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MedKoo Cat#: 534581 | Name: Nafcillin sodium
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Description:

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

Nafcillin sodium is an antibacterial chemical.

Chemical Structure

Nafcillin sodium
Nafcillin sodium
CAS#7177-50-6 (sodium hydrate)

Theoretical Analysis

MedKoo Cat#: 534581

Name: Nafcillin sodium

CAS#: 7177-50-6 (sodium hydrate)

Chemical Formula: C21H23N2NaO6S

Exact Mass: 454.1175

Molecular Weight: 454.47

Elemental Analysis: C, 55.50; H, 5.10; N, 6.16; Na, 5.06; O, 21.12; S, 7.05

Price and Availability

Size Price Availability Quantity
1g USD 235.00 2 Weeks
5g USD 420.00 2 Weeks
10g USD 670.00 2 Weeks
25g USD 1,130.00 2 Weeks
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Related CAS #
147-52-4 (free acid) 7177-50-6 (sodium hydrate) 985-16-0 (sodium)
Synonym
Nafcillin sodium; Wy 3277; Wy-3277; Wy3277; Nallpen; Unipen; Nafcil;
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, monohydrate, (2S-(2alpha,5alpha,6beta))
InChi Key
OCXSDHJRMYFTMA-KMFBOIRUSA-M
InChi Code
InChI=1S/C21H22N2O5S.Na.H2O/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);;1H2/q;+1;/p-1/t15-,16+,19-;;/m1../s1
SMILES Code
O=C([C@@H](C(C)(C)S[C@]1([H])[C@@H]2NC(C3=C4C=CC=CC4=CC=C3OCC)=O)N1C2=O)[O-].[H]O[H].[Na+]
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
>3 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
Instruction
View handling instruction
Biological target:
Nafcillin sodium monohydrate, an antibiotic, is a reversible inhibitor of β-lactamase.
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMF 15.0 33.01
DMSO 67.0 147.42
Ethanol 10.5 23.10
PBS (pH 7.2) 1.0 2.20
Water 46.0 101.22
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 454.47 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:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Twilla JD, Algrim A, Adams EH, Samarin M, Cummings C, Finch CK. Comparison of Nafcillin and Cefazolin for the Treatment of Methicillin-Susceptible Staphylococcus aureus Bacteremia. Am J Med Sci. 2020 Apr 17:S0002-9629(20)30123-3. doi: 10.1016/j.amjms.2020.04.006. Epub ahead of print. PMID: 32376001. 2: Salazar MJ, Machado H, Dillon NA, Tsunemoto H, Szubin R, Dahesh S, Pogliano J, Sakoulas G, Palsson BO, Nizet V, Feist AM. Genetic Determinants Enabling Medium-Dependent Adaptation to Nafcillin in Methicillin-Resistant Staphylococcus aureus. mSystems. 2020 Mar 31;5(2):e00828-19. doi: 10.1128/mSystems.00828-19. PMID: 32234776; PMCID: PMC7112963. 3: Montoya-Rodríguez DM, Ávila-Torres Y, Serna-Galvis EA, Torres-Palma RA. Data on treatment of nafcillin and ampicillin antibiotics in water by sonochemistry. Data Brief. 2020 Mar 2;29:105361. doi: 10.1016/j.dib.2020.105361. PMID: 32195299; PMCID: PMC7075802. 4: Campos S, Salazar R, Arancibia-Miranda N, Rubio MA, Aranda M, García A, Sepúlveda P, Espinoza LC. Nafcillin degradation by heterogeneous electro-Fenton process using Fe, Cu and Fe/Cu nanoparticles. Chemosphere. 2020 May;247:125813. doi: 10.1016/j.chemosphere.2020.125813. Epub 2020 Jan 8. PMID: 31951953. 5: Chan L, Chan-Tompkins NH, Como J, Guarascio AJ. Retrospective Analysis of Adverse Drug Events Between Nafcillin Versus Cefazolin for Treatment of Methicillin-Susceptible Staphylococcus aureus Infections. Ann Pharmacother. 2019 Dec 30:1060028019897267. doi: 10.1177/1060028019897267. Epub ahead of print. PMID: 31888347. 6: Rajput A, Poudel S, Tsunemoto H, Meehan M, Szubin R, Olson CA, Lamsa A, Seif Y, Dillon N, Vrbanac A, Sugie J, Dahesh S, Monk JM, Dorrestein PC, Knight R, Nizet V, Palsson BO, Feist AM, Pogliano J. Profiling the effect of nafcillin on HA-MRSA D712 using bacteriological and physiological media. Sci Data. 2019 Dec 17;6(1):322. doi: 10.1038/s41597-019-0331-z. PMID: 31848353; PMCID: PMC6917727. 