Flucloxacillin
Identification
- Summary
Flucloxacillin is a narrow spectrum penicillin antibiotic that exerts specific activity against Gram positive organisms in skin and soft tissue infections, except those caused by methicillin resistant staphylococcus aureus (MRSA).
- Generic Name
- Flucloxacillin
- DrugBank Accession Number
- DB00301
- Background
Antibiotic analog of cloxacillin.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 453.872
Monoisotopic: 453.056147271 - Chemical Formula
- C19H17ClFN3O5S
- Synonyms
- (2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-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
- 3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin
- Floxacillin
- Flucloxacilina
- Flucloxacillin
- Flucloxacilline
- Flucloxacillinum
- External IDs
- BRL 2039
- BRL-2039
Pharmacology
- Indication
Used to treat bacterial infection by susceptible microorganisms.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Susceptible infections •••••••••••• •••••••• •••••••••• ••••••• ••• ••••••••• •••••• •••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Flucloxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Flucloxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Flucloxacillin results from the inhibition of cell wall synthesis and is mediated through flucloxacillin binding to penicillin binding proteins (PBPs). Flucloxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
- Mechanism of action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, flucloxacillin 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 flucloxacillin interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - Absorption
Bioavailability is 50–70% following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
0.75–1 hour
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Flucloxacillin. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Flucloxacillin. Acemetacin Acemetacin may decrease the excretion rate of Flucloxacillin which could result in a higher serum level. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Flucloxacillin. Albendazole The metabolism of Albendazole can be increased when combined with Flucloxacillin. - Food Interactions
- Take on an empty stomach.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Flucloxacillin sodium LMG7C674WJ 34214-51-2 PARMJFIQRZRMHG-VICXVTCVSA-M - International/Other Brands
- Flopen (Aspen) / Floxapen (GSK) / Fluclox (ACI) / Softapen / Staphylex (Actavis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Fluclox 250 Liquid 250 mg / 5 mL Oral Ayerst Laboratories 1981-12-31 1997-08-15 Canada Fluclox 250 Cap 250mg Capsule 250 mg / cap Oral Ayerst Laboratories 1981-12-31 1997-08-15 Canada Fluclox 500 Cap 500mg Capsule 500 mg / cap Oral Ayerst Laboratories 1981-12-31 1997-08-15 Canada Fluclox-125 Pws 125mg/5ml Powder, for solution 125 mg / 5 mL Oral Wyeth Ayerst Canada Inc. 1995-12-31 1997-01-14 Canada Fluclox-250 Cap 250mg Capsule 250 mg / cap Oral Wyeth Ayerst Canada Inc. 1995-12-31 1997-08-14 Canada
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
- BSEP/ABCB11 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Penicillins
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Penicillins / N-acyl-alpha amino acids and derivatives / Chlorobenzenes / Fluorobenzenes / Aryl chlorides / Aryl fluorides / Thiazolidines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Isoxazoles show 15 more
- Substituents
- Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Azetidine / Azole / Benzenoid show 33 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:5098)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 43B2M34G2V
- CAS number
- 5250-39-5
- InChI Key
- UIOFUWFRIANQPC-JKIFEVAISA-N
- InChI
- InChI=1S/C19H17ClFN3O5S/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-chloro-6-fluorophenyl)-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=C1F)C(O)=O
References
- Synthesis Reference
Nayler, J.H.C.; U.S. Patent 3.239307; March 8,1966; assigned to Beecharn Group Limited, England.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014446
- KEGG Drug
- D04196
- KEGG Compound
- C11748
- PubChem Compound
- 21319
- PubChem Substance
- 46508276
- ChemSpider
- 20037
- BindingDB
- 50370590
- 4448
- ChEBI
- 5098
- ChEMBL
- CHEMBL222645
- ZINC
- ZINC000004102187
- Therapeutic Targets Database
- DAP001163
- PharmGKB
- PA164781042
- Wikipedia
- Flucloxacillin
