Arterolane

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Arterolane
Arterolane.png
Systematic (IUPAC) name
[(N-(2-amino-2-methylpropyl)-2-cis-dispiro(adamantane-2,3'-[1,2,4]trioxolane-5',1"-cyclohexan)-4"-yl]acetamide
Clinical data
Legal status
?
Routes oral
Identifiers
CAS number 664338-39-0 YesY
ATC code None
PubChem CID 10475633
ChemSpider 25069705 YesY
UNII 3N1TN351VB YesY
Chemical data
Formula C22H36N2O4 
Mol. mass 392.531 g/mol
 YesY (what is this?)  (verify)

Arterolane, also known as OZ277 or RBx 11160, is a substance being tested for antimalarial activity[1] by Ranbaxy Laboratories.[2] It was discovered by US and European scientists who were coordinated by the Medicines for Malaria Venture (MMV).[3] Its molecular structure is uncommon for pharmacological compounds in that it has both an ozonide group and an adamantane substituent.[4]

Phase III clinical trials of arterolane, in combination with piperaquine, began in India in 2009.[5] When clinical trial results were disappointing, the MMV withdrew support[2] and Ranbaxy continued developing the drug combination on its own.

References[edit]

  1. ^ Dong, Yuxiang; Wittlin, Sergio; Sriraghavan, Kamaraj; Chollet, Jacques; Charman, Susan A.; Charman, William N.; Scheurer, Christian; Urwyler, Heinrich et al. (2010). "The Structure−Activity Relationship of the Antimalarial Ozonide Arterolane (OZ277)". Journal of Medicinal Chemistry 53 (1): 481–91. doi:10.1021/jm901473s. PMID 19924861. 
  2. ^ a b Blow to Ranbaxy drug research plans at LiveMint.com, Sep 21 2007
  3. ^ Vennerstrom, Jonathan L.; Arbe-Barnes, Sarah; Brun, Reto; Charman, Susan A.; Chiu, Francis C. K.; Chollet, Jacques; Dong, Yuxiang; Dorn, Arnulf et al. (2004). "Identification of an antimalarial synthetic trioxolane drug development candidate". Nature 430 (7002): 900–4. doi:10.1038/nature02779. PMID 15318224. 
  4. ^ In the Pipeline: "Ozonides As Drugs: What Will They Think Of Next?", by Derek Lowe, November 23, 2009, at Corante.com
  5. ^ Indian company starts Phase III trials of synthetic artemisinin, May 4 2009, at the WorldWide Antimalarial Resistance Network[dead link]