odorless and bitter. Soluble in ethanol, soluble in water, slightly soluble in chloroform, and almost insoluble in ether. Its aqueous solution has a pH of 4.5 to 6.0. Clinically belongs to the category of anesthetics.
- Chinese name
- Bupivacaine
- Foreign name
- Bupivacaine
- CAS number
- 2180-92-9
- Molecular formula
- C18H28N2O
- Molecular weight
- 288.42800
- Density
- 1.014g / cm3
- Bupivacaine, whose chemical name is 1-n-butyl-2- (2,6-dimethylcarbamoyl) piperidine, is commonly used as its hydrochloride salt. It is a white crystalline powder, odorless and bitter. Soluble in ethanol, soluble in water, slightly soluble in chloroform, and almost insoluble in ether. Its aqueous solution has a pH of 4.5 to 6.0. Clinically belongs to the category of anesthetics.
Introduction to bupivacaine compounds
Bupivacaine Basic Information
- Chinese name: bupivacaine
- Chinese alias: bupivacaine; 1-n-butyl-2- (2,6-dimethylaminoformyl) piperidine; bupivacaine; bupivacaine; macaine; -(2,6-dimethylphenyl) piperidine-2-carboxamide;
- English name: Bupivacaine
- English alias: 1-butyl-N- (2,6-dimethylphenyl) piperidine-2-carboxamide; (RS) -bupivacaine;
- CAS number: 2180-92-9
- Molecular formula: C 18 H 28 N 2 O
- Structural formula:
- Molecular weight: 288.42800
- Exact mass: 288.22000
- PSA: 32.34000
- LogP: 3.90740 [1]
Bupivacaine physical and chemical properties
- Density: 1.014g / cm 3
- Boiling point: 436ºC at 760 mmHg
- Flash point: 140.9ºC
- Refractive index: 1.53
- Storage conditions: storeroom is ventilated, low temperature and dry, stored separately from food ingredients
- Vapor pressure: 8.4EmmHg at 25 ° C [1]
- Its hydrochloride is commonly used as a white crystalline powder, which is odorless and bitter. Soluble in ethanol, soluble in water, slightly soluble in chloroform, and almost insoluble in ether. Its aqueous solution has a pH of 4.5 to 6.0.
Bupivacaine Safety Information
- Dangerous Goods Transport Code: 2811
- Danger category code: R26 / 27/28; R38; R41
- Safety instructions: S22-S26-S36 / 37 / 39-S45 [1]
- Dangerous goods mark: T +
Bupivacaine production method
- Omega-chlorohexanoic acid is brominated and esterified to obtain ethyl 2-bromo-6-chlorohexanoate, which is cyclized with n-butylamine to form ethyl N-n-butyl-2-piperidinecarboxylic acid. It is then condensed with 2,6-xylylamine to give bupivacaine. The total yield is about 20%. [2]
Bupivacaine other
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Bupivacaine Atlas
- 1) Carbon spectrum
- 2) Proton spectrum
Bupivacaine Pharmacopoeia Standard
Bupivacaine source (name), content (potency)
- This product is a sterile aqueous solution of bupivacaine hydrochloride. Bupivacaine hydrochloride (C18H28N2O · HCl) should be 90.0% to 110.0% of the labeled amount. [3]
Bupivacaine traits
- This product is a colorless or almost colorless clear liquid. [3]
Bupivacaine identification
- (1) In the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution. [3]
- (2) Measure an appropriate amount of this product (approximately 25mg of bupivacaine hydrochloride), add 2ml of 13.5mol / L ammonia solution, shake, filter, wash the precipitate with water, dry under reduced pressure at 60 ° C for 4 hours, then add 10ml of 0.01mol / L methanolic hydrochloric acid solution, dissolve the precipitate, place in a water bath, stir, evaporate to dryness, and take the residue to dry at 105 . According to the identification (2) test under bupivacaine hydrochloride, it is the same the result of. [3]
Bupivacaine check
- 1pH [3]
- It should be 4.0 to 6.5 (Appendix VIH of Part Two of the 2010 Pharmacopoeia).
- 2 related substances [3]
- Take this product and dilute it with mobile phase to make a solution containing about 2mg of bupivacaine hydrochloride per 1ml as the test solution; take 1ml precisely, place it in a 100ml measuring bottle, dilute to the mark with mobile phase, and shake well , As a control solution. According to the method under the relevant substance of bupivacaine hydrochloride, if there are impurity peaks in the chromatogram of the test solution, the sum of the area of each impurity peak should not be greater than the area of the main peak of the control solution (1.0%).
