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MedKoo Cat#: 464064 | Name: Nafcillin-d5 sodium
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Description:

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

Nafcillin-d5 is intended for use as an internal standard for the quantification of nafcillin by GC- or LC-MS. Nafcillin is a semisynthetic and penicillinase-resistant penicillin antibiotic. It is active against 20 clinical isolates of S. aureus with minimum bactericidal concentration (MBC) values ranging from 0.078 to 0.312 µg/ml. Nafcillin (100-800 mg/kg) reduces the number of kidney colony forming units (CFUs) in a mouse model of S. aureus infection. It also reduces the number of right atrial CFUs in a rabbit model of S. aureus-induced endocarditis. Formulations containing nafcillin have been used in the treatment of various bacterial infections.

Chemical Structure

Nafcillin-d5 sodium
Nafcillin-d5 sodium
CAS#1356354-25-0

Theoretical Analysis

MedKoo Cat#: 464064

Name: Nafcillin-d5 sodium

CAS#: 1356354-25-0

Chemical Formula: C21H16D5N2NaO5S

Exact Mass: 0.0000

Molecular Weight: 441.49

Elemental Analysis: C, 57.13; H, 5.93; N, 6.35; Na, 5.21; O, 18.12; S, 7.26

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
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Related CAS #
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Synonym
Nafcillin-d5 sodium salt; Nafcillin d5 sodium salt;
IUPAC/Chemical Name
sodium (2S,5R,6R)-6-(2-(ethoxy-d5)-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
InChi Key
AYAPZOUDXCDGIF-LYVUTDJTSA-M
InChi Code
InChI=1S/C21H22N2O5S.Na/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);/q;+1/p-1/t15-,16+,19-;/m1./s1/i1D3,4D2;
SMILES Code
[O-]C([C@@H]1N2[C@@]([H])([C@H](NC(C3=C(C=CC4=C3C=CC=C4)OC([2H])(C([2H])([2H])[2H])[2H])=O)C2=O)SC1(C)C)=O.[Na+]
Appearance
Solid powder
Purity
>99% (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
Instruction
View handling instruction
Biological target:
Nafcillin-d5 is intended for use as an internal standard for the quantification of nafcillin by GC- or LC-MS.
In vitro activity:
TBD
In vivo activity:
TBD
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 441.49 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
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Life (Basel). 2020 Oct 24;10(11):253. doi: 10.3390/life10110253. PMID: 33114423; PMCID: PMC7693748. 5: Thabit AK, Shea KM, Guzman OE, Garey KW. Antibiotic utilization within 18 community hospitals in the United States: A 5-year analysis. Pharmacoepidemiol Drug Saf. 2020 Oct 23. doi: 10.1002/pds.5156. Epub ahead of print. PMID: 33094502. 6: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Nafcillin. 2020 Oct 20. PMID: 31643722. 7: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Penicillins (2nd Generation). 2020 Oct 20. PMID: 31643364. 8: Akers SM, Kinney K, Butcher MI, Moïse A. Clearance of Persistent Staphylococcus aureus Bacteremia in a Preterm Neonate With the Use of Combination Cefazolin and Ertapenem. J Pediatr Pharmacol Ther. 2020;25(6):547-551. doi: 10.5863/1551-6776-25.6.547. PMID: 32839659; PMCID: PMC7439943. 9: Bradley JS, Arrieta AC, Digtyar VA, Popejoy MW, Grandhi A, Bokesch P, Hershberger E, Dorr MB, Tan CM, Murata Y, Wolf DJ, Bensaci M. Daptomycin for Pediatric Gram-Positive Acute Hematogenous Osteomyelitis. Pediatr Infect Dis J. 2020 Sep;39(9):814-823. doi: 10.1097/INF.0000000000002790. PMID: 32639465. 10: Jenson RE, Baines SL, Howden BP, Mishra NN, Farah S, Lew C, Berti AD, Shukla SK, Bayer AS, Rose WE. Prolonged Exposure to β-Lactam Antibiotics Reestablishes Susceptibility of Daptomycin-Nonsusceptible Staphylococcus aureus to Daptomycin. Antimicrob Agents Chemother. 2020 Aug 20;64(9):e00890-20. doi: 10.1128/AAC.00890-20. PMID: 32601160; PMCID: PMC7449200. 11: Sarria JC. Methicillin-Susceptible Staphylococcus Aureus Bacteremia: Cefazolin in Prime But Nafcillin Not Ready for an Exit. Am J Med Sci. 2020 Jul;360(1):3-4. doi: 10.1016/j.amjms.2020.04.007. Epub 2020 Apr 15. PMID: 32439151. 12: Martí-Carvajal AJ, Dayer M, Conterno LO, Gonzalez Garay AG, Martí-Amarista CE. A comparison of different antibiotic regimens for the treatment of infective endocarditis. Cochrane Database Syst Rev. 2020 May 14;5(5):CD009880. doi: 10.1002/14651858.CD009880.pub3. PMID: 32407558; PMCID: PMC7527143. 13: 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 Jul;360(1):35-41. doi: 10.1016/j.amjms.2020.04.006. Epub 2020 Apr 17. PMID: 32376001. 14: 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. 15: 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. 16: Shah S, Golden M, Topal JE, McManus D. Intravenous (IV) cefazolin with oral probenecid: A novel daily regimen for the management of Methicillin Sensitive Staphylococcus aureus (MSSA) bacteremia in a patient with renal dysfunction. IDCases. 2020 Jan 29;19:e00706. doi: 10.1016/j.idcr.2020.e00706. PMID: 32055441; PMCID: PMC7005544. 17: Nguyen M, Chen YC, Tartar D. Characteristics of patients hospitalized for Drug Reaction with Eosinophilia and Systemic Symptoms (DRESS) at a Level 1 trauma center. Dermatol Online J. 2019 Dec 15;25(12):13030/qt98k1f6q4. PMID: 32045160. 18: 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. 19: 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. 2020 Jul;54(7):662-668. doi: 10.1177/1060028019897267. Epub 2019 Dec 30. PMID: 31888347. 20: Wang G, Li L, Wang X, Li X, Zhang Y, Yu J, Jiang J, You X, Xiong YQ. Hypericin enhances β-lactam antibiotics activity by inhibiting sarA expression in methicillin-resistant Staphylococcus aureus. Acta Pharm Sin B. 2019 Nov;9(6):1174-1182. doi: 10.1016/j.apsb.2019.05.002. Epub 2019 May 29. PMID: 31867163; PMCID: PMC6900551.