Drug Details

General Information of the Drug (ID: DR4436)
Name
Oxacillin
Synonyms
oxacillin; Oxazocillin; MPI-penicillin; 66-79-5; Bactocill; Prostaphlin; OXACILLIN SODIUM; 5-Methyl-3-phenyl-4-isoxazolyl-penicillin; UNII-UH95VD7V76; CHEBI:7809; C19H19N3O5S; (5-methyl-3-phenyl-4-isoxazolyl)penicillin; (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; Penicillin, (5-methyl-3-phenyl-4-isoxazolyl)-; 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid; UH95VD7V76; (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; Ossacillina; Oxacilline; Oxacillinum; Prostaphlyn; Oxacilina; Ossacillina [DCIT]; MPi-PC; Oxacillin [INN:BAN]; Oxacilina [INN-Spanish]; Oxacilline [INN-French]; Oxacillinum [INN-Latin]; 1173-88-2; Oxacilina (TN); Oxacillin (INN); EINECS 200-635-5; Oxacillin,(S); (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2alpha,5alpha,6beta))-; CHEMBL819; Epitope ID:181859; SCHEMBL3817; DTXSID8023397; GTPL10943; phenylisoxazole-4-carboxamido)-7-; ZINC3875439; BDBM50350483; DB00713; 2,2-dimethyl-6beta-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3alpha-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamide)-7-oxo-; 5-Methyl-3-phenyl-4-isooxazolylpenicillin; oxo-4-thia-1-azabicyclo[3.2.0]heptane-; X6829; C07334; D08307; (2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-; Q418725; BRD-K96786677-236-01-6; BRD-K96786677-236-02-4; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2.alpha.,5.alpha.,6.beta.))-; 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-, (2S,5R,6R)-
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Molecular Type
Small molecule
Disease Bacterial infection [ICD-11: 1A00-1C4Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 6.3 mL/min/kg
Elimination
46% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 20 - 30 minutes
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 249.10051 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.07%
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
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Formula
C19H19N3O5S
PubChem CID
6196
Canonical SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
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
CAS Number
CAS 66-79-5
ChEBI ID
CHEBI:7809
TTD Drug ID
D0MB8I
DrugBank ID
DB00713
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Alpinia purpurata lectin      Alpinia purpurata     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
Pseudomonas aeruginosa Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 ApuL-oxacillin combination showed synergistic effect on the oxacillin-resistant isolates UFPEDA-670 and 671, which were not sensitive to lectin alone.
          Bisdemethoxycurcumin      Curcumin     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression UL54  Molecule Info 
Pathway MAP
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Antimicrobial effect of BDMC combined with antibiotics was superior to treatment with that of a single agent alone.
          Juglans regia      Juglans regia     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
Streptococcus pyogenes Microorganism model Streptococcus pyogenes
Escherichia coli Microorganism model Escherichia coli
Salmonella enterica serovar Typhi Microorganism model Salmonella enterica
Shigella species Microorganism model Shigella
Salmonella Paratyphi A Microorganism model Salmonella Paratyphi
Pseudomonas aeuginosa Microorganism model Pseudomonas aeruginosa
Acinetobacter baumannii Microorganism model Acinetobacter baumannii
Klebseilla pneumoniae Microorganism model Klebseilla pneumoniae
Citrobacter freuendii Microorganism model Citrobacter freuendii
Enterobacter cloacae Microorganism model Enterobacter cloacae
Bacillus subtilis Microorganism model Bacillus subtilis
Streptococcus pneumoniae Microorganism model Streptococcus pneumoniae
Micrococcus Microorganism model Micrococcus
Helicobacter pylori Microorganism model Helicobacter pylori
Campylobacter jejuni Microorganism model Campylobacter jejuni
Pasteurella multocida Microorganism model Pasteurella multocida
                    Experimental
                    Result(s)		 Ten times reduction in MICs was observed against Staphylococcus aureus when used in combination with oxacillin.
          Palmitic acid      Myrmecophilus sp. palM     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Combinatorial therapy with a low concentration of oxacillin controlled different laboratory and highly diversified clinical MRSA strains.
          Retinol      Daucus carota     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
Staphylococcus aureus ATCC 33591 Microorganism model Staphylococcus aureus
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Rhein in combination with AM or OX could lead to the development of new combinations of antibiotics against MRSA infection.
Target and Pathway
Target(s) Bacterial Penicillin binding protein (Bact PBP)  Molecule Info  [7]
References
Reference 1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 061490.
Reference 2 Antimicrobial potential of Alpinia purpurata lectin (ApuL): Growth inhibitory action, synergistic effects in combination with antibiotics, and antibiofilm activity. Microb Pathog. 2018 Nov;124:152-162.
Reference 3 The Mechanism of Bisdemethoxycurcumin Enhances Conventional Antibiotics against Methicillin-Resistant Staphylococcus aureus. Int J Mol Sci. 2020 Oct 26;21(21):7945.
Reference 4 Synergistic antimicrobial activity of Camellia sinensis and Juglans regia against multidrug-resistant bacteria. PLoS One. 2015 Feb 26;10(2):e0118431.
Reference 5 Combination Therapy Using Low-Concentration Oxacillin with Palmitic Acid and Span85 to Control Clinical Methicillin-Resistant Staphylococcus aureus. Antibiotics (Basel). 2020 Oct 8;9(10):682.
Reference 6 Synergistic effect of rhein in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. Exp Ther Med. 2012 Apr;3(4):608-612.
Reference 7 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.
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