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Technical details about Pentosan Sulfuric Polyester, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: 37300-21-3, Pentosan sulfuric polyester, Polypentose sulfate, [(2r,3r,4s,5r)-2-hydroxy-5-[(2s,3r,4s,5r)-5-hydroxy-3,4-disulfooxyoxan-2-yl]oxy-3-sulfooxyoxan-4-yl] hydrogen sulfate, Xylan, hydrogen sulfate, Unii-f59p8b75r4
Molecular Formula
C10H18O21S4
Molecular Weight
602.5  g/mol
InChI Key
FCCNSUIJIOOXEZ-SJYYZXOBSA-N

A sulfated pentosyl polysaccharide with heparin-like properties.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(2R,3R,4S,5R)-2-hydroxy-5-[(2S,3R,4S,5R)-5-hydroxy-3,4-disulfooxyoxan-2-yl]oxy-3-sulfooxyoxan-4-yl] hydrogen sulfate
2.1.2 InChI
InChI=1S/C10H18O21S4/c11-3-1-26-10(8(31-35(22,23)24)5(3)28-32(13,14)15)27-4-2-25-9(12)7(30-34(19,20)21)6(4)29-33(16,17)18/h3-12H,1-2H2,(H,13,14,15)(H,16,17,18)(H,19,20,21)(H,22,23,24)/t3-,4-,5+,6+,7-,8-,9-,10+/m1/s1
2.1.3 InChI Key
FCCNSUIJIOOXEZ-SJYYZXOBSA-N
2.1.4 Canonical SMILES
C1C(C(C(C(O1)OC2COC(C(C2OS(=O)(=O)O)OS(=O)(=O)O)O)OS(=O)(=O)O)OS(=O)(=O)O)O
2.1.5 Isomeric SMILES
C1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2CO[C@H]([C@@H]([C@H]2OS(=O)(=O)O)OS(=O)(=O)O)O)OS(=O)(=O)O)OS(=O)(=O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Bay 946

2. Bay-946

3. Elmiron

4. Fibrocid

5. Hemoclar

6. Hoe 946

7. Hoe Bay 946

8. Hoe-946

9. Hoe-bay 946

10. Hoe-bay-946

11. Pentosan Polysulfate Sodium

12. Pentosan Polysulphate Sodium

13. Pentosan Sulfuric Polyester

14. Pentosane Sulfuric Polyester

15. Polyester, Pentosan Sulfuric

16. Polyester, Pentosane Sulfuric

17. Polypentose Sulfate

18. Polysulfate Sodium, Pentosan

19. Polysulfate, Pentosan

20. Polysulfated Xylan

21. Polysulphate Sodium, Pentosan

22. Pz 68

23. Pz-68

24. Pz68

25. Sodium, Pentosan Polysulfate

26. Sodium, Pentosan Polysulphate

27. Sp 54

28. Sp 54, Tavan

29. Sp-54

30. Sp54

31. Sp54, Xylan

32. Sulfate, Polypentose

33. Sulfate, Xylan

34. Sulfuric Polyester, Pentosan

35. Sulfuric Polyester, Pentosane

36. Tavan Sp 54

37. Xylan Sp54

38. Xylan Sulfate

39. Xylan, Polysulfated

2.2.2 Depositor-Supplied Synonyms

1. 37300-21-3

2. Pentosan Sulfuric Polyester

3. Polypentose Sulfate

4. [(2r,3r,4s,5r)-2-hydroxy-5-[(2s,3r,4s,5r)-5-hydroxy-3,4-disulfooxyoxan-2-yl]oxy-3-sulfooxyoxan-4-yl] Hydrogen Sulfate

5. Xylan, Hydrogen Sulfate

6. Unii-f59p8b75r4

7. Schembl157354

8. Chembl4073796

9. Chebi:184555

10. F59p8b75r4

11. Db00686

12. Q7165276

13. [(2r,3r,4s,5r)-2-hydroxy-5-[(2s,3r,4s,5r)-5-hydroxy-3,4-disulooxyoxan-2-yl]oxy-3-sulooxyoxan-4-yl] Hydrogen Sulate

14. [(2r,3r,4s,5r)-2-hydroxy-5-{[(2s,3r,4s,5r)-5-hydroxy-3,4-bis(sulfooxy)oxan-2-yl]oxy}-4-(sulfooxy)oxan-3-yl]oxidanesulfonic Acid

15. [(2s,3r,4s,5r)-5-hydroxy-2-{[(3r,4s,5r,6r)-6-hydroxy-4,5-bis(sulfooxy)oxan-3-yl]oxy}-4-(sulfooxy)oxan-3-yl]oxidanesulfonic Acid

16. 11096-31-4

2.3 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 602.5 g/mol
Molecular Formula C10H18O21S4
XLogP3-5.6
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count21
Rotatable Bond Count10
Exact Mass601.92234227 g/mol
Monoisotopic Mass601.92234227 g/mol
Topological Polar Surface Area356 Ų
Heavy Atom Count35
Formal Charge0
Complexity1140
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameElmiron
PubMed HealthPentosan Polysulfate Sodium (By mouth)
Drug ClassesCystitis Agent, Urinary Stone Agent
Drug LabelPentosan polysulfate sodium is a semi-synthetically produced heparin-like macromolecular carbohydrate derivative, which chemically and structurally resembles glycosaminoglycans. It is a white odorless powder, slightly hygroscopic and soluble in water...
Active IngredientPentosan polysulfate sodium
Dosage FormCapsule
RouteOral
Strength100mg
Market StatusPrescription
CompanyJanssen Pharms

2 of 2  
Drug NameElmiron
PubMed HealthPentosan Polysulfate Sodium (By mouth)
Drug ClassesCystitis Agent, Urinary Stone Agent
Drug LabelPentosan polysulfate sodium is a semi-synthetically produced heparin-like macromolecular carbohydrate derivative, which chemically and structurally resembles glycosaminoglycans. It is a white odorless powder, slightly hygroscopic and soluble in water...
Active IngredientPentosan polysulfate sodium
Dosage FormCapsule
RouteOral
Strength100mg
Market StatusPrescription
CompanyJanssen Pharms

4.2 Drug Indication

For the relief of bladder pain or discomfort associated with interstitial cystitis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Pentosan polysulfate sodium is a low molecular weight heparin-like compound. It has anticoagulant and fibrinolytic effects.


5.2 MeSH Pharmacological Classification

Anticoagulants

Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)


5.3 Absorption, Distribution and Excretion

Absorption

Slow


5.4 Biological Half-Life

4.8 hours


5.5 Mechanism of Action

Pentosan polysulfate is a polymer of xylose hydrogen sulfate and contains two sulfate groups per carbohydrate monomer. It binds Fibroblast growth factors (FGFs) as well as other heparin-binding growth factors. It has been shown to interact also with the heparin-binding site of FGFR-1. It inhibits the growth of SW13 adrenocortical cells transfected with FGF-4 and tumorigenicity of MCF-7 breast carcinoma cells transfected with FGF-1 or FGF-4.


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