Identification
- Summary
Pentosan polysulfate is a sulfated pentosyl polysaccharide used to treat bladder pain and discomfort due to interstitial cystitis.
- Brand Names
- Elmiron
- Generic Name
- Pentosan polysulfate
- DrugBank Accession Number
- DB00686
- Background
Pentosan polysulfate is a sulfated pentosyl polysaccharide with heparin-like properties.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pentosan polysulfate (DB00686)
- Weight
- Average: 602.497
Monoisotopic: 601.922340398 - Chemical Formula
- C10H18O21S4
- Synonyms
- Pentosan polysulfate
- Pentosan sulfuric polyester
- Pentosane polysulfate
- Pentosani polysulfas
- Pentosano polisulfato
- Pentosanpolysulfat
- External IDs
- CB-8061
- PZ 68
- SP 54
Pharmacology
- Indication
For the relief of bladder pain or discomfort associated with interstitial cystitis.
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- Contraindications & Blackbox Warnings
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Pentosan 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.
Target Actions Organism AFibroblast growth factor 2 antagonistHumans AFibroblast growth factor 1 antagonistHumans UFibroblast growth factor 4 inhibitorHumans - Absorption
Slow
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
4.8 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The risk or severity of adverse effects can be increased when Pentosan polysulfate is combined with Abciximab. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Pentosan polysulfate. Acemetacin The risk or severity of bleeding and hemorrhage can be increased when Pentosan polysulfate is combined with Acemetacin. Acenocoumarol Pentosan polysulfate may increase the anticoagulant activities of Acenocoumarol. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Pentosan polysulfate is combined with Acetylsalicylic acid. Albutrepenonacog alfa The therapeutic efficacy of Albutrepenonacog alfa can be decreased when used in combination with Pentosan polysulfate. Alclofenac The risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Pentosan polysulfate. Aldesleukin The risk or severity of bleeding can be increased when Pentosan polysulfate is combined with Aldesleukin. Alemtuzumab The risk or severity of bleeding can be increased when Pentosan polysulfate is combined with Alemtuzumab. Alteplase Pentosan polysulfate may increase the anticoagulant activities of Alteplase. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Taking pentosan polysulfate with anticoagulant herbs may increase bleeding risk, which is an adverse effect of pentosan polysulfate.
- Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Calcium pentosan polysulfate Not Available Not Available Not applicable Pentosan polysulfate sodium 914032762Y 140207-93-8 Not applicable - Product Images
- International/Other Brands
- Comfora (Swati Spentose Pvt. Ltd.) / Fibrase (Teofarma) / Fibrezym (Bene) / Hemoclar (Sanofi Winthrop) / Hémoclar (Sanofi-Aventis) / Tavan-SP (Sanofi-Aventis) / Thrombocid (Bene-Chemie)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Elmiron Capsule, gelatin coated 100 mg/1 Oral Physicians Total Care, Inc. 2003-12-17 Not applicable US 
Elmiron Capsule 100 mg Oral Bene Arzneimittel Gmb H 2020-12-16 Not applicable EU 
Elmiron Capsule 100 mg/1 Oral Ortho-McNeil Pharmaceutical, Inc. 2006-10-17 2006-10-17 US Elmiron Capsule, gelatin coated 100 mg/1 Oral Janssen Pharmaceuticals, Inc. 1996-09-26 Not applicable US 
Elmiron Capsule 100 mg Oral Bene Arzneimittel Gmb H 2020-12-16 Not applicable EU Elmiron Capsule, gelatin coated 100 mg/1 Oral Ortho Mc Neil Pharmaceuticals 1996-09-26 2012-05-31 US Elmiron Capsule, gelatin coated 100 mg/1 Oral Cardinal Health 1996-09-26 2018-11-30 US 
Elmiron Capsule 100 mg Oral Bene Arzneimittel Gmb H 2020-12-16 Not applicable EU Elmiron Capsule 100 mg Oral Janssen Pharmaceuticals 1993-12-31 Not applicable Canada 
Categories
- ATC Codes
- C05BA04 — Pentosan polysulfate sodium
- C05BA — Heparins or heparinoids for topical use
- C05B — ANTIVARICOSE THERAPY
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Anticoagulants
- Antivaricose Therapy
- Carbohydrates
- Drugs causing inadvertant photosensitivity
- Genito Urinary System and Sex Hormones
- Glycosaminoglycans
- Hematologic Agents
- Miscellaneous Therapeutic Agents
- Photosensitizing Agents
- Polysaccharides
- Sulfur Acids
- Sulfur Compounds
- Sulfuric Acids
- Urologicals
