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Quinupristin

July 24, 2017
Common Name

Quinupristin Description

Quinupristin/dalfopristin is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium. Dalfopristin inhibits the early phase of protein synthesis in the bacterial ribosome and quinupristin inhibits the late phase of protein synthesis. The combination of the two components acts synergistically and is more effective in vitro than each component alone. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source 5DElta-(3-quinuclidinyl)thiomethylpristinamycin iaMeSH

Chemical Formlia

C53H67N9O10S Average Molecliar Weight

1022.218 Monoisotopic Molecliar Weight

1021.473160099 IUPAC Name

N-[(3S,6S,12R,15S,16R,19S)-25-{[(3S)-1-azabicyclo[2.2.2]octan-3-ylslifanyl]methyl}-3-{[4-(dimethylamino)phenyl]methyl}-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaazatricyclo[20.4.0.0⁶,¹⁰]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide Traditional Name

quinupristin CAS Registry Number

120138-50-3 SMILES

CC[C@H]1NC(=O)[C@@H](NC(=O)C2=NC=CC=C2O)[C@@H](C)OC(=O)[C@@H](NC(=O)C2CC(=O)C(CS[C@@H]3CN4CCC3CC4)CN2C(=O)[C@H](CC2=CC=C(C=C2)N(C)C)N(C)C(=O)[C@@H]2CCCN2C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35?,37-,38+,39?,40+,43-,44+,45+/m1/s1

InChI Key

WTHRRGMBUAHGNI-MJWHERSYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regliarly alternating. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Peptidomimetics Direct Parent

Cyclic depsipeptides Alternative Parents

  • Macrolide lactams
  • Alpha amino acid esters
  • Macrolactams
  • N-acyl-alpha amino acids and derivatives
  • Pyridinecarboxamides
  • Quinuclidines
  • 2-heteroaryl carboxamides
  • Aniline and substituted anilines
  • Dialkylarylamines
  • Piperidinones
  • Hydroxypyridines
  • Pyrrolidines
  • Vinylogous acids
  • Heteroaromatic compounds
  • Tertiary carboxylic acid amides
  • Secondary carboxylic acid amides
  • Carboxylic acid esters
  • Cyclic ketones
  • Lactams
  • Lactones
  • Trialkylamines
  • Dialkylthioethers
  • Slifenyl compounds
  • Monocarboxylic acids and derivatives
  • Azacyclic compounds
  • Oxacyclic compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Organopnictogen compounds

    • Substituents

  • Cyclic depsipeptide
  • Macrolide lactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid ester
  • Macrolactam
  • Alpha-amino acid or derivatives
  • Pyridine carboxylic acid or derivatives
  • Pyridinecarboxamide
  • 2-heteroaryl carboxamide
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Quinuclidine
  • Tertiary aliphatic/aromatic amine
  • Piperidinone
  • Hydroxypyridine
  • Monocyclic benzene moiety
  • Piperidine
  • Benzenoid
  • Pyridine
  • Vinylogous acid
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Ketone
  • Lactam
  • Lactone
  • Cyclic ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Thioether
  • Slifenyl compound
  • Dialkylthioether
  • Organoheterocyclic compound
  • Amine
  • Organic oxide
  • Organooxygen compound
  • Organoslifur compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • cyclodepsipeptide (CHEBI:8732 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antibacterial Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility4.45e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.044 mg/mLALOGPS logP2.99ALOGPS logP2.18ChemAxon logS-4.4ALOGPS pKa (Strongest Acidic)7.45ChemAxon pKa (Strongest Basic)8.28ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count12ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area231.2 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity272.84 m3·mol-1ChemAxon Polarizability107.02 Å3ChemAxon Number of Rings8ChemAxon Bioavailability0ChemAxon 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

  • Cytoplasm
  • 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 DB01369

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01369

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01369 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

    26329518 KEGG Compound ID

    C08032 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Quinupristin NuGOwiki Link

    HMDB15455 Metagene Link

    HMDB15455 METLIN ID

    Not Available PubChem Compound

    23724509 PDB ID

    Not Available ChEBI ID

    Not Available

    Product: Raltitrexed

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Lamb HM, Figgitt DP, Faulds D: Quinupristin/dalfopristin: a review of its use in the management of serious gram-positive infections. Drugs. 1999 Dec;58(6):1061-97. [PubMed:10651391 ]
    2. Paradisi F, Corti G, Messeri D: Antistaphylococcal (MSSA, MRSA, MSSE, MRSE) antibiotics. Med Clin North Am. 2001 Jan;85(1):1-17. [PubMed:11190346 ]
    3. Allington DR, Rivey MP: Quinupristin/dalfopristin: a therapeutic review. Clin Ther. 2001 Jan;23(1):24-44. [PubMed:11219478 ]
    4. Manzella JP: Quinupristin-dalfopristin: a new antibiotic for severe gram-positive infections. Am Fam Physician. 2001 Dec 1;64(11):1863-6. [PubMed:11764864 ]

    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. Rubinstein E, Prokocimer P, Talbot GH: Safety and tolerability of quinupristin/dalfopristin: administration guidelines. J Antimicrob Chemother. 1999 Sep;44 Suppl A:37-46. [PubMed:10511396 ]
    2. Bearden DT: Clinical pharmacokinetics of quinupristin/dalfopristin. Clin Pharmacokinet. 2004;43(4):239-52. [PubMed:15005638 ]
    3. Delgado G Jr, Neuhauser MM, Bearden DT, Danziger LH: Quinupristin-dalfopristin: an overview. Pharmacotherapy. 2000 Dec;20(12):1469-85. [PubMed:11130220 ]

    PMID: 12878607

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