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Cellulitis 1 4 Recruiting Treatment Bone and Joint Infections / Bone Infection / Osteomyelitis / Septic Arthritis 1 4 Terminated Treatment Cellulitis / Erysipelas 1 4 Unknown Status Treatment Abscesses / Cellulitis / Wound Infections 1 4 Withdrawn Treatment Staphylococcus Aureus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Injection, powder, for solution Intramuscular Tablet Oral Injection Intramuscular; Parenteral 250 mg/g Syrup Tablet, film coated 500 mg Injection, powder, for solution 2 g Capsule Oral 500 mg Tablet Oral 1 G Tablet, coated Liquid Oral 250 mg / 5 mL Capsule Oral 500 mg / cap Powder, for solution Oral 125 mg / 5 mL Capsule Oral 250 mg / cap Injection, powder, for solution Parenteral 1000 mg Injection, powder, for solution Parenteral 2000 mg Injection, powder, for solution Parenteral 250 mg Injection, powder, for solution Parenteral 500 mg Injection, powder, for solution Parenteral 2 g Injection, powder, for solution Parenteral 4 g Injection, powder, for solution Intramuscular 1 G Injection, powder, for solution Intramuscular; Parenteral 1 G Injection, powder, for solution Parenteral 1 G Syrup 250 mg/5ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.58 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0545 mg/mL ALOGPS logP 2.69 ALOGPS logP 2.44 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 3.75 Chemaxon pKa (Strongest Basic) -0.93 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 106.85 m3·mol-1 Chemaxon Polarizability 41.69 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 + 0.9157 Blood Brain Barrier - 0.9862 Caco-2 permeable - 0.8734 P-glycoprotein substrate Non-substrate 0.6184 P-glycoprotein inhibitor I Non-inhibitor 0.8765 P-glycoprotein inhibitor II Non-inhibitor 0.9438 Renal organic cation transporter Non-inhibitor 0.965 CYP450 2C9 substrate Non-substrate 0.8279 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6012 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.926 Ames test Non AMES toxic 0.6791 Carcinogenicity Carcinogens 0.5695 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.0834 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9997 hERG inhibition (predictor II) Non-inhibitor 0.8323
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-006x-9342300000-7f180b75f0b193e6a2bf Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0190100000-e82a0767c1911c997497 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0009100000-96e0c3d3e66537f7291f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-02t9-0980100000-6adbdadb005c6ab8a57e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03dl-9058700000-105d5777a01027a3c0ba Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01p9-0290000000-bf9dffdf9c9c3d8c0918 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-9124000000-ca206d8c1bbc22cfe435 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.7093915 predictedDarkChem Lite v0.1.0 [M-H]- 195.47823 predictedDeepCCS 1.0 (2019) [M+H]+ 203.4733915 predictedDarkChem Lite v0.1.0 [M+H]+ 197.8738 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.8966915 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.78632 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Lacey RW: Mechanisms of resistance to beta-lactam antibiotics in Staphylococcus aureus. Scand J Infect Dis Suppl. 1984;42:64-71. [Article]
- Mainardi JL, Villet R, Bugg TD, Mayer C, Arthur M: Evolution of peptidoglycan biosynthesis under the selective pressure of antibiotics in Gram-positive bacteria. FEMS Microbiol Rev. 2008 Mar;32(2):386-408. doi: 10.1111/j.1574-6976.2007.00097.x. Epub 2008 Feb 11. [Article]
- Barza M: Antimicrobial spectrum, pharmacology and therapeutic use of antibiotics. Part 2: penicillins. Am J Hosp Pharm. 1977 Jan;34(1):57-67. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
- Huwyler J, Wright MB, Gutmann H, Drewe J: Induction of cytochrome P450 3A4 and P-glycoprotein by the isoxazolyl-penicillin antibiotic flucloxacillin. Curr Drug Metab. 2006 Feb;7(2):119-26. [Article]
- Dekker SJ, Dohmen F, Vermeulen NPE, Commandeur JNM: Characterization of kinetics of human cytochrome P450s involved in bioactivation of flucloxacillin: inhibition of CYP3A-catalysed hydroxylation by sulfaphenazole. Br J Pharmacol. 2019 Feb;176(3):466-477. doi: 10.1111/bph.14548. Epub 2018 Dec 26. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:51