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

Molecular Formula	C22H36N2O4
Molecular Weight	392.5322
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Comparative embryotoxicity of different antimalarial peroxides: in vitro study using the rat whole embryo culture model (WEC).	2010-12	20708075
Arterolane, a new synthetic trioxolane for treatment of uncomplicated Plasmodium falciparum malaria: a phase II, multicenter, randomized, dose-finding clinical trial.	2010-09-15	20687837
The structure-activity relationship of the antimalarial ozonide arterolane (OZ277).	2010-01-14	19924861
Development and validation of a headspace gas chromatographic method for the determination of residual solvents in arterolane (RBx11160) maleate bulk drug.	2010-01	21814428
Simultaneous determination of OZ277, a synthetic 1,2,4-trioxolane antimalarial, and its polar metabolites in rat plasma using hydrophilic interaction chromatography.	2009-10-01	19646936
The future of artemisinins: natural, synthetic or recombinant?	2008-12-15	19090980
In vitro assessment of the pharmacodynamic properties of DB75, piperaquine, OZ277 and OZ401 in cultures of Plasmodium falciparum.	2008-11	18669520
Drug metabolism and pharmacokinetics.	2008-10	21593983
Characterization of the two major CYP450 metabolites of ozonide (1,2,4-trioxolane) OZ277.	2008-03-01	18262417
In vitro susceptibility of P. falciparum populations from Colombia and Tanzania to a new synthetic peroxide (OZ277).	2007-06	17556605
In vitro and in vivo interaction of synthetic peroxide RBx11160 (OZ277) with piperaquine in Plasmodium models.	2007-03	17087929
In vitro assessment of the pharmacodynamic properties and the partitioning of OZ277/RBx-11160 in cultures of Plasmodium falciparum.	2006-07	16735432
Plasmodium vivax: in vitro susceptibility of blood stages to synthetic trioxolane compounds and the diamidine DB75.	2006-07	16458301
Infectious diseases. Source of new hope against malaria is in short supply.	2005-01-07	15637249
[Artemisinin and successors].	2005	15803790
Synthetic antimalaria drug enters clinical trials.	2004-10	15470761
Identification of an antimalarial synthetic trioxolane drug development candidate.	2004-08-19	15318224

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:13:57 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:57 GMT 2025`
Record UNII	3N1TN351VB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OZ 277

Preferred Name

English

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

arterolane [INN]

Common Name

English

Arterolane [WHO-DD]

Common Name

English

RBX-11160

Code

English

Classification Tree Code System Code

WHO-ATC

P01BX02