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Identification
NameCloxacillin
Accession NumberDB01147  (APRD00882, EXPT01068)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA semi-synthetic antibiotic that is a chlorinated derivative of oxacillin. [PubChem]
Structure
Thumb
Synonyms
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(3-(O-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin
6-(3-(O-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
Cloxacilina
CLOXACILLIN
Cloxacilline
Cloxacillinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CloxacillinCapsule500 mgOralPro Doc Limitee1994-12-312013-07-15Canada
Cloxacillin for InjectionPowder, for solution1000 mgIntravenousSterimax Inc2011-07-28Not applicableCanada
Cloxacillin for InjectionPowder, for solution2000 mgIntravenousSterimax Inc2011-07-28Not applicableCanada
Cloxacillin for InjectionPowder, for solution10 gIntravenousSterimax Inc2013-04-03Not applicableCanada
Cloxacillin for InjectionPowder, for solution500 mgIntramuscular; IntravenousSterimax Inc2011-09-14Not applicableCanada
Cloxacillin Sodium for InjectionPowder, for solution2 gIntramuscular; IntravenousTeva Canada Limited1992-12-31Not applicableCanada
Cloxacillin Sodium for InjectionPowder, for solution500 mgIntramuscular; IntravenousTeva Canada Limited1992-12-31Not applicableCanada
Cloxacillin Sodium for InjectionPowder, for solution1 gIntravenousTeva Canada Limited1992-12-31Not applicableCanada
Cloxacillin Sodium Sterile Inj 250mg/vialLiquid250 mgIntramuscular; IntravenousNovopharm Limited1992-12-312005-08-10Canada
Cloxacillin-250 CapCapsule250 mgOralPro Doc Limitee1994-12-312009-07-23Canada
Nu-cloxi Capsules 250mgCapsule250 mgOralNu Pharm Inc1990-12-312012-09-04Canada
Nu-cloxi Capsules 500mgCapsule500 mgOralNu Pharm Inc1990-12-312012-09-04Canada
Nu-cloxi Solution 125mg/5mlPowder, for solution125 mgOralNu Pharm Inc1990-12-312012-09-04Canada
Orbenin 500 Cap 500mgCapsule500 mgOralWyeth Ayerst Canada Inc.1995-12-312000-08-02Canada
Orbenin Cap 250mgCapsule250 mgOralAyerst Laboratories1963-12-311998-12-15Canada
Orbenin Cap 500mgCapsule500 mgOralAyerst Laboratories1963-12-311997-11-24Canada
Orbenin Inj 2000mgPowder, for solution2 gIntramuscular; IntravenousAyerst Laboratories1966-12-311999-04-12Canada
Orbenin Inj 250mgPowder, for solution250 mgIntramuscular; IntravenousAyerst Laboratories1964-12-311999-04-12Canada
Orbenin Inj 500mgPowder, for solution500 mgIntramuscular; IntravenousAyerst Laboratories1966-12-311999-04-12Canada
Orbenin Pwr 125mg/5mlPowder, for solution125 mgOralAyerst Laboratories1966-12-311996-09-10Canada
Orbenin Pws 125mg/5mlPowder, for solution125 mgOralWyeth Ayerst Canada Inc.1995-12-311998-01-28Canada
Riva-cloxacillin 250 Mg CapsulesCapsule250 mgOralLaboratoire Riva Inc1999-11-192003-07-28Canada
Riva-cloxacillin 500 Mg CapsulesCapsule500 mgOralLaboratoire Riva Inc1999-11-192003-07-28Canada
Taro-cloxacillin Cap 250mgCapsule250 mgOralTaro Pharmaceuticals Inc1993-12-312000-08-31Canada
Taro-cloxacillin Cap 500mgCapsule500 mgOralTaro Pharmaceuticals Inc1993-12-312000-08-31Canada
Tegopen Inj 2000mg/vialPowder, for solution2 gIntramuscular; IntravenousBristol Labs Division Of Bristol Myers Squibb1973-12-312000-08-29Canada
Tegopen Inj 250mg/vialPowder, for solution250 mgIntramuscular; IntravenousBristol Labs Division Of Bristol Myers Squibb1973-12-311996-09-09Canada
Tegopen Inj 500mg/vialPowder, for solution500 mgIntramuscular; IntravenousBristol Labs Division Of Bristol Myers Squibb1973-12-312000-08-29Canada
Teva-cloxacillinGranule, for solution125 mgOralTeva Canada Limited1980-12-31Not applicableCanada
Teva-cloxacillinCapsule250 mgOralTeva Canada Limited1975-12-31Not applicableCanada
Teva-cloxacillinCapsule500 mgOralTeva Canada Limited1975-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Cloxi Cap 250mgCapsule250 mgOralApotex Inc1984-12-31Not applicableCanada
Apo Cloxi Cap 500mgCapsule500 mgOralApotex Inc1984-12-31Not applicableCanada
Apo Cloxi for Oral Soln 125mg/5mlPowder, for solution125 mgOralApotex Inc1985-12-31Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcloxSouthshourne
Apo-CloxiApotex
Auropen Inj.Cirin
CloxacilSaiph
CloxamMacroPhar
OrbeninGlaxoSmithKline
VacloxAtlantic
VamcloxilVamsler
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cloxacillin benzathine
23736-58-5
Thumb
  • InChI Key: COCFKSXGORCFOW-VZHMHXRYSA-N
  • Monoisotopic Mass: 1110.2937878
  • Average Mass: 1112.11
DBSALT001648
Cloxacillin sodium
642-78-4
Thumb
  • InChI Key: SCLZRKVZRBKZCR-SLINCCQESA-M
  • Monoisotopic Mass: 457.047513741
  • Average Mass: 457.863
DBSALT000249
Categories
UNIIO6X5QGC2VB
CAS number61-72-3
WeightAverage: 435.881
Monoisotopic: 435.065569098
Chemical FormulaC19H18ClN3O5S
InChI KeyLQOLIRLGBULYKD-JKIFEVAISA-N
InChI
InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
IUPAC Name
(2S,5R,6R)-6-[3-(2-chlorophenyl)-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=CC=CC=C1Cl)C(O)=O
