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Substance Name: Nafcillin Sodium
RN: 985-16-0
UNII: SY07234TTS
InChIKey: AYAPZOUDXCDGIF-FRFVDRIFSA-M

Note

  • A semi-synthetic antibiotic related to penicillin.

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data

Molecular Formula

  • C21-H22-N2-O5-S.Na

Molecular Weight

  • 436.4619
 

Names and Synonyms

Results Name

  • Nafcillin sodium

Name of Substance

  • Nafcillin sodium
  • Nafcillin sodium anhydrous

Synonyms

  • 6-(2-Ethoxy-1-naphthamido)penicillin sodium
  • BRL 1383
  • EINECS 213-574-4
  • Nafcillin sodium
  • Nafcillin sodium salt
  • Naftopen
  • Nallpen
  • Nallpen in plastic container
  • Sodium 6-(2-ethoxy-1-naphthamido)penicillanate
  • Sodium nafcillin
  • UNII-SY07234TTS
  • Unipen
  • Unipen in plastic container

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amido)-3,3-dimethyl-7-oxo-, monosodium salt, (2S,5R,6R)-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-, monosodium salt
  • Sodium (2S-(2alpha,5alpha,6beta))-6-(((2-ethoxy-1-naphthyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

Registry Numbers

CAS Registry Number

  • 985-16-0

FDA UNII

  • SY07234TTS

Related Registry Number

  • 147-52-4 (Parent)

System Generated Number

  • 0000985160

Molecular Formulas

Molecular Formula

  • C21-H22-N2-O5-S.Na

Molecular Formula Fragments

  • C21-H22-N2-O5-S
  • COMPONENT
  • Na

Structure Descriptors

InChI

1S/C21H22N2O5S.Na/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);/q;+1/p-1/t15-,16+,19-;/m1./s1

InChIKey

AYAPZOUDXCDGIF-FRFVDRIFSA-M

Smiles

CCOc1ccc2ccccc2c1C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].[Na+]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 450mg/kg/3D (450mg/kg) BLOOD: LEUKOPENIA

BLOOD: EOSINOPHILIA

LIVER: OTHER CHANGES
American Journal of Diseases of Children. Vol. 135, Pg. 52, 1981.
dog LD50 intravenous 633mg/kg (633mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 6, Pg. 220, 1964.
mammal (species unspecified) LD50 intramuscular 2955mg/kg (2955mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Toxicology and Applied Pharmacology. Vol. 6, Pg. 220, 1964.
mammal (species unspecified) LD50 intraperitoneal 1266mg/kg (1266mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toxicology and Applied Pharmacology. Vol. 6, Pg. 220, 1964.
man TDLo intravenous 429mg/kg/23D- (429mg/kg) BLOOD: AGRANULOCYTOSIS JAMA, Journal of the American Medical Association. Vol. 232, Pg. 1152, 1975.
man TDLo intravenous 3100mg/kg/18D (3100mg/kg) KIDNEY, URETER, AND BLADDER: PROTEINURIS

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: HEMATURIA
JAMA, Journal of the American Medical Association. Vol. 244, Pg. 2609, 1980.
mouse LD50 intravenous 1gm/kg (1000mg/kg)   Russian Pharmacology and Toxicology Vol. 37, Pg. 69, 1974.
women TDLo intravenous 3200mg/kg/20D (3200mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Gastroenterology. Vol. 88, Pg. 1960, 1993.
women TDLo intravenous 4560mg/kg/19D (4560mg/kg) BLOOD: AGRANULOCYTOSIS JAMA, Journal of the American Medical Association. Vol. 232, Pg. 1150, 1975.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -1.070 (none)   EST
Atmospheric OH Rate Constant 1.08E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.