7: Timbrook TT, McKay L, Sutton JD, Spivak ES. Disproportionality Analysis of Safety with Nafcillin and Oxacillin with the FDA Adverse Event Reporting System (FAERS). Antimicrob Agents Chemother. 2020 Feb 21;64(3):e01818-19. doi: 10.1128/AAC.01818-19. PMID: 31844017; PMCID: PMC7038239. 8: Beganovic M, Cusumano JA, Lopes V, LaPlante KL, Caffrey AR. Comparative Effectiveness of Exclusive Exposure to Nafcillin or Oxacillin, Cefazolin, Piperacillin/Tazobactam, and Fluoroquinolones Among a National Cohort of Veterans With Methicillin-Susceptible Staphylococcus aureus Bloodstream Infection. Open Forum Infect Dis. 2019 Jun 6;6(7):ofz270. doi: 10.1093/ofid/ofz270. PMID: 31281864; PMCID: PMC6602898. 9: Poudel S, Tsunemoto H, Meehan M, Szubin R, Olson CA, Lamsa A, Seif Y, Dillon N, Vrbanac A, Sugie J, Dahesh S, Monk JM, Dorrestein PC, Pogliano J, Knight R, Nizet V, Palsson BO, Feist AM. Characterization of CA-MRSA TCH1516 exposed to nafcillin in bacteriological and physiological media. Sci Data. 2019 Apr 26;6(1):43. doi: 10.1038/s41597-019-0051-4. PMID: 31028276; PMCID: PMC6486602. 10: Burrelli CC, Broadbent EK, Margulis A, Snyder GM, Gold HS, McCoy C, Mahoney MV, Hirsch EB. Does the Beta-Lactam Matter? Nafcillin versus Cefazolin for Methicillin-Susceptible Staphylococcus aureus Bloodstream Infections. Chemotherapy. 2018;63(6):345-351. doi: 10.1159/000499033. Epub 2019 Apr 9. PMID: 30965335. 11: Lewis PO, Sevinsky RE, Patel PD, Krolikowski MR, Cluck DB. Vancomycin plus nafcillin salvage for the treatment of persistent methicillin-resistant Staphylococcus aureus bacteremia following daptomycin failure: a case report and literature review. Ther Adv Infect Dis. 2018 Sep 10;6:2049936118797404. doi: 10.1177/2049936118797404. PMID: 30891239; PMCID: PMC6416679. 12: Casado F, Mudunuru SA, Nasr R. A Case of Hypokalemia Possibly Induced by Nafcillin. Antibiotics (Basel). 2018 Dec 12;7(4):108. doi: 10.3390/antibiotics7040108. PMID: 30545049; PMCID: PMC6315441. 13: King CA, Babcock KM, Godios RJ, King BS. Significant drug-drug interaction between warfarin and nafcillin. Ther Adv Drug Saf. 2018 Aug 31;9(11):667-671. doi: 10.1177/2042098618796186. PMID: 30479741; PMCID: PMC6243422. 14: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Nafcillin. 2018 Oct 31. PMID: 30000101. 15: Miller MA, Fish DN, Barber GR, Barron MA, Goolsby TA, Moine P, Mueller SW. A comparison of safety and outcomes with cefazolin versus nafcillin for methicillin-susceptible Staphylococcus aureus bloodstream infections. J Microbiol Immunol Infect. 2020 Apr;53(2):321-327. doi: 10.1016/j.jmii.2018.07.006. Epub 2018 Aug 18. PMID: 30190234. 16: Rukma P, Mohsena A, Sunil M. Nafcillin-Associated Hypokalemia. Am J Ther. 2018 Nov/Dec;25(6):e755-e756. doi: 10.1097/MJT.0000000000000760. PMID: 29672332. 17: Vidal J, Huiliñir C, Santander R, Silva-Agredo J, Torres-Palma RA, Salazar R. Effective removal of the antibiotic Nafcillin from water by combining the Photoelectro-Fenton process and Anaerobic Biological Digestion. Sci Total Environ. 2018 May 15;624:1095-1105. doi: 10.1016/j.scitotenv.2017.12.159. Epub 2017 Dec 27. PMID: 29625524. 18: Monogue ML, Ortwine JK, Wei W, Eljaaly K, Bhavan KP. Nafcillin versus cefazolin for the treatment of methicillin-susceptible Staphylococcus aureus bacteremia. J Infect Public Health. 2018 Sep-Oct;11(5):727-731. doi: 10.1016/j.jiph.2018.02.004. Epub 2018 Mar 8. PMID: 29526442. 19: Oh DH, Kim JJ, Kim J, Seong H, Lee SJ, Kim YC, Kim EJ, Jung IY, Jeong WY, Jeong SJ, Ku NS, Han SH, Choi JY, Song YG, Kim JM. Comparison of the efficacy of nafcillin and glycopeptides as definitive therapy for patients with methicillin- susceptible Staphylococcus aureus bacteremia: a retrospective cohort study. BMC Infect Dis. 2018 Jan 30;18(1):60. doi: 10.1186/s12879-018-2978-z. PMID: 29378565; PMCID: PMC5789670. 20: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Nafcillin. 2018 Jan 3. PMID: 31643722.

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