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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16Cl2N3O5S.Na
Molecular Weight 492.3099
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICLOXACILLIN SODIUM ANHYDROUS

SMILES

Cc1c(c(-c2c(cccc2Cl)Cl)no1)C(=N[C@]3([H])C(=O)N4[C@@]([H])(C(=O)O)C(C)(C)S[C@]34[H])[O-].[Na+]

InChI

InChIKey=GXOMMGAFBINOJY-SLINCCQESA-M
InChI=1S/C19H17Cl2N3O5S.Na/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);/q;+1/p-1/t13-,14+,17-;/m1./s1

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.drugbank.ca/drugs/DB00485 | https://www.ncbi.nlm.nih.gov/pubmed/6559051 | https://www.ncbi.nlm.nih.gov/pubmed/3923593 | https://www.ncbi.nlm.nih.gov/pubmed/20308386

Dicloxacillin sodium USP is a semisynthetic antibiotic substance which resists destruction by the enzyme penicillinase (beta-lactamase). It is monosodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-4- isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]heptane-2-carboxylate monohydrate. Like other β-lactam antibiotics, dicloxacillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. Dicloxacillin is administered orally via capsule form or powder for reconstitution.

Originator

Sources: Arzneimittel-Forschung Volume14 Issue11 Pages1238-41

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PATHOCIL

Approved Use

Indications and Usage. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Dicloxacillin sodium capsules USP and other antibacterial drugs, Dicloxacillin sodium capsules USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Dicloxacillin is indicated in the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug. Cultures and susceptibility tests should be performed initially to determine the causative organisms and their sensitivity to the drug (see CLINICAL PHARMACOLOGY – Susceptibility Plate Testing). Dicloxacillin may be used to initiate therapy in suspected cases of resistant staphylococcal infections prior to the availability of laboratory test results. The penicillinase-resistant penicillins should not be used in infections caused by organisms susceptible to penicillin G. If the susceptibility tests indicate that the infection is due to an organism other than a resistant staphylococcus, therapy should not be continued with a penicillinase-resistant penicillin.

Launch Date

-52099200000
Curative
PATHOCIL

Approved Use

Indications and Usage. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Dicloxacillin sodium capsules USP and other antibacterial drugs, Dicloxacillin sodium capsules USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Dicloxacillin is indicated in the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug. Cultures and susceptibility tests should be performed initially to determine the causative organisms and their sensitivity to the drug (see CLINICAL PHARMACOLOGY – Susceptibility Plate Testing). Dicloxacillin may be used to initiate therapy in suspected cases of resistant staphylococcal infections prior to the availability of laboratory test results. The penicillinase-resistant penicillins should not be used in infections caused by organisms susceptible to penicillin G. If the susceptibility tests indicate that the infection is due to an organism other than a resistant staphylococcus, therapy should not be continued with a penicillinase-resistant penicillin.

Launch Date

-52099200000
Curative
PATHOCIL

Approved Use

Indications and Usage. To reduce the development of drug-resistant bacteria and maintain the effectiveness of Dicloxacillin sodium capsules USP and other antibacterial drugs, Dicloxacillin sodium capsules USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Dicloxacillin is indicated in the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug. Cultures and susceptibility tests should be performed initially to determine the causative organisms and their sensitivity to the drug (see CLINICAL PHARMACOLOGY – Susceptibility Plate Testing). Dicloxacillin may be used to initiate therapy in suspected cases of resistant staphylococcal infections prior to the availability of laboratory test results. The penicillinase-resistant penicillins should not be used in infections caused by organisms susceptible to penicillin G. If the susceptibility tests indicate that the infection is due to an organism other than a resistant staphylococcus, therapy should not be continued with a penicillinase-resistant penicillin.

Launch Date

-52099200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
45.02 μg/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
79.97 μg/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13.62 μg/mL
0.25 g single, oral
dose: 0.25 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
24.28 μg/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
17 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
110.93 μg × h/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
207.4 μg × h/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
32.78 μg × h/mL
0.25 g single, oral
dose: 0.25 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
62.43 μg × h/mL
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.51 h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.71 h
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.38 h
0.25 g single, oral
dose: 0.25 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1.44 h
0.5 g single, oral
dose: 0.5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.7 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DICLOXACILLIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
25 mg/kg multiple, oral
dose: 25 mg/kg
route: oral
experiment_type: multiple
dose_type:
co-adm with
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/8396081/
    unhealthy, 2-12
    population: unhealthy
    age: 2-12
    sex:
    food_status:
    n:
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/8396081/
    Other AEs: Abdominal pain...
    Other AEs:
    Abdominal pain

    data_source:
    https://pubmed.ncbi.nlm.nih.gov/8396081/
    2 g single, oral
    dose: 2 g
    route: oral
    experiment_type: single
    dose_type:
    co-adm with
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/26527863/
      healthy, 22.2
      population: healthy
      age: 22.2
      sex: M+F
      food_status:
      n:
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/26527863/
      0.5 g 4 times / day single, oral
      dose: 0.5 g 4 times / day
      route: oral
      experiment_type: single
      dose_type:
      co-adm with
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/26527863/
        healthy, 22.3
        population: healthy
        age: 22.3
        sex: M+F
        food_status:
        n:
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/26527863/
        AEs

