U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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:: 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.

Originator

Sources: Arzneimittel-Forschung Volume14 Issue11 Pages1238-41

Approval Year

Targets

Targets

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

-5.2099199E10
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

-5.2099199E10
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

-5.2099199E10
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
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)
Vomiting (mild, 1 patient)
Sources:
2 g single, oral
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
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

AEs

AESignificanceDosePopulation
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

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: 457.0
PubMed

PubMed

TitleDatePubMed
Effect of dicloxacillin, oxacillin, and nafcillin upon staphylococcal population and rate of healing of soft-tissue lesions.
1966
Prosthetic heart valve thrombosis during dicloxacillin therapy.
1999
Nephrotoxicity by dicloxacillin and gentamicin in 163 patients with intertrochanteric hip fractures.
2000
Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic.
2001
A rare case of osteomyelitis of the sternum in an adult with sickle cell disease.
2001 Feb
Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate.
2001 Feb
Metal complexes of antibiotic drugs. Studies on dicluxacillin complexes of FeII, FeIII, CoII NiII and CuII.
2001 Jul
Generation of class-selective monoclonal antibodies against the penicillin group.
2001 Jul
Verotoxin-producing Escherichia coli--an environment-induced emerging zoonosis in and around Calcutta.
2001 Mar
Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry.
2001 Mar 16
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization.
2001 Sep
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.
2002
PKQuest: a general physiologically based pharmacokinetic model. Introduction and application to propranolol.
2002 Aug 15
Clinical significance and epidemiology of NO-1, an unusual bacterium associated with dog and cat bites.
2002 Feb
A comparison of previous antibiotic therapy following isolation of MRSA versus MSSA in nursing home residents: a preliminary investigation.
2002 Nov-Dec
Antibiotic concentrations in serum and wound fluid after local gentamicin or intravenous dicloxacillin prophylaxis in cardiac surgery.
2003
Photorhabdus species: bioluminescent bacteria as emerging human pathogens?
2003 Feb
The use of a physiologically based pharmacokinetic model to evaluate deconvolution measurements of systemic absorption.
2003 Mar 19
Cowpox with severe generalized eruption, Finland.
2003 Nov
Large-volume sample stacking combined with separation by 2-hydroxypropyl-beta-cyclodextrin for analysis of isoxyzolylpenicillins by capillary electrophoresis.
2003 Sep
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
Community-acquired methicillin-resistant Staphylococcus aureus among military recruits.
2004 May
Interaction of dicloxacillin with warfarin.
2004 May
Biodegradable polymer releasing antibiotic developed for drainage catheter of cerebrospinal fluid: in vitro results.
2005 Apr
Rapidly growing mycobacteria in King Chulalongkorn Memorial Hospital and review of the literature in Thailand.
2005 Aug
Catheter-related septic thrombophlebitis of the great central veins successfully treated with low-dose streptokinase thrombolysis and antimicrobials.
2005 Aug 22
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
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 SDS and two anionic hydrotropes on the micellized state of the triblock copolymer E71G7E71.
2006 Apr 15
Recurrent staphylococcal conjunctivitis associated with facial impetigo contagiosa.
2006 Jan
Human physiologically based pharmacokinetic model for ACE inhibitors: ramipril and ramiprilat.
2006 Jan 6
Surface and bulk properties of two anionic amphiphilic penicillins in a selective solvent.
2006 Jul 20
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
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
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. 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
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