DrugBank: Dicloxacillin (DB00485)

targets (7) transporters (2)

Identification

Name

Dicloxacillin

Accession Number

DB00485 (APRD00916)

Type

small molecule

Groups

approved

Description

One of the penicillins which is resistant to penicillinase. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Diclossacillina [DCIT]
Dicloxacilin
Dicloxacilina [INN-Spanish]
Dicloxacillin Sodium
Dicloxacilline [INN-French]
Dicloxacillinum [INN-Latin]
Dicloxacycline

Brand names

Dycill
Dynapen
Maclicine
Pathocil

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Penicillins

CAS number

3116-76-5

Weight

Average: 470.326
Monoisotopic: 469.026596773

Chemical Formula

C₁₉H₁₇Cl₂N₃O₅S

InChI Key

InChIKey=YFAGHNZHGGCZAX-JKIFEVAISA-N

InChI

InChI=1S/C19H17Cl2N3O5S/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)/t13-,14+,17-/m1/s1

Plain Text

IUPAC Name

(2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl)C(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Phenylpropenes
Penicillins
Cinnamaldehydes

Substructures

Hydroxy Compounds
Acetates
Amino Ketones
Phenylpropenes
Benzene and Derivatives
Aliphatic and Aryl Amines
Isoxazoles
Aryl Halides
Carboxylic Acids and Derivatives
Halobenzenes
Beta Lactams
Penicillins
Thiazoles
Heterocyclic compounds
Aromatic compounds
Cinnamaldehydes
Carboxamides and Derivatives
Oxazoles
Lactams
Imines
Azetidines
Thiazolidines

Pharmacology

Indication

Used to treat infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug.

Pharmacodynamics

Dicloxacillin is a beta-lactamase resistant penicillin similar to oxacillin. Dicloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of dicloxacillin results from the inhibition of cell wall synthesis and is mediated through dicloxacillin binding to penicillin binding proteins (PBPs). Dicloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.

Mechanism of action

Dicloxacillin exerts a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication. All penicillins inhibit the biosynthesis of the bacterial cell wall. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, dicloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that dicloxacillin interferes with an autolysin inhibitor.

Absorption

Absorption of the isoxazolyl penicillins after oral administration is rapid but incomplete: peak blood levels are achieved in 1-1.5 hours. Oral absorption of cloxacillin, dicloxacillin, oxacillin and nafcillin is delayed when the drugs are administered after meals.

Volume of distribution

Not Available

Protein binding

Binds to serum protein, mainly albumin.

Metabolism

Route of elimination

Dicloxacillin sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.

Half life

The elimination half-life for dicloxacillin is about 0.7 hour.

Clearance

Not Available

Toxicity

Oral LD₅₀ in rat is 3579 mg/kg. Symptoms of overexposure include irritation, rash, labored breathing, hives, itching, wheezing, nausea, chills, and fever.

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Sandoz inc
Teva pharmaceuticals usa inc
Glaxosmithkline
Wyeth ayerst laboratories
Apothecon inc div bristol myers squibb

Packagers

Apotheca Inc.
Apothecon
A-S Medication Solutions LLC
Bryant Ranch Prepack
Comprehensive Consultant Services Inc.
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Golden State Medical Supply Inc.
H.J. Harkins Co. Inc.
Innoviant Pharmacy Inc.
Kaiser Foundation Hospital
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Major Pharmaceuticals
Mead Johnson and Co.
Murfreesboro Pharmaceutical Nursing Supply
Novopharm Ltd.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prescription Dispensing Service Inc.
Redpharm Drug
Sandoz
Southwood Pharmaceuticals
Teva Pharmaceutical Industries Ltd.

Dosage forms

Form	Route	Strength
Capsule	Oral
Powder, for solution	Oral

Prices

Unit description	Cost	Unit
Dicloxacillin Sodium 500 mg capsule	1.25 USD	capsule
Dicloxacillin 500 mg capsule	1.2 USD	capsule
Dicloxacillin Sodium 250 mg capsule	0.69 USD	capsule
Dicloxacillin 250 mg capsule	0.66 USD	capsule

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Property	Value	Source
water solubility	3.63 mg/L	PhysProp
logP	3.7	PhysProp

