Arterolane

Arterolane
Clinical data
Routes of; administration	Oral
ATC code	P01BX02 (WHO) (combination with piperaquine);
Identifiers
	IUPAC name [(N-(2-amino-2-methylpropyl)-2-cis-dispiro(adamantane-2,3'-[1,2,4]trioxolane-5',1"-cyclohexan)-4"-yl]acetamide;
CAS Number	664338-39-0 ;
PubChem CID	10475633;
ChemSpider	25069705 ;
UNII	3N1TN351VB;
ChEBI	CHEBI:136054;
CompTox Dashboard (EPA)	DTXSID50985095 ;
Chemical and physical data
Formula	C22H36N2O4
Molar mass	392.540 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(N)CN=C(O)C[C@H]1CC[C@]2(CC1)OO[C@]1(O2)[C@H]2C[C@@H]3C[C@H](C2)C[C@H]1C3;
	InChI 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- ; Key:VXYZBLXGCYNIHP-SSPKTAKCSA-N ;
	(verify)

Arterolane, also known as OZ277 or RBx 11160, is an antimalarial compound marketed by Ranbaxy Laboratories.^[1] It was discovered by US and European scientists coordinated by the Medicines for Malaria Venture (MMV).^[2] Its molecular structure is uncommon for pharmacological compounds in that it has both an ozonide (trioxolane) group and an adamantane substituent.^[3]^[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 arterolane in combination with another drug.^[1] In 2009, Ranbaxy started a Phase II clinical trial of arterolane in combination with piperaquine, and it was published in 2015.^[6]^[7]

In 2012, Ranbaxy obtained approval to market an arterolane/piperaquine combination drug in India, under the brand name Synriam.^[5] In 2014, the product was also approved in Nigeria, Uganda, Senegal, Cameroon, Guinea, Kenya and Ivory Coast.^[8]

References

^ ^a ^b Unnikrishnan CH (21 September 2007). "Blow to Ranbaxy drug research plans". LiveMint.com. Archived from the original on 25 September 2007.
^ Vennerstrom JL, Arbe-Barnes S, Brun R, Charman SA, Chiu FC, Chollet J, et al. (August 2004). "Identification of an antimalarial synthetic trioxolane drug development candidate". Nature. 430 (7002): 900–4. Bibcode:2004Natur.430..900V. doi:10.1038/nature02779. PMID 15318224. S2CID 4320974.
^ Dong Y, Wittlin S, Sriraghavan K, Chollet J, Charman SA, Charman WN, et al. (January 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.
^ Lowe D (23 November 2009). "Ozonides As Drugs: What Will They Think Of Next?". In the Pipeline. Sciencemag.org. Retrieved 17 November 2015.
^ ^a ^b Rathi A (3 May 2012). "Ranbaxy launches new anti-malarial Synriam". Chemistry World.
^ "Phase II trial of dispersible fixed dose combination of arterolane (RBx 11160) maleate and piperaquine phosphate in pediatric patients with acute uncomplicated Plasmodium falciparum malaria". India Clinical trials registry.
^ Toure OA, Rulisa S, Anvikar AR, Rao BS, Mishra P, Jalali RK, et al. (November 2015). "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". Malaria Journal. 14: 469. doi:10.1186/s12936-015-0982-y. PMC 4660726. PMID 26608469.
^ Staff (16 December 2014). "Ranbaxy receives approval for malaria drug Synriam from 7 African countries". Business Standard.

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[livemint-1] Unnikrishnan CH (21 September 2007). "Blow to Ranbaxy drug research plans". LiveMint.com. Archived from the original on 25 September 2007.

[2] Vennerstrom JL, Arbe-Barnes S, Brun R, Charman SA, Chiu FC, Chollet J, et al. (August 2004). "Identification of an antimalarial synthetic trioxolane drug development candidate". Nature. 430 (7002): 900–4. Bibcode:2004Natur.430..900V. doi:10.1038/nature02779. PMID 15318224. S2CID 4320974.

[3] Dong Y, Wittlin S, Sriraghavan K, Chollet J, Charman SA, Charman WN, et al. (January 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.

[4] Lowe D (23 November 2009). "Ozonides As Drugs: What Will They Think Of Next?". In the Pipeline. Sciencemag.org. Retrieved 17 November 2015.

[launch-5] Rathi A (3 May 2012). "Ranbaxy launches new anti-malarial Synriam". Chemistry World.

[6] "Phase II trial of dispersible fixed dose combination of arterolane (RBx 11160) maleate and piperaquine phosphate in pediatric patients with acute uncomplicated Plasmodium falciparum malaria". India Clinical trials registry.

[pmid26608469-7] Toure OA, Rulisa S, Anvikar AR, Rao BS, Mishra P, Jalali RK, et al. (November 2015). "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". Malaria Journal. 14: 469. doi:10.1186/s12936-015-0982-y. PMC 4660726. PMID 26608469.

[8] Staff (16 December 2014). "Ranbaxy receives approval for malaria drug Synriam from 7 African countries". Business Standard.

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