You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NamePentosan Polysulfate
Accession NumberDB00686  (APRD01175)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
Pentosan sulfuric polyester
Pentosane polysulfate
Pentosani polysulfas
Pentosano polisulfato
Pentosanpolysulfat
External Identifiers
  • CB-8061
  • PZ 68
  • SP 54
  • UNII-F59P8B75R4
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Elmironcapsule, gelatin coated100 mg/1oralJanssen Pharmaceuticals, Inc.1996-09-26Not applicableUs
Elmironcapsule100 mgoralJanssen Inc1993-12-31Not applicableCanada
Elmironcapsule, gelatin coated100 mg/1oralCardinal Health1996-09-26Not applicableUs
Elmironcapsule, gelatin coated100 mg/1oralPhysicians Total Care, Inc.2003-12-17Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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
Calcium pentosan polysulfate
ThumbNot applicableDBSALT001142
Pentosan polysulfate sodium
ThumbNot applicableDBSALT000991
Categories
UNIIF59P8B75R4
CAS number37300-21-3
WeightAverage: 602.497
Monoisotopic: 601.922340398
Chemical FormulaC10H18O21S4
InChI KeyInChIKey=FCCNSUIJIOOXEZ-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)[[email protected]](OS(O)(=O)=O)[[email protected]]2OS(O)(=O)=O)[[email protected]](OS(O)(=O)=O)[[email protected]]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.
Related Articles
AbsorptionSlow
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.8387
CYP450 2D6 inhibitorNon-inhibitor0.8982
CYP450 2C19 inhibitorNon-inhibitor0.8044
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Capsuleoral100 mg
Capsule, gelatin coatedoral100 mg/1
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
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5180715 No1993-01-192010-01-19Us
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 References
  1. Ghosh P, Smith M: Osteoarthritis, genetic and molecular mechanisms. Biogerontology. 2002;3(1-2):85-8. [PubMed:12014849 ]
External Links
ATC CodesC05BA04G04BX15
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelDownload (59.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Abciximab.
AcenocoumarolPentosan Polysulfate may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Acetylsalicylic acid.
AnagrelideThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Anagrelide.
ApixabanPentosan Polysulfate may increase the anticoagulant activities of Apixaban.
ArgatrobanPentosan Polysulfate may increase the anticoagulant activities of Argatroban.
BivalirudinPentosan Polysulfate may increase the anticoagulant activities of Bivalirudin.
CangrelorThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Cangrelor.
CilostazolThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Cilostazol.
CitalopramThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Citalopram.
Citric AcidPentosan Polysulfate may increase the anticoagulant activities of Citric Acid.
ClopidogrelThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Clopidogrel.
Dabigatran etexilatePentosan Polysulfate may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinPentosan Polysulfate may increase the anticoagulant activities of Dalteparin.
DanaparoidPentosan Polysulfate may increase the anticoagulant activities of Danaparoid.
DesirudinPentosan Polysulfate may increase the anticoagulant activities of Desirudin.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Desvenlafaxine.
DiclofenacThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Diclofenac.
DicoumarolPentosan Polysulfate may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Diflunisal.
DipyridamoleThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Dipyridamole.
DuloxetineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Duloxetine.
Edetic AcidPentosan Polysulfate may increase the anticoagulant activities of Edetic Acid.
EdoxabanPentosan Polysulfate may increase the anticoagulant activities of Edoxaban.
EnoxaparinPentosan Polysulfate may increase the anticoagulant activities of Enoxaparin.
EptifibatideThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Eptifibatide.
EscitalopramThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Escitalopram.
Ethyl biscoumacetatePentosan Polysulfate may increase the anticoagulant activities of Ethyl biscoumacetate.
EtodolacThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Etodolac.
FenoprofenThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Fenoprofen.
FloctafenineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Floctafenine.
FluoxetineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Fluoxetine.
FlurbiprofenThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Flurbiprofen.
FluvoxamineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Fluvoxamine.
Fondaparinux sodiumPentosan Polysulfate may increase the anticoagulant activities of Fondaparinux sodium.
HeparinPentosan Polysulfate may increase the anticoagulant activities of Heparin.
IbuprofenThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ibuprofen.
IndomethacinThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Indomethacin.
KetoprofenThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ketorolac.
LevomilnacipranThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Levomilnacipran.
Mefenamic acidThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Mefenamic acid.
MeloxicamThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Meloxicam.
MilnacipranThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Milnacipran.
NabumetoneThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Nabumetone.
NadroparinPentosan Polysulfate may increase the anticoagulant activities of Nadroparin.
NaproxenThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Naproxen.
OxaprozinThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Oxaprozin.
ParoxetineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Paroxetine.
PhenindionePentosan Polysulfate may increase the anticoagulant activities of Phenindione.
PhenprocoumonPentosan Polysulfate may increase the anticoagulant activities of Phenprocoumon.
PiroxicamThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Piroxicam.
PrasugrelThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Prasugrel.
RivaroxabanPentosan Polysulfate may increase the anticoagulant activities of Rivaroxaban.
SertralineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Sertraline.
SulindacThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Sulindac.
SulodexidePentosan Polysulfate may increase the anticoagulant activities of Sulodexide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Tiaprofenic acid.
TicagrelorThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ticagrelor.
TiclopidineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ticlopidine.
TinzaparinPentosan Polysulfate may increase the anticoagulant activities of Tinzaparin.
TirofibanThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Tirofiban.
TolmetinThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Tolmetin.
TreprostinilPentosan Polysulfate may increase the anticoagulant activities of Treprostinil.
VenlafaxineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Venlafaxine.
VilazodoneThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Vilazodone.
VorapaxarThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Vorapaxar.
VortioxetineThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Vortioxetine.
WarfarinPentosan Polysulfate may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take on an empty stomach, 1 hour before or 2 hours after meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Ligand-dependent nuclear receptor transcription coactivator activity
Specific Function:
Plays an important role in the regulation of cell survival, cell division, angiogenesis, cell differentiation and cell migration. Functions as potent mitogen in vitro.
Gene Name:
FGF2
Uniprot ID:
P09038
Molecular Weight:
30769.715 Da
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:10667230 ]
  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:12375053 ]
  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:7692072 ]
  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:8738610 ]
  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:17071728 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
S100 protein binding
Specific Function:
Plays an important role in the regulation of cell survival, cell division, angiogenesis, cell differentiation and cell migration. Functions as potent mitogen in vitro.
Gene Name:
FGF1
Uniprot ID:
P05230
Molecular Weight:
17459.58 Da
References
  1. Pascu C, Ljungh A, Wadstrom T: Staphylococci bind heparin-binding host growth factors. Curr Microbiol. 1996 Apr;32(4):201-7. [PubMed:8867461 ]
  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:8946244 ]
  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:17071728 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Heparin binding
Specific Function:
Plays an important role in the regulation of embryonic development, cell proliferation, and cell differentiation. Required for normal limb and cardiac valve development during embryogenesis.
Gene Name:
FGF4
Uniprot ID:
P08620
Molecular Weight:
22047.355 Da
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:1279186 ]
  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:8738610 ]
  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:1708834 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 16, 2015 10:20