Uses
ChemicalBook > CAS DataBase List > Levobupivacaine hydrochloride

Levobupivacaine hydrochloride

Uses
Product Name
Levobupivacaine hydrochloride
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
More
Less

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
InChIKey
SIEYLFHKZGLBNX-NTISSMGPSA-N
CAS DataBase Reference
27262-48-2(CAS DataBase Reference)
More
Less

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
More
Less

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.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1092
Product name
Levobupivacaine hydrochloride
Purity
≥98% (HPLC)
Packaging
10mg
Price
$77.2
Updated
2021/03/22
Sigma-Aldrich
Product number
B5274
Product name
Bupivacaine hydrochloride monohydrate
Purity
analytical standard, for drug analysis
Packaging
1 g
Price
$81.5
Updated
2021/03/22
Sigma-Aldrich
Product number
B5274
Product name
Bupivacaine hydrochloride monohydrate
Purity
analytical standard, for drug analysis
Packaging
5 g
Price
$138
Updated
2021/03/22
Sigma-Aldrich
Product number
SML1092
Product name
Levobupivacaine hydrochloride
Purity
≥98% (HPLC)
Packaging
50mg
Price
$299
Updated
2021/03/22
Sigma-Aldrich
Product number
B5274
Product name
Bupivacaine hydrochloride monohydrate
Purity
analytical standard, for drug analysis
Packaging
15 g
Price
$327
Updated
2021/03/22
More
Less

Levobupivacaine hydrochloride Chemical Properties,Usage,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

