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Basic information

  • Name:

  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, sodiumsalt (1:1), (2S,5R,6R)-

  • CAS No.:

  • 985-16-0

  • Formula:
  • C21H22 N2 O5 S . Na
  • Synonyms:
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-, monosodium salt (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, monosodium salt,(2S,5R,6R)- (9CI); 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, monosodiumsalt, [2S-(2a,5a,6b)]-;6-(2-Ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid sodium salt; 6-(2-Ethoxy-1-naphthamido)penicillin sodium salt; BRL 1383;Nafcil; Nafcillin sodium; Nafcillin sodium salt; Naftopen; Naphthicillin;Sodium6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;Sodium 6-(2-ethoxy-1-naphthamido)penicillanate; Sodium nafcillin; Unipen; Wy3277

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Chemistry

Empirical Formula of Nafcillin Sodium (CAS NO.985-16-0): C21H21N2NaO5S
Molecular Weight: 436.4566 
EINECS: 213-574-4
storage temp.: Store at 0-5 °C 
Flash Point: 385.7 °C
Enthalpy of Vaporization: 109.6 kJ/mol
Boiling Point: 714.1 °C at 760 mmHg
Vapour Pressure: 2.11E-21 mmHg at 25 °C
Structure of Nafcillin Sodium (CAS NO.985-16-0):
              
IUPAC Name of Nafcillin Sodium (CAS NO.985-16-0): Sodium(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES: CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].[Na+]
Isomeric SMILES: CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].[Na+]
InChI: 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
 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 450mg/kg/3D (450mg/kg) LIVER: OTHER CHANGES
BLOOD: LEUKOPENIA
BLOOD: EOSINOPHILIA		 American Journal of Diseases of Children. Vol. 135, Pg. 52, 1981.
dog LD50 intravenous 633mg/kg (633mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Toxicology and Applied Pharmacology. Vol. 6, Pg. 220, 1964.
mammal (species unspecified) LD50 intramuscular 2955mg/kg (2955mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
BEHAVIORAL: MUSCLE WEAKNESS		 Toxicology and Applied Pharmacology. Vol. 6, Pg. 220, 1964.
mammal (species unspecified) LD50 intraperitoneal 1266mg/kg (1266mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
BEHAVIORAL: MUSCLE WEAKNESS
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: INTERSTITIAL NEPHRITIS
KIDNEY, URETER, AND BLADDER: PROTEINURIS
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) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
LIVER: "JAUNDICE, CHOLESTATIC"
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.
 

Safety Profile

Moderately toxic by intraperitoneal and intravenous routes. Human systemic effects by intravenous route: interstitial nephritis (kidney damage), proteinuria (protein in the urine), hematuria (blood in the urine), leukopenia (reduced number of leukocytes in the blood), rosinophilia, agranulocytosis (reduced levels of granulocytes) and liver changes. When heated to decomposition it emits very toxic fumes of NOx, SOx, and Na2O.

Specification

 Nafcillin Sodium ,its cas register number is 985-16-0. It also can be called 6-(2-Ethoxy-1-naphthamido)penicillin sodium ; Nafcillin and Sodium nafcillin .As a beta-lactamase-resistant penicillin, Nafcillin Sodium (CAS NO.985-16-0) is used to treat infections caused by Gram-positive bacteria, that are resistant to other penicillins. It is particularly indicated in the treatment of staphylococcal infections, except those caused by MRSA.

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