Levobupivacaine hydrochloride

Base Information Edit

Chemical Name:Levobupivacaine hydrochloride
CAS No.:27262-48-2
Molecular Formula:C₁₈H₂₈N₂O*ClH
Molecular Weight:324.894
Hs Code.:2942000000
European Community (EC) Number:642-955-1,690-037-4
UNII:J998RDZ51I
DSSTox Substance ID:DTXSID9046071
Wikidata:Q27114682
NCI Thesaurus Code:C61805
ChEMBL ID:CHEMBL1200749
Mol file:27262-48-2.mol

Synonyms:Chirocaine;levobupivacaine;levobupivacaine hydrochloride

Suppliers and Price of Levobupivacaine hydrochloride

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
(S)-(-)-BupivacaineHydrochloride
500mg
$ 495.00

Sigma-Aldrich
Bupivacaine hydrochloride monohydrate analytical standard, for drug analysis
1 g
$ 81.50

Sigma-Aldrich
Levobupivacaine hydrochloride ≥98% (HPLC)
10mg
$ 77.20

Sigma-Aldrich
Bupivacaine hydrochloride monohydrate analytical standard, for drug analysis
5 g
$ 138.00

Sigma-Aldrich
Bupivacaine hydrochloride monohydrate analytical standard, for drug analysis
15 g
$ 327.00

Sigma-Aldrich
Levobupivacaine hydrochloride ≥98% (HPLC)
50mg
$ 299.00

Medical Isotopes, Inc.
(S)-(-)-BupivacaineHCl
50 mg
$ 610.00

Matrix Scientific
(S)-Bupivacaine hydrochloride 95+%
1g
$ 1260.00

Matrix Scientific
(S)-Bupivacaine hydrochloride 95+%
250mg
$ 567.00

DC Chemicals
LevobupivacaineHCL >99%
250 mg
$ 600.00

Total 207 raw suppliers

Chemical Property of Levobupivacaine hydrochloride Edit

Chemical Property:

Appearance/Colour:white crystalline powder
Vapor Pressure:2.24E-07mmHg at 25°C
Melting Point:254 °C (dec.)(lit.)
Boiling Point:423.4 °C at 760 mmHg
Flash Point:209.9 °C
PSA：23.55000
LogP:4.74080
Storage Temp.:2-8°C
Solubility.:H2O: soluble20mg/mL, clear
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:324.1968412
Heavy Atom Count:22
Complexity:321

Purity/Quality:

99%, ^*data from raw suppliers

(S)-(-)-BupivacaineHydrochloride ^*data from reagent suppliers

Safty Information:

Pictogram(s): T+, Xn
Hazard Codes:T+,Xn
Statements: 26/27/28-20/21/22-28
Safety Statements: 22-36/37/39-45-36/37-53

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
Isomeric SMILES:CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C.Cl
Recent ClinicalTrials:TAP Block Versus Local Anesthesia Wound Infiltration for Postoperative Pain Relief After Appendicectomy in Children
Recent EU Clinical Trials:PAIN CONTROL WITH THE USE OF WALANT IN TOTAL TRAPEZECTOMY. RANDOMIZED CLINICAL TRIAL
Recent NIPH Clinical Trials:Randomized clinical trial on patient-controlled epidural analgesia versus intravenous patient-controlled analgesia for laparoscopiccoloectomy within an enhanced recovery pathway.
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.
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.
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.

Technology Process of Levobupivacaine hydrochloride

There total 6 articles about Levobupivacaine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

: 109-65-9
1-bromo-butane

: 15883-20-2,27262-40-4,27262-43-7,78341-12-5
2',6'-pipecoloxylidide

: 14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2
bupivacaine hydrochloride

Guidance literature:: 1-bromo-butane; 2',6'-pipecoloxylidide; With tetrabutylammomium bromide; potassium carbonate; In toluene; at 80 - 85 ℃; for 5h; Green chemistry;

With hydrogenchloride; In water; toluene; Reagent/catalyst; Green chemistry;

Reference yield: 92.0%

: 14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2
bupivacaine hydrochloride

Guidance literature:: With tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 80 - 85 ℃; for 8.5h;

With hydrogenchloride; In isopropyl alcohol; acetone; toluene; at 40 ℃;

Reference yield:

: 4043-87-2,83680-83-5
pipecolic Acid

: 14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2
bupivacaine hydrochloride

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 12 h / 20 °C

2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 18 h / 20 °C

3.1: palladium on activated charcoal; hydrogen / methanol / 0.5 h / 50 °C / Autoclave

4.1: N,N-dimethyl-formamide / 12 h / 20 - 80 °C

4.2: 20 °C

With palladium on activated charcoal; hydrogen; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;