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Identification
NamePentosan Polysulfate
Accession NumberDB00686  (APRD01175)
TypeSmall Molecule
GroupsApproved
Description

A sulfated pentosyl polysaccharide with heparin-like properties. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
Pentosan sulfuric polyesterNot AvailableIS
Pentosane polysulfateFrenchINN
Pentosani polysulfasLatinINN
Pentosano polisulfatoSpanishINN
PentosanpolysulfatGermanINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Elmironcapsule, gelatin coated100 mgoralJanssen Pharmaceuticals, Inc.1996-09-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elmironcapsule, gelatin coated100 mgoralPhysicians Total Care, Inc.2003-12-17Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Elmironcapsule, gelatin coated100 mgoralCardinal Health1996-09-26Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
ComforaSwati Spentose Pvt. Ltd.
FibraseTeofarma
FibrezymBene
HemoclarSanofi Winthrop
HémoclarSanofi-Aventis
Tavan-SPSanofi-Aventis
ThrombocidBene-Chemie
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pentosan Polysulphate Sodium
ThumbNot applicableDBSALT000991
CategoriesNot Available
CAS number37300-21-3
WeightAverage: 602.497
Monoisotopic: 601.922340398
Chemical FormulaC10H18O21S4
InChI KeyFCCNSUIJIOOXEZ-SJYYZXOBSA-N
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
IUPAC Name
[(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
SMILES
O[C@@H]1CO[C@@H](O[C@@H]2CO[C@@H](O)[C@H](OS(O)(=O)=O)[C@H]2OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Oxane
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the relief of bladder pain or discomfort associated with interstitial cystitis.
PharmacodynamicsPentosan polysulfate sodium is a low molecular weight heparin-like compound. It has anticoagulant and fibrinolytic effects.
Mechanism of actionPentosan 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.
AbsorptionSlow
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half life4.8 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5
Blood Brain Barrier+0.8606
Caco-2 permeable-0.6462
P-glycoprotein substrateNon-substrate0.7185
P-glycoprotein inhibitor IInhibitor0.6326
P-glycoprotein inhibitor IINon-inhibitor0.9889
Renal organic cation transporterNon-inhibitor0.8869
CYP450 2C9 substrateNon-substrate0.9008
CYP450 2D6 substrateNon-substrate0.8275
CYP450 3A4 substrateNon-substrate0.6053
CYP450 1A2 substrateNon-inhibitor0.8007
CYP450 2C9 substrateNon-inhibitor0.8387
CYP450 2D6 substrateNon-inhibitor0.8982
CYP450 2C19 substrateNon-inhibitor0.8044
CYP450 3A4 substrateNon-inhibitor0.9891
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.964
Ames testNon AMES toxic0.6383
CarcinogenicityNon-carcinogens0.5703
BiodegradationNot ready biodegradable0.8772
Rat acute toxicity2.3876 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8908
hERG inhibition (predictor II)Non-inhibitor0.7929
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Capsule, gelatin coatedoral100 mg
Prices
Unit descriptionCostUnit
Elmiron 100 mg capsule3.32USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States51807151993-01-192010-01-19
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-8Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.49 mg/mLALOGPS
logP-2.5ALOGPS
logP-11ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-2.9ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area322.55 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity96.38 m3·mol-1ChemAxon
Polarizability46.17 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Pandurang Balwant Deshpande, Parvenkumar Luthra, Anand Kumar Pandey, Dinesh Jayntibhai Paghdar, Phani,Sharma,Gowthamaiah Vemavarapu Govardhana, “PROCESS FOR THE PREPARATION OF PENTOSAN POLYSULFATE OR SALTS THEREOF.” U.S. Patent US20100105889, issued April 29, 2010.

US20100105889
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (59.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
EptifibatidePentosan can potentiate adverse effects of antiplatelet agents and thus increase bleeding risk. Combination must be used with caution.
Food Interactions
  • Take on an empty stomach, 1 hour before or 2 hours after meals.

Targets

1. Fibroblast growth factor 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Fibroblast growth factor 2 P09038 Details

References:

  1. Zugmaier G, Favoni R, Jaeger R, Rosen N, Knabbe C: Polysulfated heparinoids selectively inactivate heparin-binding angiogenesis factors. Ann N Y Acad Sci. 1999;886:243-8. Pubmed
  2. Mucha S, Melen-Mucha G, Stepien T, Godlewski A, Stepien H: Effects of pentosan polysulfate sodium on the estrogen-induced pituitary prolactinoma in Fischer 344 rats. Oncol Rep. 2002 Nov-Dec;9(6):1385-9. Pubmed
  3. Pluda JM, Shay LE, Foli A, Tannenbaum S, Cohen PJ, Goldspiel BR, Adamo D, Cooper MR, Broder S, Yarchoan R: Administration of pentosan polysulfate to patients with human immunodeficiency virus-associated Kaposi’s sarcoma. J Natl Cancer Inst. 1993 Oct 6;85(19):1585-92. Pubmed
  4. McLeskey SW, Zhang L, Kharbanda S, Kurebayashi J, Lippman ME, Dickson RB, Kern FG: Fibroblast growth factor overexpressing breast carcinoma cells as models of angiogenesis and metastasis. Breast Cancer Res Treat. 1996;39(1):103-17. Pubmed
  5. Jerebtsova M, Wong E, Przygodzki R, Tang P, Ray PE: A novel role of fibroblast growth factor-2 and pentosan polysulfate in the pathogenesis of intestinal bleeding in mice. Am J Physiol Heart Circ Physiol. 2007 Feb;292(2):H743-50. Epub 2006 Oct 27. Pubmed

2. Fibroblast growth factor 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Fibroblast growth factor 1 P05230 Details

References:

  1. Pascu C, Ljungh A, Wadstrom T: Staphylococci bind heparin-binding host growth factors. Curr Microbiol. 1996 Apr;32(4):201-7. Pubmed
  2. Zenjari C, Boilly-Marer Y, Desbiens X, Oudghir M, Hondermarck H, Boilly B: Experimental evidence for FGF-1 control of blastema cell proliferation during limb regeneration of the amphibian Pleurodeles waltl. Int J Dev Biol. 1996 Oct;40(5):965-71. Pubmed
  3. Jerebtsova M, Wong E, Przygodzki R, Tang P, Ray PE: A novel role of fibroblast growth factor-2 and pentosan polysulfate in the pathogenesis of intestinal bleeding in mice. Am J Physiol Heart Circ Physiol. 2007 Feb;292(2):H743-50. Epub 2006 Oct 27. Pubmed

3. Fibroblast growth factor 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Fibroblast growth factor 4 P08620 Details

References:

  1. Zugmaier G, Lippman ME, Wellstein A: Inhibition by pentosan polysulfate (PPS) of heparin-binding growth factors released from tumor cells and blockage by PPS of tumor growth in animals. J Natl Cancer Inst. 1992 Nov 18;84(22):1716-24. Pubmed
  2. McLeskey SW, Zhang L, Kharbanda S, Kurebayashi J, Lippman ME, Dickson RB, Kern FG: Fibroblast growth factor overexpressing breast carcinoma cells as models of angiogenesis and metastasis. Breast Cancer Res Treat. 1996;39(1):103-17. Pubmed
  3. Wellstein A, Zugmaier G, Califano JA 3rd, Kern F, Paik S, Lippman ME: Tumor growth dependent on Kaposi’s sarcoma-derived fibroblast growth factor inhibited by pentosan polysulfate. J Natl Cancer Inst. 1991 May 15;83(10):716-20. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 13, 2014 10:55