Arterolane | CAS# 664338-39-0 | Antimalarial Agent

MedKoo Cat#: 565079 | Name: Arterolane

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arterolane is an antimalarial agent.

Chemical Structure

Arterolane

CAS#664338-39-0 (free base)

Theoretical Analysis

MedKoo Cat#: 565079

Name: Arterolane

CAS#: 664338-39-0 (free base)

Chemical Formula: C22H36N2O4

Exact Mass: 392.2675

Molecular Weight: 392.54

Elemental Analysis: C, 67.32; H, 9.24; N, 7.14; O, 16.30

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

664338-39-0 (free base) 959520-73-1 (maleate) 959520-79-7 (acetate) 664338-40-3 (tosylate) 959520-82-2 (tartrate) 959520-83-3 (citrate)

Synonym

OZ-277; OZ277; OZ 277; RBx 11160; RBx-11160; RBx11160; Arterolane

IUPAC/Chemical Name

N-(2-Amino-2-methylpropyl)-2-{dispiro[adamantane-2,2'-[1,3,5]trioxolane-4',1''-cyclohexane]-4''-yl}acetamide

InChi Key

VXYZBLXGCYNIHP-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C(NCC(C)(N)C)CC(CC1)CCC21OC3(OO2)C4CC5CC(C4)CC3C5

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 392.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Varo R, Bassat Q. Arterolane-based combinations for the treatment of uncomplicated falciparum malaria in Kenyan children. Lancet Infect Dis. 2021 Oct;21(10):1338-1339. doi: 10.1016/S1473-3099(21)00004-9. Epub 2021 Jun 7. PMID: 34111411. 2: Patil C, Katare S, Baig M, Doifode S. Fixed dose combination of arterolane and piperaquine: a newer prospect in antimalarial therapy. Ann Med Health Sci Res. 2014 Jul;4(4):466-71. doi: 10.4103/2141-9248.139270. PMID: 25221689; PMCID: PMC4160665. 3: Hamaluba M, van der Pluijm RW, Weya J, Njuguna P, Ngama M, Kalume P, Mwambingu G, Ngetsa C, Wambua J, Boga M, Mturi N, Lal AA, Khuroo A, Taylor WRJ, Gonçalves S, Miotto O, Dhorda M, Mutinda B, Mukaka M, Waithira N, Hoglund RM, Imwong M, Tarning J, Day NPJ, White NJ, Bejon P, Dondorp AM. Arterolane- piperaquine-mefloquine versus arterolane-piperaquine and artemether-lumefantrine in the treatment of uncomplicated Plasmodium falciparum malaria in Kenyan children: a single-centre, open-label, randomised, non-inferiority trial. Lancet Infect Dis. 2021 Oct;21(10):1395-1406. doi: 10.1016/S1473-3099(20)30929-4. Epub 2021 Jun 7. PMID: 34111412; PMCID: PMC8461080. 4: Fontaine SD, Spangler B, Gut J, Lauterwasser EM, Rosenthal PJ, Renslo AR. Drug delivery to the malaria parasite using an arterolane-like scaffold. ChemMedChem. 2015 Jan;10(1):47-51. doi: 10.1002/cmdc.201402362. Epub 2014 Oct 14. PMID: 25314098; PMCID: PMC4420023. 5: 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. Arterolane maleate plus piperaquine phosphate for treatment of uncomplicated Plasmodium falciparum malaria: a comparative, multicenter, randomized clinical trial. Clin Infect Dis. 2012 Sep;55(5):663-71. doi: 10.1093/cid/cis475. Epub 2012 May 14. PMID: 22586253. 6: Valecha N, Looareesuwan S, Martensson A, Abdulla SM, Krudsood S, Tangpukdee N, Mohanty S, Mishra SK, Tyagi PK, Sharma SK, Moehrle J, Gautam A, Roy A, Paliwal JK, Kothari M, Saha N, Dash AP, Björkman A. Arterolane, a new synthetic trioxolane for treatment of uncomplicated Plasmodium falciparum malaria: a phase II, multicenter, randomized, dose-finding clinical trial. Clin Infect Dis. 2010 Sep 15;51(6):684-91. doi: 10.1086/655831. PMID: 20687837. 7: Niguram P, Kate AS. Comprehensive metabolite identification study of arterolane using hydrophilic interaction liquid chromatography with quadrupole- time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2022 Aug 30;36(16):e9335. doi: 10.1002/rcm.9335. PMID: 35706363. 8: Bansal R, Singh R, Kaur K. Quantitative analysis of doxorubicin hydrochloride and arterolane maleate by mid IR spectroscopy using transmission and reflectance modes. BMC Chem. 2021 Apr 24;15(1):27. doi: 10.1186/s13065-021-00752-3. PMID: 33894779; PMCID: PMC8070331. 9: Blank BR, Gut J, Rosenthal PJ, Renslo AR. Enantioselective Synthesis and in Vivo Evaluation of Regioisomeric Analogues of the Antimalarial Arterolane. J Med Chem. 2017 Jul 27;60(14):6400-6407. doi: 10.1021/acs.jmedchem.7b00699. Epub 2017 Jul 10. PMID: 28692297; PMCID: PMC5535261. 