Nafcillin sodium salt monohydrate

Names

[ Name ]:
Nafcillin sodium salt monohydrate

[Synonym ]:
nafcillin sodium monohydrate
MFCD01941128
Nafcillin sodium salt monohydrate
NAFCILLINSODIUMSTERILE
nafcillin sodium
Unipen (tn)
Sodium (2S,5R,6R)-6-[(2-ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate (1:1:1)
Nafcillin monohydrate sodium salt
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, sodium salt, (2S,5R,6R)-, hydrate (1:1:1)
Nafcillin (sodium monohydrate)

Biological Activity

[Description]:

Nafcillin sodium monohydrate is a semi-synthetic antibiotic related to penicillin.Target: AntibacterialNafcillin sodium is a narrow-spectrum, beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins. Nafcillin is considered therapeutically equivalent to oxacillin, although its safety profile is somewhat different. Nafcillin was shown to reversibly inhibit beta-lactamase from Staphylococcus aureus PC1 with characteristics indicative of a type A inhibitor [Citri, Samuni & Zyk (1976) Proc. Natl. Acad. Sci. U.S.A. 73, 1048-1052]. At nafcillin concentrations above 80 mM, complete inactivation occurred within 200 s. Upon removal of the excess nafcillin the inhibited enzyme was re-activated completely, with a rate constant of 2.0 x 10(-3) s-1 (25 degrees C) [1, 2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Tan, A.K. and A.L. Fink, Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase. Biochem J, 1992. 281 ( Pt 1): p. 191-6.

[2]. Palmer, D.L., S.B. Pett, and B.F. Akl, Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics. Ann Thorac Surg, 1995. 59(3): p. 626-31.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.42 g/cm3

[ Boiling Point ]:
714.1ºC at 760 mmHg

[ Molecular Formula ]:
C₂₁H₂₃N₂NaO₆S

[ Molecular Weight ]:
454.472

[ Flash Point ]:
385.7ºC

[ Exact Mass ]:
454.117462

[ PSA ]:
133.30000

[ LogP ]:
1.41360

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H317-H319-H334-H335

[ Precautionary Statements ]:
P261-P280-P284-P304 + P340-P305 + P351 + P338-P342 + P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Effect of NaCl and nafcillin on penicillin-binding protein 2a and heterogeneous expression of methicillin resistance in Staphylococcus aureus.

Antimicrob. Agents Chemother. 31 , 1982-1988, (1987)

Expression of methicillin resistance in heterogeneous strains of Staphylococcus aureus is enhanced by 2 to 5% NaCl in the medium and by selection with beta-lactam antibiotics. Resistance is associated...

Co-trimoxazole versus nafcillin in the therapy of experimental meningitis due to Staphylococcus aureus.

J. Antimicrob. Chemother. 19 , 647-658, (1987)

Co-trimoxazole was compared with nafcillin against Staphylococcus aureus in vitro and in the therapy of experimental Staph. aureus meningitis in rabbits. Co-trimoxazole (trimethoprim:sulphamethoxazole...