ARTEROLANE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H36N2O4
Molecular Weight	392.5322
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0
Stereo Comments	CIS

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(N)CNC(=O)C[C@H]1CC[C@@]2(CC1)OO[C@@]3(O2)C4CC5CC(C4)CC3C5

InChI

InChIKey=VXYZBLXGCYNIHP-ACBWXVLLSA-N

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-

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15318224 | https://www.ncbi.nlm.nih.gov/pubmed/29020247 | https://www.business-standard.com/content/b2b-pharma/ranbaxy-receives-approval-for-malaria-drug-synriam-from-7-african-countries-114121700050_1.html

Arterolane is an anti-malarial drug developed by Ranbaxy Laboratories. Arterolane belongs to peroxidic antimalarial compounds. Upon administration, the drug is activated by heme of hemoglobin digested by malarial parasite. Activation produces free radicals, leading to alkylation of heme and proteins, critical for the survival of the parasite. Arterolane was approved for marketing in India in 2012 and received marketing authorization in several African countries in 2014.

Approval Year

PubMed

Title	Date	PubMed
Infectious diseases. Source of new hope against malaria is in short supply.	2005 Jan 7	15637249
In vitro assessment of the pharmacodynamic properties and the partitioning of OZ277/RBx-11160 in cultures of Plasmodium falciparum.	2006 Jul	16735432
Plasmodium vivax: in vitro susceptibility of blood stages to synthetic trioxolane compounds and the diamidine DB75.	2006 Jul	16458301
In vitro susceptibility of P. falciparum populations from Colombia and Tanzania to a new synthetic peroxide (OZ277).	2007 Jun	17556605
In vitro and in vivo interaction of synthetic peroxide RBx11160 (OZ277) with piperaquine in Plasmodium models.	2007 Mar	17087929
The future of artemisinins: natural, synthetic or recombinant?	2008 Dec 15	19090980
Characterization of the two major CYP450 metabolites of ozonide (1,2,4-trioxolane) OZ277.	2008 Mar 1	18262417
Drug metabolism and pharmacokinetics.	2008 Oct	21593983
Simultaneous determination of OZ277, a synthetic 1,2,4-trioxolane antimalarial, and its polar metabolites in rat plasma using hydrophilic interaction chromatography.	2009 Oct 1	19646936
Comparative embryotoxicity of different antimalarial peroxides: in vitro study using the rat whole embryo culture model (WEC).	2010 Dec	20708075
Development and validation of a headspace gas chromatographic method for the determination of residual solvents in arterolane (RBx11160) maleate bulk drug.	2010 Jan	21814428
The structure-activity relationship of the antimalarial ozonide arterolane (OZ277).	2010 Jan 14	19924861
Arterolane, a new synthetic trioxolane for treatment of uncomplicated Plasmodium falciparum malaria: a phase II, multicenter, randomized, dose-finding clinical trial.	2010 Sep 15	20687837

Name

Type

Language

ARTEROLANE

Official Name

English

OZ-277

Code

English

RBX11160

Code

English

DISPIRO(CYCLOHEXANE-1,3'-(1,2,4)TRIOXOLANE-5',2''-TRICYCLO(3.3.1.13,7)DECANE)-4-ACETAMIDE, N-(2-AMINO-2-METHYLPROPYL)-, CIS-

Common Name

English

OZ 277

Code

English

arterolane [INN]

Common Name

English

Arterolane [WHO-DD]

Common Name

English

RBX-11160

Code

English

Classification Tree Code System Code

WHO-ATC

P01BX02