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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:40:01 UTC
HMDB IDHMDB0014628
Secondary Accession Numbers
  • HMDB14628
Metabolite Identification
Common NameDicloxacillin
DescriptionDicloxacillin is only found in individuals that have used or taken this drug. It is one of the penicillins which is resistant to penicillinase. [PubChem]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.
Structure
Data?1582753201
Synonyms
ValueSource
(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 acidChEBI
DicloxacilinaChEBI
DicloxacillineChEBI
DicloxacillinumChEBI
(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-carboxylateGenerator
DiclossacillinaHMDB
DicloxacilinHMDB
DicloxacyclineHMDB
Bristol myers squibb brand OF dicloxacillin sodiumHMDB
DicloxaciclinHMDB
Dicloxacillin, monosodium salt, mono-hydrateHMDB
PosipenHMDB
Sanfer brand OF dicloxacillin sodiumHMDB
Sigma brand OF dicloxacillin sodiumHMDB
Sodium, dicloxacillinHMDB
Alphapharm brand OF dicloxacillin sodiumHMDB
Antibioticos brand OF dicloxacillin sodiumHMDB
CilpenHMDB
DiclocilHMDB
DitterolinaHMDB
DynapenHMDB
Infectopharm brand OF dicloxacillin sodiumHMDB
Bristol-myers squibb brand OF dicloxacillin sodiumHMDB
DichloroxacillinHMDB
DicloxsigHMDB
DistaphHMDB
Geneva brand OF dicloxacillin sodiumHMDB
InfectoStaphHMDB
PathocilHMDB
SmithKline beecham brand OF dicloxacillin sodiumHMDB
Dicloxacillin sodiumHMDB
Dicloxacillin, monosodium salt, anhydrousHMDB
DycillHMDB
Fustery brand OF dicloxacillin sodiumHMDB
Wyeth brand OF dicloxacillin sodiumHMDB
Chemical FormulaC19H17Cl2N3O5S
Average Molecular Weight470.326
Monoisotopic Molecular Weight469.026596773
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
Traditional Namedicloxacillin
CAS Registry Number3116-76-5
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
InChI Identifier
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
InChI KeyYFAGHNZHGGCZAX-JKIFEVAISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • Penam
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Monocyclic benzene moiety
  • Azole
  • Isoxazole
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Beta-lactam
  • Heteroaromatic compound
  • Azetidine
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hemithioaminal
  • Monocarboxylic acid or derivatives
  • Thioether
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.03 g/LNot Available
LogP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.44 m³·mol⁻¹ChemAxon
Polarizability42.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9323100000-c8806eaea476ee681443Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9101010000-09418080881eaa1e2c3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1926600000-2819aa19376902b7bbc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2963100000-d32486357adcfc7196e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0900-4950000000-26919912afad41b9ef63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009100000-eb6339e06bab6641dd24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0059100000-aef2e49cd1687d6bd205Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-2953000000-61a1b22f6ec123b74f59Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00485 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00485 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00485
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID17358
KEGG Compound IDC06950
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDicloxacillin
METLIN IDNot Available
PubChem Compound18381
PDB IDNot Available
ChEBI ID4511
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. [PubMed:18505790 ]

Transporters

General function:
Involved in 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:
78805.3
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 ]
General function:
Involved in transporter 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:
81782.8
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 ]