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Substance Name: Nafcillin [INN:BAN]
RN: 147-52-4
UNII: 4CNZ27M7RV
InChIKey: GPXLMGHLHQJAGZ-JTDSTZFVSA-N

Note

  • A semi-synthetic antibiotic related to penicillin.

Molecular Formula

  • C21-H22-N2-O5-S

Molecular Weight

  • 414.4798
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Human Data

Names and Synonyms

Name of Substance

  • Nafcillin
  • Nafcillin [INN:BAN]

MeSH Heading

  • Nafcillin

Synonyms

  • (2-Ethoxy-1-naphthyl)penicillin
  • 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-
  • BRN 0862393
  • EINECS 205-690-9
  • HSDB 3133
  • Nafcilin-1
  • Nafcilina
  • Nafcilina [INN-Spanish]
  • Nafcillin
  • Nafcilline
  • Nafcilline [INN-French]
  • Nafcillinum
  • Nafcillinum [INN-Latin]
  • Naphcillin
  • Penicillin, (2-ethoxy-1-naphthalenyl)-
  • Penicillin, (2-ethoxy-1-naphthyl)-
  • UNII-4CNZ27M7RV

Systematic Names

  • 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-
  • Nafcillin

Registry Numbers

CAS Registry Number

  • 147-52-4

FDA UNII

  • 4CNZ27M7RV

Related Registry Number

  • 985-16-0 (mono-hydrochloride salt, anhydrous)

System Generated Number

  • 0000147524

Structure Descriptors

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

InChIKey

GPXLMGHLHQJAGZ-JTDSTZFVSA-N

Smiles

CCOc1ccc2ccccc2c1C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo unreported 1050mg/kg/1W- (1050mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS JAMA, Journal of the American Medical Association. Vol. 225, Pg. 178, 1973.