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MedKoo Cat#: 562858 | Name: Bupivacaine tartrate

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 tartrate
Bupivacaine tartrate
CAS#175082-90-3 (tartrate)

Theoretical Analysis

MedKoo Cat#: 562858

Name: Bupivacaine tartrate

CAS#: 175082-90-3 (tartrate)

Chemical Formula: C22H34N2O7

Exact Mass: 0.0000

Molecular Weight: 438.52

Elemental Analysis: C, 60.26; H, 7.82; N, 6.39; O, 25.54

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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 HCl; Bupivacaine Hydrochloride; Vivacaine;
IUPAC/Chemical Name
1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide L-tartrate
InChi Key
RJNAJMHSZCZJJT-LREBCSMRSA-N
InChi Code
InChI=1S/C18H28N2O.C4H6O6/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;5-1(3(7)8)2(6)4(9)10/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
SMILES Code
O=C(C1N(CCCC)CCCC1)NC2=C(C)C=CC=C2C.O[C@H]([C@H](C(O)=O)O)C(O)=O
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 438.52 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
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.