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
Structure for Dicloxacillin (DB00485)
- 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.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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.
Target Actions Organism APenicillin-binding protein 3 inhibitorListeria monocytogenes serotype 4b str. LL195 APenicillin-binding protein 1b inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2a inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 3 inhibitorStreptococcus pneumoniae APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2B inhibitorStreptococcus 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be increased when combined with Dicloxacillin. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Dicloxacillin. Acemetacin Acemetacin may decrease the excretion rate of Dicloxacillin which could result in a higher serum level. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Dicloxacillin. Albendazole The metabolism of Albendazole can be increased when combined with Dicloxacillin. Alectinib The metabolism of Alectinib can be increased when combined with Dicloxacillin. Alpelisib The metabolism of Alpelisib can be increased when combined with Dicloxacillin. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Dicloxacillin. Aminophylline The metabolism of Aminophylline can be increased when combined with Dicloxacillin. Amiodarone The metabolism of Amiodarone can be increased when combined with Dicloxacillin. 
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- Take on an empty stomach. Food decreases bioavailability.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Dicloxacillin sodium 4HZT2V9KX0 13412-64-1 SIGZQNJITOWQEF-VICXVTCVSA-M Dicloxacillin sodium anhydrous 4CKS6MOL6Z 343-55-5 GXOMMGAFBINOJY-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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dicloxacillin Sodium Capsule 250 mg/1 Oral Liberty Pharmaceuticals, Inc. 1971-04-01 Not applicable US 
Dicloxacillin Sodium Capsule 500 mg/1 Oral Physicians Total Care, Inc. 1992-10-21 Not applicable US 
Dicloxacillin Sodium Capsule 250 mg/1 Oral Sandoz Inc 1971-04-01 Not applicable US 
Dicloxacillin Sodium Capsule 500 mg/1 Oral AvKARE, Inc. 2017-03-30 2020-02-03 US Dicloxacillin Sodium Capsule 250 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1990-09-30 Not applicable US Dicloxacillin Sodium Capsule 250 mg/1 Oral Rebel Distributors 1971-04-01 Not applicable US 
Dicloxacillin Sodium Capsule 250 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 1990-09-30 Not applicable US Dicloxacillin Sodium Capsule 250 mg/1 Oral Avera McKennan Hospital 2016-06-14 2017-05-24 US Dicloxacillin Sodium Capsule 250 mg/1 Oral A-S Medication Solutions 1971-04-01 2018-11-30 US 
Dicloxacillin Sodium Capsule 500 mg/1 Oral A S Medication Solutions 1990-09-30 Not applicable US 
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- Beta-Lactamase Resistant Penicillins
- beta-Lactams
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Penicillins
- Sulfur Compounds
- 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
- External Links
- Human Metabolome Database
- HMDB0014628
- KEGG Drug
- D02348
- KEGG Compound
- C06950
- PubChem Compound
- 18381
- PubChem Substance
- 46508182
- ChemSpider
- 17358
- BindingDB
- 50350476
- 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
Phase Status Purpose Conditions Count 4 Recruiting Treatment Bone and Joint Infections / Bone Infection / Joint Infections / Osteomyelitis / Septic Arthritis 1 4 Unknown Status Treatment Bacteremia 1 3 Completed Treatment Bacteremia / Bacterial Infections / Infections, Gram-Positive Bacterial 1 1 Completed Treatment Healthy Volunteers 1 0 Terminated Treatment Osteomyelitis 1
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 Capsule Oral Powder, for suspension Oral 5 g Powder, for solution Oral Capsule, coated Oral 500 mg Suspension Oral Capsule Oral 250 mg/1 Capsule Oral 500 mg/1 Capsule, coated Oral Tablet, film coated Powder, for suspension Oral Capsule Oral 500 mg Powder; syrup Oral Capsule Oral 250 mg - Prices
Unit description Cost Unit Dicloxacillin Sodium 500 mg capsule 1.25USD capsule Dicloxacillin 500 mg capsule 1.2USD capsule Dicloxacillin Sodium 250 mg capsule 0.69USD capsule Dicloxacillin 250 mg capsule 0.66USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
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 0.0296 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 111.44 m3·mol-1 ChemAxon Polarizability 42.86 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.891 CYP450 2D6 inhibitor Non-inhibitor 0.918 CYP450 2C19 inhibitor Non-inhibitor 0.8832 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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
- Uniprot Name
- Penicillin-binding protein 1b
- Molecular Weight
- 89479.92 Da
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: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
- Uniprot Name
- Penicillin-binding protein 2a
- Molecular Weight
- 80797.94 Da
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: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
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 45209.84 Da
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: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
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
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:7447421]
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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]
Drug created on June 13, 2005 13:24 / Updated on May 06, 2021 01:23