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MedKoo Cat#: 317356 | Name: Bupivacaine HCl
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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 HCl
Bupivacaine HCl
CAS#18010-40-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 317356

Name: Bupivacaine HCl

CAS#: 18010-40-7 (HCl)

Chemical Formula: C18H29ClN2O

Exact Mass: 288.2202

Molecular Weight: 324.89

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 90.00 Ready to ship
1g USD 150.00 Ready to Ship
2g USD 250.00 Ready to Ship
5g USD 450.00 2 Weeks
10g USD 750.00 2 Weeks
25g USD 1,250.00 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
Bupivacaine, Marcaine; AH-250; HSDB 7790; SKY 0402; SKY0402, Win 11318; AH 250; AH250; HSDB7790; HSDB-7790; SKY-0402; Win-11318; Win11318
IUPAC/Chemical Name
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride
InChi Key
SIEYLFHKZGLBNX-UHFFFAOYSA-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
SMILES Code
O=C(C1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C
Appearance
White crystalline 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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# T21C03I08
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Bupivacaine hydrochloride is a Na+ channel blocker which has local narcotic effect.
In vitro activity:
The in vitro effects of bupivacaine on cartilaginous tumor cells were evaluated. Multiple different cartilaginous tumors were evaluated, including enchondromas, chondroblastomas, a low-grade chondrosarcoma, which were harvested from patients during tumor resection, and a grade-II chondrosarcoma SW1535 (ATCC HTB-94). The tumor cells were treated with 0.25% and 0.5% bupivacaine at various times points, and the result was compared with that of untreated tumor cells. Increasing periods of exposure to bupivacaine decreased the cell viability in all tumor samples. The cytotoxicity of 0.5% bupivacaine was significantly greater than that of 0.25% bupivacaine in all tumor cells tested. Reference: J Am Acad Orthop Surg. 2019 Apr 1;27(7):e337-e345. https://journals.lww.com/jaaos/Abstract/2019/04010/The_In_Vitro_Effects_of_Bupivacaine_on.10.aspx
In vivo activity:
The role of Bupivacaine in painful diabetic neuropathy was evaluated. Mouse model with painful diabetic neuropathy was established, and then treated with different concentrations of Bupivacaine. Bupivacaine ameliorated the mechanical allodynia, thermal hyperalgesia, and thermal allodynia in mice with painful diabetic neuropathy, and is more effective at low concentration. Moreover, low concentration of Bupivacaine inhibited inflammation and promoted miR-23a expression in mice with painful diabetic neuropathy and in microglia induced by high glucose. Reference: Eur J Pharmacol. 2021 Jan 15;891:173719. https://www.sciencedirect.com/science/article/abs/pii/S0014299920308116?via%3Dihub
Solvent mg/mL mM
Solubility
DMSO 40.1 123.46
DMF 30.0 92.34
Water 38.8 119.27
Ethanol 47.5 146.20
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.54
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.

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. Chapman GL, Zuckerman LM, Mirshahidi S. The In Vitro Effects of Bupivacaine on Cartilage-forming Tumor Cells. J Am Acad Orthop Surg. 2019 Apr 1;27(7):e337-e345. doi: 10.5435/JAAOS-D-17-00407. PMID: 30278011. 2. Flenner F, Arlt N, Nasib M, Schobesberger S, Koch T, Ravens U, Friedrich F, Nikolaev V, Christ T, Stehr SN. In Vitro Negative Inotropic Effect of Low Concentrations of Bupivacaine Relates to Diminished Ca2+ Sensitivity but Not to Ca2+ Handling or β-Adrenoceptor Signaling. Anesthesiology. 2018 Jun;128(6):1175-1186. doi: 10.1097/ALN.0000000000002180. PMID: 29547406. 3. Wang T, Hurwitz O, Shimada SG, Tian D, Dai F, Zhou J, Ma C, LaMotte RH. Anti-nociceptive effects of bupivacaine-encapsulated PLGA nanoparticles applied to the compressed dorsal root ganglion in mice. Neurosci Lett. 2018 Mar 6;668:154-158. doi: 10.1016/j.neulet.2018.01.031. Epub 2018 Feb 3. PMID: 29355697; PMCID: PMC5829013. 4. Zhang X, Xia L, Xie A, Liao O, Ju F, Zhou Y. Low concentration of Bupivacaine ameliorates painful diabetic neuropathy by mediating miR-23a/PDE4B axis in microglia. Eur J Pharmacol. 2021 Jan 15;891:173719. doi: 10.1016/j.ejphar.2020.173719. Epub 2020 Nov 1. PMID: 33144067.
In vitro protocol:
1. Chapman GL, Zuckerman LM, Mirshahidi S. The In Vitro Effects of Bupivacaine on Cartilage-forming Tumor Cells. J Am Acad Orthop Surg. 2019 Apr 1;27(7):e337-e345. doi: 10.5435/JAAOS-D-17-00407. PMID: 30278011. 2. Flenner F, Arlt N, Nasib M, Schobesberger S, Koch T, Ravens U, Friedrich F, Nikolaev V, Christ T, Stehr SN. In Vitro Negative Inotropic Effect of Low Concentrations of Bupivacaine Relates to Diminished Ca2+ Sensitivity but Not to Ca2+ Handling or β-Adrenoceptor Signaling. Anesthesiology. 2018 Jun;128(6):1175-1186. doi: 10.1097/ALN.0000000000002180. PMID: 29547406.
In vivo protocol:
1. Wang T, Hurwitz O, Shimada SG, Tian D, Dai F, Zhou J, Ma C, LaMotte RH. Anti-nociceptive effects of bupivacaine-encapsulated PLGA nanoparticles applied to the compressed dorsal root ganglion in mice. Neurosci Lett. 2018 Mar 6;668:154-158. doi: 10.1016/j.neulet.2018.01.031. Epub 2018 Feb 3. PMID: 29355697; PMCID: PMC5829013. 2. Zhang X, Xia L, Xie A, Liao O, Ju F, Zhou Y. Low concentration of Bupivacaine ameliorates painful diabetic neuropathy by mediating miR-23a/PDE4B axis in microglia. Eur J Pharmacol. 2021 Jan 15;891:173719. doi: 10.1016/j.ejphar.2020.173719. Epub 2020 Nov 1. PMID: 33144067.
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.