A semisynthetic and penicillinase-resistant penicillin antibiotic
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Labeled Version(s)
33468Nafcillin-d5 (sodium salt)
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Nafcillin (sodium salt hydrate)

Item No. 21008

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, monosodium salt, monohydrate
CAS Number
7177-50-6
Molecular Formula
C21H21N2O5S • Na [H2O]
Formula Weight
454.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
226, 228, 279, 333 nm
SMILES
O=C(N[C@@H]1C(N2[C@]1([H])SC(C)(C)[C@@H]2C([O-])=O)=O)C3=C(C=CC=C4)C4=CC=C3OCC.[Na+].O
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
InChi Key
OCXSDHJRMYFTMA-KMFBOIRUSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Nafcillin is a semisynthetic and penicillinase-resistant penicillin antibiotic.1 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.2 It also reduces the number of right atrial CFUs in a rabbit model of S. aureus-induced endocarditis.3 Formulations containing nafcillin have been used in the treatment of various bacterial infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tuazon, C.U., Lin, M.Y., and Sheagren, J.N. In vitro activity of rifampin alone and in combination with nafcillin and vancomycin against pathogenic strains of Staphylococcus aureus. Antimicrob. Agents Chemother. 13(5), 759-761 (1978).

    2. Yuchenco, J.A., Hopper, M.W., Vince, T.D., et al. Nafcillin and oxacillin: Comparative antistaphylococcal activity in mice. J. Antibiot. (Tokyo) 29(4), 460-465 (1976).

    3. Carrizosa, J., Kobasa, W.D., and Kaye, D. Effectiveness of nafcillin, methicillin, and cephalothin in experimental Staphylococcus aureus endocarditis. Antimicrob. Agents Chemother. 15(5), 735-737 (1979).