CAS 147-52-4: Nafcillin

Description:Nafcillin is a semisynthetic penicillin antibiotic that is primarily used to treat infections caused by penicillinase-producing staphylococci. It is characterized by its beta-lactam structure, which is essential for its antibacterial activity. Nafcillin is resistant to degradation by certain beta-lactamases, making it effective against specific strains of bacteria that would typically be resistant to natural penicillins. The compound is typically administered via injection, as it is poorly absorbed from the gastrointestinal tract. Nafcillin exhibits a broad spectrum of activity against Gram-positive bacteria, particularly Staphylococcus aureus, and is less effective against Gram-negative organisms. Its pharmacokinetics involve rapid distribution in body tissues, with a relatively short half-life, necessitating multiple doses for effective treatment. Common side effects may include allergic reactions, gastrointestinal disturbances, and potential impacts on liver function. As with all antibiotics, appropriate susceptibility testing is recommended to ensure its effectiveness against the targeted bacterial strain.

Formula:C₂₁H₂₂N₂O₅S

InChI:InChI=1S/C21H22N2O5S/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)/t15-,16+,19-/m1/s1

InChI key:InChIKey=GPXLMGHLHQJAGZ-JTDSTZFVSA-N

SMILES:O=C(O)C1N2C(=O)C(NC(=O)C3=C(OCC)C=CC=4C=CC=CC43)C2SC1(C)C

Synonyms:
(2-Ethoxy-1-naphthyl)penicillin
(2S,5R,6R)-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-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-(2alpha,5alpha,6beta))-
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-
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)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-
6-(2-Ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Brn 0862393
Hsdb 3133
See more synonyms
Nafcilin-1
Nafcilina
Nafcilina [INN-Spanish]
Nafcilline
Nafcilline [INN-French]
Nafcillinum
Nafcillinum [INN-Latin]
Nallpen
Naphcillin
Penicillin, (2-ethoxy-1-naphthalenyl)-
Penicillin, (2-ethoxy-1-naphthyl)-
Unii-4Cnz27M7Rv
sodium (5R,6R)-6-[(2-ethoxynaphthalen-1-yl)carbamoyl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate