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Cloxacillin Sodium

Names

[ CAS No. ]:
642-78-4

[ Name ]:
Cloxacillin Sodium

[Synonym ]:
Tegopen
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-, sodium salt, (2S,5R,6R)-, hydrate (1:1:1)
Staphybiotic
Sodium cloxacillin
cloxacillin sodium hydrate
Ankerbin
Cloxapen
Austrastaph
(2S,5R,6R)-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 Sodium Salt Monohydrate
Prevencilina P
Cloxacillin sodium salt hydrate
Sodium cloxacillin monohydrate
cloxacillin sodium monohydrate
Orbenin
Sodium (2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate (1:1:1)
MFCD00150735
Prostaphilin A
Ekvacillin
[(2S,5R,6R)-6-({[3-(2-Chlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylato-κO]sodium hydrate (1:1)
sodium, [(2S,5R,6R)-6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylato-κO]-, hydrate (1:1)
Cloxacillin Sodium Salt
EINECS 211-390-9
Gelstaph
Monosodium (2S,5R,6R)-6-(3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Monohydrate
Cloxacillin Sodium

Biological Activity

[Description]:

Cloxacillin sodium exhibits antibiotic efficacy, with a MIC of 256 mg/L for Staphylococcus aureus 25923[1][2][3].

[Related Catalog]:

Research Areas >> Infection
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Cloxacillin is an antibiotic useful for the study of a number of bacterial infections[1]. Cell Viability Assay[1] Cell Line: Strains M12 and M60. Concentration: 0.5 μg/mL. Incubation Time: 4-24 h. Result: Significantly reduced the bacterial numbers.

[In Vivo]

Cloxacillin sodium (50 mg/kg, Subcutaneously) results a significant antibiotic efficacy against S. aureus[3] Animal Model: Mice[2]. Dosage: 10 mg/kg (Pharmacological Analysis). Administration: Given subcutaneously. Result: Reached a maximal concentration in plasma of 8.4 μg/mL at 10 min and had a half-life of approximately 15 min. Animal Model: Mice injected with approximately 2 × 106 CFU of bacteria in 0.1 mL saline were aseptically injected into the right thigh muscle[3]. Dosage: 0–500 mg/kg. Administration: Subcutaneously in the nuchal region at 1 h after infection. Result: Resulted in a significant decrease in the number of viable S. aureus measured 18 h thereafter.

[References]

[1]. J C Anderson, et al. The Effect of Incorporation of Cloxacillin in Liposomes on Treatment of Experimental Staphylococcal Mastitis in Mice. J Vet Pharmacol Ther. 1986 Sep;9(3):303-9.

[2]. W Calame, et al. Influence of Etoposide and Cyclophosphamide on the Efficacy of Cloxacillin and Erythromycin in an Experimental Staphylococcal Infection. Antimicrob Agents Chemother. 1989 Jun;33(6):980-2.

[3]. Peter H Nibbering, et al. 99mTc-Labeled UBI 29-41 Peptide for Monitoring the Efficacy of Antibacterial Agents in Mice Infected With Staphylococcus Aureus. J Nucl Med. 2004 Feb;45(2):321-6.

Chemical & Physical Properties

[ Melting Point ]:
170ºC

[ Molecular Formula ]:
C19H17ClN3NaO5S

[ Molecular Weight ]:
475.878

[ Exact Mass ]:
475.058075

[ PSA ]:
140.87000

[ LogP ]:
1.54280

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents. Refrigerate.

[ Water Solubility ]:
H2O: 50 mg/mL, clear, colorless

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XH8750000
CHEMICAL NAME :
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(o-chlorophenyl)-5-methyl- 4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-, monosodium salt
CAS REGISTRY NUMBER :
642-78-4
LAST UPDATED :
199806
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C19-H17-C1-N3-O5-S.Na
MOLECULAR WEIGHT :
434.45
WISWESSER LINE NOTATION :
T45 ANV ESTJ F1 F1 GVQ CMV- DT5NOJ C1 ER BG &-NA-

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,232,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,322,1965
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,232,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1660 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,232,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,232,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,232,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,232,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
916 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 31,232,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1117 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,401,1995 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4495 No. of Facilities: 203 (estimated) No. of Industries: 2 No. of Occupations: 8 No. of Employees: 4409 (estimated) No. of Female Employees: 2017 (estimated)

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
36/37/38-42/43

[ Safety Phrases ]:
S22

[ WGK Germany ]:
2

[ RTECS ]:
XH8920000

[ HS Code ]:
2941109900

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2941109900


Related Compounds