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Identification
NameDicloxacillin
Accession NumberDB00485  (APRD00916)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
DicloxacilinaSpanishINN
DicloxacillinGermanINN
DicloxacillinaNot AvailableDCIT
DicloxacillineFrenchINN
DicloxacillinumLatinINN
Salts
Name/CAS Structure Properties
Dicloxacillin Sodium
343-55-5
Thumb
  • InChI Key: GXOMMGAFBINOJY-SLINCCQESA-M
  • Monoisotopic Mass: 491.008541416
  • Average Mass: 492.308
DBSALT000495
Brand names
NameCompany
AmcidilMacroPhar
BetacloxEskayef
CloxagenGenamerica
DacocilinCCPC
DamacirDamacir
DicillinSandoz
DiclexMeiji
DiclocilBristol-Myers Squibb
DicloplusIcofarma
DiclosonUnison
DicloxalMagma
DicloxgenGeneral Drugs House
DicloxinaECU
DyclobiotMedifarma
DynapenNot Available
PosipenGlaxoSmithKline
QuimocyclarArmofar
StakloxActavis
TerbocloxilTerbol
ZiefmycinYung Shin
Brand mixtures
Brand NameIngredients
ADCDicloxacillin and Ampicillin
Kai Li DaDicloxacillin and Amoxicillin
RampiclixDicloxacillin and Ampicillin
Categories
CAS number3116-76-5
WeightAverage: 470.326
Monoisotopic: 469.026596773
Chemical FormulaC19H17Cl2N3O5S
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentPenicillins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Dichlorobenzenes; Aryl Chlorides; Isoxazoles; Thiazolidines; Tertiary Carboxylic Acid Amides; Secondary Carboxylic Acid Amides; Azetidines; Tertiary Amines; Hemiaminals; Thioethers; Enolates; Carboxylic Acids; Polyamines; Aminals; Organochlorides
Substituentsn-acyl-alpha amino acid or derivative; 1,3-dichlorobenzene; chlorobenzene; aryl halide; benzene; aryl chloride; thiazolidine; azole; isoxazole; tertiary carboxylic acid amide; azetidine; secondary carboxylic acid amide; hemiaminal; tertiary amine; carboxamide group; polyamine; aminal; enolate; thioether; carboxylic acid; carboxylic acid derivative; amine; organohalogen; organonitrogen compound; organochloride
Classification descriptionThis compound belongs to the penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
Pharmacology
IndicationUsed to treat infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drug.
PharmacodynamicsDicloxacillin 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 actionDicloxacillin 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.
AbsorptionAbsorption 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 distributionNot Available
Protein bindingBinds to serum protein, mainly albumin.
Metabolism
Route of eliminationDicloxacillin sodium is rapidly excreted as unchanged drug in the urine by glomerular filtration and active tubular secretion.
Half lifeThe elimination half-life for dicloxacillin is about 0.7 hour.
ClearanceNot Available
ToxicityOral 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8368
Blood Brain Barrier - 0.9903
Caco-2 permeable - 0.8957
P-glycoprotein substrate Non-substrate 0.6204
P-glycoprotein inhibitor I Non-inhibitor 0.8951
P-glycoprotein inhibitor II Non-inhibitor 0.9204
Renal organic cation transporter Non-inhibitor 0.9629
CYP450 2C9 substrate Non-substrate 0.8262
CYP450 2D6 substrate Non-substrate 0.905
CYP450 3A4 substrate Substrate 0.5977
CYP450 1A2 substrate Inhibitor 0.8592
CYP450 2C9 substrate Non-inhibitor 0.891
CYP450 2D6 substrate Non-inhibitor 0.918
CYP450 2C19 substrate Non-inhibitor 0.8832
CYP450 3A4 substrate Non-inhibitor 0.819
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9186
Ames test Non AMES toxic 0.6979
Carcinogenicity Carcinogens 0.5672
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 1.9946 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9996
hERG inhibition (predictor II) Non-inhibitor 0.8486
Pharmacoeconomics
Manufacturers
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Glaxosmithkline
  • Wyeth ayerst laboratories
  • Apothecon inc div bristol myers squibb
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
Powder, for solutionOral
Prices
Unit descriptionCostUnit
Dicloxacillin Sodium 500 mg capsule1.25USDcapsule
Dicloxacillin 500 mg capsule1.2USDcapsule
Dicloxacillin Sodium 250 mg capsule0.69USDcapsule
Dicloxacillin 250 mg capsule0.66USDcapsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubility3.63 mg/LNot Available
logP2.91HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility2.96e-02 g/lALOGPS
logP3.19ALOGPS
logP2.91ChemAxon
logS-4.2ALOGPS
pKa (strongest acidic)3.75ChemAxon
pKa (strongest basic)-0.71ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count2ChemAxon
polar surface area112.74ChemAxon
rotatable bond count3ChemAxon
refractivity111.44ChemAxon
polarizability42.86ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD02348
KEGG CompoundC06950
PubChem Compound18381
PubChem Substance46508182
ChemSpider17358
ChEBI4511
ChEMBLCHEMBL893
Therapeutic Targets DatabaseDAP000435
PharmGKBPA164749649
RxListhttp://www.rxlist.com/cgi/generic2/diclox.htm
Drugs.comhttp://www.drugs.com/cdi/dicloxacillin.html
WikipediaDicloxacillin
ATC CodesJ01CF01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(51.3 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolDicloxacillin may decrease the anticoagulant effect of acenocoumarol.
AnisindioneDicloxacillin may decrease the anticoagulant effect of anisindione.
DemeclocyclinePossible antagonism of action
DicoumarolDicloxacillin may decrease the anticoagulant effect of dicumarol.
DoxycyclinePossible antagonism of action
Ethinyl EstradiolThis anti-infectious agent could decrease the effect of the oral contraceptive
MestranolThis anti-infectious agent could decrease the effect of the oral contraceptive
MethacyclinePossible antagonism of action
MethotrexateThe penicillin increases the effect and toxicity of methotrexate
MinocyclinePossible antagonism of action
OxytetracyclinePossible antagonism of action
RolitetracyclinePossible antagonism of action
TetracyclinePossible antagonism of action
WarfarinDicloxacillin may decrease the anticoagulant effect of warfarin.
Food Interactions
  • Take on an empty stomach, food decreases the availability.

1. Penicillin-binding protein 3 (Pbp 3) (Pspb20)

Kind: protein

Organism: Listeria monocytogenes serotype 4a (strain HCC23)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 3 (Pbp 3) (Pspb20) B8DCL9 Details

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. D-alanyl-D-alanine carboxypeptidase DacA (DD-peptidase) (DD-carboxypeptidase) (CPase) (Penicillin-binding protein5) (PBP-5)

Kind: protein

Organism: Listeria monocytogenes serotype 4a (strain HCC23)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
D-alanyl-D-alanine carboxypeptidase DacA (DD-peptidase) (DD-carboxypeptidase) (CPase) (Penicillin-binding protein5) (PBP-5) B8DD61 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1b Q7CRA4 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2a Q8DNB6 Details

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

Kind: protein

Organism: Streptococcus pneumoniae

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 3 Q75Y35 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8DR59 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2B P0A3M6 Details

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

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

1. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 1 P46059 Details

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. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 2 Q16348 Details

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 September 16, 2013 17:10