        AEs

        AESignificanceDosePopulation
        Abdominal pain 1 pts%
        25 mg/kg multiple, oral
        dose: 25 mg/kg
        route: oral
        experiment_type: multiple
        dose_type:
        co-adm with
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/8396081/
          unhealthy, 2-12
          population:
          age:
          sex:
          food_status:
          n:
          data_source:
          https://pubmed.ncbi.nlm.nih.gov/8396081/
          Overview

          Overview

          CYP3A4CYP2C9CYP2D6hERG



          OverviewOther

          Other InhibitorOther SubstrateOther Inducer





          Drug as perpetrator​Drug as victim

          Drug as victim

          TargetModalityActivityMetaboliteClinical evidence
          yes
          yes (co-administration study)
          Comment: ketoconazole decreased flux of dicloxacillin
          Page: 457
          PubMed

          PubMed

          TitleDatePubMed
          Necrotizing surgical site infection after tension-free vaginal tape.
          2004 Dec
          Application of ion-exchange cartridge clean-up in food analysis. VI. Determination of six penicillins in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry.
          2004 Jul 9
          Liquid chromatographic assay for dicloxacillin in plasma.
          2004 Jun 15
          Community-acquired methicillin-resistant Staphylococcus aureus among military recruits.
          2004 May
          Cases from the aerospace medicine residents' teaching file: furunculosis.
          2004 Nov
          Interactions of two amphiphilic penicillins with myoglobin in aqueous buffered solutions: a thermodynamic and spectroscopy study.
          2004 Nov-Dec
          Methicillin-resistant Staphylococcus aureus in Europe, 1999-2002.
          2004 Sep
          Laser-mediated photodynamic therapy of actinic cheilitis.
          2004 Sep-Oct
          Biodegradable polymer releasing antibiotic developed for drainage catheter of cerebrospinal fluid: in vitro results.
          2005 Apr
          Effect of the MDR1 C3435T variant and P-glycoprotein induction on dicloxacillin pharmacokinetics.
          2005 Apr
          Rapidly growing mycobacteria in King Chulalongkorn Memorial Hospital and review of the literature in Thailand.
          2005 Aug
          Comparative assessment of antibiotic susceptibility of coagulase-negative staphylococci in biofilm versus planktonic culture as assessed by bacterial enumeration or rapid XTT colorimetry.
          2005 Aug
          Catheter-related septic thrombophlebitis of the great central veins successfully treated with low-dose streptokinase thrombolysis and antimicrobials.
          2005 Aug 22
          Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics.
          2005 Aug 24
          Diagnosis and management of staphylococcal infections of vascular grafts and stents.
          2005 Dec
          Diagnosis and management of staphylococcal infections of pacemakers and cardiac defibrillators.
          2005 Dec
          Antibiotics currently used in the treatment of infections caused by Staphylococcus aureus.
          2005 Dec
          Thermodynamic study of the effect of ethanol on two amphiphilic penicillins.
          2005 Dec 1
          [Treatment of chronic bovine endometritis and factors for treatment success].
          2005 Jan
          Local gentamicin reduces sternal wound infections after cardiac surgery: a randomized controlled trial.
          2005 Jan
          Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
          2005 Jan
          Risk of cholestatic liver disease associated with flucloxacillin and flucloxacillin prescribing habits in the UK: cohort study using data from the UK General Practice Research Database.
          2005 Jul
          Methicillin-resistant Staphylococcus aureus in community-acquired skin infections.
          2005 Jun
          The relationship between inhibition of bacterial adhesion to a solid surface by sub-MICs of antibiotics and subsequent development of a biofilm.
          2005 Jun-Jul
          Confirmatory and quantitative analysis of beta-lactam antibiotics in bovine kidney tissue by dispersive solid-phase extraction and liquid chromatography-tandem mass spectrometry.
          2005 Mar 1
          Influence of sub-inhibitory concentrations of antimicrobial agents on biofilm formation in indwelling medical devices.
          2005 Nov
          Cheilitis glandularis in an African-American woman: response to antibiotic therapy.
          2005 Nov-Dec
          Clonal spread of Staphylococcus aureus with reduced susceptibility to oxacillin in a dermatological hospital unit.
          2006
          Influence of SDS and two anionic hydrotropes on the micellized state of the triblock copolymer E71G7E71.
          2006 Apr 15
          Positive effect of natural and negatively charged cyclodextrins on the stabilization of penicillins towards beta-lactamase degradation due to inclusion and external guest-host association. An NMR and MS study.
          2006 Apr 7
          Pseudomonas aeruginosa otochondritis complicating localized cutaneous leishmaniasis: prevention of mutilation by early antibiotic therapy.
          2006 Aug
          Placental transfer of antibiotics administered to the mother: a review.
          2006 Feb
          Recurrent staphylococcal conjunctivitis associated with facial impetigo contagiosa.
          2006 Jan
          Efficient approach for the reliable quantification and confirmation of antibiotics in water using on-line solid-phase extraction liquid chromatography/tandem mass spectrometry.
          2006 Jan 20
          Human physiologically based pharmacokinetic model for ACE inhibitors: ramipril and ramiprilat.
          2006 Jan 6
          Development of a validated HPLC method for the determination of four penicillin antibiotics in pharmaceuticals and human biological fluids.
          2006 Jul
          Surface and bulk properties of two anionic amphiphilic penicillins in a selective solvent.
          2006 Jul 20
          Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays.
          2006 Mar 15
          Spectrophotometric determination of flucloxacillin and dicloxacillin in pure and dosage forms.
          2006 May 1
          In vitro activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains.
          2006 Oct 12
          Determination of antimicrobials in sludge from infiltration basins at two artificial recharge plants by pressurized liquid extraction-liquid chromatography-tandem mass spectrometry.
          2006 Oct 13
          Spectrophotometric study of the reaction mechanism between DDQ as pi-acceptor and potassium iodate and flucloxacillin and dicloxacillin drugs and their determination in pure and in dosage forms.
          2006 Sep
          Clinical manifestations and outcome in Staphylococcus aureus endocarditis among injection drug users and nonaddicts: a prospective study of 74 patients.
          2006 Sep 11
          Antibiotic resistance of lactic acid bacteria and Bifidobacterium spp. isolated from dairy and pharmaceutical products.
          2007 Apr 1
          Direct extraction of penicillin G and derivatives from aqueous samples using a stoichiometrically imprinted polymer.
          2007 Jan 15
          Analysis of different beta-lactams antibiotics in pharmaceutical preparations using micellar electrokinetic capillary chromatography.
          2007 Jan 17
          Heterogeneity of human adipose blood flow.
          2007 Jan 20
          Oral beta-lactams applied to uncomplicated infections of skin and skin structures.
          2007 Mar
          Characterisation of KLUA-9, a beta-lactamase from extended-spectrum cephalosporin-susceptible Kluyvera ascorbata, and genetic organisation of bla(KLUA-9).
          2007 Mar
          Identification and characterization of degradation products of dicloxacillin in bulk drug and pharmaceutical dosage forms.
          2007 Mar 12
          Patents

