NAFCILLIN SODIUM SALT Chemical Properties

Melting point:

>167°C (dec.)

storage temp. 

Store at 0-5°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

pKa 2.65(H2O,t = 25±0.1,c=0.006) (Uncertain)

color 

Off-White to Pale Yellow

Safety Information

Hazard Codes 

Xn

Risk Statements 

42/43

Safety Statements 

22-36/37-45

WGK Germany 

3

RTECS 

XI0175000

NAFCILLIN SODIUM SALT Usage And Synthesis

Originator

Unipen,Wyeth,US,1964

Uses

Nafcillin Sodium Salt is an antibiotic of the penicillin class that is resistant to beta-lactamase. It can also be used as analyte for biological study and analytical study of hybrid quadrupole-orbitrap mass spectrometry analysis for high-throughput screening and quantification of multi-xenobiotics in honey.

Uses

Nafcillin SodiuM Salt can be used as narcotic antagonist

Uses

As a synthetic beta-lactamase-resistant penicillin, Nafcillin SodiuM Salt can be used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.

Definition

ChEBI: Nafcillin sodium is an organic sodium salt. It contains a nafcillin(1-).

Indications

It is effective against Gram-positive cocci and staphylococci that produce penicillinase. It is used for the same indications as methicillin. Synonyms of this drug are nafcil, nalpen, unipen, and others.
Another type of semisynthetic penicillin that should undoubtedly be considered is penicillin derivatives of heteroylcarboxylic acids (as a rule an isoxazol) in the third position of which is present a substituted or nonsubstituted phenyl radical (oxacillin, cloxacillin, dicloxacillin), which plays the role of the radical in the acyl side group. These penicillins (oxacillin, cloxacillin, dicloxacillin), which are resistant to penicillinase, are active with respect to penicillin-G-resistant staphylococci. Their antimicrobial spectrum is restricted to Gram-positive microorganisms.
Penicillins that are resistant to penicillinase are the drug of choice for infections resistant to penicillin G, Staph. aureus, or coagulase-negative staphylococci. They are also effective for infections caused by nonenterococcus types of streptococci, such as streptococci groups A, B, C, and G, as well as pneumococci.

Manufacturing Process

A stirred suspension of 12.6 grams 6-aminopenicillanic acid in 130 ml dry alcohol-free chloroform was treated with 16 ml triethylamine and then with 13.8 grams of a solution of 2-ethoxy-1-naphthoyl chloride in 95 ml chloroform. After being washed successively with 58 ml each of 1 N and then 0.1 N hydrochloric acid the chloroform solution was extracted with N aqueous sodium bicarbonate (58 ml + 6 ml). The combined bicarbonate extracts were washed with 20 ml ether and then evaporated at low temperature and pressure to give the crude sodium salt of 2-ethoxy-1-naphthylpenicillin [also called sodium 6-(2-ethoxy-1-naphthamido)penicillinate] as a yellow powder (20.3 grams). This was dissolved in 20 ml water at 30°C and diluted with 180 ml n-butanol, also at 30°C, with stirring. Slow cooling to 0°C gave colorless needles of the product.

brand name

Nallpen (GlaxoSmithKline).

Therapeutic Function

Antibacterial

Antimicrobial activity

The antibacterial spectrum is similar to that of the isoxazolylpenicillins but it is more active against streptococci and pneumococci. Activity in vitro is depressed in the presence of serum. It is more stable than the isoxazolylpenicillins to staphylococcal β-lactamase. There is complete cross-resistance with other group 3 penicillins.

Pharmacokinetics

Oral absorption: c. 35%
C_max 1 g intramuscular:8 mg/L after 1 h
500 mg intravenous:30 mg/L after 5 min
Plasma half-life: 0.5 h
Plasma protein binding: 90%
Absorption and distribution
Nafcillin is poorly absorbed after oral administration, and absorption is further depressed if the drug is given with food. Most dosing is now intravenous. Penetration into tissues is similar to that of the isoxazolylpenicillins. Penetration into normal meninges is low, but is higher in inflamed meninges.
Metabolism and excretion
About 60–70% is inactivated in the liver. Following intramuscular administration, about 30% appears in the urine, producing concentrations up to 1000 mg/L. Administration of probenecid reduces the urinary excretion and raises and prolongs the plasma level. About 8% of the dose is excreted in the bile.

Clinical Use

Uses are those of group 3 penicillins . Nafcillin has been particularly recommended for the treatment of staphylococcal bacteremia caused by susceptible strains.

Side effects

There is cross-allergenicity with other penicillins. Its side effects are similar to the penicillins. Pseudomembranous colitis has been reported.

Synthesis

Nafcillin, [2S-(2α,5α,6β)]-3,3-dimethyl-7-oxo-6-(2-ethoxy-1-naphthamido)-4- thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.4), is synthesized by acylating 6-APA with 2-ethoxy-1-naphthoic acid chloride in the presence of triethylamine.

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