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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
Salts
Name/CAS Structure Properties
Pentosan Polysulphate Sodium
Thumb Not applicable DBSALT000991
Brand names
NameCompany
ComforaSwati Spentose Pvt. Ltd.
ElmironOrtho-McNeil Pharmaceutical
FibraseTeofarma
FibrezymBene
HemoclarSanofi Winthrop
HémoclarSanofi-Aventis
Tavan-SPSanofi-Aventis
ThrombocidBene-Chemie
Brand mixturesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassDisaccharides
Direct parentDihexoses
Alternative parentsO-glycosyl Compounds; Sulfuric Acid Monoesters; Oxanes; Secondary Alcohols; Hemiacetals; Polyamines; Acetals
Substituentsglycosyl compound; o-glycosyl compound; sulfuric acid monoester; oxane; sulfate-ester; sulfuric acid derivative; hemiacetal; secondary alcohol; acetal; polyamine; ether; alcohol
Classification descriptionThis compound belongs to the dihexoses. These are disaccharides containing two hexose carbohydrates.
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
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 substrate Non-inhibitor 0.8387
CYP450 2D6 substrate Non-inhibitor 0.8982
CYP450 2C19 substrate Non-inhibitor 0.8044
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
Prices
Unit descriptionCostUnit
Elmiron 100 mg capsule3.32USDcapsule
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 solubility3.49e+00 g/lALOGPS
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 area322.55ChemAxon
rotatable bond count10ChemAxon
refractivity96.38ChemAxon
polarizability46.17ChemAxon
number of rings2ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
PubChem Compound37720
PubChem Substance46509187
ChemSpider34595
Therapeutic Targets DatabaseDAP001025
PharmGKBPA164774806
Drug Product Database2082101
RxListhttp://www.rxlist.com/cgi/generic2/pento.htm
ATC CodesC05BA04
AHFS Codes
  • 92:00.00
PDB EntriesNot Available
FDA labelshow(59.2 KB)
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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