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- O-glycosyl compounds
- Alternative Parents
- Disaccharides / Sulfuric acid monoesters / Oxanes / Alkyl sulfates / Secondary alcohols / Hemiacetals / Oxacyclic compounds / Acetals / Organic oxides / Hydrocarbon derivatives
- Substituents
- Acetal / Alcohol / Aliphatic heteromonocyclic compound / Alkyl sulfate / Disaccharide / Hemiacetal / Hydrocarbon derivative / O-glycosyl compound / Organic oxide / Organic sulfuric acid or derivatives
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- F59P8B75R4
- CAS number
- 37300-21-3
- InChI Key
- 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)[C@H](OS(O)(=O)=O)[C@H]2OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O
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
- Ghosh P, Smith M: Osteoarthritis, genetic and molecular mechanisms. Biogerontology. 2002;3(1-2):85-8. [Article]
- External Links
- Human Metabolome Database
- HMDB0014824
- PubChem Compound
- 37720
- PubChem Substance
- 46509187
- ChemSpider
- 34595
- 155046
- ChEBI
- 184555
- ChEMBL
- CHEMBL4073796
- ZINC
- ZINC000014879975
- Therapeutic Targets Database
- DAP001025
- PharmGKB
- PA164774806
- RxList
- RxList Drug Page
- Wikipedia
- Pentosan_polysulfate
- FDA label
- Download (59.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Terminated Treatment Interstitial Cystitis 1 3 Completed Supportive Care Diarrhea / Enteritis Caused by Radiation 1 3 Not Yet Recruiting Treatment Osteoarthritis of the Knee 1 2 Completed Treatment Bipolar Disorder (BD) / Psychosis / Schizoaffective Disorders / Schizophrenia 1 2 Completed Treatment Prostatitis 1 2 Terminated Prevention BCG / Bladder Carcinoma / Lower Urinary Tract Symptoms (LUTS) 1 2, 3 Recruiting Treatment Osteoarthritis of the Knee 1 2, 3 Recruiting Treatment Radiation Cystitis 1
Pharmacoeconomics
- Manufacturers
- Ortho mcneil janssen pharmaceuticals inc
- Packagers
- Alza Corp.
- A-S Medication Solutions LLC
- Ivax Pharmaceuticals
- Janssen-Ortho Inc.
- McNeil Laboratories
- Murfreesboro Pharmaceutical Nursing Supply
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Capsule Oral 100 mg/1 Capsule Oral 100 mg Capsule, gelatin coated Oral 100 mg/1 Injection, solution Intramuscular; Intravenous Ointment Topical Capsule, coated Oral 100 mg Gel Topical 1.5 g Gel Topical 1.5 % - Prices
Unit description Cost Unit Elmiron 100 mg capsule 3.32USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5180715 No 1993-01-19 2010-01-19 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -8 Not Available - Predicted Properties
Property Value Source Water Solubility 3.49 mg/mL ALOGPS logP -2.5 ALOGPS logP -11 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) -2.9 Chemaxon pKa (Strongest Basic) -3.6 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 17 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 322.55 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 96.38 m3·mol-1 Chemaxon Polarizability 46.22 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier + 0.8606 Caco-2 permeable - 0.6462 P-glycoprotein substrate Non-substrate 0.7185 P-glycoprotein inhibitor I Inhibitor 0.6326 P-glycoprotein inhibitor II Non-inhibitor 0.9889 Renal organic cation transporter Non-inhibitor 0.8869 CYP450 2C9 substrate Non-substrate 0.9008 CYP450 2D6 substrate Non-substrate 0.8275 CYP450 3A4 substrate Non-substrate 0.6053 CYP450 1A2 substrate Non-inhibitor 0.8007 CYP450 2C9 inhibitor Non-inhibitor 0.8387 CYP450 2D6 inhibitor Non-inhibitor 0.8982 CYP450 2C19 inhibitor Non-inhibitor 0.8044 CYP450 3A4 inhibitor Non-inhibitor 0.9891 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.964 Ames test Non AMES toxic 0.6383 Carcinogenicity Non-carcinogens 0.5703 Biodegradation Not ready biodegradable 0.8772 Rat acute toxicity 2.3876 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8908 hERG inhibition (predictor II) Non-inhibitor 0.7929
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Fibroblast growth factor 2
- Molecular Weight
- 30769.715 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Fibroblast growth factor 1
- Molecular Weight
- 17459.58 Da
References
- Pascu C, Ljungh A, Wadstrom T: Staphylococci bind heparin-binding host growth factors. Curr Microbiol. 1996 Apr;32(4):201-7. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Fibroblast growth factor 4
- Molecular Weight
- 22047.355 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 29, 2023 23:14