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OXACILLIN

Names

[ CAS No. ]:
66-79-5

[ Name ]:
OXACILLIN

[Synonym ]:
OXACILLIN
[2S-(2,5,6)]-3,3-dimethyl-6-(methyl-3-phenylisoxaz-4-ole-carboxamide-7-oxy-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Oxazina
(2S,5R,6R)-3,3-Dimethyl-6-[(5-methyl-3-phenylisoxazol-4-yl)carbonylamino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Penstapho
(5-methyl-3-phenyl-isoxazol-4-yl)-penicillin
Bactocil
oxazocillin

Biological Activity

[Description]:

Oxacillin is an orally active synthetic penicillin with good bactericidal activity against staphylococci and other gram-positive pathogens[1].

[Related Catalog]:

Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Oxacillin inhibits gram positive pathogens with MICs of 0.05, 0.09, 0.32 and 0.80 μg/mL against group A streptococci, Pneutnococci, susceptible staphylococci and penicillin-resistant staphylococci, respectively[1]. The Oxacillin-resistant strains are highly resistant to other penicillins[1].

[In Vivo]

Oxacillin (50-800 mg/kg; s.c.; once) shows curative dose (CD50) of 253.3 mg/kg in mice infected with Staphylococcus aureus Evans. The oral CD50 of Oxacillin is 187.2 mg/kg[2]. Animal Model: CD-1 strain male albino mice infected with S. aureus Evans[2] Dosage: 50, 100, 200, 400 and 800 mg/kg Administration: Subcutaneous injection, once Result: Showed therapeutic activity with CD50 of 253.3 mg/kg.

Chemical & Physical Properties

[ Melting Point ]:
188ºC

[ Molecular Formula ]:
C19H19N3O5S

[ Molecular Weight ]:
401.43600

[ Exact Mass ]:
401.10500

[ PSA ]:
138.04000

[ LogP ]:
2.22410

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XH9000000
CHEMICAL NAME :
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4- isoxazolecarboxamide)-7-oxo-
CAS REGISTRY NUMBER :
66-79-5
LAST UPDATED :
199606
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C19-H19-N3-O5-S
MOLECULAR WEIGHT :
401.47
WISWESSER LINE NOTATION :
T45 ANV ESTJ F1 F1 GVQ CMV- DT5NOJ C1 FR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
200 mg/kg/10D-I
TOXIC EFFECTS :
Gastrointestinal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3800 mg/kg/19D-I
TOXIC EFFECTS :
Blood - agranulocytosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
2550 mg/kg/17D-I
TOXIC EFFECTS :
Blood - agranulocytosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
3800 mg/kg/19D-I
TOXIC EFFECTS :
Blood - agranulocytosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
5560 mg/kg/20D-I
TOXIC EFFECTS :
Blood - agranulocytosis
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1490 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
28 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
120 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Microorganism - not otherwise specified
DOSE/DURATION :
4 mg/L
REFERENCE :
JOBAAY Journal of Bacteriology. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1916- Volume(issue)/page/year: 170,1831,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3709 No. of Facilities: 231 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 11502 (estimated) No. of Female Employees: 9533 (estimated)

Synthetic Route

Precursor & DownStream


Related Compounds