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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Flucloxacillin (DB00301)

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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

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Pharmacology

Indication

Used to treat bacterial infection by susceptible microorganisms.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Susceptible infections		••••••••••••			•••••••• •••••••••• ••••••• ••• ••••••••• •••••• ••••••

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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	inhibitor	Clostridium 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

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Abemaciclib	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.

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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
Fluclox 250 Cap 250mg	Capsule	250 mg / cap	Oral	Ayerst Laboratories	1981-12-31	1997-08-15
Fluclox 500 Cap 500mg	Capsule	500 mg / cap	Oral	Ayerst Laboratories	1981-12-31	1997-08-15
Fluclox-125 Pws 125mg/5ml	Powder, for solution	125 mg / 5 mL	Oral	Wyeth Ayerst Canada Inc.	1995-12-31	1997-01-14
Fluclox-250 Cap 250mg	Capsule	250 mg / cap	Oral	Wyeth Ayerst Canada Inc.	1995-12-31	1997-08-14

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

J01CF05 — Flucloxacillin

• J01CF — Beta-lactamase resistant penicillins
• 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 / Secondary carboxylic acid amides / Azetidines / Thiohemiaminal derivatives / Oxacyclic compounds / Azacyclic compounds / Carboxylic acids / Dialkylthioethers / Monocarboxylic acids and derivatives / Organonitrogen compounds / Carbonyl compounds / Organofluorides / Organochlorides / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds

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Substituents

Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Azetidine / Azole / Benzenoid / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid / Chlorobenzene / Dialkylthioether / Fluorobenzene / Halobenzene / Hemithioaminal / Heteroaromatic compound / Hydrocarbon derivative / Isoxazole / Lactam / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / N-acyl-alpha amino acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organochloride / Organofluoride / Organohalogen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Penam / Penicillin / Secondary carboxylic acid amide / Tertiary carboxylic acid amide / Thiazolidine / Thioether

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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

RxNav

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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	predicted	DarkChem Lite v0.1.0
[M-H]-	195.47823	predicted	DeepCCS 1.0 (2019)
[M+H]+	203.4733915	predicted	DarkChem Lite v0.1.0
[M+H]+	197.8738	predicted	DeepCCS 1.0 (2019)
[M+Na]+	199.8966915	predicted	DarkChem Lite v0.1.0
[M+Na]+	203.78632	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Penicillin-binding protein 1A

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

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
2. 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]
3. Lacey RW: Mechanisms of resistance to beta-lactam antibiotics in Staphylococcus aureus. Scand J Infect Dis Suppl. 1984;42:64-71. [Article]
4. 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]
5. Barza M: Antimicrobial spectrum, pharmacology and therapeutic use of antibiotics. Part 2: penicillins. Am J Hosp Pharm. 1977 Jan;34(1):57-67. [Article]

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Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:51