Dicloxacillin

Title: Dicloxacillin
CAS Registry Number: 3116-76-5
CAS Name: (2S,5R,6R)-6-[[[3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: 6-[3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido]penicillanic acid; 3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylpenicillin
Manufacturers' Codes: BRL-1702
Trademarks: Maclicine (Christiaens)
Molecular Formula: C19H17Cl2N3O5S
Molecular Weight: 470.33
Percent Composition: C 48.52%, H 3.64%, Cl 15.08%, N 8.93%, O 17.01%, S 6.82%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn: J. H. C. Naylor, GB 978299; eidem, US 3239507 (1965, 1969 to Beecham). Toxicity data: C. Gloxhuber et al., Arzneim.-Forsch. 15, 322 (1965). Series of articles on chemistry, pharmacology and toxicology: ibid. 322-348; Matsuzaki, Jpn. J. Antibiot. 21, 274, 284 (1968), C.A. 70, 95267z, 95265x (1969).
Derivative Type: Sodium salt monohydrate
CAS Registry Number: 13412-64-1
Additional Names: Sodium dicloxacillin monohydrate
Manufacturers' Codes: P-1011
Trademarks: Brispen; Dichlor-Stapenor (Bayer); Diclocil (BMS); Dycill (SKB); Dynapen (Apothecon); Noxaben (Unifa); Pathocil (Wyeth); Pen-Sint (Cophar); Syntarpen (Polfa); Veracillin (Ayerst)
Molecular Formula: C19H16Cl2N3NaO5S.H2O
Molecular Weight: 510.32
Percent Composition: C 44.72%, H 3.56%, Cl 13.89%, N 8.23%, Na 4.50%, O 18.81%, S 6.28%
Properties: Crystals, dec 222-225°. [a]D20 +127.2° (water). Sol in water, methanol; less sol in butanol; slightly sol in acetone and the usual organic solvents. LD50 in mice (g/kg): 0.9 i.v.; in rats (g/kg): 0.63 i.p.; >5 orally (Gloxhuber).
Optical Rotation: [a]D20 +127.2° (water)
Toxicity data: LD50 in mice (g/kg): 0.9 i.v.; in rats (g/kg): 0.63 i.p.; >5 orally (Gloxhuber)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.
Dicobalt Octacarbonyl Dicofol Dicrotophos Dicryl Dictamnine

Dicloxacillin
Dicloxacillin.svg
Systematic (IUPAC) name
(2S,5R,6R)-6-{[3-(2,6-dichlorophenyl)-5-methyl-
oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-
1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a685017
Pregnancy cat. B2 (AU) B (US)
Legal status Prescription Only (S4) (AU) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 60 to 80%
Protein binding 98%
Metabolism Hepatic
Half-life 0.7 hours
Excretion Renal and biliary
Identifiers
CAS number 3116-76-5 YesY
ATC code J01CF01 QJ51CF01
PubChem CID 18381
DrugBank DB00485
ChemSpider 17358 YesY
UNII COF19H7WBK YesY
KEGG D02348 YesY
ChEBI CHEBI:4511 YesY
ChEMBL CHEMBL893 YesY
Chemical data
Formula C19H17Cl2N3O5S 
Mol. mass 470.327 g/mol
 YesY (what is this?)  (verify)

Dicloxacillin (INN) is a narrow-spectrum beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus,[1] which would otherwise be resistant to most penicillins. It is very similar to flucloxacillin and these two agents are considered interchangeable. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).