Synonym
Levobupivacaine, Levobupivacaine HCl; Levobupivacaine hydrochloride; Chirocaine, Novabupi
IUPAC/Chemical Name
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride
InChi Key
SIEYLFHKZGLBNX-NTISSMGPSA-N
InChi Code
InChI=1S/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-;/m0./s1
SMILES Code
O=C([C@H]1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C.[H]Cl
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 hydrochloride is a sodium channel blocker.
In vitro activity:
This study aimed to test the hypothesis that levobupivacaine has anti-tumour effects on breast cancer cells. The effects of levobupivacaine on cellular signalling and molecular response were studied with Quantitative Polymerase Chain Reaction and western blot. Induction of apoptosis was confirmed by cell viability, morphological changes showed cell shrinkage, rounding, and detachments from plates. The results of the western blot and Quantitative Polymerase Chain Reaction indicated activation of active caspase-3 and inhibition of FOXO1. The results of the flow Cytometry confirmed that levobupivacaine inhibited breast cancer cell proliferation and enhanced apoptosis of breast cancer cells. Quantitative Polymerase Chain Reaction and Western blot analysis showed increased p21 and decreased cyclin D. Quantitative Polymerase Chain Reaction and western blot analysis showed that levobupivacaine significantly increased Bax expression, accompanied by a significant decreased Bcl-2 expression and inhibition of PI3K/Akt/mTOR signalling pathway. These findings suggested that levobupivacaine inhibits proliferation and promotes breast cancer cells apoptosis in vitro.
Reference: BMC Res Notes. 2020; 13: 386. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7430121/
In vivo activity:
The impact of levobupivacaine on gastric cancer cell growth was assessed in vivo. It was observed that SGC7901 cell growth was significantly inhibited by levobupivacaine in the nude mice (Figures 2A–C). Meanwhile, IHC analysis showed that the levels of SLC7A11 were repressed by levobupivacaine in the mice (Figure 2D). The lipid ROS accumulation was enhanced by levobupivacaine in the mice (Figure 2E). The data showed that levobupivacaine repressed gastric cancer cell growth in vitro and in vivo. Levobupivacaine may be applied as an anti-cancer agent in gastric cancer, especially in the combination treatment with other anticancer drugs.
Reference: World J Gastroenterol. 2010 May 28; 16(20): 2537–2541. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2877184/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
55.0 |
169.29 |
|
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
324.89
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. Mao SH, Zhu CH, Nie Y, Yu J, Wang L. Levobupivacaine Induces Ferroptosis by miR-489-3p/SLC7A11 Signaling in Gastric Cancer. Front Pharmacol. 2021 Jun 9;12:681338. doi: 10.3389/fphar.2021.681338. PMID: 34177591; PMCID: PMC8220201.
3. Duman U, Yilmazlar A, Ozturk E, Aker S, Sarandol E, Yilmazlar T. Anti-inflammatory efficiency of levobupivacaine in an experimental colitis model. World J Gastroenterol. 2010 May 28;16(20):2537-41. doi: 10.3748/wjg.v16.i20.2537. PMID: 20503454; PMCID: PMC2877184.
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. Mao SH, Zhu CH, Nie Y, Yu J, Wang L. Levobupivacaine Induces Ferroptosis by miR-489-3p/SLC7A11 Signaling in Gastric Cancer. Front Pharmacol. 2021 Jun 9;12:681338. doi: 10.3389/fphar.2021.681338. PMID: 34177591; PMCID: PMC8220201.
In vivo protocol:
1.Duman U, Yilmazlar A, Ozturk E, Aker S, Sarandol E, Yilmazlar T. Anti-inflammatory efficiency of levobupivacaine in an experimental colitis model. World J Gastroenterol. 2010 May 28;16(20):2537-41. doi: 10.3748/wjg.v16.i20.2537. PMID: 20503454; PMCID: PMC2877184.
2. Mao SH, Zhu CH, Nie Y, Yu J, Wang L. Levobupivacaine Induces Ferroptosis by miR-489-3p/SLC7A11 Signaling in Gastric Cancer. Front Pharmacol. 2021 Jun 9;12:681338. doi: 10.3389/fphar.2021.681338. PMID: 34177591; PMCID: PMC8220201.
1: Lv BS, Wang W, Wang ZQ, Wang XW, Wang JH, Fang F, Mi WD. Efficacy and safety of local anesthetics bupivacaine, ropivacaine and levobupivacaine in combination with sufentanil in epidural anesthesia for labor and delivery: a meta-analysis. Curr Med Res Opin. 2014 Nov;30(11):2279-89. doi: 10.1185/03007995.2014.946127. Epub 2014 Aug 5. Review. PubMed PMID: 25050590.
2: Sanford M, Keating GM. Levobupivacaine: a review of its use in regional anaesthesia and pain management. Drugs. 2010 Apr 16;70(6):761-91. doi: 10.2165/11203250-000000000-00000. Review. PubMed PMID: 20394458.
3: Taya K, Shimizu S. [Levobupivacaine hydrochloride injection (POPSCAINE): pharmacological characteristics and clinical study result]. Nihon Yakurigaku Zasshi. 2009 Mar;133(3):159-67. Review. Japanese. PubMed PMID: 19282620.
4: Leone S, Di Cianni S, Casati A, Fanelli G. Pharmacology, toxicology, and clinical use of new long acting local anesthetics, ropivacaine and levobupivacaine. Acta Biomed. 2008 Aug;79(2):92-105. Review. PubMed PMID: 18788503.
5: Zink W, Graf BM. The toxicity of local anesthetics: the place of ropivacaine and levobupivacaine. Curr Opin Anaesthesiol. 2008 Oct;21(5):645-50. doi: 10.1097/ACO.0b013e32830c214c. Review. PubMed PMID: 18784493.
6: Urbanek B, Kapral S. [Levobupivacaine for regional anesthesia. A systematic review]. Anaesthesist. 2006 Mar;55(3):296-313. Review. German. PubMed PMID: 16341730.
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.
13: Ivani G, Borghi B, van Oven H. Levobupivacaine. Minerva Anestesiol. 2001 Sep;67(9 Suppl 1):20-3. Review. PubMed PMID: 11778089.
14: McLeod GA, Burke D. Levobupivacaine. Anaesthesia. 2001 Apr;56(4):331-41. Review. PubMed PMID: 11284819.
15: Foster RH, Markham A. Levobupivacaine: a review of its pharmacology and use as a local anaesthetic. Drugs. 2000 Mar;59(3):551-79. Review. PubMed PMID: 10776835.
16: McClellan KJ, Spencer CM. Levobupivacaine. Drugs. 1998 Sep;56(3):355-62; discussion 363-4. Review. PubMed PMID: 9777312.
