Posted inUncategorized

Azidocillin

July 24, 2017
Common Name

Azidocillin Description

Azidocillin is only found in individuals that have used or taken this drug. It is a penicillin antibiotic similir to ampicillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Azidocillin 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 Azidocillin interferes with an autolysin inhibitor. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI AzidocilinaChEBI AzidocillineChEBI AzidocillinumChEBI D-(-)-(alpha-Azidobenzyl)penicillinChEBI (2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator D-(-)-(a-Azidobenzyl)penicillinGenerator D-(-)-(α-azidobenzyl)penicillinGenerator Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta))-isomerMeSH Azidocillin, monosodium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomerMeSH 6-(azido-2-phenylacetamido)Penicillanic acidMeSH Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(r*)))-isomerMeSH Azidocillin, 2S-(2alpha,5alpha,6beta)MeSH AzidobenzylpenicillinMeSH Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomerMeSH

Chemical Formlia

C16H17N5O4S Average Molecliar Weight

375.402 Monoisotopic Molecliar Weight

375.100124747 IUPAC Name

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

azidocillin CAS Registry Number

17243-38-8 SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1

InChI Key

ODFHGIPNGIAMDK-NJBDSQKTSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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 slifur atom at position 1]. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Lactams Direct Parent

Penicillins Alternative Parents

  • N-acyl-alpha amino acids and derivatives
  • Phenylacetamides
  • Thiazolidines
  • Tertiary carboxylic acid amides
  • Azetidines
  • Secondary carboxylic acid amides
  • Azo compounds
  • Azo imides
  • Azacyclic compounds
  • Thiohemiaminal derivatives
  • Carboxylic acids
  • Dialkylthioethers
  • Monocarboxylic acids and derivatives
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Monocyclic benzene moiety
  • Benzenoid
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Azetidine
  • Secondary carboxylic acid amide
  • Azo compound
  • Azo imide
  • Carboxamide group
  • Dialkylthioether
  • Azacycle
  • Hemithioaminal
  • Thioether
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • penicillin (CHEBI:51758 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antibacterial 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 Solubility6.11e-01 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.61 mg/mLALOGPS logP2.32ALOGPS logP1.19ChemAxon logS-2.8ALOGPS pKa (Strongest Acidic)3.32ChemAxon pKa (Strongest Basic)-6.4ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area116.14 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity92.16 m3·mol-1ChemAxon Polarizability35.87 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 DB08795

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08795

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB08795 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

    16735689 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Azidocillin NuGOwiki Link

    HMDB15685 Metagene Link

    HMDB15685 METLIN ID

    Not Available PubChem Compound

    15574941 PDB ID

    Not Available ChEBI ID

    51758

    Product: BQ-789 (sodium salt)

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

    Transporters

    General function:
    Involved in ion transmembrane transporter activity
    Specific function:
    Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
    Gene Name:
    SLC22A5
    Uniprot ID:
    O76082
    Molecular weight:
    62751.1
    References
    1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]
    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. Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [PubMed:8956326 ]
    2. Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [PubMed:10087037 ]
    3. 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 ]
    4. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
    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. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
    2. 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 ]

    PMID: 18587423

    Last updated on