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]
Staphylococcal pneumonia N.A. Approved [2]
Staphylococcus aureus infection N.A. Approved [2]
Sinusitis CA0A.Z Investigative [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 401.4
Logarithm of the Partition Coefficient (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 [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 6.3 mL/min/kg [4]
Elimination
46% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 20 - 30 minutes [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 249.10051 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.07% [4]
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 [4]
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
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
PenA beta-lactamase (penA1)
Main DME
DE2ARDZ O08350_BURCE Substrate [7]
Molecular Interaction Atlas (MIA) 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] [8]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Oxacillin due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [9]
Probenecid DMMFWOJ Minor Decreased elimination of Oxacillin caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [10]

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
⏷ 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 Oxacillin FDA Label
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 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
6 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.
7 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.
8 Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
9 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
10 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]