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2D Structure
Also known as: Kelacid, Sazio, Gum levan, Levan gum, E400
Molecular Formula
C12H20O12P2
Molecular Weight
418.23  g/mol
InChI Key
FHVDTGUDJYJELY-UHFFFAOYSA-N

Salts and esters of ALGINIC ACID that are used as HYDROGELS; DENTAL IMPRESSION MATERIALS, and as absorbent materials for surgical dressings (BANDAGES, HYDROCOLLOID). They are also used to manufacture MICROSPHERES and NANOPARTICLES for DIAGNOSTIC REAGENT KITS and DRUG DELIVERY SYSTEMS.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(6-carboxy-3,4-dihydroxy-5-phosphanyloxan-2-yl)oxy-4,5-dihydroxy-6-phosphanyloxyoxane-2-carboxylic acid
2.1.2 InChI
InChI=1S/C12H20O12P2/c13-1-3(15)12(24-26)22-6(9(17)18)5(1)21-11-4(16)2(14)8(25)7(23-11)10(19)20/h1-8,11-16H,25-26H2,(H,17,18)(H,19,20)
2.1.3 InChI Key
FHVDTGUDJYJELY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1(C(C(OC(C1OC2C(C(C(C(O2)C(=O)O)P)O)O)C(=O)O)OP)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Alginate, Barium

2. Alginate, Calcium

3. Alginate, Copper

4. Alginate, Potassium

5. Alginate, Sodium

6. Alginate, Sodium Calcium

7. Alginates

8. Alginic Acid, Barium Salt

9. Alginic Acid, Calcium Salt

10. Alginic Acid, Copper Salt

11. Alginic Acid, Potassium Salt

12. Alginic Acid, Sodium Salt

13. Alloid G

14. Barium Alginate

15. Calcium Alginate

16. Calcium Alginate, Sodium

17. Calginat

18. Copper Alginate

19. Kalrostat

20. Kalrostat 2

21. Kaltostat

22. Poly(mannuronic Acid), Sodium Salt

23. Potassium Alginate

24. Sodium Alginate

25. Sodium Calcium Alginate

26. Vocoloid

27. Xantalgin

2.2.2 Depositor-Supplied Synonyms

1. Kelacid

2. Sazio

3. Gum Levan

4. Levan Gum

5. E400

2.3 Create Date
2017-10-31
3 Chemical and Physical Properties
Molecular Weight 418.23 g/mol
Molecular Formula C12H20O12P2
XLogP3-4
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count5
Exact Mass418.04300006 g/mol
Monoisotopic Mass418.04300006 g/mol
Topological Polar Surface Area192 Ų
Heavy Atom Count26
Formal Charge0
Complexity534
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count10
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Indicated for the management of gastric reflux, reflux oesophagitis, hiatus hernia, heartburn (including heartburn of pregnancy) and similar gastric distress.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Alginic acid reduces reflux via its floating, foaming, and viscous properties. Alginic acid precipitates upon contact with gastric acid to create a mechanical barrier, or a "raft", that displaces the postprandial acid pocket. The formation of a raft is thought to occur rapidly, often within a few seconds of dosing. In clinical trials, alginic acid was effective in reducing the symptoms of gastroesophageal reflux disease (GERD). In healthy volunteers, alginic acid in combination with an antacid was effective in decreasing postprandial reflux in the upright position. Alginic acid is able to bind to cations when ingested.


5.2 Absorption, Distribution and Excretion

Absorption

The absorption into the systemic circulation from oral formulations of alginic acid is reported to be minimal, as the mode of action of alginic acid is physical.


Route of Elimination

This pharmacokinetic parameter is unlikely to apply for alginic acid.


Volume of Distribution

This pharmacokinetic parameter is unlikely to apply for alginic acid.


Clearance

This pharmacokinetic parameter is unlikely to apply for alginic acid.


5.3 Metabolism/Metabolites

This pharmacokinetic parameter is unlikely to apply for alginic acid.


5.4 Biological Half-Life

This pharmacokinetic parameter is unlikely to apply for alginic acid.


5.5 Mechanism of Action

Once orally administered, alginic acid reacts with gastric acid to form a floating "raft" of alginic acid gel on the gastric acid pool. Alginate-based raft-forming formulations commonly contain sodium or bicarbonate; bicarbonate ions are converted to carbon dioxide in presence of gastric acid and get entrapped within the gel precipitate, converting it into a foam which floats on the surface of the gastric contents, much like a raft on water. The "raft" has a near neutral pH due to carbon dioxide and floats on the stomach contents and potentially functions as a barrier to impede gastroesophageal reflux. In severe cases, the raft itself may be refluxed into the oesophagus in preference to the stomach contents and exert a demulcent effect.