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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
Molecular Weight:
324.89
MDL Number:
MFCD01704265
MOL File:
27262-48-2.mol
Last updated:2024-03-27 14:23:05

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
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)
FDA UNII J998RDZ51I
NCI Drug Dictionary levobupivacaine hydrochloride

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-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
NFPA 704
0
2 0

Levobupivacaine hydrochloride price More Price(33)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML1092 Levobupivacaine hydrochloride ≥98% (HPLC) 27262-48-2 10mg $92.2 2024-03-01 Buy
Sigma-Aldrich SML1092 Levobupivacaine hydrochloride ≥98% (HPLC) 27262-48-2 50mg $357 2024-03-01 Buy
Alfa Aesar H37643 Levobupivacaine hydrochloride 98% 27262-48-2 250mg $148.05 2023-01-06 Buy
Alfa Aesar H37643 Levobupivacaine hydrochloride 98% 27262-48-2 1g $438.9 2023-01-06 Buy
TRC B689675 (S)-(-)-BupivacaineHydrochloride 27262-48-2 500mg $495 2021-12-16 Buy
Product number Packaging Price Buy
SML1092 10mg $92.2 Buy
SML1092 50mg $357 Buy
H37643 250mg $148.05 Buy
H37643 1g $438.9 Buy
B689675 500mg $495 Buy

Levobupivacaine hydrochloride Chemical Properties,Uses,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

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View Lastest Price from Levobupivacaine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Levobupivacaine hydrochloride pictures 2024-03-29 Levobupivacaine hydrochloride
27262-48-2
US $6.00-1.00 / g 10g 99% 60tons Hebei Dangtong Import and export Co LTD
Levobupivacaine HCl pictures 2024-03-28 Levobupivacaine HCl
27262-48-2
US $0.00 / kg 25kg 98% Inquiry PNP Biotech Co. Ltd
Levobupivacaine hydrochloride pictures 2024-03-27 Levobupivacaine hydrochloride
27262-48-2
US $20.00 / kg 1kg 99 1000kg Shaanxi Franta Biotechnology Co., Ltd

Levobupivacaine hydrochloride Spectrum

TIMTEC-BB SBB001337 (S)-(-)-BUPIVACAINE HCL (S)-(-)-BUPIVACAINE HYDROCHLORIDE (S)-(-)-1-N-BUTYL-2',6'-DIMETHYL-2-PIPERIDINCARBOXANILID HYDROCHLORIDE (S)-(-)-1-BUTYL-2-(2,6-XYLYLCARBAMOYL)-PIPERIDINE HYDROCHLORIDE s-(-)-1-butyl-2',6'-pipecoloxylidide hydrochloride (s)-1-butyl-2’,6’-piperidinecarboxamidemonohydrochloride (s)-1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamidemonohydrochloride (S)-1-Butyl-N-(2,6-diMethylphenyl)piperidine-2-carboxaMide hydrochloride (2S)-1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, hydrochloride (1:1) Levobupivacaine hydrochloride S-(-)-1-Butyl-2',6'-pipecoloxylidide hydrochloride levobupivacaine hydrochloride (anhydrous) Levobupivacaine HCL //Levobupivacaine LEVAMISOLHCLSALT (S)-(-)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride 2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride, (-) (S)-(-)-Bupivacaine hydrochloride,99% 6’-pipecoloxylidide,1-butyl-,hydrochloride,(-)-2 bupicainehydrochloride(-) BUPIVACAINE HYDROCHLORIDE, MONOHYDRATE BUPIVACAINE HCL LEVOBUPIVACAINE HCL LEVOBUPIVACAINE HYDROCHLORIDE L-BUPIVACAINE HYDROCHLORIDE (S)-(-)-Bupivacaine monohydrochloride (S)-(-)-BUPIVACAINEHYDROCHLORIDEMONOHYDRATE (S)-(-)-Bupivacaine (S)-Bupivacaine 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)- 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (S)- L-(-)-Bupivacaine 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (2S)- 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (S)- Levobupivacaine hydrochloride 27262-48-2 A Ropivacaine Impurity A(EP) Bupivacaine Impurity 1 Ropivacaine EP Impurity A HBr (S)-Bupivacaine HCl (Levobupivacaine HCl) Levobupivacaine hydrochloride USP/EP/BP Levobupivacaine hydrochloride Impurities Levobupivacaine HCl (S-Bupivacaine) Levo-Bupivacaine hydrochlorideQ: What is Levo-Bupivacaine hydrochloride Q: What is the CAS Number of Levo-Bupivacaine hydrochloride Ropivacaine Impurity A(EP) Levobupivacaine HCI Levobupivacaine hcl Anesthetic Raw Powder API Levobupivacaine hydrochloride Powder Dosage Usage Effect and Benefit 27262-48-2 27626-48-2 27626-47-1 15252-80-3 C18H28N2OHCl C18H29ClN2O API Inhibitors Active Pharmaceutical Ingredients Pharmaceutical Raw Materials BDO