Pentosan polysulfate

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Pentosan polysulfate
Clinical data
Trade namesElmiron, Zycosan
Other namesPPS, (1->4)-β-Xylan 2,3-bis(hydrogen sulfate) with a 4 O-methyl-α-D-glucuronate
AHFS/Drugs.comMonograph
License data
By mouth, intramuscular
ATC code
Legal status
Legal status
JSmol)
  • 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
  • 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
  • Key:FCCNSUIJIOOXEZ-SJYYZXOBSA-N
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Pentosan polysulfate, sold under the brand name Elmiron among others, is a medication used for the treatment of interstitial cystitis.[1] It was approved for medical use in the United States in 1996.[1][2][3]

Medical uses

Pentosan polysulfate sodium is

indicated for the relief of bladder pain or discomfort associated with interstitial cystitis.[1]

Adverse effects

Patients who have taken pentosan polysulfate orally report a variety of side effects, primarily

Hair loss, headache, rash, and insomnia have also been reported.[4] Due to Elmiron's anticoagulant effects, some patients report bruising more easily. In some cases, patients are asked to stop taking the medication before any major surgical procedures to reduce the likelihood of bleeding. Recent report based on clinical observation hypothesizes that chronic exposure to pentosan polysulfate can cause retinal toxicity, mimicking pigmentary pattern dystrophy.[2][5][6][7]

Mechanism of action

In interstitial cystitis, pentosan polysulfate is believed to work by providing a protective coating to the damaged bladder wall. Pentosan polysulfate is similar in structure to the natural glycosaminoglycan coating of the inner lining of the bladder, and may replace or repair the lining, reducing its permeability.[5]

History

The calcium salt of pentosan polysulfate was one of the first reported disease-modifying osteoarthritis drugs (DMOAD).[6]

Society and culture

Names

The

IUPAC name for pentosan polysulfate is [(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.[8]

There are 40 synonyms listed for pentosan polysulfate on PubChem including BAY-946, HOE-946, pentosan sulfuric polyester, polypentose sulfate, polysulfated xylan, PZ-68, SP-54, xylan SP54 and xylan sulfate.[9]

Various brand names include Elmiron (as sodium salt), Hemoclar, Anarthron, Fibrase, Fibrocid, Thrombocid and SP54. Pentosan polysulfate capsules are sold in India under the brand names Comfora, Pentossan-100, Cystopen and For-IC. In the veterinary field, pentosan polysulfate is sold as Cartrophen Vet and Sylvet by Biopharm Australia, Pentosan by Naturevet Australia, Anarthron by Randlab Australia and Zydax by Parnell.[10]

Research

Osteoarthritis

Pentosan polysulfate has been studied in knee osteoarthritis, though evidence to support such use is poor as of 2003.[11] There is some theoretical evidence that it should help.[12]

Transmissible spongiform encephalopathies

Pentosan polysulfate is being studied as a potential treatment of Creutzfeldt–Jakob disease (CJD). The rationale for this treatment was unclear but it was subsequently shown in prion-infected mouse neuroblastoma cells that pentosan polysulfate could rapidly reduce the levels of abnormal (scrapie) prion without affecting the normal cellular isoform.[13] As pentosan polysulfate can bind to the cellular isoform of the prion protein, it may stabilise this form and prevent its conversion to the pathological (scrapie) isoform.[14]

The treatment[15] of one patient in Northern Ireland and around six other patients in mainland Britain was reported in the press.[16]

Veterinary uses

Dogs

Read et al. (1996)

cranial cruciate ligament instability and found to hasten recovery, as measured by more rapidly improved ground reaction forces, over 48 weeks.[20]

Horses

Zycosan, for horses, is a heparin-like compound and is the first injectable pentosan product to receive approval by the US Food and Drug Administration (FDA).[21]

In December 2022, the US Food and Drug Administration (FDA) approved pentosan polysulfate (Zycosan) for the control of clinical signs associated with osteoarthritis in horses.[21] Zycosan is for intramuscular use in horses only and is not for use in humans.[21] Zycosan is sponsored by Anzac Animal Health LLC, based in Maryland Heights, Missouri.[21]

Pentosan polysulfate is being used for this osteoarthritis in Australia. When administered to racing thoroughbreds with chronic osteoarthritis (2 to 3 mg/kg, intramuscularly, once weekly for 4 weeks, then as required), pentosan polysulfate treatment improved but did not eliminate clinical signs of joint disease.[22] Articular cartilage fibrillation was substantially reduced by similar NaPPS treatment intramuscularly in nine horses with experimentally-induced carpal osteoarthritis.[23]

References

  1. ^ a b c d e "Elmiron- pentosan polysulfate sodium capsule, gelatin coated". DailyMed. 10 November 2022. Retrieved 21 December 2022.
  2. ^
    S2CID 234767956
    .
  3. ^ "Elmiron (pentosan polysulfate sodium)" (PDF). FDA approval letter. U.S. Food and Drug Administration. 25 September 1996.
  4. ^ a b Pubmed Health (2012). "Pentosan Polysulfate". U.S. National Library of Medicine. Retrieved 2 October 2012.
  5. ^
    PMID 7904388
    .
  6. ^
    S2CID 33755966
    .
  7. PMID 31486843
    .
  8. ^ "Pentosan polysulfate". PubChem. U.S. National Library of Medicine. Retrieved 8 November 2022.
  9. ^ "Pentosan polysulfate". PubChem. U.S. National Library of Medicine. Retrieved 8 November 2022.
  10. PMID 12779171
    .
  11. PMID 12954956
    .
  12. PMID 10073500
    .
  13. PMID 25181483
    .
  14. PMID 23081827
    .
  15. S2CID 37400744
    .
  16. ^ "Research will now assess CJD drug". 1 March 2005 – via news.bbc.co.uk.
  17. PMID 8683953
    .
  18. PMID 11812016
    .
  19. S2CID 46623547
    .
  20. PMID 17461948
    .
  21. ^ a b c d "FDA Approves First Injectable Pentosan for Osteoarthritis in Horses". U.S. Food and Drug Administration (FDA). 20 December 2022. Retrieved 21 December 2022. Public Domain This article incorporates text from this source, which is in the public domain.
  22. ^ Little CB, Ghosh P (1996). McIlwraith CW, Trotter GW (eds.). Joint Disease in the Horse. Philadelphia: WB Saunders Company. pp. 281–292.
  23. PMID 22533393
    .
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