Predicted Properties

Property	Value	Source
water solubility	2.96e-02 g/l	ALOGPS
logP	3.19	ALOGPS
logP	2.91	ChemAxon Molconvert
logS	-4.20	ALOGPS
pKa	13.64	ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	2	ChemAxon Molconvert
polar surface area	112.74	ChemAxon Molconvert
rotatable bond count	3	ChemAxon Molconvert
refractivity	111.44	ChemAxon Molconvert
polarizability	42.86	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D02348
KEGG Compound	C06950
PubChem Compound	18381
PubChem Substance	46508182
ChemSpider	17358
ChEBI	4511
ChEMBL	4511
Therapeutic Targets Database	DAP000435
PharmGKB	PA449296
Drug Product Database	0
RxList	http://www.rxlist.com/cgi/generic2/diclox.htm
Drugs.com	http://www.drugs.com/cdi/dicloxacillin.html
Wikipedia	http://en.wikipedia.org/wiki/Dicloxacillin

ATC Codes

J01CF01

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (51.3 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Take on an empty stomach, food decreases the availability.

Targets
1. Penicillin-binding protein 3 Pharmacological action: yes Actions: inhibitor UniProt ID: B8DCL9 Gene: LMHCC_2184 SNPs: SNPJam Report References: Gutkind GO, Ogueta SB, de Urtiaga AC, Mollerach ME, de Torres RA: Participation of PBP 3 in the acquisition of dicloxacillin resistance in Listeria monocytogenes. J Antimicrob Chemother. 1990 May;25(5):751-8. Pubmed 2. Penicillin-binding protein5 Pharmacological action: yes Actions: inhibitor UniProt ID: B8DD61 Gene: LMHCC_2773 SNPs: SNPJam Report References: Gutkind GO, Ogueta SB, de Urtiaga AC, Mollerach ME, de Torres RA: Participation of PBP 3 in the acquisition of dicloxacillin resistance in Listeria monocytogenes. J Antimicrob Chemother. 1990 May;25(5):751-8. Pubmed 3. Penicillin-binding protein 1b Pharmacological action: yes Actions: inhibitor Organism class: bacterial UniProt ID: Q7CRA4 Gene: pbp1b Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed 4. Penicillin-binding protein 2a Pharmacological action: yes Actions: inhibitor UniProt ID: Q8DNB6 Gene: pbp2a SNPs: SNPJam Report References: Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed 5. Penicillin-binding protein 3 Pharmacological action: yes Actions: inhibitor UniProt ID: Q75Y35 Gene: pbp3 SNPs: SNPJam Report References: Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed 6. Penicillin-binding protein 1A Pharmacological action: yes Actions: inhibitor Cell wall formation Organism class: bacterial UniProt ID: Q8DR59 Gene: pbpA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed 7. Penicillin-binding protein 2B Pharmacological action: yes Actions: inhibitor Organism class: bacterial UniProt ID: P0A3M6 Gene: penA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

Targets

1. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: B8DCL9 Link_out

Gene: LMHCC_2184
SNPs: SNPJam Report Link_out

References:

Gutkind GO, Ogueta SB, de Urtiaga AC, Mollerach ME, de Torres RA: Participation of PBP 3 in the acquisition of dicloxacillin resistance in Listeria monocytogenes. J Antimicrob Chemother. 1990 May;25(5):751-8. Pubmed

2. Penicillin-binding protein5

Pharmacological action: yes
Actions: inhibitor
UniProt ID: B8DD61 Link_out

Gene: LMHCC_2773
SNPs: SNPJam Report Link_out

References:

Gutkind GO, Ogueta SB, de Urtiaga AC, Mollerach ME, de Torres RA: Participation of PBP 3 in the acquisition of dicloxacillin resistance in Listeria monocytogenes. J Antimicrob Chemother. 1990 May;25(5):751-8. Pubmed

3. Penicillin-binding protein 1b

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q7CRA4 Link_out

Gene: pbp1b Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

4. Penicillin-binding protein 2a

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q8DNB6 Link_out

Gene: pbp2a
SNPs: SNPJam Report Link_out

References:

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

5. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out

Gene: pbp3
SNPs: SNPJam Report Link_out

References:

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

6. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q8DR59 Link_out

Gene: pbpA Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

7. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M6 Link_out

Gene: penA Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

Transporters
1. Oligopeptide transporter, small intestine isoform Actions: inhibitor Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products UniProt ID: P46059 Gene: SLC15A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed 2. Oligopeptide transporter, kidney isoform Actions: inhibitor Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides UniProt ID: Q16348 Gene: SLC15A2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

Transporters

1. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products

UniProt ID: P46059 Link_out

Gene: SLC15A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

2. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out

Gene: SLC15A2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.