Levobupivacaine free base
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MedKoo CAT#: 319941

CAS#: 27262-47-1 (free base)

Description: Levobupivacaine is a local anaesthetic drug belonging to the amino amide group. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by Abbott under the trade name Chirocaine. Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 percent less potent (by molarity) than racemic bupivacaine and has a longer motor block onset time.

Chemical Structure

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Levobupivacaine free base
CAS# 27262-47-1 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319941
Name: Levobupivacaine free base
CAS#: 27262-47-1 (free base)
Chemical Formula: C18H28N2O
Exact Mass: 288.22
Molecular Weight: 288.435
Elemental Analysis: C, 74.96; H, 9.79; N, 9.71; O, 5.55

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
100g USD 2950 Ready to ship
500g USD 5450 Ready to ship
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Related CAS #: 27262-47-1 (free base)   27262-48-2 (HCl)    

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

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 (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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 58.0 201.09
Ethanol 58.0 201.09

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.

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. 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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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.

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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.