More
Less

Levobupivacaine hydrochloride Suppliers

Anhui Rencheng Technology Co., Ltd
Tel
Email
admin@ahrencheng.com
Country
China
ProdList
42
Advantage
58
Jinan Chenghui Shuangda Chemical Co., Ltd.
Tel
0531-58897046-
Fax
0531-58897046
Email
1057567120@qq.com
Country
China
ProdList
250
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
Energy Chemical
Tel
021-58432009-
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
43499
Advantage
61
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078;021-50426030
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
10006
Advantage
60
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202- ; ;
Email
jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com
Country
China
ProdList
43255
Advantage
64
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-2580635- ;0712-2580635
Email
1791901229@qq.com;1791901229@qq.com;
Country
China
ProdList
8935
Advantage
52
Shanghai Ennopharm Co., Ltd.
Tel
+86 (21) 6435-5022
Email
market@ennopharm.com
Country
China
ProdList
4271
Advantage
65
Jinan Chenghui-shuangda Chemical Co.,Ltd.
Tel
0531-58897051-
Fax
0531-58897093
Email
jnchsd@qq.com
Country
China
ProdList
68
Advantage
62
Wuhan Fortuna Chemical Co., Ltd
Tel
027-59207852-
Fax
QQ3130921841
Email
buy@fortunachem.com
Country
China
ProdList
2950
Advantage
58
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
;
Fax
0755 28094224
Email
3001280422@qq.com;marketing@phystandard.com
Country
China
ProdList
6544
Advantage
50
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
17727448752;0755-83725681-603
Fax
+86 755 28094224
Country
China
ProdList
4508
Advantage
50
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12341
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9914
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
86-21-58998985
Fax
(86) 21-58955996
Email
apisales@chemexpress.com.cn
Country
China
ProdList
7557
Advantage
61
Candia Thamtech Company Limited
Tel
0371-86615086 18203638366 0371-86159066 13526786601
Fax
0371-86159066
Email
sales@candiapharm.com candiazhang@candiapharm.com.candiali@candiapharm.com
Country
China
ProdList
2017
Advantage
60
China Nobel Chem Co., Limited
Tel
+86(0)21 60484900
Fax
+86(0)21 60484900
Email
sales@nobelchem.com
Country
China
ProdList
765
Advantage
50
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399-
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4575
Advantage
55
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810- ;025-57798810-
Fax
025-57019371
Email
sales@sunlidabio.com;sales@sunlidabio.com
Country
China
ProdList
3756
Advantage
55
Shanghai TaoShu Biochemical Technology Co., Ltd.
Tel
021-33632979-
Fax
021-33632979
Email
service1@targetmol.com
Country
China
ProdList
7962
Advantage
58
Cato Research Chemicals Inc.
Tel
+1-541-2553640
Fax
+1-541-2553641
Email
info@cato-chem.com
Country
China
ProdList
1958
Advantage
55
Wuhan DKY Technology Co.,Ltd.
Tel
27-81302488- ;27-81302488-
Fax
027-81302088
Email
info@dkybpc.com;2851686510@qq.com
Country
China
ProdList
2025
Advantage
58
Hubei XinyuanShun Chemical Co., Ltd.
Tel
13971561712 / 13995564702 / 027-50664929
Fax
027-50664927
Email
hbeixys2001@163.com
Country
China
ProdList
3130
Advantage
55
Vientiane Tianjin Hengyuan Technology Co., Ltd.
Tel
15722085254
Fax
022-26358246
Email
phytochemical@126.com
Country
China
ProdList
813
Advantage
55
Shanghai JONLN Reagent Co., Ltd.
Tel
400-0066400;021-60496031
Fax
021-55660885
Email
422131432@qq.com;422131432@qq.com
Country
China
ProdList
9998
Advantage
55
ChemStrong Scientific Co.,Ltd
Tel
0755-66853366-
Email
sales@chem-strong.com
Country
China
ProdList
26487
Advantage
56
Finetech Industry Limited
Tel
027-87465837-
Fax
027-8777-2287
Email
sales@finetechnology-ind.com;
Country
China
ProdList
9375
Advantage
58
HangZhou YuHao Chemical Technology Co., Ltd.
Tel
0571-82693216
Fax
0571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
1853
Advantage
58
Wuhan Dahua Pharmaceutical Co., Ltd.
Tel
027-59262863 13277907145 QQ:3091977954
Fax
027-59420980
Email
dh.luna@whdhwy.com
Country
China
ProdList
4957
Advantage
58
Shanghai Kewel Chemical Co., Ltd.
Tel
021-64609169-
Fax
021-64609160
Email
kewelchemexp@yahoo.com
Country
China
ProdList
9839
Advantage
50
Hangzhou J&H Chemical Co., Ltd.
Tel
0571-87396432-
Fax
0571-87396431
Email
sales@jhechem.com
Country
China
ProdList
13966
Advantage
53
Shanghai HuanChuan Industry Co.,Ltd.
Tel
021-61478794
Fax
021-61478794
Email
sales@hcshhai.com
Country
China
ProdList
9804
Advantage
50
Wuhan Dahua Weiye Pharmaceutical Chemical Co., Ltd.
Tel
027-59420981/18702770802
Fax
027-83322098
Email
dh.luna@whdhwy.com
Country
China
ProdList
1980
Advantage
50
Wuhan Biocar Bio-Pharm Co., Ltd.
Tel
Fax
86-13343428090
Email
85776233@qq.com
Country
China
ProdList
2000
Advantage
50
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
Tel
025-66099280-
Email
sales01@aikonchem.com
Country
China
ProdList
15390
Advantage
50
Hubei Jusheng Technology Co.,Ltd
Tel
027-59599241- ;027-59599240-
Fax
027-59599241
Email
1400878000@qq.com;1400868000@qq.com
Country
China
ProdList
9841
Advantage
58
Sigma-Aldrich
Tel
021-61415566- ;
Email
orderCN@merckgroup.com;orderCN@merckgroup.com
Country
China
ProdList
50837
Advantage
80
Nanjing Chempioneer Pharmaceutical Co., Ltd.
Tel
18068075658;QQ 2689309269
Fax
-
Email
sales@chempioneer.com
Country
China
ProdList
1813
Advantage
58
Shanghai Biolang biotechnology Co.,Ltd
Tel
Fax
13669031409
Email
Jason@biolang.cn
Country
China
ProdList
838
Advantage
55
Shanghai Biolang biotechnology Co.,Ltd
Tel
Fax
13669031409
Email
Jason@biolang.cn
Country
China
ProdList
838
Advantage
55
Hubei kangmingde Pharmaceutical Chemical Co., Ltd
Tel
027-89771658-
Fax
027-89771658
Email
hbtcky@163.com
Country
China
ProdList
4870
Advantage
56
Wuhan Kai Lun new material Chemical Co Ltd
Tel
025-87787262;15071332665
Fax
025-87787262
Email
wshun@51chemall.com
Country
China
ProdList
499
Advantage
58
Shanghai Synchem Pharma Co., ltd
Tel
021-61984905-1
Email
synchempharma@aliyun.com
Country
China
ProdList
6136
Advantage
55
Jiangsu Aosaikang Pharmaceutical Co. Ltd.
Tel
025-85090179
Fax
025-85090192
Email
normal@ask-pharm.com
Country
China
ProdList
15
Advantage
58
Jinan Putubio Tech Co., Ltd.
Tel
+86 (531) 8099-2215
Fax
+86 (531) 8099-2215
Email
putubio@outlook.com
Country
China
ProdList
1263
Advantage
55
Pharmacodia (Beijing) Co.,Ltd
Tel
+86-400-851-9921;+86-10-82826195
Fax
+86-10-82826195
Email
sales@pharmacodia.com
Country
China
ProdList
2320
Advantage
55
Hubei Yuancheng Saichuang Technology Co., Ltd.
Tel
18062666868/13048470578 QQ2355779403/2355880551
Fax
023-60363599,027-68886696
Email
andy@ycgmp.com;2355880551@qq.com;2355779403@qq.com
Country
China
ProdList
5053
Advantage
58
Henan CoreyChem Co., Ltd
Tel
0371-86658258
Fax
0371-60996044
Email
info@coreychem.com
Country
China
ProdList
10462
Advantage
58
Guangzhou QiYun Biotechnology Co., Ltd.
Tel
020-61288194 61288195
Fax
020-61288700
Email
505721671@qq.com
Country
China
ProdList
3872
Advantage
58
More
Less

