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MedKoo Cat#: 540052 | Name: Bupivacaine free base
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Description:

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

Bupivacaine is a BK/SK, Kv1, Kv3, TASK-2 K Channel and voltage-gated Na channel blocker used as an anesthetic. It maybe neurotoxic at high does, inducing apoptosis in neuroblastoma cells. It acts by binding to the intracellular portion of voltage-gated sodium channels and blocking sodium influx into nerve cells.

Chemical Structure

Bupivacaine free base
Bupivacaine free base
CAS#38396-39-3 (free base)

Theoretical Analysis

MedKoo Cat#: 540052

Name: Bupivacaine free base

CAS#: 38396-39-3 (free base)

Chemical Formula: C18H28N2O

Exact Mass: 288.2202

Molecular Weight: 288.43

Elemental Analysis: C, 74.96; H, 9.79; N, 9.71; O, 5.55

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
2g USD 400.00 2 Weeks
5g USD 750.00 2 Weeks
10g USD 1,050.00 2 Weeks
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Related CAS #
18010-40-7 (HCl) 38396-39-3 (free base) 2180-92-9 (free base) 175082-90-3 (tartrate) 73360-54-0 (HCl hydrate) 221376-60-9 (phosphate)
Synonym
AH 250; AH250; AH-250; Anekain; Bupivacaina; SKY 0402; SKY0402; SKY-0402;
IUPAC/Chemical Name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
InChi Key
LEBVLXFERQHONN-UHFFFAOYSA-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)
SMILES Code
O=C(C1N(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
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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# C21M11C01
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
A sodium channel blocker and local anesthetic.
In vitro activity:
Bupivacaine suppressed proliferation and induced apoptosis of HepG2 and SNU-449 cells in a time- and dose-dependent manner. Bupivacaine treatment also decreased colony formation, migration, and invasion of HepG2 and SNU-449 cells. Reference: J Biochem Mol Toxicol. 2021 Aug 2:e22871. https://pubmed.ncbi.nlm.nih.gov/34338398/
In vivo activity:
CAL-27 cells were subcutaneously injected to form xenograft tumors in vivo. The results showed that tumor weight and volume treated with 40 µmol/kg Bupi (bupivacaine) were obviously lower compared with the control group (Figure 7A,B). The apoptotic cells were increased, and the number of Ki67+ expression was decreased (Figure 7C,D,E). Neferine treatment also down-regulated the expression of SOX2, NANOG, and OCT4 proteins (Figure 7F). Reference: Ann Transl Med. 2021 May; 9(10): 839. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8184410/
Solvent mg/mL mM
Solubility
DMSO 25.0 86.68
DMF 30.0 104.01
Ethanol 30.0 104.01
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.73
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 288.43 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. Wang L, Guo W, Guan H, Yan N, Cai X, Zhu L. Local anesthetic bupivacaine inhibits proliferation and metastasis of hepatocellular carcinoma cells via suppressing PI3K/Akt and MAPK signaling. J Biochem Mol Toxicol. 2021 Aug 2:e22871. doi: 10.1002/jbt.22871. Epub ahead of print. PMID: 34338398. 2. Gu JH, Liu CC, Xie JL, Ma B, Cui SM, Yang GZ, He SC. The Local Anesthetic Bupivacaine Inhibits the Progression of Non-Small Cell Lung Cancer by Inducing Autophagy Through Akt/mTOR Signaling. Front Oncol. 