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Substance Name: Oxacillin [INN:BAN]
RN: 66-79-5
UNII: UH95VD7V76
InChIKey: UWYHMGVUTGAWSP-JKIFEVAISA-N

Note

  • An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.

Molecular Formula

  • C19-H19-N3-O5-S

Molecular Weight

  • 401.4411
 

Classification Codes

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

Names and Synonyms

Name of Substance

  • Oxacillin
  • Oxacillin [INN:BAN]

MeSH Heading

  • Oxacillin

Synonyms

  • 5-Methyl-3-phenyl-4-isoxazolyl-penicillin
  • EINECS 200-635-5
  • MPi-PC
  • MPI-penicillin
  • Ossacillina
  • Ossacillina [DCIT]
  • Oxacilina
  • Oxacilina [INN-Spanish]
  • Oxacillin
  • Oxacilline
  • Oxacilline [INN-French]
  • Oxacillinum
  • Oxacillinum [INN-Latin]
  • Oxazocillin
  • Penicillin, (5-methyl-3-phenyl-4-isoxazolyl)-
  • Prostaphlyn
  • UNII-UH95VD7V76

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamide)-7-oxo-
  • Oxacillin

Registry Numbers

CAS Registry Number

  • 66-79-5

FDA UNII

  • UH95VD7V76

Related Registry Numbers

  • 1173-88-2 (anhydrous monosodium salt)
  • 7240-38-2 (monosodium salt, monohydrate)

System Generated Number

  • 0000066795

Structure Descriptors

InChI

1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1

InChIKey

UWYHMGVUTGAWSP-JKIFEVAISA-N

Smiles

Cc1c(c(no1)c2ccccc2)C(=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 intravenous 2550mg/kg/17D (2550mg/kg) BLOOD: AGRANULOCYTOSIS Journal of Pediatrics. Vol. 90, Pg. 668, 1977.
guinea pig LD50 unreported 120mg/kg (120mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977.
infant TDLo intravenous 3800mg/kg/19D (3800mg/kg) BLOOD: AGRANULOCYTOSIS Journal of Pediatrics. Vol. 89, Pg. 769, 1976.
man TDLo intravenous 3800mg/kg/19D (3800mg/kg) BLOOD: AGRANULOCYTOSIS Journal of Pediatrics. Vol. 89, Pg. 769, 1976.
mouse LD50 intravenous 1490mg/kg (1490mg/kg)   Pharmaceutical Chemistry Journal Vol. 1, Pg. 245, 1967.
mouse LD50 oral 6500mg/kg (6500mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 95, 1982.
mouse LD50 unreported 28gm/kg (28000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977.
rat LD50 unreported 10gm/kg (10000mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 42(9), Pg. 10, 1977.
women TDLo intravenous 40mg/kg/7H-I (40mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Annals of Pharmacotherpy. Vol. 33, Pg. 1060, 1999.
women TDLo intravenous 5560mg/kg/20D (5560mg/kg) BLOOD: AGRANULOCYTOSIS Southern Medical Journal. Vol. 70, Pg. 1245, 1977.
women TDLo oral 200mg/kg/10D- (200mg/kg) GASTROINTESTINAL: OTHER CHANGES Southern Medical Journal. Vol. 77, Pg. 532, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 188 deg C   EXP
pKa Dissociation Constant 2.72 (none)   EXP
log P (octanol-water) 2.38 (none)   EXP
Water Solubility 27.8 mg/L 25 EST
Vapor Pressure 5.51E-15 mm Hg 25 EST
Henry's Law Constant 2.55E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.68E-11 cm3/molecule-sec 25 EST

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