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MedKoo Cat#: 318469 | Name: Pentosan Polysulfate sodium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pentosan polysulfate is a semi-synthetic polysulfated xylan sold for the relief of various medical conditions including thrombi and interstitial cystitis in humans. Pentosan polysulfate is a sulfated pentosyl polysaccharide with heparin-like properties.

Chemical Structure

Pentosan Polysulfate sodium
Pentosan Polysulfate sodium
CAS#116001-96-8 (sodium)

Theoretical Analysis

MedKoo Cat#: 318469

Name: Pentosan Polysulfate sodium

CAS#: 116001-96-8 (sodium)

Chemical Formula:

Exact Mass:

Molecular Weight:

Elemental Analysis:

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
116001-96-8 (sodium) 37300-21-3 (free acid)
Synonym
Pentosan Polysulfate; Elmiron; Polypentose sulfate; Pentosan sulfuric polyester; Xylan, hydrogen sulfate; AC1L1YAW;
IUPAC/Chemical Name
[(2R,3R,4S,5R)-2-hydroxy-5-[(2S,3R,4S,5R)-5-hydroxy-3,4-disulfooxyoxan-2-yl]oxy-3-sulfooxyoxan-4-yl] hydrogen sulfate
InChi Key
FCCNSUIJIOOXEZ-SJYYZXOBSA-N
InChi Code
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
SMILES Code
C1C(C(C(C(O1)OC2COC(C(C2OS(=O)(=O)O)OS(=O)(=O)O)O)OS(=O)(=O)O)OS(=O)(=O)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 0.00 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Guan Z, Singletary ST, Cha H, Van Beusecum JP, Cook AK, Pollock JS, Pollock DM, Inscho EW. Pentosan polysulfate preserves renal microvascular P2X1 receptor reactivity and autoregulatory behavior in DOCA-salt hypertensive rats. Am J Physiol Renal Physiol. 2016 Mar 15;310(6):F456-65. doi: 10.1152/ajprenal.00110.2015. Epub 2015 Dec 23. PubMed PMID: 26697978. 2: Oehme D, Ghosh P, Goldschlager T, Itescu S, Shimon S, Wu J, McDonald C, Troupis JM, Rosenfeld JV, Jenkin G. Reconstitution of degenerated ovine lumbar discs by STRO-3-positive allogeneic mesenchymal precursor cells combined with pentosan polysulfate. J Neurosurg Spine. 2016 Jan 22:1-12. [Epub ahead of print] PubMed PMID: 26799116. 3: Herrero LJ, Foo SS, Sheng KC, Chen W, Forwood MR, Bucala R, Mahalingam S. Pentosan Polysulfate: a Novel Glycosaminoglycan-Like Molecule for Effective Treatment of Alphavirus-Induced Cartilage Destruction and Inflammatory Disease. J Virol. 2015 Aug;89(15):8063-76. doi: 10.1128/JVI.00224-15. Epub 2015 May 27. PubMed PMID: 26018160; PubMed Central PMCID: PMC4505659. 4: Delille M, Fröhlich L, Müller RS, Hartmann K, Dorsch R. Efficacy of intravesical pentosan polysulfate sodium in cats with obstructive feline idiopathic cystitis. J Feline Med Surg. 2015 Jun 26. pii: 1098612X15588934. [Epub ahead of print] PubMed PMID: 26116618. 5: Nickel JC, Herschorn S, Whitmore KE, Forrest JB, Hu P, Friedman AJ, Baseman AS. Pentosan polysulfate sodium for treatment of interstitial cystitis/bladder pain syndrome: insights from a randomized, double-blind, placebo controlled study. J Urol. 2015 Mar;193(3):857-62. doi: 10.1016/j.juro.2014.09.036. Epub 2014 Sep 20. PubMed PMID: 25245489. 6: Kramer CM, Tsang AS, Koenig T, Jeffcott LB, Dart CM, Dart AJ. Survey of the therapeutic approach and efficacy of pentosan polysulfate for the prevention and treatment of equine osteoarthritis in veterinary practice in Australia. Aust Vet J. 2014 Dec;92(12):482-7. doi: 10.1111/avj.12266. PubMed PMID: 25424761. 7: Newman PK, Todd NV, Scoones D, Mead S, Knight RS, Will RG, Ironside JW. Postmortem findings in a case of variant Creutzfeldt-Jakob disease treated with intraventricular pentosan polysulfate. J Neurol Neurosurg Psychiatry. 2014 Aug;85(8):921-4. doi: 10.1136/jnnp-2013-305590. Epub 2014 Feb 19. PubMed PMID: 24554103; PubMed Central PMCID: PMC4112497. 8: Koenig TJ, Dart AJ, McIlwraith CW, Horadagoda N, Bell RJ, Perkins N, Dart C, Krockenberger M, Jeffcott LB, Little CB. Treatment of experimentally induced osteoarthritis in horses using an intravenous combination of sodium pentosan polysulfate, N-acetyl glucosamine, and sodium hyaluronan. Vet Surg. 2014 Jul;43(5):612-22. doi: 10.1111/j.1532-950X.2014.12203.x. Epub 2014 May 13. PubMed PMID: 24819506. 