2021 Mar 11;11:616445. doi: 10.3389/fonc.2021.616445. PMID: 33777755; PMCID: PMC7991299. 3. Wang Z, Zhang J, Wen Y, Wang P, Fan L. Bupivacaine inhibits the malignant biological behavior of oral squamous cell carcinoma cells by inhibiting the activation of ERK1/2 and STAT3. Ann Transl Med. 2021 May;9(10):839. doi: 10.21037/atm-21-1414. PMID: 34164473; PMCID: PMC8184410. 4. Liu B, Yan X, Hou Z, Zhang L, Zhang D. Impact of Bupivacaine on malignant proliferation, apoptosis and autophagy of human colorectal cancer SW480 cells through regulating NF-κB signaling path. Bioengineered. 2021 Dec;12(1):2723-2733. doi: 10.1080/21655979.2021.1937911. PMID: 34151717.
In vitro protocol:
1. Wang L, Guo W, Guan H, Yan N, Cai X, Zhu L. Local anesthetic bupivacaine inhibits proliferation and metastasis of hepatocellular carcinoma cells via suppressing PI3K/Akt and MAPK signaling. J Biochem Mol Toxicol. 2021 Aug 2:e22871. doi: 10.1002/jbt.22871. Epub ahead of print. PMID: 34338398. 2. Gu JH, Liu CC, Xie JL, Ma B, Cui SM, Yang GZ, He SC. The Local Anesthetic Bupivacaine Inhibits the Progression of Non-Small Cell Lung Cancer by Inducing Autophagy Through Akt/mTOR Signaling. Front Oncol. 2021 Mar 11;11:616445. doi: 10.3389/fonc.2021.616445. PMID: 33777755; PMCID: PMC7991299.
In vivo protocol:
1. Wang Z, Zhang J, Wen Y, Wang P, Fan L. Bupivacaine inhibits the malignant biological behavior of oral squamous cell carcinoma cells by inhibiting the activation of ERK1/2 and STAT3. Ann Transl Med. 2021 May;9(10):839. doi: 10.21037/atm-21-1414. PMID: 34164473; PMCID: PMC8184410. 2. Liu B, Yan X, Hou Z, Zhang L, Zhang D. Impact of Bupivacaine on malignant proliferation, apoptosis and autophagy of human colorectal cancer SW480 cells through regulating NF-κB signaling path. Bioengineered. 2021 Dec;12(1):2723-2733. doi: 10.1080/21655979.2021.1937911. PMID: 34151717.
1: Prabhakar A, Ward CT, Watson M, Sanford J, Fiza B, Moll V, Kaye RJ, Morgan Hall O, Cornett EM, Urman RD, Kaye AD. Liposomal bupivacaine and novel local anesthetic formulations. Best Pract Res Clin Anaesthesiol. 2019 Dec;33(4):425-432. doi: 10.1016/j.bpa.2019.07.012. Epub 2019 Jul 19. PMID: 31791561. 2: Beiranvand S, Moradkhani MR. Bupivacaine Versus Liposomal Bupivacaine For Pain Control. Drug Res (Stuttg). 2018 Jul;68(7):365-369. doi: 10.1055/s-0043-121142. Epub 2017 Nov 6. PMID: 29108087. 3: Vyas KS, Rajendran S, Morrison SD, Shakir A, Mardini S, Lemaine V, Nahabedian MY, Baker SB, Rinker BD, Vasconez HC. Systematic Review of Liposomal Bupivacaine (Exparel) for Postoperative Analgesia. Plast Reconstr Surg. 2016 Oct;138(4):748e-756e. doi: 10.1097/PRS.0000000000002547. PMID: 27673545. 4: Shafiei FT, McAllister RK, Lopez J. Bupivacaine. 2020 Jun 22. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2021 Jan–. PMID: 30422478. 5: Casati A, Putzu M. Bupivacaine, levobupivacaine and ropivacaine: are they clinically different? Best Pract Res Clin Anaesthesiol. 2005 Jun;19(2):247-68. doi: 10.1016/j.bpa.2004.12.003. PMID: 15966496. 6: Balocco AL, Van Zundert PGE, Gan SS, Gan TJ, Hadzic A. Extended release bupivacaine formulations for postoperative analgesia: an update. Curr Opin Anaesthesiol. 2018 Oct;31(5):636-642. doi: 10.1097/ACO.0000000000000648. PMID: 30074492. 