Levobupivacaine HCl
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318096

CAS#: 27262-48-2 (HCl)

Description: Levobupivacaine is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action.


Chemical Structure

img
Levobupivacaine HCl
CAS# 27262-48-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 318096
Name: Levobupivacaine HCl
CAS#: 27262-48-2 (HCl)
Chemical Formula: C18H29ClN2O
Exact Mass: 0.00
Molecular Weight: 324.893
Elemental Analysis: C, 66.54; H, 9.00; Cl, 10.91; N, 8.62; O, 4.92

Price and Availability

Size Price Availability Quantity
500mg USD 150 Ready to ship
1g USD 250 Ready to ship
5g USD 550 Ready to ship
10g USD 850 Ready to ship
Bulk inquiry

Related CAS #: 27262-47-1 (free base)   27262-48-2 (HCl)    

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

Appearance: Solid powder

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

More Info:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 55.0 169.29

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.

Recalculate based on batch purity %
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.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.