Levobupivacaine hydrochloride
- Product Name
- Levobupivacaine hydrochloride
- CAS No.
- 27262-48-2
- Chemical Name
- Levobupivacaine hydrochloride
- Synonyms
- BUPIVACAINE HCL;(S)-Bupivacaine;LEVAMISOLHCLSALT;L-(-)-Bupivacaine;TIMTEC-BB SBB001337;LEVOBUPIVACAINE HCL;(S)-(-)-Bupivacaine;Levobupivacaine HCI;Bupivacaine Impurity 1;(S)-(-)-BUPIVACAINE HCL
- CBNumber
- CB3408801
- Molecular Formula
- C18H29ClN2O
- Formula Weight
- 324.89
- MOL File
- 27262-48-2.mol
Levobupivacaine hydrochloride Property
- 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
- InChI
- InChI=1/C18H28N2O.ClH/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);1H/t16-;/s3
- InChIKey
- SIEYLFHKZGLBNX-NTISSMGPSA-N
- SMILES
- C([C@@H]1CCCCN1CCCC)(=O)NC1C(=CC=CC=1C)C.Cl |&1:1,r|
- CAS DataBase Reference
- 27262-48-2(CAS DataBase Reference)
Safety
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML1092
- Product name
- Levobupivacaine hydrochloride
- Purity
- ≥98% (HPLC)
- Packaging
- 10mg
- Price
- $92.2
- Updated
- 2024/03/01
- Product number
- SML1092
- Product name
- Levobupivacaine hydrochloride
- Purity
- ≥98% (HPLC)
- Packaging
- 50mg
- Price
- $357
- Updated
- 2024/03/01
- Product number
- H37643
- Product name
- Levobupivacaine hydrochloride
- Purity
- 98%
- Packaging
- 250mg
- Price
- $148.05
- Updated
- 2023/01/06
- Product number
- H37643
- Product name
- Levobupivacaine hydrochloride
- Purity
- 98%
- Packaging
- 1g
- Price
- $438.9
- Updated
- 2023/01/06
- Product number
- B689675
- Product name
- (S)-(-)-BupivacaineHydrochloride
- Packaging
- 500mg
- Price
- $495
- Updated
- 2021/12/16
Levobupivacaine hydrochloride Chemical Properties,Usage,Production
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
Levobupivacaine hydrochloride has been used as an analyte in tandem mass spectrometry. It may be used to test its inhibitory effect on phosphorylation of extracellular signal-regulated kinase (ERK) mediated by capsaicin It may also be used as a component of poly(D,L-lactide-co-glycolide) (PLGA) microparticles for testing its sustainable release by electrospraying technique.
Definition
ChEBI: Levobupivacaine hydrochloride (anhydrous) is the monohydrochloride salt of levobupivacaine. It has a role as a local anaesthetic, an adrenergic antagonist, an amphiphile, an EC 3.1.1.8 (cholinesterase) inhibitor and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It contains a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine hydrochloride (anhydrous).
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.
General Description
Levobupivacaine belongs to the N-alkyl substituted pipecoloxylidide family and comprises amino-amide group.
Biochem/physiol Actions
Levobupivacaine hydrochloride is a sodium channel blocker used as a long-acting local anaesthetic for epidural anesthesia. Levobupivacaine is the (S)-isomer of bupivacaine, with efficacy similar to that of bupivacaine with a reduced risk of cardiotoxicity.
Mode of action
Levobupivacaine Hydrochloride is the hydrochloride salt of levobupivacaine, an amide derivative with anesthetic property. Levobupivacaine reversibly binds voltage-gated sodium channels to modulate ionic flux and prevent the initiation and transmission of nerve impulses (stabilizing neuronal membrane), thereby resulting in analgesia and anesthesia. In comparison with racemic bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action.
Levobupivacaine hydrochloride Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Levobupivacaine hydrochloride manufacturers
- Product
- Levobupivacaine hydrochloride 27262-48-2
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 500
- Release date
- 2023-07-14
- Product
- Levobupivacaine hydrochloride 27262-48-2
- Price
- US $3.00-1.00/kg
- Min. Order
- 1kg
- Purity
- 99.9%
- Supply Ability
- 10 tons
- Release date
- 2024-04-19
- Product
- Levobupivacaine hydrochloride 27262-48-2
- Price
- US $1.00/mg
- Min. Order
- 1000mg
- Purity
- 99
- Supply Ability
- 5ton/month
- Release date
- 2022-05-27