View Lastest Price from Levobupivacaine hydrochloride manufacturers

Shanxi Lianxu New Material Co., LTD
Product
Levobupivacaine hydrochloride 27262-48-2
Price
US $54.00/KG
Min. Order
1KG
Purity
99.9%
Supply Ability
1000kg/month
Release date
2021-10-20
Xingtai Haoxun Import and Export Trade Co., Ltd.
Product
Levobupivacaine hydrochloride 27262-48-2
Price
US $5.00/KG
Min. Order
10g
Purity
99
Supply Ability
1tons
Release date
2020-07-20
Xingtai Haoxun Import and Export Trade Co., Ltd.
Product
Levobupivacaine hydrochloride 27262-48-2
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10tons
Release date
2020-07-17

27262-48-2, Levobupivacaine hydrochlorideRelated Search:


  • 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 hydrochloride 27262-48-2
  • A Ropivacaine Impurity A(EP)
  • Bupivacaine Impurity 1
  • 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)-
  • Ropivacaine EP Impurity A HBr
  • (S)-Bupivacaine HCl (Levobupivacaine HCl)
  • Levobupivacaine hydrochloride USP/EP/BP
  • Levobupivacaine hydrochloride Impurities
  • 27262-48-2
  • 27262-48-2
  • 27626-48-2
  • 27626-47-1
  • 15252-80-3
  • C18H28N2OHCl
  • C18H29ClN2O
  • API
  • Inhibitors
  • Active Pharmaceutical Ingredients
  • Pharmaceutical Raw Materials