          Sample Use Guides

          Usual Adult Dose for Bronchitis: 250 to 500 mg orally every 6 hours for 10 days, depending on the nature and severity of the infection.
          Route of Administration: Oral
          Bacteria strains ATCC 25923 and E19977 at a density of 10-6 Colony-forming unit /ml were exposed to Dicloxacillin concentrations that varied over a wide range (to obtain a full description of the pharmacological response), and quantification of the numbers of Colony-forming unit was performed after 5 and 24 h of incubation. The MICs of Dicloxacillin at pH 7.4 was 0.125 mg/liter (ATCC 25923) and 0.5 mg/liter (E19977).
          Name Type Language
          DICLOXACILLIN SODIUM ANHYDROUS
          Common Name English
          4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, MONOSODIUM SALT, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-
          Common Name English
          4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, SODIUM SALT (1:1), (2S,5R,6R)-
          Common Name English
          MONOSODIUM (2S,5R,6R)-6-(3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLECARBOXAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE
          Systematic Name English
          Code System Code Type Description
          EPA CompTox
          343-55-5
          Created by admin on Sat Jun 26 12:20:18 UTC 2021 , Edited by admin on Sat Jun 26 12:20:18 UTC 2021
          PRIMARY
          PUBCHEM
          23667628
          Created by admin on Sat Jun 26 12:20:18 UTC 2021 , Edited by admin on Sat Jun 26 12:20:18 UTC 2021
          PRIMARY
          ECHA (EC/EINECS)
          206-444-3
          Created by admin on Sat Jun 26 12:20:18 UTC 2021 , Edited by admin on Sat Jun 26 12:20:18 UTC 2021
          PRIMARY
          CAS
          343-55-5
          Created by admin on Sat Jun 26 12:20:18 UTC 2021 , Edited by admin on Sat Jun 26 12:20:18 UTC 2021
          PRIMARY
          DRUG BANK
          DBSALT000495
          Created by admin on Sat Jun 26 12:20:18 UTC 2021 , Edited by admin on Sat Jun 26 12:20:18 UTC 2021
          PRIMARY
          FDA UNII
          4CKS6MOL6Z
          Created by admin on Sat Jun 26 12:20:18 UTC 2021 , Edited by admin on Sat Jun 26 12:20:18 UTC 2021
          PRIMARY