Basic information
- CAS
37300-21-3- Standard SMILES
O=S(=O)(O)O[C@@H]1[C@@H](OS(=O)(=O)O)[C@H](O[C@@H]2CO[C@@H](O)[C@H](OS(=O)(=O)O)[C@H]2OS(=O)(=O)O)OC[C@H]1O- InChIKey
FCCNSUIJIOOXEZ-SJYYZXOBSA-N- Molecular formula
- C10H18O21S4
- Average molar mass
- 602.5 g/mol
- Monoisotopic mass
- 601.92234227
Overview
[(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 is a glycoside.
Names & identifiers
- Preferred name
- Xylan Sulfate
- IUPAC
- [(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
- English name
- Pentosan Sulfuric Polyester
- Molecular formula
- C10H18O21S4
- Molecular weight
- 0
Names & synonyms
37300-21-3Xylan, hydrogen sulfateF59P8B75R4[(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 acidXylan hydrogen sulfateXylan Sulfate((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 acidRefChem:8526GlyTouCan:G69706YRDTXSID601026229G69706YRCB-8061
Show more names
ElmironXylan polysulfateXylofuranan sulfatePENTOSAN POLYSULFATE SODPentosan Sulfuric Polyester[(2R,3R,4S,5R)-2-hydroxy-5-[(2S,3R,4S,5R)-5-hydroxy-3,4-disulfooxy-oxan-2-yl]oxy-3-sulfooxy-oxan-4-yl] hydrogen sulfatesulfuric acid [(2R,3R,4S,5R)-2-hydroxy-5-[(2S,3R,4S,5R)-5-hydroxy-3,4-disulfoxy-tetrahydropyran-2-yl]oxy-3-sulfoxy-tetrahydropyran-4-yl] ester
140207-92-7[(2R,3R,4S,5R)-2-hydroxy-5-[(2S,3R,4S,5R)-5-hydroxy-3,4-disulfooxyoxan-2-yl]oxy-3-sulfooxyoxan-4-yl] hydrogen sulfate11096-31-4UNII-F59P8B75R42763886-11-7Pentosan PolysulfonateSCHEMBL157354CHEMBL4073796
Properties
Computed structural properties
- XLogP
- -5.6
- Topological polar surface area
- 356 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 21
- Rotatable bonds
- 10
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 1,140
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP-8
Solubility3.49e+00 g/L
Physical DescriptionSolid
Physicochemical properties
- form
- Solid
- color
- White to off-white
- FDA UNII
- 59 P8B75R4 · F59P8B75R4
Chemistry & industry
Pharmacology
PharmacodynamicsPentosan polysulfate sodium is a low molecular weight heparin-like compound. It has anticoagulant and fibrinolytic effects.
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.
Biological Half-Life4.8 hours
FDA Pharmacological Classification
F59P8B75R4
PENTOSAN POLYSULFATE
Established Pharmacologic Class [EPC] - Glycosaminoglycan
Chemical Structure [CS] - Glycosaminoglycans
Pentosan polysulfate is a Glycosaminoglycan.
MeSH Pharmacological ClassificationAgents that prevent BLOOD CLOTTING.
Absorption, Distribution and ExcretionSlow
Applications
HistoryPentosan polysulfate sodium (Elmiron) was synthesized at Baker Norton Pharmaceuticals in the early 1980s as a heparin analogue for interstitial cystitis; after orphan designation (1985) and compassionate use (1986–1995) it received FDA approval on 26 September 1996 under an NDA that listed no individually named inventors, and its efficacy was later questioned when the first controlled trial (Nickel, 2014) proved negative.
Suppliers12 total
Related reactions
0 records
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Compound notes
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