Pharmacology
IndicationUsed to treat infections caused by penicillinase-producing staphylococci, including pneumococci, group A beta-hemolytic streptococci, and penicillin G-sensitive and penicillin G-resistant staphylococci.
Structured Indications
PharmacodynamicsCloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is for use against staphylococci that produce beta-lactamase.
Mechanism of actionBy binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cloxacillin 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 cloxacillin interferes with an autolysin inhibitor.
TargetKindPharmacological actionActionsOrganismUniProt ID
Penicillin-binding protein 1AProteinyes
inhibitor
Clostridium perfringens (strain 13 / Type A)Q8XJ01 details
Beta-lactamaseProteinunknown
inducer
Escherichia coli (strain K12)P00811 details
Penicillin-binding protein 2aProteinyes
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)Q8DNB6 details
Penicillin-binding protein 2BProteinyes
inhibitor
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)P0A3M5 details
Cell division proteinProteinyes
inhibitor
Pseudomonas aeruginosaQ51504 details
D-alanyl-D-alanine carboxypeptidase DacAProteinunknown
inhibitor
Escherichia coli O6:H1 (strain CFT073 / ATCC 700928 / UPEC)P0AEB3 details
Related Articles
AbsorptionWell absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein binding95%
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral LD50 in rat and mouse is 5000 mg/kg. Intravenous LD50 in rat is 1660 mg/kg. Symptoms of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, and swelling of face, lips, tongue, or throat.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolCloxacillin may decrease the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Cloxacillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Cloxacillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Cloxacillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Cloxacillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Cloxacillin.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Cloxacillin.Investigational
ChlortetracyclineThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Chlortetracycline.Approved, Vet Approved
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Cloxacillin.Approved
DemeclocyclineThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Demeclocycline.Approved
DicoumarolCloxacillin may decrease the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Cloxacillin.Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Cloxacillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Cloxacillin.Approved
Ethyl biscoumacetateCloxacillin may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCloxacillin may decrease the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Cloxacillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Cloxacillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Cloxacillin.Experimental
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Cloxacillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Cloxacillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Cloxacillin.Investigational
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Cloxacillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Cloxacillin.Approved
MinocyclineThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Cloxacillin resulting in a loss in efficacy.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Cloxacillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Cloxacillin.Approved
OxytetracyclineThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Oxytetracycline.Approved, Vet Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Cloxacillin.Approved, Investigational
PhenindioneCloxacillin may decrease the anticoagulant activities of Phenindione.Approved
PhenprocoumonCloxacillin may decrease the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cloxacillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Cloxacillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Cloxacillin.Approved, Withdrawn
ProbenecidThe serum concentration of Cloxacillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Cloxacillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Cloxacillin.Approved
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Cloxacillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Cloxacillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Cloxacillin.Approved
TetracyclineThe therapeutic efficacy of Cloxacillin can be decreased when used in combination with Tetracycline.Approved, Vet Approved
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Cloxacillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Cloxacillin.Approved
WarfarinCloxacillin may decrease the anticoagulant activities of Warfarin.Approved
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Cloxacillin.Experimental
Food Interactions
  • Take on an empty stomach.
References
Synthesis Reference