7: Hamilton TW, Athanassoglou V, Mellon S, Strickland LH, Trivella M, Murray D, Pandit HG. Liposomal bupivacaine infiltration at the surgical site for the management of postoperative pain. Cochrane Database Syst Rev. 2017 Feb 1;2(2):CD011419. doi: 10.1002/14651858.CD011419.pub2. PMID: 28146271; PMCID: PMC6464293. 8: Malik O, Kaye AD, Kaye A, Belani K, Urman RD. Emerging roles of liposomal bupivacaine in anesthesia practice. J Anaesthesiol Clin Pharmacol. 2017 Apr- Jun;33(2):151-156. doi: 10.4103/joacp.JOACP_375_15. PMID: 28781438; PMCID: PMC5520585. 9: Uppal V, Retter S, Shanthanna H, Prabhakar C, McKeen DM. Hyperbaric Versus Isobaric Bupivacaine for Spinal Anesthesia: Systematic Review and Meta-analysis for Adult Patients Undergoing Noncesarean Delivery Surgery. Anesth Analg. 2017 Nov;125(5):1627-1637. doi: 10.1213/ANE.0000000000002254. PMID: 28708665. 10: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Bupivacaine. 2020 Nov 16. PMID: 30000385. 11: Sorenson E, Chesnut C. Liposomal Bupivacaine: A Review and Applications to Dermatologic Surgery. Dermatol Surg. 2019 Jan;45(1):68-73. doi: 10.1097/DSS.0000000000001628. PMID: 30148736. 12: Tong YC, Kaye AD, Urman RD. Liposomal bupivacaine and clinical outcomes. Best Pract Res Clin Anaesthesiol. 2014 Mar;28(1):15-27. doi: 10.1016/j.bpa.2014.02.001. Epub 2014 Mar 15. PMID: 24815964. 13: Uskova A, O'Connor JE. Liposomal bupivacaine for regional anesthesia. Curr Opin Anaesthesiol. 2015 Oct;28(5):593-7. doi: 10.1097/ACO.0000000000000240. PMID: 26308513. 14: Lonner JH, Scuderi GR, Lieberman JR. Potential utility of liposome bupivacaine in orthopedic surgery. Am J Orthop (Belle Mead NJ). 2015 Mar;44(3):111-7. PMID: 25750943. 15: Ilfeld BM, Eisenach JC, Gabriel RA. Clinical Effectiveness of Liposomal Bupivacaine Administered by Infiltration or Peripheral Nerve Block to Treat Postoperative Pain. Anesthesiology. 2021 Feb 1;134(2):283-344. doi: 10.1097/ALN.0000000000003630. PMID: 33372949. 16: Ma TT, Wang YH, Jiang YF, Peng CB, Yan C, Liu ZG, Xu WX. Liposomal bupivacaine versus traditional bupivacaine for pain control after total hip arthroplasty: A meta-analysis. Medicine (Baltimore). 2017 Jun;96(25):e7190. doi: 10.1097/MD.0000000000007190. PMID: 28640101; PMCID: PMC5484209. 17: Manchikanti L, Knezevic NN, Parr A, Kaye AD, Sanapati M, Hirsch JA. Does Epidural Bupivacaine with or Without Steroids Provide Long-Term Relief? A Systematic Review and Meta-analysis. Curr Pain Headache Rep. 2020 Apr 25;24(6):26. doi: 10.1007/s11916-020-00859-7. PMID: 32335757. 18: Lambrechts M, O'Brien MJ, Savoie FH, You Z. Liposomal extended-release bupivacaine for postsurgical analgesia. Patient Prefer Adherence. 2013 Sep 6;7:885-90. doi: 10.2147/PPA.S32175. PMID: 24043932; PMCID: PMC3772762. 19: Yan Z, Chen Z, Ma C. Liposomal bupivacaine versus interscalene nerve block for pain control after shoulder arthroplasty: A meta-analysis. Medicine (Baltimore). 2017 Jul;96(27):e7226. doi: 10.1097/MD.0000000000007226. PMID: 28682872; PMCID: PMC5502145. 20: Ngo AL, Urits I, Yilmaz M, Fortier L, Anya A, Oh JH, Berger AA, Kassem H, Sanchez MG, Kaye AD, Urman RD, Herron EW, Cornett EM, Viswanath O. Postherpetic Neuralgia: Current Evidence on the Topical Film-Forming Spray with Bupivacaine Hydrochloride and a Review of Available Treatment Strategies. Adv Ther. 2020 May;37(5):2003-2016. doi: 10.1007/s12325-020-01335-9. Epub 2020 Apr 15. PMID: 32297285; PMCID: PMC7467465.