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Pentosan Polysulfate

Pentosan polysulfate

Synopsis, Chemistry

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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

Pentosan polysulfate

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 Formula	C₁₀H₁₈O₂₁S₄
Molecular Weight	602.5 g/mol
XLogP3	-5.6
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	21
Rotatable Bond Count	10
Exact Mass	601.92234227 g/mol
Monoisotopic Mass	601.92234227 g/mol
Topological Polar Surface Area	356 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	1140
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Elmiron
PubMed Health	Pentosan Polysulfate Sodium (By mouth)
Drug Classes	Cystitis Agent, Urinary Stone Agent
Drug Label	Pentosan 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 Ingredient	Pentosan polysulfate sodium
Dosage Form	Capsule
Route	Oral
Strength	100mg
Market Status	Prescription
Company	Janssen Pharms

2 of 2
Drug Name	Elmiron
PubMed Health	Pentosan Polysulfate Sodium (By mouth)
Drug Classes	Cystitis Agent, Urinary Stone Agent
Drug Label	Pentosan 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 Ingredient	Pentosan polysulfate sodium
Dosage Form	Capsule
Route	Oral
Strength	100mg
Market Status	Prescription
Company	Janssen 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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