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    CAS 9005-27-0

    BUILDING BLOCK

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 9005-27-0, Starch, 2-hydroxyethyl ether, 2-hydroxyethyl starch, (2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;2-[[(2r,3r,4s,5r,6s)-3,4,5,6-tetrakis(2-hydroxyethoxy)oxan-2-yl]methoxy]ethanol, Hydroxyethyl starch 130/0.4, Starch, 2-hydroxyethyl ether, base-hydrolyzed
    Molecular Formula
    C22H44O17
    Molecular Weight
    580.6  g/mol
    InChI Key
    DNZMDASEFMLYBU-RNBXVSKKSA-N
    Hydroxyethyl starch (HES/HAES) is a nonionic starch derivative. Hydroxyethyl starches (HES) are synthetic colloids commonly used for fluid resuscitation to replace intravascular volume. HES is a general term and can be sub-classified according to average molecular weight, molar substitution, concentration, C2/C6 ratio and Maximum Daily Dose.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;2-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(2-hydroxyethoxy)oxan-2-yl]methoxy]ethanol
    2.1.2 InChI
    InChI=1S/C16H32O11.C6H12O6/c17-1-6-22-11-12-13(23-7-2-18)14(24-8-3-19)15(25-9-4-20)16(27-12)26-10-5-21;7-1-2-3(8)4(9)5(10)6(11)12-2/h12-21H,1-11H2;2-11H,1H2/t12-,13-,14+,15-,16+;2-,3-,4+,5-,6+/m11/s1
    2.1.3 InChI Key
    DNZMDASEFMLYBU-RNBXVSKKSA-N
    2.1.4 Canonical SMILES
    C(COCC1C(C(C(C(O1)OCCO)OCCO)OCCO)OCCO)O.C(C1C(C(C(C(O1)O)O)O)O)O
    2.1.5 Isomeric SMILES
    C(COC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OCCO)OCCO)OCCO)OCCO)O.C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. 9005-27-0

    2. Starch, 2-hydroxyethyl Ether

    3. 2-hydroxyethyl Starch

    4. (2s,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol;2-[[(2r,3r,4s,5r,6s)-3,4,5,6-tetrakis(2-hydroxyethoxy)oxan-2-yl]methoxy]ethanol

    5. Hydroxyethyl Starch 130/0.4

    6. Starch, 2-hydroxyethyl Ether, Base-hydrolyzed

    7. 68512-26-5

    8. Chembl1730764

    9. Akos030254900

    10. Hydroxyethyl Starch (high Mw), European Pharmacopoeia (ep) Reference Standard

    11. Hydroxyethyl Starch (medium Mw), European Pharmacopoeia (ep) Reference Standard

    2.3 Create Date
    2007-07-12
    3 Chemical and Physical Properties
    Molecular Weight 580.6 g/mol
    Molecular Formula C22H44O17
    Hydrogen Bond Donor Count10
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count17
    Exact Mass580.25784993 g/mol
    Monoisotopic Mass580.25784993 g/mol
    Topological Polar Surface Area267 Ų
    Heavy Atom Count39
    Formal Charge0
    Complexity497
    Isotope Atom Count0
    Defined Atom Stereocenter Count10
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    An intravenous solution of hydroxyethyl starch is used to prevent shock following severe blood loss caused by trauma, surgery, or other issues.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    After isovolemic exchange of blood with 500 mL of HES in healthy volunteers, blood volume is maintained for at least 6 hours

    5.2 Absorption, Distribution and Excretion

    Absorption

    Peak concentration (C(max), 4.34 mg/mL)

    Route of Elimination

    Approximately 62 % of HES was excreted as hydroxyethyl starch molecules in urine within 72 hours.

    Volume of Distribution

    5.9 L.

    Clearance

    31.4 mL/min

    5.3 Metabolism/Metabolites

    When given intravenously, molecules smaller than the renal threshold (60,000-70,000 daltons) are readily and rapidly excreted in the urine, while molecules with higher molecular weights are metabolized by plasma -amylase prior to excretion via the renal route.

    5.4 Biological Half-Life

    Terminal half-life is 16.1 h. Elimination half-life is 12 h.

    5.5 Mechanism of Action

    Hydroxyethyl starch (HES) is one of the most frequently used plasma substitutes. Recent studies have indicated that HES may reduce capillary leakage.