Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H16Cl2N3O5S.Na.H2O |
Molecular Weight | 510.323 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(C)ON=C3C4=C(Cl)C=CC=C4Cl)C([O-])=O
InChI
InChIKey=SIGZQNJITOWQEF-VICXVTCVSA-M
InChI=1S/C19H17Cl2N3O5S.Na.H2O/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);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1
DescriptionSources: https://www.drugs.com/pro/dicloxacillin.htmlCurator's Comment: description was created based on several sources, including
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
Sources: https://www.drugs.com/pro/dicloxacillin.html
Curator's Comment: description was created based on several sources, including
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2362973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
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Target ID: GO:0009252 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6559051 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | PATHOCIL Approved UseIndications 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 Date1968 |
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Curative | PATHOCIL Approved UseIndications 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 Date1968 |
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Curative | PATHOCIL Approved UseIndications 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 Date1968 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45.02 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
110.93 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.51 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527863 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
25 mg/kg multiple, oral Dose: 25 mg/kg Route: oral Route: multiple Dose: 25 mg/kg Sources: |
unhealthy, 2-12 n = 49 Health Status: unhealthy Condition: skin infection Age Group: 2-12 Population Size: 49 Sources: |
Other AEs: Abdominal pain, Vomiting... Other AEs: Abdominal pain (mild, 1 patient) Sources: Vomiting (mild, 1 patient) |
2 g single, oral |
healthy, 22.2 n = 16 Health Status: healthy Age Group: 22.2 Sex: M+F Population Size: 16 Sources: |
|
0.5 g 4 times / day single, oral Dose: 0.5 g, 4 times / day Route: oral Route: single Dose: 0.5 g, 4 times / day Sources: |
healthy, 22.3 n = 16 Health Status: healthy Age Group: 22.3 Sex: M+F Population Size: 16 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abdominal pain | mild, 1 patient | 25 mg/kg multiple, oral Dose: 25 mg/kg Route: oral Route: multiple Dose: 25 mg/kg Sources: |
unhealthy, 2-12 n = 49 Health Status: unhealthy Condition: skin infection Age Group: 2-12 Population Size: 49 Sources: |
Vomiting | mild, 1 patient | 25 mg/kg multiple, oral Dose: 25 mg/kg Route: oral Route: multiple Dose: 25 mg/kg Sources: |
unhealthy, 2-12 n = 49 Health Status: unhealthy Condition: skin infection Age Group: 2-12 Population Size: 49 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: abstract |
no | |||
Page: 516.0 |
unlikely | |||
Page: 517.0 |
unlikely | |||
Page: 20.0 |
yes | |||
Page: 516.0 |
yes | |||
Page: 516.0 |
yes | |||
Page: 516.0 |
yes | yes (co-administration study) Comment: dicloxacillin decreased omeprazole AUC 67%, Cmax 60% Page: 516.0 |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 457.0 |
yes | yes (co-administration study) Comment: ketoconazole decreased flux of dicloxacillin Page: 457.0 |
PubMed
Title | Date | PubMed |
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Effect of dicloxacillin, oxacillin, and nafcillin upon staphylococcal population and rate of healing of soft-tissue lesions. | 1966 |
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Clinical, laboratory, and pharmacological studies of dicloxacillin. | 1966 |
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Necrotizing surgical site infection after tension-free vaginal tape. | 2004 Dec |
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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 |
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Cases from the aerospace medicine residents' teaching file: furunculosis. | 2004 Nov |
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Interactions of two amphiphilic penicillins with myoglobin in aqueous buffered solutions: a thermodynamic and spectroscopy study. | 2004 Nov-Dec |
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Methicillin-resistant Staphylococcus aureus in Europe, 1999-2002. | 2004 Sep |
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Laser-mediated photodynamic therapy of actinic cheilitis. | 2004 Sep-Oct |
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Biodegradable polymer releasing antibiotic developed for drainage catheter of cerebrospinal fluid: in vitro results. | 2005 Apr |
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Effect of the MDR1 C3435T variant and P-glycoprotein induction on dicloxacillin pharmacokinetics. | 2005 Apr |
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Rapidly growing mycobacteria in King Chulalongkorn Memorial Hospital and review of the literature in Thailand. | 2005 Aug |
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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 |
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Catheter-related septic thrombophlebitis of the great central veins successfully treated with low-dose streptokinase thrombolysis and antimicrobials. | 2005 Aug 22 |
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Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics. | 2005 Aug 24 |
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Diagnosis and management of staphylococcal infections of vascular grafts and stents. | 2005 Dec |
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Diagnosis and management of staphylococcal infections of pacemakers and cardiac defibrillators. | 2005 Dec |
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Antibiotics currently used in the treatment of infections caused by Staphylococcus aureus. | 2005 Dec |
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Thermodynamic study of the effect of ethanol on two amphiphilic penicillins. | 2005 Dec 1 |
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[Treatment of chronic bovine endometritis and factors for treatment success]. | 2005 Jan |
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Local gentamicin reduces sternal wound infections after cardiac surgery: a randomized controlled trial. | 2005 Jan |
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Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. | 2005 Jan |
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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 |
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Methicillin-resistant Staphylococcus aureus in community-acquired skin infections. | 2005 Jun |
