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
Clinical, laboratory, and pharmacological studies of dicloxacillin.
1966
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.
2002
In vitro susceptibility of Staphylococcus aureus towards amoxycillin-clavulanic acid, penicillin-clavulanic acid, dicloxacillin and cefuroxime.
2002 Aug
Staphylococcal scalded skin syndrome complicating acute generalized pustular psoriasis.
2002 Aug
Shorter courses of parenteral antibiotic therapy do not appear to influence response rates for children with acute hematogenous osteomyelitis: a systematic review.
2002 Aug 14
PKQuest: measurement of intestinal absorption and first pass metabolism - application to human ethanol pharmacokinetics.
2002 Aug 15
PKQuest: a general physiologically based pharmacokinetic model. Introduction and application to propranolol.
2002 Aug 15
[Staphylococcus aureus infections--the clinical picture and treatment].
2002 Aug 5
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.
2002 Jul-Aug
Compatibility between active components of a commercial drug.
2002 Oct
Photorhabdus species: bioluminescent bacteria as emerging human pathogens?
2003 Feb
High-performance thin-layer chromatography-bioautography for multiple antibiotic residues in cow's milk.
2003 Feb 5
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
Residues of beta-lactam antibiotics in bovine milk: confirmatory analysis by liquid chromatography tandem mass spectrometry after microbial assay screening.
2003 Jun
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
Necrotizing surgical site infection after tension-free vaginal tape.
2004 Dec
Dicloxacillin and erythromycin at high concentrations increase ICAM-1 expression by endothelial cells: a possible factor in the pathogenesis of infusion phlebitis.
2004 Feb
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
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
Catheter-related septic thrombophlebitis of the great central veins successfully treated with low-dose streptokinase thrombolysis and antimicrobials.
2005 Aug 22
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
Local gentamicin reduces sternal wound infections after cardiac surgery: a randomized controlled trial.
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
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
Influence of SDS and two anionic hydrotropes on the micellized state of the triblock copolymer E71G7E71.
2006 Apr 15
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
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
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
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