Synonym
Levobupivacaine free base; (S)-1-Butyl-2',6'-pipecoloxylidide; L(-)-Bupivacaine
IUPAC/Chemical Name
(S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
InChi Key
LEBVLXFERQHONN-INIZCTEOSA-N
InChi Code
InChI=1S/C18H28N2O/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)/t16-/m0/s1
SMILES Code
O=C([C@H]1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Levobupivacaine (Chirocaine, (S)-(-)-Bupivacaine, L-(-)-Bupivacaine) inhibits the opening of voltage-gated sodium channels.
In vitro activity:
In the present study, the role of levobupivacaine on the expression of PI3K, Akt, and mTOR was investigated to illustrate the potential molecular mechanism. This study observed a significantly decreased expression of p-Akt, p-PI3K, p-mTOR and subsequent decreased expression of FOXO, Cyclin D1 and Bcl-2 following levobupivacaine treatment which correlated with decreased breast cancer cells proliferation and increased apoptosis. These emerging pieces of evidence suggest that levobupivacaine may inhibit proliferation and promote apoptosis by suppressing PI3K/Akt/mTOR signalling pathway, which demonstrated an anti-tumour effect on breast cancer cells in this study.
Reference: BMC Res Notes. 2020; 13: 386. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7430121/
In vivo activity:
The CNAP depression eff ect of levobupivacaine on isolated rat sciatic nerves is given in Fig. 2. This sample CNAP recording demonstrates that levobupivacaine administration suppresses the CNAPs recorded from isolated nerves in a time-dependent manner, completely abolishing the CNAPs within 25 min. This eff ect was found to be reversible. Changes in the area under CNAP, CNAP amplitude, conduction velocities of the fastest (CVinit) and medium velocity (CVpeak) fiber groups were computed using CNAP data at 5-min intervals aft er the administration (t = 0) of levobupivacaine (Fig. 3).
Reference: Acta Pharm. 2017 Sep 1;67(3):293-307. https://sciendo.com/article/10.1515/acph-2017-0025
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
58.0 |
201.09 |
|
| Ethanol |
58.0 |
201.09 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
288.44
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Kwakye AK, Kampo S, Lv J, Ramzan MN, Richard SA, Falagán AA, Agudogo J, Atito-Narh E, Yan Q, Wen QP. Levobupivacaine inhibits proliferation and promotes apoptosis of breast cancer cells by suppressing the PI3K/Akt/mTOR signalling pathway. BMC Res Notes. 2020 Aug 17;13(1):386. doi: 10.1186/s13104-020-05191-2. PMID: 32807213; PMCID: PMC7430121.
2. Jose C, Hebert-Chatelain E, Dias Amoedo N, Roche E, Obre E, Lacombe D, Rezvani HR, Pourquier P, Nouette-Gaulain K, Rossignol R. Redox mechanism of levobupivacaine cytostatic effect on human prostate cancer cells. Redox Biol. 2018 Sep;18:33-42. doi: 10.1016/j.redox.2018.05.014. Epub 2018 May 31. PMID: 29935387; PMCID: PMC6019688.
3. Tuncer S, Tuncer Peker T, Burat İ, Kiziltan E, İlhan B, Dalkiliç N. Axonal excitability and conduction alterations caused by levobupivacaine in rat. Acta Pharm. 2017 Sep 1;67(3):293-307. doi: 10.1515/acph-2017-0025. PMID: 28858839.
4. Özcan MS, Kalem M, Özçelik M, Şahin E, Çakar S, Hayırlı N, Evirgen O, Ökten F. The effect of intra-articular levobupivacaine on shoulder cartilage at different doses-experimental study. Braz J Anesthesiol. 2017 Jan-Feb;67(1):42-49. doi: 10.1016/j.bjane.2015.08.008. Epub 2016 Apr 20. PMID: 28017169.
In vitro protocol:
1. Kwakye AK, Kampo S, Lv J, Ramzan MN, Richard SA, Falagán AA, Agudogo J, Atito-Narh E, Yan Q, Wen QP. Levobupivacaine inhibits proliferation and promotes apoptosis of breast cancer cells by suppressing the PI3K/Akt/mTOR signalling pathway. BMC Res Notes. 2020 Aug 17;13(1):386. doi: 10.1186/s13104-020-05191-2. PMID: 32807213; PMCID: PMC7430121.
2. Jose C, Hebert-Chatelain E, Dias Amoedo N, Roche E, Obre E, Lacombe D, Rezvani HR, Pourquier P, Nouette-Gaulain K, Rossignol R. Redox mechanism of levobupivacaine cytostatic effect on human prostate cancer cells. Redox Biol. 2018 Sep;18:33-42. doi: 10.1016/j.redox.2018.05.014. Epub 2018 May 31. PMID: 29935387; PMCID: PMC6019688.
In vivo protocol:
1. Tuncer S, Tuncer Peker T, Burat İ, Kiziltan E, İlhan B, Dalkiliç N. Axonal excitability and conduction alterations caused by levobupivacaine in rat. Acta Pharm. 2017 Sep 1;67(3):293-307. doi: 10.1515/acph-2017-0025. PMID: 28858839.
2. Özcan MS, Kalem M, Özçelik M, Şahin E, Çakar S, Hayırlı N, Evirgen O, Ökten F. The effect of intra-articular levobupivacaine on shoulder cartilage at different doses-experimental study. Braz J Anesthesiol. 2017 Jan-Feb;67(1):42-49. doi: 10.1016/j.bjane.2015.08.008. Epub 2016 Apr 20. PMID: 28017169.
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7: Celleno D, Parpaglioni R, Frigo MG, Barbati G. Intrathecal levobupivacaine and ropivacaine for cesarean section. New perspectives. Minerva Anestesiol. 2005 Sep;71(9):521-5. Review. PubMed PMID: 16166911.
8: Casati A, Putzu M. Bupivacaine, levobupivacaine and ropivacaine: are they clinically different? Best Pract Res Clin Anaesthesiol. 2005 Jun;19(2):247-68. Review. PubMed PMID: 15966496.
9: De Cosmo G, Mascia A, Clemente A, Congedo E, Aceto P. Use of levobupivacaine for the treatment of postoperative pain after thoracotomies. Minerva Anestesiol. 2005 Jun;71(6):347-51. Review. PubMed PMID: 15886599.
10: Kuczkowski KM. Levobupivacaine and ropivacaine: the new choices for labor analgesia. Int J Clin Pract. 2004 Jun;58(6):604-5. Review. PubMed PMID: 15311561.
11: Bremerich DH, Zwissler B. [Levobupivacaine in obstetric analgesia and anaesthesia. Where is its place?]. Anaesthesist. 2004 Jul;53(7):637-44. Review. German. PubMed PMID: 15221118.
12: Capogna G, Celleno D, Camorcia M. [Levobupivacaine in obstetric analgesia and anaesthesia]. Minerva Anestesiol. 2001 Sep;67(9 Suppl 1):24-8. Review. Italian. PubMed PMID: 11778090.
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16: McClellan KJ, Spencer CM. Levobupivacaine. Drugs. 1998 Sep;56(3):355-62; discussion 363-4. Review. PubMed PMID: 9777312.
