Details of the Drug

General Information of Drug (ID: DMTAFY4)

Drug Name

Oxacillin

Synonyms

Bactocill; Ossacillina; Oxacilina; Oxacilline; Oxacillinum; Oxazocillin; Oxazocilline; Prostaphlin; Prostaphlyn; OXACILLIN SODIUM; Ossacillina [DCIT]; Sodium oxacillin; Bactocill (TN); MPI-penicillin; MPi-PC; Oxacilina (TN); Oxacilina [INN-Spanish]; Oxacillin (INN); Oxacillin [INN:BAN]; Oxacilline [INN-French]; Oxacillinum [INN-Latin]; Penicillin, Methylphenylisoxazolyl; Oxacillin, Monosodium Salt, Anhydrous; (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; (2S,5R,6R)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (5-methyl-3-phenyl-4-isoxazolyl)penicillin; 2,2-dimethyl-6beta-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3alpha-carboxylic acid; 5-Methyl-3-phenyl-4-isoxazolyl-penicillin; 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid

Indication

Disease Entry	ICD 11	Status	REF
Bacterial infection	1A00-1C4Z	Approved	[1]

Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

401.4

Topological Polar Surface Area (xlogp)

2.4

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

7

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Clearance: The drug present in the plasma can be removed from the body at the rate of 6.3 mL/min/kg [3]
Elimination: 46% of drug is excreted from urine in the unchanged form [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 20 - 30 minutes [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 249.10051 micromolar/kg/day [4]
Unbound Fraction: The unbound fraction of drug in plasma is 0.07% [3]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.19 L/kg [3]

Chemical Identifiers

Formula: C19H19N3O5S
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
Canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI: InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
InChIKey: UWYHMGVUTGAWSP-JKIFEVAISA-N

Cross-matching ID

PubChem CID: 6196
ChEBI ID: CHEBI:7809
CAS Number: 66-79-5
DrugBank ID: DB00713
TTD ID: D0MB8I
VARIDT ID: DR00647
INTEDE ID: DR2321
ACDINA ID: D01306

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Binder	[5]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
PenA beta-lactamase (penA1)_{Main DME}	DE2ARDZ	O08350_BURCE	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Oxacillin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Anisindione	DM2C48U	Moderate	Increased risk of bleeding by the combination of Oxacillin and Anisindione.	Coagulation defect [3B10]	[16]
Mycophenolic acid	DMU65NK	Moderate	Altered absorption of Oxacillin due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[17]
Probenecid	DMMFWOJ	Minor	Decreased elimination of Oxacillin caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[18]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Hydrochloric acid	E00015	313	Acidulant
Dextrose monohydrate	E00538	22814120	Binding agent; Diluent; Flavoring agent; Tonicity agent
Disodium hydrogenorthophosphate	E00283	24203	Buffering agent; Complexing agent
Sodium citrate dihydrate	E00369	71474	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Sodium phosphate dibasic dihydrate	E00498	6451167	Buffering agent; Complexing agent
Water	E00035	962	Solvent
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⏷ Show the Full List of 7 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Oxacillin 1g/50ml solution	1g/50ml	Solution	Intravenous
Oxacillin 10g/100ml powder	10g/100ml	Powder	Intravenous
Oxacillin 1g/20ml powder	1g/20ml	Powder	Intravenous

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 061490.
2	BDDCS applied to over 900 drugs
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Novel anion liposome-encapsulated antisense oligonucleotide restores susceptibility of methicillin-resistant Staphylococcus aureus and rescues mice... Antimicrob Agents Chemother. 2009 Jul;53(7):2871-8.
6	Characterization of the penA and penR genes of Burkholderia cepacia 249 which encode the chromosomal class A penicillinase and its LysR-type transcriptional regulator. Antimicrob Agents Chemother. 1997 Nov;41(11):2399-405.
7	Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80.
8	Bacteriological characteristics of Staphylococcus aureus isolates from humans and bulk milk. J Dairy Sci. 2008 Feb;91(2):564-9.
9	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10	Activities of antibiotics against methicillin-resistant Staphylococcus aureus with particular reference to synergetic effect between ticarcillin and fosfomycin on penicillinase non-producing methicillin-resistant S. aureus. Jpn J Antibiot. 1993 Jun;46(6):421-7.
11	Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
12	Penicillin-binding protein sensitive to cephalexin in sporulation of Bacillus cereus. Microbiol Res. 1997 Sep;152(3):227-32.
13	Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30.
14	Relationship between penicillin-binding protein patterns and beta-lactamases in clinical isolates of Bacteroides fragilis with different susceptibility to beta-lactam antibiotics. J Med Microbiol. 2004 Mar;53(Pt 3):213-21.
15	Resistance of Pseudomonas aeruginosa to cefsulodin: modification of penicillin-binding protein 3 and mapping of its chromosomal gene. J Antimicrob Chemother. 1990 Apr;25(4):513-23.
16	Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
17	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
18	Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]