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Identification
Name Dicloxacillin
Accession Number DB00485 (APRD00916)
Type small molecule
Groups approved
Description

One of the penicillins which is resistant to penicillinase. [PubChem]
Structure Thumb
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
Salts Not Available
Brand names
Name Company
Dycill
Dynapen
Maclicine
Pathocil
Brand 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 Not Available
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
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility 3.63 mg/L Not Available
logP 2.91 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 2.96e-02 g/l ALOGPS
logP 3.19 ALOGPS
logP 2.91 ChemAxon
logS -4.2 ALOGPS
pKa (strongest acidic) 3.75 ChemAxon
pKa (strongest basic) -0.71 ChemAxon
physiological charge -1 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 112.74 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 111.44 ChemAxon
polarizability 42.86 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D02348 Link_out
KEGG Compound C06950 Link_out
PubChem Compound 18381 Link_out
PubChem Substance 46508182 Link_out
ChemSpider 17358 Link_out
ChEBI 4511 Link_out
ChEMBL 4511 Link_out
Therapeutic Targets Database DAP000435 Link_out
PharmGKB PA164749649 Link_out
RxList http://www.rxlist.com/cgi/generic2/diclox.htm Link_out
Drugs.com http://www.drugs.com/cdi/dicloxacillin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Dicloxacillin Link_out
ATC Codes
  • J01CF01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (51.3 KB)
Interactions
Drug Interactions
Drug Interaction
Acenocoumarol Dicloxacillin may decrease the anticoagulant effect of acenocoumarol.
Anisindione Dicloxacillin may decrease the anticoagulant effect of anisindione.
Demeclocycline Possible antagonism of action
Dicumarol Dicloxacillin may decrease the anticoagulant effect of dicumarol.
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
Methacycline Possible antagonism of action
Methotrexate The penicillin increases the effect and toxicity of methotrexate
Minocycline Possible antagonism of action
Oxytetracycline Possible antagonism of action
Rolitetracycline Possible antagonism of action
Tetracycline Possible antagonism of action
Warfarin Dicloxacillin may decrease the anticoagulant effect of warfarin.
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 Link_out
Gene: LMHCC_2184
SNPs: SNPJam Report Link_out

References:
  1. 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:
  1. 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:
  1. 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:
  1. 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:
  1. 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:
  1. 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:
  1. 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
Enzymes

1. Cytochrome P450 3A4

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yasuda K, Ranade A, Venkataramanan R, Strom S, Chupka J, Ekins S, Schuetz E, Bachmann K: A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug Metab Dispos. 2008 Aug;36(8):1689-97. Epub 2008 May 27. 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:
  1. 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:
  1. 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 February 08, 2013 16:19