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Meticillin

July 24, 2017
Common Name

Meticillin Description

Meticillin is only found in individuals that have used or taken this drug. It is one of the penicillins which is resistant to penicillinase but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection. [PubChem]Like other beta-lactam antibiotics, meticillin acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI 6beta-(2,6-dimethoxybenzamido)Penicillanic acidChEBI MeticilinaChEBI MeticillineChEBI MeticillinumChEBI (2S,5R,6R)-6-[(2,6-Dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator 6b-(2,6-dimethoxybenzamido)PenicillanateGenerator 6b-(2,6-dimethoxybenzamido)Penicillanic acidGenerator 6beta-(2,6-dimethoxybenzamido)PenicillanateGenerator 6β-(2,6-dimethoxybenzamido)penicillanateGenerator 6β-(2,6-dimethoxybenzamido)penicillanic acidGenerator (2,6-Dimethoxyphenyl)penicillinHMDB 6-(2,6-dimethoxybenzamido)Penicillanic acidHMDB MethicillinumHMDB MethycillinHMDB StaphcillinMeSH CSL Brand OF methicillin sodiumMeSH Dimethoxyphenyl penicillinMeSH Penicillin, dimethoxyphenylMeSH Methicillin hydrate, monosodium saltMeSH Methicillin monohydrate, monosodium saltMeSH Methicillin sodiumMeSH MetinMeSH

Chemical Formlia

C17H20N2O6S Average Molecliar Weight

380.415 Monoisotopic Molecliar Weight

380.104207072 IUPAC Name

(2S,5R,6R)-6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Traditional Name

methicillin CAS Registry Number

61-32-5 SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OC)C=CC=C1OC)C(O)=O

InChI Identifier

InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1

InChI Key

RJQXTJLFIWVMTO-TYNCELHUSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Dipeptides Alternative Parents

  • Penicillins
  • N-acyl-alpha amino acids and derivatives
  • Dimethoxybenzenes
  • Benzamides
  • Anisoles
  • Benzoyl derivatives
  • Phenoxy compounds
  • Alkyl aryl ethers
  • Tertiary carboxylic acid amides
  • Thiazolidines
  • Azetidines
  • Secondary carboxylic acid amides
  • Monocarboxylic acids and derivatives
  • Dialkylthioethers
  • Carboxylic acids
  • Thiohemiaminal derivatives
  • Azacyclic compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Organopnictogen compounds

    • Substituents

  • Alpha-dipeptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Benzoic acid or derivatives
  • Benzamide
  • Penam
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Beta-lactam
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • penicillin (CHEBI:6827 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Bacterial Agents
  • Penicillins

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility3.10e-01 g/LNot Available LogP1.22HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.31 mg/mLALOGPS logP1.79ALOGPS logP0.79ChemAxon logS-3.1ALOGPS pKa (Strongest Acidic)2.96ChemAxon pKa (Strongest Basic)-1.8ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area105.17 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity93.4 m3·mol-1ChemAxon Polarizability37.27 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01603

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01603

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01603 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5862 KEGG Compound ID

    C07177 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Methicillin NuGOwiki Link

    HMDB15541 Metagene Link

    HMDB15541 METLIN ID

    Not Available PubChem Compound

    6087 PDB ID

    MII ChEBI ID

    6827

    Product: AMD 3466

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    PMID: 17505012

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