Chemistry:Perfluoro tert-butylcyclohexane

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Short description: Chemical compound


Perfluoro tert-butylcyclohexane
The skeletal structure of an organic molecule
Clinical data
Trade namesOxycyte
Identifiers
CAS Number
PubChem CID
DrugBank
UNII
Chemical and physical data
FormulaC10F20
Molar mass500.078 g·mol−1
3D model (JSmol)

Perfluoro tert-butylcyclohexane is a perfluorinated chemical compound (or perfluorocarbon, PFC). It is a component of the empirical therapeutic oxygen carrier called Oxycyte.[1]

Chemical properties

Perfluoro tert-butyl-cyclo-hexane is a saturated alicyclic perfluorocarbon with the molecular formula C10F20.[2][3] Fluorocarbons are known for their strong gas-dissolving properties which, when used with oxygen, serve a dual role of healing the tissue as well as imaging. It fits the imaging role promisingly due to its biocompatibility and half-life. A similar compound, perfluoro-butane, is already used for ultrasound imaging.[4][5] Healing decompression sickness with oxygen has a similar mechanism of action to healing brain anemia, and so Oxycyte can be used for this.[6][7]

Oxycyte

Oxycyte is a perfluorocarbon (PFC) product composed of submicron particles of perfluoro(t-butylcyclohexane) in a 60% w/v concentration with an egg phospholipid emulsifier.[1]

Oxycyte was invented by Leland Clark and developed by Tenex Therapeutics, formerly Oxygen Biotherapeutics, Inc. and Synthetic Blood International.[8] It is designed to enhance oxygen delivery to damaged tissues. Through a collaborative agreement, Oxycyte (under the development code name of ABL-101) was being developed by Aurum Biosciences Ltd, with an initial indication in acute ischemic stroke.[9]

Tenex claims that Oxycyte can carry oxygen with up to 5 times the efficiency of hemoglobin when used as an intravenous emulsion, making it an effective means of transporting oxygen to tissues and carrying carbon dioxide to the lungs for disposal.[10] However, because Oxycyte is a PFC and not based on hemoglobin, it does not have the safety issues associated with hemoglobin-based products. There have been no adverse events in company clinical trials related to Oxycyte. Tenex believed Oxycyte has a very favorable risk-benefit profile for its potential indications.

Aurum Biosciences promoted Oxycyte as having potential use in multiple indications, including cardiology, oncology, and treating epilepsy and neurodegenerative diseases. These claims raised Tenex's stock price to its peak. Since then, the stock price has plummeted with no signs of recovery.[11][12]

Around September 2004, Oxycyte completed Phase I trials with few mild side effects.[13] Clinical interest in Oxycyte began to grow during this period, culminating in 2013.[14]

Aurum Biosciences received a Wellcome Trust HICF funding to conduct a Phase I clinical trial with Oxycyte in stroke patients. This study investigated both therapeutic potential and its ability to enhance the diagnostic potential of an MRI in suspected stroke patients.[15][16][17]

In September 2014, Oxygen Biotherapeutics announced the discontinuation of a Phase IIB trial for its Oxycyte drug candidate, citing "difficulties enrolling patients".[18] Clinical interest in Oxycyte has since tapered off.[14]

Oxycyte has been linked to potentially dangerous variations in blood viscosity.[19]

References

  1. ↑ 1.0 1.1 "The Emulsified PFC Oxycyte® Improved Oxygen Content and Lung Injury Score in a Swine Model of Oleic Acid Lung Injury (OALI)". Lung 194 (6): 945–957. December 2016. doi:10.1007/s00408-016-9941-9. PMID 27704259. 
  2. ↑ "Chapter 27 – Rational Development of Oxyfluor". Blood Substitutes. Academic Press. 2006. p. 303. ISBN 978-0127597607. https://books.google.com/books?id=kkbJ5D2n4koC&dq=C10F20&pg=PA303. 
  3. ↑ Huvard G, Kiral R, Quitaro M, Thompson DP, Grossman A, Clauson G, Sandhu G, "Perfluorocarbon gel formulations", US patent 2013096190, published 18 April 2013, assigned to Oxygen Biotherapeutics, Inc..
  4. ↑ "A characterization of ABL-101 as a potential tracer for clinical fluorine-19 MRI". NMR in Biomedicine 33 (1): e4212. January 2020. doi:10.1002/nbm.4212. PMID 31724252. https://serval.unil.ch/resource/serval:BIB_F9103E2AE976.P001/REF.pdf. 
  5. ↑ "Ultrasound Contrast Agent Sonazoid® for Injection Released for Sale". Daiichi Sankyo Company, Ltd.. January 10, 2007. https://www.daiichisankyo.com/files/news/pressrelease/pdf/005564/news2007_01_10_69_en.pdf. 
  6. ↑ "Cardiovascular parameters in a mixed-sex swine study of severe decompression sickness treated with the emulsified perfluorocarbon Oxycyte". Journal of Applied Physiology 118 (1): 71–79. January 2015. doi:10.1152/japplphysiol.00727.2014. PMID 25342702. 
  7. ↑ "The emulsified perfluorocarbon Oxycyte improves spinal cord injury in a swine model of decompression sickness". Spinal Cord 51 (3): 188–192. March 2013. doi:10.1038/sc.2012.135. PMID 23165506. 
  8. ↑ "Oxycyte | Tenax Therapeutics" (in en-US). http://www.tenaxthera.com/pipeline/oxycyte/. 
  9. ↑ "Aurum Biosciences" (in en-GB). http://www.aurumbiosciences.com/. 
  10. ↑ "Oxygen Biotherapeutics, Inc.". http://oxybiomed.com. 
  11. ↑ "Man Made Life Saver 50x Better Than Blood". December 15, 2006. https://www.trendhunter.com/trends/oxycyte-man-made-life-saver-50x-better-than-blood. 
  12. ↑ "Tenax Therapeutics Stock Price Today (NASDAQ: TENX) Quote, Market Cap, Chart | WallStreetZen". https://www.wallstreetzen.com/stocks/us/nasdaq/tenx. 
  13. ↑ "Synthetic Blood International Announces Preliminary Analysis of Oxycyte Phase I Study Results - O-STA". https://o-sta.si/en/1819/synthetic-blood-international-announces-preliminary-analysis-of-oxycyte-phase-i-study-results. 
  14. ↑ 14.0 14.1 "Oxycyte - Search Results" (in en). PubMed. U.S. National Library of Medicine. https://pubmed.ncbi.nlm.nih.gov/?term=Oxycyte&sort=date. 
  15. ↑ "Health Innovation Challenge Fund: projects we've funded" (in en). Wellcome. UK. https://wellcome.org/what-we-do/directories/health-innovation-challenge-fund-projects-funded. 
  16. ↑ "Technology and Products" (in en-GB). Aurum Biosciences. http://www.aurumbiosciences.com/technology-and-products/. 
  17. ↑ Santosh C, Brennan D, "Method of imaging metabolic function", US patent 9144392, issued 9 September 2015, assigned to The Greater Glasgow Health Board.
  18. ↑ "Oxygen Biotherapeutics Announces Halt of Oxycyte Phase IIb Traumatic Brain Injury Trial". September 11, 2014. https://www.businesswire.com/news/home/20140911006403/en/Oxygen-Biotherapeutics-Announces-Halt-Oxycyte-Phase-IIb. 
  19. ↑ "In vitro alteration of hematological parameters and blood viscosity by the perfluorocarbon: Oxycyte". International Journal of Hematology 103 (5): 584–591. May 2016. doi:10.1007/s12185-016-1955-9. PMID 26886450. 

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