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Levobupivacaine hydrochloride

Uses
Levobupivacaine hydrochloride
Levobupivacaine hydrochloride structure
CAS No.
27262-48-2
Chemical Name:
Levobupivacaine hydrochloride
Synonyms
27262-48-2;BUPIVACAINE HCL;(S)-Bupivacaine;LEVAMISOLHCLSALT;L-(-)-Bupivacaine;TIMTEC-BB SBB001337;LEVOBUPIVACAINE HCL;(S)-(-)-Bupivacaine;Bupivacaine Impurity 1;(S)-(-)-BUPIVACAINE HCL
CBNumber:
CB3408801
Molecular Formula:
C18H29ClN2O
Formula Weight:
324.89
MOL File:
27262-48-2.mol

Levobupivacaine hydrochloride Properties

Melting point:
254 °C (dec.)(lit.)
alpha 
-12.5 º (c=2, water)
storage temp. 
2-8°C
solubility 
H2O: soluble20mg/mL, clear
form 
powder
color 
white to beige
optical activity
[α]/D -10 to -14°, c = 1.0 in H2O
InChIKey
SIEYLFHKZGLBNX-NTISSMGPSA-N
CAS DataBase Reference
27262-48-2(CAS DataBase Reference)
FDA UNII
J998RDZ51I
NCI Drug Dictionary
levobupivacaine hydrochloride
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  T+,Xn
Risk Statements  26/27/28-20/21/22-28
Safety Statements  22-36/37/39-45-36/37-53
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS  TK6125000

Levobupivacaine hydrochloride price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML1092 Levobupivacaine hydrochloride ≥98% (HPLC) 27262-48-2 10mg $77.2 2021-03-22 Buy
Sigma-Aldrich B5274 Bupivacaine hydrochloride monohydrate analytical standard, for drug analysis 27262-48-2 1 g $81.5 2021-03-22 Buy
Sigma-Aldrich B5274 Bupivacaine hydrochloride monohydrate analytical standard, for drug analysis 27262-48-2 5 g $138 2021-03-22 Buy
Sigma-Aldrich SML1092 Levobupivacaine hydrochloride ≥98% (HPLC) 27262-48-2 50mg $299 2021-03-22 Buy
Sigma-Aldrich B5274 Bupivacaine hydrochloride monohydrate analytical standard, for drug analysis 27262-48-2 15 g $327 2021-03-22 Buy

Levobupivacaine hydrochloride Chemical Properties,Uses,Production

Uses

(S)-(-)-Bupivacaine Hydrochloride is the salt analogue of a local anaesthetic used for epidural and intrathecal anaesthesia.

Description

Levobupivacaine was first launched in the US for the production of local anesthesia for surgery and obstetrics and for post-operative pain management. It is the (S)-enantiomer of the long acting, highly potent local anesthetic bupivacaine (Marcaine) that can be prepared by a three step sequence from (S)-pipecolic acid or from (S)-lysine by oxidative deamination and stereospecific ring closure to (S)-pipecolamide core structure. Levobupivacaine exhibits its long-acting local anesthetic effect by blocking neuronal sodium channel ion flow in nerve axons. Clinical studies demonstrated an efficacy and a general profile closely resembling those of the racemic bupivacaine currently in use; however, it produced an enhanced safety profile, in particular substantially reduced (about one-third) cardiotoxicity (less effect on myocardial contractility and QT, prolongation) and CNS depressive side effects. Onset and duration of blockade were also equivalent or even better.

Chemical Properties

white crystalline powder

Originator

Chiroscience (UK)

Uses

Local anesthetic; analgesic.

Definition

ChEBI: The monohydrochloride salt of levobupivacaine.

Manufacturing Process

Synthesis of L-pipecolic acid 2,6-xylidide (Patent US 4,695,576)
130 g of pipecolic acid and 158.6 g of Laevo (+)-tartaric acid are dissolved under stirring in 2 L 95% ethyl alcohol and 125 ml water at 80°C. The solution is allowed to cool to room temperature and after two days the crystallized D-pipecolic-tartrate is separated. The L-pipecolic-tartrate remains in solution. The filtrate is evaporated and dissolved in 5% acetic acid. Finally the solution is treated with Amberlite IR 45* in an ion exchanger. The eluate thus obtained is evaporated and the resulting crystalline residue is dried with potassium hydroxide in vacuo. The product obtained consists of L-pipecolic acid [α]D24 = -26.2°(C = 5, H2O).
4 g of phosphorus pentachloride was added to a suspension of 4 g of Lpipecolic acid hydrochloride in 40 ml acetylchloride. The initial reaction is effected at a temperature of about 35°C under stirring for 2 hours. The chlorination is completed by adding during a time period of about 10 minutes an additional two grams of phosphorus pentachloride and stirring over a further period of 4 hours while maintaining the suspension at a temperature of about 35°C. The resulting L-pipecolic acid chloride hydrochloride is filtered and washed with toluene and acetone. The crystalline residue is then dried in vacuo, m.p. 155°C.
A mixture of 2.7 ml 2,6-dimethylaniline, 4 ml acetone, and 4 ml Nmethylpyrrolidone is gradually added under stirring for 2 hours at 70°C to a suspension of 4 g of L-pipecolic acid chloride hydrochloride. This yields a crystalline product, which is filtered, washed with acetone and dried. This crystalline product is then dissolved in water and the base is precipitated by the addition of ammonia. The base is then extracted by the use of toluene and is recovered by evaporation. The base is recrystallized from a mixture of hexane and ethanol to yield L-pipecolic acid 2,6-xylidide. The melting point of this compound is 129-130°C.
Preparation of L-N-n-butylpipecilic acid 2,6-xylidide may de carried out by analogy with the preparation of L-N-n-propylpipecolic acid 2,6-xylidide (Patent US 5,777,124).
n-Butylbromide and potassium carbonate are added to a solution of L-pipecolic acid 2,6-xylidide dissolved in isopropyl alcohol. Thereafter, 5 ml of water is added to the mixture and the reaction is carried out for 4 hours at 72°C.
To complete the reaction, a further 0.8 ml n-butylbromide are added under continuous stirring and heating for 4 hours. The residue is treated with a mixture of 250 ml toluene and an equal amount of water at 50°C. The toluene layer is separated and washed three times with 100 ml warm water (40°C). A 175 ml portion of the toluene is removed by evaporation and the remainder is stored at +5°C for 6 hours to achieve crude crystalline L-N-n-butylpipecilic acid 2,6-xylidide. The crystalline product is separated by filtration, washed with some cooled toluene and dried at 70°C. Recrystallization may be carried from toluene. This product is dissolved in 100 ml ethanol and neutralized with concentrated hydrochloric acid. Ethanol is removed by evaporation and the hydrochloride product obtained is vacuum dried. Finally the latter is recrystallized from isopropyl alcohol.

brand name

Chirocaine (Purdue).

Therapeutic Function

Local anesthetic

Biological Functions

Levobupivacaine hydrochloride (Chirocaine) is the S-enantiomer of bupivacaine. It too has long action. Animal studies show that it has less CNS and cardiac toxicity than does bupivacaine. It also is slightly more motor sparing than is bupivacaine.

Levobupivacaine hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products


Levobupivacaine hydrochloride Suppliers

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View Lastest Price from Levobupivacaine hydrochloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-04 Levobupivacainehydrochloride
27262-48-2
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-12-04 Levobupivacainehydrochloride
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-12-04 Levobupivacaine HCL
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD

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