Doyle, F.P. and Nayler, J.H.C.; British Patent 905,778; September 12, 1962; assigned to Beecham Research Laboratories, Ltd.
Doyle, F.P. and Nayler, J.H.C.; US. Patent 2,996,501; August 15, 1961.

General ReferencesNot Available
External Links
ATC CodesJ01CF02
AHFS Codes
  • 08:12.16.12
PDB Entries
FDA labelNot Available
MSDSDownload (38 KB)
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
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral250 mg
CapsuleOral500 mg
Powder, for solutionOral125 mg
Powder, for solutionIntravenous10 g
Powder, for solutionIntravenous1000 mg
Powder, for solutionIntravenous2000 mg
Powder, for solutionIntramuscular; Intravenous2 g
Powder, for solutionIntramuscular; Intravenous500 mg
Powder, for solutionIntravenous1 g
LiquidIntramuscular; Intravenous250 mg
Powder, for solutionIntramuscular; Intravenous250 mg
Granule, for solutionOral125 mg
Prices
Unit descriptionCostUnit
Cloxacillin Sodium 2 g/vial7.69USD vial
Cloxacillin Sodium 1 g/vial5.89USD vial
Cloxacillin Sodium 500 mg/vial4.79USD vial
Apo-Cloxi 500 mg Capsule0.38USD capsule
Novo-Cloxin 500 mg Capsule0.38USD capsule
Nu-Cloxi 500 mg Capsule0.38USD capsule
Apo-Cloxi 250 mg Capsule0.19USD capsule
Novo-Cloxin 250 mg Capsule0.19USD capsule
Nu-Cloxi 250 mg Capsule0.19USD capsule
Apo-Cloxi 25 mg/ml Liquid0.05USD ml
Novo-Cloxin 25 mg/ml Liquid0.05USD ml
Nu-Cloxi 25 mg/ml Liquid0.05USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility13.9 mg/LNot Available
logP2.48SANGSTER (1994)
pKa2.78SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0532 mg/mLALOGPS
logP2.61ALOGPS
logP2.3ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.64 m3·mol-1ChemAxon
Polarizability41.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  • 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

Targets

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 strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Kleppe G, Yu W, Strominger JL: Penicillin-binding proteins in Bacillus subtilis mutants. Antimicrob Agents Chemother. 1982 Jun;21(6):979-83. [PubMed:6810758 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
Actions
inducer
General Function:
Beta-lactamase activity
Specific Function:
This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
Gene Name:
ampC
Uniprot ID:
P00811
Molecular Weight:
41555.3 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Mirelis B, Rivera A, Miro E, Mesa RJ, Navarro F, Coll P: A simple phenotypic method for differentiation between acquired and chromosomal AmpC beta-lactamases in Escherichia coli. Enferm Infecc Microbiol Clin. 2006 Jun-Jul;24(6):370-2. [PubMed:16792938 ]
  4. Ruppe E, Bidet P, Verdet C, Arlet G, Bingen E: First detection of the Ambler class C 1 AmpC beta-lactamase in Citrobacter freundii by a new, simple double-disk synergy test. J Clin Microbiol. 2006 Nov;44(11):4204-7. Epub 2006 Sep 13. [PubMed:16971653 ]
  5. Guan XZ, Liu YN, Luo YP, She DY, Zhou G, Chen LA, Xu YP: [A new member of CMY type cephalosporinase prevailing in Escherichia coli]. Zhonghua Yi Xue Za Zhi. 2004 Nov 17;84(22):1872-5. [PubMed:15631796 ]
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 serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M5
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 ]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
Not Available
Gene Name:
pbpB
Uniprot ID:
Q51504
Molecular Weight:
62855.78 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
Escherichia coli O6:H1 (strain CFT073 / ATCC 700928 / UPEC)
Pharmacological action
unknown
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name:
dacA
Uniprot ID:
P0AEB3
Molecular Weight:
44443.62 Da
References
  1. Nicola G, Tomberg J, Pratt RF, Nicholas RA, Davies C: Crystal structures of covalent complexes of beta-lactam antibiotics with Escherichia coli penicillin-binding protein 5: toward an understanding of antibiotic specificity. Biochemistry. 2010 Sep 21;49(37):8094-104. doi: 10.1021/bi100879m. [PubMed:20726582 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. [PubMed:1031216 ]
  2. Friedman LA, Lewis PJ: The effect of semisynthetic penicillins on the binding of bilirubin by neonatal serum. Br J Clin Pharmacol. 1980 Jan;9(1):61-5. [PubMed:7356894 ]
  3. Okore VC: Effect of ascorbic acid on the binding of cloxacillin sodium to bovine serum albumin. Arzneimittelforschung. 1994 May;44(5):671-3. [PubMed:8024646 ]

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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:48