- 3bacterial endotoxins [3]
- Take this product, you can use high-sensitivity plutonium reagents above 0.06 EU / ml, check according to law (Appendix E of the second edition of the Pharmacopoeia 2010 edition), the amount of endotoxin in 1 mg bupivacaine hydrochloride should be less than 0.080 EU.
- 4 others [3]
- It should comply with the relevant provisions under the injection (Appendix IB of Part Two of the 2010 Pharmacopoeia).
Determination of bupivacaine
- It was determined by high performance liquid chromatography (Appendix VD of Part Two of the Pharmacopoeia, 2010 Edition).
- 1 Chromatographic conditions and system suitability test [3]
- Use octadecylsilane-bonded silica gel as the filler (pH range is greater than 8.0); 0.02mol / L phosphate buffer (take 2.72g of potassium dihydrogen phosphate and 0.75g of sodium hydroxide, add 1000ml of water to dissolve, Adjust the pH to 8.0)-Acetonitrile (35:65) is the mobile phase; the detection wavelength is 240nm. The resolution of the bupivacaine hydrochloride peak from the adjacent impurity peaks should meet the requirements.
- 2 determination method [3]
- Precisely measure the appropriate amount of this product, add mobile phase dilution to make a solution containing about 25g per 1ml, accurately measure 20l into the liquid chromatograph, and record the chromatogram; also take bupivacaine hydrochloride reference substance for the same method. Calculate the peak area according to the external standard method.
Bupivacaine Drug Description
Bupivacaine Pharmacology and Toxicology
- It is an amide long-acting local anesthetic. Its anesthesia time is 2-3 times longer than lidocaine hydrochloride, and the dispersion is similar to lidocaine hydrochloride. It has less impact on circulation and breathing, has no irritating effect on tissues, and does not produce Methemoglobin, the commonly used amount has no effect on cardiovascular function. When the amount is large, it can cause blood pressure to drop and heart rate to slow. Have obvious blocking effect on -receptor. No obvious rapid tolerance. The blood concentration of the drug in the mother is 4 times that of the fetus. [4]
Bupivacaine pharmacokinetics
- Generally, the effect begins in 5-10 minutes after administration, reaches a peak in 15-20 minutes, and is maintained for 3-6 hours or longer. The plasma protein binding rate of this product is about 95%. Most of the products are excreted by the kidneys after being metabolized by the liver, only about 5% is excreted in the original form with urine. [4]
Bupivacaine indications
- For local infiltration anesthesia, peripheral nerve block and spinal block. [4]
Bupivacaine dosage
- (1) Brachial plexus block, 0.25% solution, 20-30ml or 0.375% 20ml (50-75mg); [4]
- (2) sacral block, 0.25%, 15-30ml (37.5-75.0mg), or 0.5%, 15-20ml (75-100mg); [4]
- (3) For epidural space block, 0.25% -0.375% (10-20ml) can be analgesic, 0.5% (10-20ml) can be used for general abdominal surgery, etc. [4]
- (4) Local infiltration, the total dosage is generally limited to 175-200mg (0.25%, 70-80ml), and divided into doses within 24 hours, with a daily maximum of 400mg; [4]
- (5) The total amount of sympathetic ganglion block is 50-125mg (0.25%, 20-50ml); [4]
- (6) Subarachnoid block, commonly used amount is 5-15mg, and 10% glucose is added to high-density fluid or diluted with cerebrospinal fluid to approximately equal density fluid. [4]
Bupivacaine adverse reactions
- (1) A small number of patients may experience headache, nausea, vomiting, urinary retention and slow heart rate. If severe side effects occur, ephedrine or atropine can be given intravenously. [4]
- (2) Excessive or accidental entry into the blood vessel can produce serious toxic reactions, and once myocardial toxicity occurs, there is little hope of recovery. [4]
Bupivacaine contraindications
- Those who are allergic to this product are prohibited. [4]
Bupivacaine precautions
- (1) This product is 4 times more toxic than lidocaine. Cardiotoxicity should be especially noted. It causes a lower ratio of circulatory failure and convulsions (CC / CNS = 3.7 ± 0.5). Cardiotoxic symptoms appear earlier and often circulatory failure. Concurrent with convulsions, resuscitation is difficult once the heart is arrested. [4]
- (2) 0.1% concentration for children with local infiltration anesthesia. [4]
- Medication for children
- Use with caution in children under 12 years of age. [4]
Bupivacaine drug interactions
- Compatibility with alkaline drugs will cause precipitation to lose its effect. [4]
Bupivacaine overdose
- Do not overdose when used. Overdose can cause hypertension, convulsions, cardiac arrest, respiratory depression and convulsions. [4]
Bupivacaine specifications
- (1) 5ml: 12.5mg (2) 5ml: 25mg (3) 5ml: 37.5mg [4]