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
Identification of an antimalarial synthetic trioxolane drug development candidate.	2004 Aug 19	15318224
Synthetic antimalaria drug enters clinical trials.	2004 Oct	15470761
In vitro assessment of the pharmacodynamic properties and the partitioning of OZ277/RBx-11160 in cultures of Plasmodium falciparum.	2006 Jul	16735432
In vitro and in vivo interaction of synthetic peroxide RBx11160 (OZ277) with piperaquine in Plasmodium models.	2007 Mar	17087929
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
Development and validation of a headspace gas chromatographic method for the determination of residual solvents in arterolane (RBx11160) maleate bulk drug.	2010 Jan	21814428

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