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Substance Name: Cloxacillin [INN:BAN]
RN: 61-72-3
UNII: O6X5QGC2VB
InChIKey: LQOLIRLGBULYKD-JKIFEVAISA-N

Note

  • A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.

Molecular Formula

  • C19-H18-Cl-N3-O5-S

Molecular Weight

  • 435.8862
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Human Data
  • Mutation Data
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Names and Synonyms

Name of Substance

  • Cloxacillin
  • Cloxacillin [INN:BAN]

MeSH Heading

  • Cloxacillin

Synonyms

  • (3-(o-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(O-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
  • 6-(((3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 6-(3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
  • BRL 1621
  • Clossacillina
  • Clossacillina [DCIT]
  • Cloxacilina
  • Cloxacilina [INN-Spanish]
  • Cloxacillin
  • Cloxacilline
  • Cloxacilline [INN-French]
  • Cloxacillinum
  • Cloxacillinum [INN-Latin]
  • EINECS 200-514-7
  • HSDB 3042
  • Methocillin S
  • Methylchlorphenylisoxazoryl-penicillin
  • Syntarpen
  • UNII-O6X5QGC2VB

Systematic Names

  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(o-chlorophenyl)-S-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
  • Cloxacillin

Registry Numbers

CAS Registry Number

  • 61-72-3

FDA UNII

  • O6X5QGC2VB

Other Registry Numbers

  • 50763-55-8
  • 8056-79-9

System Generated Number

  • 0000061723

Structure Descriptors

InChI

1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1

InChIKey

LQOLIRLGBULYKD-JKIFEVAISA-N

Smiles

Cc1c(c(no1)c2ccccc2Cl)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 oral 5600mg/kg/5W- (5600mg/kg)   Israel Journal of Medical Sciences. Vol. 27, Pg. 159, 1991.
child TDLo oral 5600mg/kg/5W- (5600mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Israel Journal of Medical Sciences. Vol. 27, Pg. 159, 1991.
man TDLo oral 429mg/kg/10D- (429mg/kg) BLOOD: EOSINOPHILIA

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Annals of Pharmacotherpy. Vol. 26, Pg. 1241, 1992.
mouse LD50 intracrebral 8100ug/kg (8.1mg/kg)   Chemotherapy Vol. 17, Pg. 1111, 1969.
women TDLo intravenous 1680mg/kg/14D (1680mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

LIVER: LIVER FUNCTION TESTS IMPAIRED

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Postgraduate Medical Journal. Vol. 74, Pg. 59, 1998.
women TDLo oral 200mg/kg/5D-I (200mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: LIVER FUNCTION TESTS IMPAIRED
American Journal of Gastroenterology. Vol. 81, Pg. 1082, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 2.78 (none)   EXP
log P (octanol-water) 2.48 (none)   EXP
Water Solubility 13.9 mg/L 25 EST
Vapor Pressure 1.37E-15 mm Hg 25 EST
Henry's Law Constant 1.89E-17 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.44E-11 cm3/molecule-sec 25 EST

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