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Arterolane

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Arterolane
Clinical data
Routes of
administration		Oral
ATC code
Identifiers
  • [(N-(2-amino-2-methylpropyl)-2-cis-dispiro(adamantane-2,3'-[1,2,4]trioxolane-5',1"-cyclohexan)-4"-yl]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H36N2O4
Molar mass392.531 g/mol g·mol−1
3D model (JSmol)
  • C2C1CC5CC2CC(C5)C1(O3)OOC3(CC4)CCC4CC(=O)NCC(C)(C)N
  • InChI=1S/C22H36N2O4/c1-20(2,23)13-24-19(25)12-14-3-5-21(6-4-14)26-22(28-27-21)17-8-15-7-16(10-17)11-18(22)9-15/h14-18H,3-13,23H2,1-2H3,(H,24,25)/t14-,15-,16+,17-,18+,21+,22- checkY
  • Key:VXYZBLXGCYNIHP-SSPKTAKCSA-N checkY
  (verify)

Arterolane, also known as OZ277 or RBx 11160, is a substance that was 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 a ozonide (trioxolane) group and an adamantane substituent.[4]

Initial results were disappointing, and in 2007 MMV withdrew support, after having invested $20M in the research;[5] Ranbaxy said at the time that it intended to continue developing the drug combination on its own.[2] Ranbaxy started a Phase II clinical trial of arterolane, in combination with piperaquine in 2009 that published in 2015.[6][7]

In 2012, Ranbaxy obtained approval to market the arterolane/piperaquine combination drug in India, under the brand name Synriam,[5] and in 2014 received approval to market it in Nigeria, Uganda, Senegal, Cameroon, Guinea, Kenya and Ivory Coast; it had already received approval in Uganda.[8]

References

  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; published November 23, 2009; retrieved November 17, 2015; at Sciencemag.org
  5. ^ a b Akshat Rathi for Chemistry World. 3 May 2012 Ranbaxy launches new anti-malarial Synriam
  6. ^ India Clinical trials registry CTRI/2009/091/000531
  7. ^ Toure OA et al. Efficacy and safety of fixed dose combination of arterolane maleate and piperaquine phosphate dispersible tablets in paediatric patients with acute uncomplicated Plasmodium falciparum malaria: a phase II, multicentric, open-label study. Malar J. 2015 Nov 25;14(1):469. Clinical Trial Registry India: CTRI/2009/091/000531. PMID 26608469 PMC4660726
  8. ^ Staff, Business Standard. December 16, 2014 Ranbaxy receives approval for malaria drug Synriam from 7 African countries


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