9: Oehme D, Ghosh P, Shimmon S, Wu J, McDonald C, Troupis JM, Goldschlager T, Rosenfeld JV, Jenkin G. Mesenchymal progenitor cells combined with pentosan polysulfate mediating disc regeneration at the time of microdiscectomy: a preliminary study in an ovine model. J Neurosurg Spine. 2014 Jun;20(6):657-69. doi: 10.3171/2014.2.SPINE13760. Epub 2014 Apr 4. PubMed PMID: 24702507. 10: Nakamura T, Satoh K, Fukuda T, Kinoshita I, Nishiura Y, Nagasato K, Yamauchi A, Kataoka Y, Nakamura T, Sasaki H, Kumagai K, Niwa M, Noguchi M, Nakamura H, Nishida N, Kawakami A. Pentosan polysulfate treatment ameliorates motor function with increased serum soluble vascular cell adhesion molecule-1 in HTLV-1-associated neurologic disease. J Neurovirol. 2014 Jun;20(3):269-77. doi: 10.1007/s13365-014-0244-8. Epub 2014 Mar 27. PubMed PMID: 24671717. 11: Lander EB, See JR. Intravesical instillation of pentosan polysulfate encapsulated in a liposome nanocarrier for interstitial cystitis. Am J Clin Exp Urol. 2014 Jul 12;2(2):145-8. eCollection 2014. PubMed PMID: 25374916; PubMed Central PMCID: PMC4219302. 12: Yamasaki T, Suzuki A, Hasebe R, Horiuchi M. Comparison of the anti-prion mechanism of four different anti-prion compounds, anti-PrP monoclonal antibody 44B1, pentosan polysulfate, chlorpromazine, and U18666A, in prion-infected mouse neuroblastoma cells. PLoS One. 2014 Sep 2;9(9):e106516. doi: 10.1371/journal.pone.0106516. eCollection 2014. PubMed PMID: 25181483; PubMed Central PMCID: PMC4152300. 13: Frohbergh M, Ge Y, Meng F, Karabul N, Solyom A, Lai A, Iatridis J, Schuchman EH, Simonaro CM. Dose responsive effects of subcutaneous pentosan polysulfate injection in mucopolysaccharidosis type VI rats and comparison to oral treatment. PLoS One. 2014 Jun 25;9(6):e100882. doi: 10.1371/journal.pone.0100882. eCollection 2014. PubMed PMID: 24964042; PubMed Central PMCID: PMC4071040. 14: Vistnes M, Aronsen JM, Lunde IG, Sjaastad I, Carlson CR, Christensen G. Pentosan polysulfate decreases myocardial expression of the extracellular matrix enzyme ADAMTS4 and improves cardiac function in vivo in rats subjected to pressure overload by aortic banding. PLoS One. 2014 Mar 3;9(3):e89621. doi: 10.1371/journal.pone.0089621. eCollection 2014. PubMed PMID: 24595230; PubMed Central PMCID: PMC3940660. 15: Schuchman EH, Ge Y, Lai A, Borisov Y, Faillace M, Eliyahu E, He X, Iatridis J, Vlassara H, Striker G, Simonaro CM. Pentosan polysulfate: a novel therapy for the mucopolysaccharidoses. PLoS One. 2013;8(1):e54459. doi: 10.1371/journal.pone.0054459. Epub 2013 Jan 24. PubMed PMID: 23365668; PubMed Central PMCID: PMC3554761. 16: Kwan C, Bell R, Koenig T, Bischofberger A, Horadagoda N, Perkins NR, Jeffcott LB, Dart AJ. Effects of intra-articular sodium pentosan polysulfate and glucosamine on the cytology, total protein concentration and viscosity of synovial fluid in horses. Aust Vet J. 2012 Aug;90(8):315-20. doi: 10.1111/j.1751-0813.2012.00959.x. PubMed PMID: 22827626. 17: Sunaga T, Oh N, Hosoya K, Takagi S, Okumura M. Inhibitory effects of pentosan polysulfate sodium on MAP-kinase pathway and NF-κB nuclear translocation in canine chondrocytes in vitro. J Vet Med Sci. 2012 Jun;74(6):707-11. Epub 2011 Dec 28. PubMed PMID: 22214865. 18: McIlwraith CW, Frisbie DD, Kawcak CE. Evaluation of intramuscularly administered sodium pentosan polysulfate for treatment of experimentally induced osteoarthritis in horses. Am J Vet Res. 2012 May;73(5):628-33. doi: 10.2460/ajvr.73.5.628. PubMed PMID: 22533393. 19: Honda H, Sasaki K, Minaki H, Masui K, Suzuki SO, Doh-Ura K, Iwaki T. Protease-resistant PrP and PrP oligomers in the brain in human prion diseases after intraventricular pentosan polysulfate infusion. Neuropathology. 2012 Apr;32(2):124-32. doi: 10.1111/j.1440-1789.2011.01245.x. Epub 2011 Aug 1. PubMed PMID: 21801238. 20: Troeberg L, Mulloy B, Ghosh P, Lee MH, Murphy G, Nagase H. Pentosan polysulfate increases affinity between ADAMTS-5 and TIMP-3 through formation of an electrostatically driven trimolecular complex. Biochem J. 2012 Apr 1;443(1):307-15. doi: 10.1042/BJ20112159. PubMed PMID: 22299597; PubMed Central PMCID: PMC3369482.