Dicloxacillin

Identification

Summary

Dicloxacillin is a penicillin used to treat penicillinase-producing bacterial infections that are susceptible to the drug.

Generic Name
Dicloxacillin
DrugBank Accession Number
DB00485
Background

One of the penicillins which is resistant to penicillinase.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 470.326
Monoisotopic: 469.026596773
Chemical Formula
C19H17Cl2N3O5S
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 IDs
  • Bayer 5488
  • BRL 1702
  • BRL-1702
  • P 1011
  • R 13423
  • R-13423

Pharmacology

Indication

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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.

TargetActionsOrganism
APenicillin-binding protein 3
inhibitor
Listeria monocytogenes serotype 4b str. LL195
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
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

Adverse Effects
Medicalerrors
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Dicloxacillin.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Dicloxacillin.
AcemetacinAcemetacin may decrease the excretion rate of Dicloxacillin which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be increased when combined with Dicloxacillin.
AlbendazoleThe metabolism of Albendazole can be increased when combined with Dicloxacillin.
AlectinibThe metabolism of Alectinib can be increased when combined with Dicloxacillin.
AlpelisibThe metabolism of Alpelisib can be increased when combined with Dicloxacillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Dicloxacillin.
AminophyllineThe metabolism of Aminophylline can be increased when combined with Dicloxacillin.
AmiodaroneThe metabolism of Amiodarone can be increased when combined with Dicloxacillin.
Interactions
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Food Interactions
  • Take on an empty stomach. Food decreases bioavailability.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Dicloxacillin sodium4HZT2V9KX013412-64-1SIGZQNJITOWQEF-VICXVTCVSA-M
Dicloxacillin sodium anhydrous4CKS6MOL6Z343-55-5GXOMMGAFBINOJY-SLINCCQESA-M
Product Images
International/Other Brands
Amcidil (MacroPhar) / Betaclox (Eskayef) / Cloxagen (Genamerica) / Dacocilin (CCPC) / Damacir (Damacir) / Dicillin (Sandoz) / Diclex (Meiji) / Diclocil (Bristol-Myers Squibb) / Dicloplus (Icofarma) / Dicloson (Unison) / Dicloxal (Magma) / Dicloxgen (General Drugs House) / Dicloxina (ECU) / Dyclobiot (Medifarma) / Dynapen / Posipen (GlaxoSmithKline) / Quimocyclar (Armofar) / Staklox (Actavis) / Terbocloxil (Terbol) / Ziefmycin (Yung Shin)
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dicloxacillin SodiumCapsule250 mg/1OralAvera McKennan Hospital2016-06-142017-05-24US flag
Dicloxacillin SodiumCapsule500 mg/1Oralbryant ranch prepack1990-09-302012-01-01US flag
Dicloxacillin SodiumCapsule500 mg/1OralRed Pharm Drug, Inc.2011-01-20Not applicableUS flag67296 012220180907 15195 1qzqsvp
Dicloxacillin SodiumCapsule500 mg/1OralAvera McKennan Hospital2016-01-282017-05-24US flag
Dicloxacillin SodiumCapsule250 mg/1OralA-S Medication Solutions1990-09-30Not applicableUS flag50090 011620180907 15195 1chacwq
Dicloxacillin SodiumCapsule250 mg/1OralAvera McKennan Hospital2015-10-012017-05-24US flag69189 224820180907 15195 p6yekv
Dicloxacillin SodiumCapsule250 mg/1OralLiberty Pharmaceuticals, Inc.1971-04-01Not applicableUS flag00440 138020210506 12874 192lylu
Dicloxacillin SodiumCapsule500 mg/1OralAsclemed Usa, Inc.1990-09-30Not applicableUS flag
Dicloxacillin SodiumCapsule500 mg/1OralPhysicians Total Care, Inc.1992-10-21Not applicableUS flag00781 2258 01 nlmimage10 2f3e97b4
Dicloxacillin SodiumCapsule500 mg/1OralPD-Rx Pharmaceuticals, Inc.1990-09-30Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
COMPLICILLINDicloxacillin (125 MG) + Amoxicillin (250 MG)Capsuleบริษัท แมคโครฟาร์ จำกัด2018-03-222020-06-01Thailand flag
COMPLISCANDicloxacillin (125 mg) + Amoxicillin (250 mg)Capsuleบริษัท แมคโครฟาร์ จำกัด2004-02-132020-06-01Thailand flag
แคมพลิคอนDicloxacillin (125 mg) + Amoxicillin (250 mg)Capsuleห้างหุ้นส่วนสามัญนิติบุคคล โรงงานเภสัชกรรมพอนด์เคมีคอลประเทศไทย2017-04-112020-06-01Thailand flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CF01 — Dicloxacillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Penams / Dichlorobenzenes / Aryl chlorides / Thiazolidines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Isoxazoles / Azetidines / Thiohemiaminal derivatives / Azacyclic compounds
show 12 more
Substituents
1,3-dichlorobenzene / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azetidine / Azole / Benzenoid / Beta-lactam / Carbonyl group
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dichlorobenzene, penicillin (CHEBI:4511)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
COF19H7WBK
CAS number
3116-76-5
InChI Key
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

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 References
Not Available
Human Metabolome Database
HMDB0014628
KEGG Drug
D02348
KEGG Compound
C06950
PubChem Compound
18381
PubChem Substance
46508182
ChemSpider
17358
BindingDB
50350476
RxNav
3356
ChEBI
4511
ChEMBL
CHEMBL893
ZINC
ZINC000003978006
Therapeutic Targets Database
DAP000435
PharmGKB
PA164749649
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dicloxacillin
MSDS
Download (51.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentBone and Joint Infections / Bone Infection / Joint Infections / Osteomyelitis / Septic Arthritis1
4Unknown StatusTreatmentBacteremia1
3CompletedTreatmentBacteremia / Bacterial Infections / Infections, Gram-Positive Bacterial1
1CompletedTreatmentHealthy Volunteers1
0TerminatedTreatmentOsteomyelitis1

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
FormRouteStrength
Capsule
CapsuleOral
Capsule, coatedOral250 mg
Capsule, coatedOral542 mg
Powder, for suspensionOral2.5 g
Powder, for suspensionOral125 mg
Powder, for suspensionOral2500 mg
Powder, for suspensionOral5 g
Powder, for suspensionOral5.41 g
Powder, for solutionOral5.7375 g
Capsule, coatedOral500 mg
SuspensionOral2.5 g
CapsuleOral250 mg/1
CapsuleOral500 mg/1
SuspensionOral5 g
Powder, for suspensionOral62.5 mg/5ml
Tablet, film coated250 mg
Powder, for suspensionOral125 mg/5ml
CapsuleOral500 mg
Powder; syrupOral62.5 mg/5ml
CapsuleOral250 mg
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.
Patents
Not Available

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Listeria monocytogenes serotype 4b str. LL195
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
pbpC
Uniprot ID
A0A0E1R3H3
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
75015.58 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. [Article]
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
Uniprot Name
Penicillin-binding protein 1b
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. [Article]
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
Uniprot Name
Penicillin-binding protein 2a
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. [Article]
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
Uniprot Name
Penicillin-binding protein 3
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. [Article]
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
Uniprot Name
Penicillin-binding protein 1A
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. [Article]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
penA
Uniprot ID
P0A3M6
Uniprot Name
Penicillin-binding protein 2B
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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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. [Article]

Transporters

Kind
Protein
Organism
Humans
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
Uniprot Name
Solute carrier family 15 member 1
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. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Solute carrier family 15 member 2
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. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 06, 2021 01:23