Arterolane

• CAT Number: I002868
• CAS Number: 664338-39-0
• Molecular Formula: C22H36N2O4
• Molecular Weight: 392.54
• Purity: ≥95%
• Synonyms: Arterolane maleate; OZ-277; RBx-11160; OZ 277; RBx 11160; OZ277; RBx11160;N-(2-AMINO-2-METHYLPROPYL)-2-{DISPIRO[ADAMANTANE-2,2/’-[1,3,5]TRIOXOLANE-4/’,1/’/’-CYCLOHEXANE]-4/’/’-YL}ACETAMIDE
• Target: ATPase inhibitor
• Solubility: Soluble in DMSO
• Storage: 0 - 4 °Cfor short term (days to weeks), or -20 °C for long term (months).
• 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)
• InChIKey: VXYZBLXGCYNIHP-UHFFFAOYSA-N
• SMILES: CC(C)(CNC(=O)CC1CCC2(CC1)OC3(C4CC5CC(C4)CC3C5)OO2)N

Arterolane (Cat.No:I002868), also known as Arterolane maleate, is an adenosine triphosphatase inhibitor potentially for the treatment of malaria.

Reference

1:A Phase 3, Double-Blind, Randomized Study of Arterolane Maleate-Piperaquine Phosphate vs Artemether-Lumefantrine for Falciparum Malaria in Adolescent and Adult Patients in Asia and Africa. Toure OA, Valecha N, Tshefu AK, Thompson R, Krudsood S, Gaye O, Rao BHK, Sagara I, Bose TK, Mohanty S, Rao BS, Anvikar AR, Mwapasa V, Noedl H, Arora S, Roy A, Iyer SS, Sharma P, Saha N, Jalali RK; AM–PQP Study Team., Tiacoh L, Enosse S, Tangpukdee N, Kokolomami J, Ndiaye JL, Rao D, Yumva NN, Sidibe B, Mohanty R, Jha AC, Nyirenda M, Starzengruber P, Swoboda P.Clin Infect Dis. 2016 Apr 15;62(8):964-971. doi: 10.1093/cid/ciw029. Epub 2016 Feb 21. PMID: 26908796 Free PMC Article2:Monoclonal Antibodies That Recognize the Alkylation Signature of Antimalarial Ozonides OZ277 (Arterolane) and OZ439 (Artefenomel). Jourdan J, Matile H, Reift E, Biehlmaier O, Dong Y, Wang X, Mäser P, Vennerstrom JL, Wittlin S.ACS Infect Dis. 2016 Jan 8;2(1):54-61. Epub 2015 Sep 28. PMID: 26819968 Free PMC Article3:Comparison of the safety and efficacy of fixed-dose combination of arterolane maleate and piperaquine phosphate with chloroquine in acute, uncomplicated Plasmodium vivax malaria: a phase III, multicentric, open-label study. Valecha N, Savargaonkar D, Srivastava B, Rao BH, Tripathi SK, Gogtay N, Kochar SK, Kumar NB, Rajadhyaksha GC, Lakhani JD, Solanki BB, Jalali RK, Arora S, Roy A, Saha N, Iyer SS, Sharma P, Anvikar AR.Malar J. 2016 Jan 27;15:42. doi: 10.1186/s12936-016-1084-1. PMID: 26818020 Free PMC Article4: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. Toure OA, Rulisa S, Anvikar AR, Rao BS, Mishra P, Jalali RK, Arora S, Roy A, Saha N, Iyer SS, Sharma P, Valecha N.Malar J. 2015 Nov 25;14:469. doi: 10.1186/s12936-015-0982-y. PMID: 26608469 Free PMC Article5:Drug delivery to the malaria parasite using an arterolane-like scaffold. Fontaine SD, Spangler B, Gut J, Lauterwasser EM, Rosenthal PJ, Renslo AR.ChemMedChem. 2015 Jan;10(1):47-51. doi: 10.1002/cmdc.201402362. Epub 2014 Oct 14. PMID: 25314098 Free PMC Article6:Fixed dose combination of arterolane and piperaquine: a newer prospect in antimalarial therapy. Patil C, Katare S, Baig M, Doifode S.Ann Med Health Sci Res. 2014 Jul;4(4):466-71. doi: 10.4103/2141-9248.139270. Review. PMID: 25221689 Free PMC Article7:Ex vivo activity of endoperoxide antimalarials, including artemisone and arterolane, against multidrug-resistant Plasmodium falciparum isolates from Cambodia. Lanteri CA, Chaorattanakawee S, Lon C, Saunders DL, Rutvisuttinunt W, Yingyuen K, Bathurst I, Ding XC, Tyner SD.Antimicrob Agents Chemother. 2014 Oct;58(10):5831-40. doi: 10.1128/AAC.02462-14. Epub 2014 Jul 21. PMID: 25049252 Free PMC Article8:Safety, tolerability and pharmacokinetic profile of single and multiple oral doses of arterolane (RBx11160) maleate in healthy subjects. Saha N, Moehrle JJ, Zutshi A, Sharma P, Kaur P, Iyer SS.J Clin Pharmacol. 2014 Apr;54(4):386-93. doi: 10.1002/jcph.232. Epub 2013 Dec 17. PMID: 24242999 9:Arterolane maleate plus piperaquine phosphate for treatment of uncomplicated Plasmodium falciparum malaria: a comparative, multicenter, randomized clinical trial. Valecha N, Krudsood S, Tangpukdee N, Mohanty S, Sharma SK, Tyagi PK, Anvikar A, Mohanty R, Rao BS, Jha AC, Shahi B, Singh JP, Roy A, Kaur P, Kothari M, Mehta S, Gautam A, Paliwal JK, Arora S, Saha N.Clin Infect Dis. 2012 Sep;55(5):663-71. doi: 10.1093/cid/cis475. Epub 2012 May 14. PMID: 22586253 10:Pharmacokinetics and pharmacodynamics of arterolane maleate following multiple oral doses in adult patients with P. falciparum malaria. Gautam A, Ahmed T, Sharma P, Varshney B, Kothari M, Saha N, Roy A, Moehrle JJ, Paliwal J.J Clin Pharmacol. 2011 Nov;51(11):1519-28. doi: 10.1177/0091270010385578. Epub 2010 Dec 8. PMID: 21148048