WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 317356
CAS#: 18010-40-7 (HCl)
Description: 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.
MedKoo Cat#: 317356
Name: Bupivacaine HCl
CAS#: 18010-40-7 (HCl)
Chemical Formula: C18H29ClN2O
Exact Mass: 288.22016
Molecular Weight: 324.893
Elemental Analysis: C, 66.54; H, 9.00; Cl, 10.91; N, 8.62; O, 4.92
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
The following data is based on the product molecular weight 324.893 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 |
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.
