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Identification
NameDicloxacillin
Accession NumberDB00485  (APRD00916)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

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

Structure
Thumb
Synonyms
(2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Dicloxacilina
Dicloxacillin
Dicloxacillina
Dicloxacilline
Dicloxacillinum
External Identifiers
  • Bayer 5488
  • BRL 1702
  • P 1011
  • R 13423
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dicloxacillin Sodiumcapsule500 mg/1oralA S Medication Solutions Llc1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralPd Rx Pharmaceuticals, Inc.2011-01-20Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralPhysicians Total Care, Inc.2004-08-17Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralRebel Distributors Corp1971-04-01Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralA S Medication Solutions Llc1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralH.J. Harkins Company, Inc.2011-01-20Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralSTAT Rx USA LLC2011-01-20Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralAvera Mc Kennan Hospital2015-10-01Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralA S Medication Solutions Llc1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralSandoz Inc1971-04-01Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralA S Medication Solutions Llc1971-04-01Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralSandoz Inc1971-04-01Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralRed Pharm Drug Inc.2011-01-20Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralA S Medication Solutions Llc1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralLiberty Pharmaceuticals, Inc.1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralPd Rx Pharmaceuticals, Inc.2011-01-20Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-19Not applicableUs
Dicloxacillin Sodiumcapsule250 mg/1oralLiberty Pharmaceuticals, Inc.1971-04-01Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralPd Rx Pharmaceuticals, Inc.1971-04-01Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralPd Rx Pharmaceuticals, Inc.1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Dicloxacillin Sodiumcapsule500 mg/1oralPhysicians Total Care, Inc.1992-10-21Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
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 mixturesNot Available
Salts
Name/CASStructureProperties
Dicloxacillin sodium
343-55-5
Thumb
  • InChI Key: GXOMMGAFBINOJY-SLINCCQESA-M
  • Monoisotopic Mass: 491.008541416
  • Average Mass: 492.308
DBSALT000495
Dicloxacillin sodium monohydrate
ThumbNot applicableDBSALT001622
Categories
UNIICOF19H7WBK
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)[[email protected]]2NC(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 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].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Oxazole
  • Isoxazole
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Oxacycle
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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.
Related Articles
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.
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.8368
Blood Brain Barrier-0.9903
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.6204
P-glycoprotein inhibitor INon-inhibitor0.8951
P-glycoprotein inhibitor IINon-inhibitor0.9204
Renal organic cation transporterNon-inhibitor0.9629
CYP450 2C9 substrateNon-substrate0.8262
CYP450 2D6 substrateNon-substrate0.905
CYP450 3A4 substrateSubstrate0.5977
CYP450 1A2 substrateInhibitor0.8592
CYP450 2C9 inhibitorNon-inhibitor0.891
CYP450 2D6 inhibitorNon-inhibitor0.918
CYP450 2C19 inhibitorNon-inhibitor0.8832
CYP450 3A4 inhibitorNon-inhibitor0.819
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9186
Ames testNon AMES toxic0.6979
CarcinogenicityCarcinogens 0.5672
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.9946 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9996
hERG inhibition (predictor II)Non-inhibitor0.8486
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Glaxosmithkline
  • Wyeth ayerst laboratories
  • Apothecon inc div bristol myers squibb
Packagers
Dosage forms
FormRouteStrength
Capsuleoral250 mg/1
Capsuleoral500 mg/1
Prices
Unit descriptionCostUnit
Dicloxacillin Sodium 500 mg capsule1.25USD capsule
Dicloxacillin 500 mg capsule1.2USD capsule
Dicloxacillin Sodium 250 mg capsule0.69USD capsule
Dicloxacillin 250 mg capsule0.66USD capsule
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 Solubility0.0296 mg/mLALOGPS
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 Area112.74 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.44 m3·mol-1ChemAxon
Polarizability42.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Sallmann, A. and Pfister, R.; U.S.Patent 3,558,690; January 26,1971; assigned to Geigy Chemical Corporation.
Sallmann, A. and Pfister, R.; US. Patent 3,652,762; March 28,1972; assigned to Ciba Geigy Corporation.

General ReferencesNot Available
External Links
ATC CodesJ01CF01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (51.3 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolDicloxacillin may decrease the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Dicloxacillin.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Dicloxacillin.
BiotinThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Biotin.
DemeclocyclineThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Demeclocycline.
DicoumarolDicloxacillin may decrease the anticoagulant activities of Dicoumarol.
DoxycyclineThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Doxycycline.
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Dicloxacillin.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Dicloxacillin.
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Dicloxacillin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Dicloxacillin.
MinocyclineThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Minocycline.
Mycophenolate mofetilThe serum concentration of the active metabolites of Mycophenolate mofetil can be reduced when Mycophenolate mofetil is used in combination with Dicloxacillin resulting in a loss in efficacy.
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Dicloxacillin resulting in a loss in efficacy.
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Dicloxacillin.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Dicloxacillin.
OxytetracyclineThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Oxytetracycline.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Dicloxacillin.
ProbenecidThe serum concentration of Dicloxacillin can be increased when it is combined with Probenecid.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Dicloxacillin.
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Dicloxacillin.
TetracyclineThe therapeutic efficacy of Dicloxacillin can be decreased when used in combination with Tetracycline.
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Dicloxacillin.
WarfarinDicloxacillin may decrease the anticoagulant activities of Warfarin.
Food Interactions
  • Take on an empty stomach, food decreases the availability.

Targets

Kind
Protein
Organism
Listeria monocytogenes serotype 4a (strain HCC23)
Pharmacological action
yes
Actions
inhibitor
General Function:
Involved in response to antibiotic
Specific Function:
Not Available
Gene Name:
LMHCC_2184
Uniprot ID:
B8DCL9
Molecular Weight:
74541.995 Da
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:2115510 ]
Kind
Protein
Organism
Listeria monocytogenes serotype 4a (strain HCC23)
Pharmacological action
yes
Actions
inhibitor
General Function:
Involved in serine-type D-Ala-D-Ala carboxypeptidase activity
Specific Function:
Not Available
Gene Name:
LMHCC_2773
Uniprot ID:
B8DD61
Molecular Weight:
48182.67 Da
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:2115510 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp1b
Uniprot ID:
Q7CRA4
Molecular Weight:
89479.92 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Not Available
Gene Name:
pbp2a
Uniprot ID:
Q8DNB6
Molecular Weight:
80797.94 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not Available
Gene Name:
pbp3
Uniprot ID:
Q75Y35
Molecular Weight:
45209.84 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Cell wall formation.
Gene Name:
pbpA
Uniprot ID:
Q8DR59
Molecular Weight:
79700.9 Da
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:7447421 ]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M6
Molecular Weight:
73872.305 Da
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:7447421 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
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 xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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. doi: 10.1124/dmd.108.020701. Epub 2008 May 27. [PubMed:18505790 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
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.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
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:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
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:15567297 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on February 04, 2016 11:46