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Levobupivacaine

Product Name
Levobupivacaine
CAS No.
27262-47-1
Chemical Name
Levobupivacaine
Synonyms
Chirocaine;1-Butyl-N-(2;Levobupivacaine;(-)-Bupivacaine;Levobupivacaine base;1-Butyl-N-(2,6-dimet;Levobupivacaine free base;Levo Bupivacaine HCl (HIS);Levobupivacaine HCl (base);2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-
CBNumber
CB52130881
Molecular Formula
C18H28N2O
Formula Weight
288.43
MOL File
27262-47-1.mol
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Levobupivacaine Property

Melting point:
136-137°C
alpha 
D25 -80.9° (c = 5 in methanol)
Boiling point:
430.65°C (rough estimate)
Density 
1.0238 (rough estimate)
refractive index 
1.5700 (estimate)
storage temp. 
Refrigerator
solubility 
DMSO:58.0(Max Conc. mg/mL);201.09(Max Conc. mM)
Ethanol:58.0(Max Conc. mg/mL);201.09(Max Conc. mM)
pka
14.85±0.70(Predicted)
form 
Solid
color 
White to Off-White
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H311Toxic in contact with skin

H330Fatal if inhaled

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P310Immediately call a POISON CENTER or doctor/physician.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P320Specific treatment is urgent (see … on this label).

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P363Wash contaminated clothing before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC
Product number
B689546
Product name
(S)-(-)-Bupivacaine
Packaging
25mg
Price
$95
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB19357
Product name
1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide
Packaging
5mg
Price
$100
Updated
2021/12/16
AK Scientific
Product number
E583
Product name
Levobupivacaine
Packaging
25mg
Price
$128
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB19357
Product name
1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide
Packaging
10g
Price
$160
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0009248
Product name
LEVOBUPIVACAINE
Purity
97.00%
Packaging
25MG
Price
$263.55
Updated
2021/12/16
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Levobupivacaine Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Chirocaine,Abbott Laboratories

Uses

Local anaesthetic used for epidural and intrathecal anaesthesia.

Definition

ChEBI: Levobupivacaine is the (S)-(-)-enantiomer of bupivacaine. 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 is a conjugate base of a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine.

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.

Therapeutic Function

Local anesthetic

General Description

Levobupivacaine is the pure “S” enantiomer of bupivacaineand in vivo and in vitro studies confirm that it does notundergo metabolic inversion to R(+) bupivacaine. The pKaof the tertiary nitrogen is 8.09, the same as bupivacaine’s pKa. Levobupivacaine is available in solution for epiduraladministration, peripheral nerve block administration, andinfiltration anesthesia. Clinical trials have shown thatlevobupivacaine and bupivacaine have similar anestheticeffects. Levobupivacaine has lower CNS and cardiotoxicitythan bupivacaine although unintended intravenousinjection when performing nerve blocks may result intoxicity. Racemic bupivacaine is metabolized extensivelywith no unchanged drug found in the urine or feces. Liverenzymes including the CYP3A4 and CYP1A2 isoforms areresponsible for N-dealkylation and 3-hydroxylation oflevobupivacaine followed by glucuronidation or sulfation.

Pharmacology

This is the laevo (S–) enantiomer of bupivacaine, with similar properties to the racemic mixture, though it has slightly higher protein binding and clearance and hence a lower potential for cardiac and CNS toxicity. In practice, several other factors contribute to local anaesthetic toxicity, and the recommended maximum doses remain the same. Its formulation is expressed as percentage weight per unit volume of free base; racemic bupivacaine is expressed as percentage weight per unit volume of hydrochloride salt. Levobupivacaine therefore contains 13% more active molecules for a given dose.

Levobupivacaine Preparation Products And Raw materials

Raw materials

Preparation Products

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Levobupivacaine Suppliers

YICHANG TIANRUI BIOPHARM CO., LTD
Tel
0717-4065884 18671799682
Email
yctr@renfu.com.cn
Country
China
ProdList
25
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
021-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6013
Advantage
61
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10194
Advantage
62
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070 13913916777;
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
17839
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32344
Advantage
50
Jinan Chenghui Shuangda biological Co., LTD
Tel
0531-58897003 15550412551
Fax
0531-58897003
Email
market@jnchsd.com
Country
China
ProdList
209
Advantage
62
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
TargetMol Chemicals Inc.
Tel
021-33632979 15002134094
Fax
021-33632979
Email
marketing@targetmol.com
Country
China
ProdList
7934
Advantage
58
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View Lastest Price from Levobupivacaine manufacturers

Shanghai Aosiris new Material Technology Co., LTD
Product
Levobupivacaine 27262-47-1
Price
US $3.00-1.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10 tons
Release date
2024-03-20
Shanghai Affida new material science and technology center
Product
Levobupivacaine 27262-47-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99
Supply Ability
10 tons
Release date
2024-03-19
Sigma Audley
Product
Levobupivacaine 27262-47-1
Price
US $45.00-35.00/kg
Min. Order
1kg
Purity
99.8%
Supply Ability
200tons/year
Release date
2024-02-21

27262-47-1, LevobupivacaineRelated Search:


  • 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide
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