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    Pentosan Polysulphate Sodium

    ACTIVE PHARMA INGREDIENTS

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    $ API Ref.Price (USD/KG) : 2,560Xls

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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.