Arterolane
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| 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 | |
| Routes of administration | Oral |
| Identifiers | |
| CAS Number |
664338-39-0  |
| ATC code | none |
| PubChem | CID 10475633 |
| ChemSpider |
25069705 |
| UNII |
3N1TN351VB |
| Chemical data | |
| Formula | C22H36N2O4 |
| Molar mass | 392.531 g/mol |
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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
- ↑ 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.
- 1 2 Blow to Ranbaxy drug research plans at LiveMint.com, Sep 21 2007
- ↑ 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.
- ↑ 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
- 1 2 Akshat Rathi for Chemistry World. 3 May 2012 [http://www.rsc.org/chemistryworld/2012/05/ranbaxy-launches-new-anti-malarial-synriam Ranbaxy launches new anti-malarial Synriam
- ↑ India Clinical trials registry CTRI/2009/091/000531
- ↑ 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
- ↑ Staff, Business Standard. December 16, 2014 Ranbaxy receives approval for malaria drug Synriam from 7 African countries
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