Arterolane

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]

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 Y
PubChem CID	10475633
ChemSpider	25069705 Y
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- Y Key:VXYZBLXGCYNIHP-SSPKTAKCSA-N Y
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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]