Oxacillin

Oxacillin: Oxacillin

Systematic (IUPAC) name

(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-
1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-
azabicyclo[3.2.0]heptane-2-carboxylic acid

Clinical data

Trade names Bactocill

AHFS/Drugs.com monograph

MedlinePlus a685020

Pregnancy cat. ?

Legal status ?

Identifiers

CAS number 66-79-5^Y

ATC code J01CF04 QJ51CF04

PubChem CID 6098

DrugBank DB00713

ChemSpider 5873^Y

UNII UH95VD7V76^Y

KEGG D08307^Y

ChEBI CHEBI:49566^N

ChEMBL CHEMBL891^Y

Chemical data

Formula C₁₉H₁₉N₃O₅S

Mol. mass 401.436 g/mol

SMILES eMolecules & PubChem

InChI

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^Y
Key:LQOLIRLGBULYKD-JKIFEVAISA-N^Y

Physical data

Density 1.49 g/cm³

Boiling point 686.8 °C (1268 °F)

N(what is this?) (verify)

Oxacillin sodium (trade name Bactocill) is a narrow spectrum beta-lactam antibiotic of the penicillin class.

It was developed by Beecham.^[1]

Uses

Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by Staphylococcus aureus, it is widely used clinically in the US to treat penicillin-resistant Staphylococcus aureus. However, resistant strains called oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) are highly prevalent in the U.S. and the U.K.

References

^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 9780199534845. http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124. Retrieved 18 November 2010.

v · d · eAntibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)

Glycopeptide
inhibit PG chain elongation: Vancomycin^# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins/
(penams)

Extended sp.

aminopenicillins: Amoxicillin^# • Ampicillin^# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin

carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin

ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin

Narrow sp.

β-lactamase sensitive

Benzylpenicillin (G)^#: Clometocillin • Benzathine benzylpenicillin^# • Procaine benzylpenicillin^# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V)^#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin

β-lactamase resistant

Cloxacillin^# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/
(cephems)

1st (P Ec K)

Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)

Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd

Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)

Cefepime • Cefozopran • Cefpirome • Cefquinome

5th

Ceftobiprole • Ceftaroline fosamil

Veterinary

Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Tabtoxin

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam

Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

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Oxacillin

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Systematic (IUPAC) name
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl- 1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1- azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names	Bactocill
AHFS/Drugs.com	monograph
MedlinePlus	a685020
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	66-79-5^Y
ATC code	J01CF04 QJ51CF04
PubChem	CID 6098
DrugBank	DB00713
ChemSpider	5873^Y
UNII	UH95VD7V76^Y
KEGG	D08307^Y
ChEBI	CHEBI:49566^N
ChEMBL	CHEMBL891^Y
Chemical data
Formula	C₁₉H₁₉N₃O₅S
Mol. mass	401.436 g/mol
SMILES	eMolecules & PubChem
InChI 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^Y Key:LQOLIRLGBULYKD-JKIFEVAISA-N^Y
Physical data
Density	1.49 g/cm³
Boiling point	686.8 °C (1268 °F)
N(what is this?) (verify)

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Oxacillin

Uses

References

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