| Identification | Back Directory | [Name]
nafcillin | [CAS]
147-52-4 | [Synonyms]
C07250
Nafcilin 1
Nafcillin acid
Westwood acid, naphthalene
6α-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]penicillanic acid
6-(2-Ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-(2-Ethoxy-1-naphthoylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- | [EINECS(EC#)]
205-690-9 | [Molecular Formula]
C21H22N2O5S | [MDL Number]
MFCD00864927 | [MOL File]
147-52-4.mol | [Molecular Weight]
414.48 |
| Hazard Information | Back Directory | [Originator]
Unipen,Wyeth,US,1964 | [Uses]
Antibacterial. | [Definition]
ChEBI: Nafcillin is a penicillin in which the substituent at position 6 of the penam ring is a (2-ethoxy-1-naphthoyl)amino group. It has a role as an antibacterial drug. It is a penicillin and a penicillin allergen. It is a conjugate acid of a nafcillin(1-). | [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 |
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