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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 |
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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 |
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Influence of sub-inhibitory concentrations of antimicrobial agents on biofilm formation in indwelling medical devices. | 2005 Nov |
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Cheilitis glandularis in an African-American woman: response to antibiotic therapy. | 2005 Nov-Dec |
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Clonal spread of Staphylococcus aureus with reduced susceptibility to oxacillin in a dermatological hospital unit. | 2006 |
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Influence of SDS and two anionic hydrotropes on the micellized state of the triblock copolymer E71G7E71. | 2006 Apr 15 |
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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 |
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Pseudomonas aeruginosa otochondritis complicating localized cutaneous leishmaniasis: prevention of mutilation by early antibiotic therapy. | 2006 Aug |
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Placental transfer of antibiotics administered to the mother: a review. | 2006 Feb |
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Recurrent staphylococcal conjunctivitis associated with facial impetigo contagiosa. | 2006 Jan |
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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 |
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Human physiologically based pharmacokinetic model for ACE inhibitors: ramipril and ramiprilat. | 2006 Jan 6 |
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Development of a validated HPLC method for the determination of four penicillin antibiotics in pharmaceuticals and human biological fluids. | 2006 Jul |
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Surface and bulk properties of two anionic amphiphilic penicillins in a selective solvent. | 2006 Jul 20 |
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Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays. | 2006 Mar 15 |
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Spectrophotometric determination of flucloxacillin and dicloxacillin in pure and dosage forms. | 2006 May 1 |
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In vitro activity effects of combinations of cephalothin, dicloxacillin, imipenem, vancomycin and amikacin against methicillin-resistant Staphylococcus spp. strains. | 2006 Oct 12 |
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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 |
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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 |
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Clinical manifestations and outcome in Staphylococcus aureus endocarditis among injection drug users and nonaddicts: a prospective study of 74 patients. | 2006 Sep 11 |
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Antibiotic resistance of lactic acid bacteria and Bifidobacterium spp. isolated from dairy and pharmaceutical products. | 2007 Apr 1 |
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Direct extraction of penicillin G and derivatives from aqueous samples using a stoichiometrically imprinted polymer. | 2007 Jan 15 |
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Analysis of different beta-lactams antibiotics in pharmaceutical preparations using micellar electrokinetic capillary chromatography. | 2007 Jan 17 |
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Heterogeneity of human adipose blood flow. | 2007 Jan 20 |
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Oral beta-lactams applied to uncomplicated infections of skin and skin structures. | 2007 Mar |
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Characterisation of KLUA-9, a beta-lactamase from extended-spectrum cephalosporin-susceptible Kluyvera ascorbata, and genetic organisation of bla(KLUA-9). | 2007 Mar |
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Identification and characterization of degradation products of dicloxacillin in bulk drug and pharmaceutical dosage forms. | 2007 Mar 12 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/dicloxacillin.html
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.
Usual Adult Dose for Pneumonia: 500 mg orally every 6 hours for up to 21 days, depending on the nature and severity of the infection.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20308386
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).
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1500
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52019
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13412-64-1
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756726
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SUB11900MIG
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DBSALT001622
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23675786
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1189009
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267257
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DICLOXACILLIN SODIUM
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PRIMARY | Description: A white or almost white, crystalline powder.Solubility: Freely soluble in water and methanol R; soluble in ethanol (~750 g/l) TS.Category: Antibacterial drug.Storage: Dicloxacillin sodium should be kept in a tightly closed container, protected from light.Additional information: Even in the absence of light, Dicloxacillin sodium is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures.Definition: Dicloxacillin sodium contains not less than 88.0% of total penicillins calculated as dicloxacillin free acid (C19H17Cl2N3O5S) and with reference to the anhydrous substance. | ||
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34691
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DTXSID2049002
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4HZT2V9KX0
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CHEMBL893
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4HZT2V9KX0
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100000087924
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Dicloxacillin sodium
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SUB01675MIG
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m4364
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C47985
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ACTIVE MOIETY
SUBSTANCE RECORD