10: 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. 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. Malar J. 2016 Jan 27;15:42. doi: 10.1186/s12936-016-1084-1. PMID: 26818020; PMCID: PMC4728808. 11: Niguram P, Goswami A, Kate AS. A novel hydrophilic interaction liquid chromatography method for the analysis of arterolane; Isolation and structural elucidation of its major degradation product by LC-HRMS and NMR. J Pharm Biomed Anal. 2020 Jul 15;186:113279. doi: 10.1016/j.jpba.2020.113279. Epub 2020 Apr 19. PMID: 32361471. 12: Dong Y, Wittlin S, Sriraghavan K, Chollet J, Charman SA, Charman WN, Scheurer C, Urwyler H, Santo Tomas J, Snyder C, Creek DJ, Morizzi J, Koltun M, Matile H, Wang X, Padmanilayam M, Tang Y, Dorn A, Brun R, Vennerstrom JL. The structure-activity relationship of the antimalarial ozonide arterolane (OZ277). J Med Chem. 2010 Jan 14;53(1):481-91. doi: 10.1021/jm901473s. PMID: 19924861. 13: Saha N, Moehrle JJ, Zutshi A, Sharma P, Kaur P, Iyer SS. Safety, tolerability and pharmacokinetic profile of single and multiple oral doses of arterolane (RBx11160) maleate in healthy subjects. J Clin Pharmacol. 2014 Apr;54(4):386-93. doi: 10.1002/jcph.232. Epub 2013 Dec 17. PMID: 24242999. 14: Valecha N, Goyal VK, Mishra DN, Das RR, Jauhri N, Bhardwaj AC, Khurana O, Choudhury R, Pandey M, Baliga BS, Ghosh SK, Srivastava B, Soans ST, Bahl RK, Punj A, Roy A, Sharma SK, Nasa A, Jalali RK, Anvikar AR. Efficacy and safety of fixed dose combination of arterolane maleate and piperaquine phosphate in comparison with chloroquine phosphate in children with acute uncomplicated Plasmodium vivax malaria: A phase III, randomised, multicentric study. J Vector Borne Dis. 2020 Jul-Sep;57(3):213-220. doi: 10.4103/0972-9062.311781. PMID: 34472504. 15: Gupta A, Singh Y, Srinivas KS, Jain G, Sreekumar VB, Semwal VP. Development and validation of a headspace gas chromatographic method for the determination of residual solvents in arterolane (RBx11160) maleate bulk drug. J Pharm Bioallied Sci. 2010 Jan;2(1):32-7. doi: 10.4103/0975-7406.62706. PMID: 21814428; PMCID: PMC3146089. 16: Gautam A, Ahmed T, Sharma P, Varshney B, Kothari M, Saha N, Roy A, Moehrle JJ, Paliwal J. Pharmacokinetics and pharmacodynamics of arterolane maleate following multiple oral doses in adult patients with P. falciparum malaria. J Clin Pharmacol. 2011 Nov;51(11):1519-28. doi: 10.1177/0091270010385578. Epub 2010 Dec 8. PMID: 21148048. 17: Jourdan J, Matile H, Reift E, Biehlmaier O, Dong Y, Wang X, Mäser P, Vennerstrom JL, Wittlin S. Monoclonal Antibodies That Recognize the Alkylation Signature of Antimalarial Ozonides OZ277 (Arterolane) and OZ439 (Artefenomel). ACS Infect Dis. 2016 Jan 8;2(1):54-61. doi: 10.1021/acsinfecdis.5b00090. Epub 2015 Sep 28. PMID: 26819968; PMCID: PMC4718528. 18: Toure OA, Rulisa S, Anvikar AR, Rao BS, Mishra P, Jalali RK, Arora S, Roy A, Saha N, Iyer SS, Sharma P, Valecha N. 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;14:469. doi: 10.1186/s12936-015-0982-y. PMID: 26608469; PMCID: PMC4660726. 19: Toure OA, Mwapasa V, Sagara I, Gaye O, Thompson R, Maheshwar AV, Mishra P, Behra N, Tshefu AK, Das RR, Anvikar AR, Sharma P, Roy A, Sharma SK, Nasa A, Jalali RK, Valecha N; Arterolane Maleate-Piperaquine Phosphate (AM-PQP) Study Team. Assessment of Efficacy and Safety of Arterolane Maleate-Piperaquine Phosphate Dispersible Tablets in Comparison With Artemether-Lumefantrine Dispersible Tablets in Pediatric Patients With Acute Uncomplicated Plasmodium falciparum Malaria: A Phase 3, Randomized, Multicenter Trial in India and Africa. Clin Infect Dis. 2017 Oct 30;65(10):1711-1720. doi: 10.1093/cid/cix617. PMID: 29020247. 20: Fügi MA, Wittlin S, Dong Y, Vennerstrom JL. Probing the antimalarial mechanism of artemisinin and OZ277 (arterolane) with nonperoxidic isosteres and nitroxyl radicals. Antimicrob Agents Chemother. 2010 Mar;54(3):1042-6. doi: 10.1128/AAC.01305-09. Epub 2009 Dec 22. PMID: 20028825; PMCID: PMC2825978.