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targets (3)
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Identification
Name Pentosan Polysulfate
Accession Number DB00686 (APRD01175)
Type small molecule
Groups approved
Description

A sulfated pentosyl polysaccharide with heparin-like properties. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Elmiron
Brand mixtures Not Available
Categories
  • Anticoagulants
  • Enzyme Inhibitors
CAS number 37300-21-3
Weight Average: 602.497
Monoisotopic: 601.922340398
Chemical Formula C10H18O21S4
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbohydrates
Substructures
  • Carbohydrates
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Acetals and Derivatives
  • Sulfuric Acids and Derivatives
  • Sulfonyls
  • Ethers
  • Sulfate Esters
  • Heterocyclic compounds
  • Alcohols and Polyols
Pharmacology
Indication For the relief of bladder pain or discomfort associated with interstitial cystitis.
Pharmacodynamics 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.
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
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Prices
Unit description Cost Unit
Elmiron 100 mg capsule 3.32 USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Country Patent Number Approved Expires (estimated)
United States 5180715 1993-01-19 2010-01-19
Properties
State solid
Experimental Properties
Property Value Source
logP -8 Not Available
Predicted Properties
Property Value Source
water solubility 3.49e+00 g/l 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 ChemAxon
rotatable bond count 10 ChemAxon
refractivity 96.38 ChemAxon
polarizability 46.17 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 37720 Link_out
PubChem Substance 46509187 Link_out
ChemSpider 34595 Link_out
Therapeutic Targets Database DAP001025 Link_out
PharmGKB PA164774806 Link_out
Drug Product Database 2082101 Link_out
RxList http://www.rxlist.com/cgi/generic2/pento.htm Link_out
ATC Codes
  • C05BA04
AHFS Codes
  • 92:00.00
PDB Entries Not Available
FDA label show (59.2 KB)
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Take on an empty stomach, 1 hour before or 2 hours after meals.
Targets

1. Heparin-binding growth factor 2

Pharmacological action: yes
Actions: antagonist

The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors

Organism class: human
UniProt ID: P09038 Link_out
Gene: FGF2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors

Organism class: human
UniProt ID: P05230 Link_out
Gene: FGF1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: unknown
Actions: inhibitor

Can transform NIH 3T3 cells from a human stomach tumor (hst) and from karposi's sarcoma (KS3). It has a mitogenic activity

Organism class: human
UniProt ID: P08620 Link_out
Gene: FGF4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19