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Hydroxyethyl Starch

Synopsis, Chemistry

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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

Hydroxyethyl Starch

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 Formula	C₂₂H₄₄O₁₇
Molecular Weight	580.6 g/mol
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	17
Exact Mass	580.25784993 g/mol
Monoisotopic Mass	580.25784993 g/mol
Topological Polar Surface Area	267 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	497
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.