U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ARTEROLANE

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

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

PubMed

TitleDatePubMed
In vitro assessment of the pharmacodynamic properties and the partitioning of OZ277/RBx-11160 in cultures of Plasmodium falciparum.
2006 Jul
In vitro and in vivo interaction of synthetic peroxide RBx11160 (OZ277) with piperaquine in Plasmodium models.
2007 Mar
Drug metabolism and pharmacokinetics.
2008 Oct
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
Comparative embryotoxicity of different antimalarial peroxides: in vitro study using the rat whole embryo culture model (WEC).
2010 Dec
The structure-activity relationship of the antimalarial ozonide arterolane (OZ277).
2010 Jan 14
Arterolane, a new synthetic trioxolane for treatment of uncomplicated Plasmodium falciparum malaria: a phase II, multicenter, randomized, dose-finding clinical trial.
2010 Sep 15
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:30:03 GMT 2023
Edited
by admin
on Fri Dec 15 18:30:03 GMT 2023
Record UNII
3N1TN351VB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEROLANE
INN   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
Code System Code Type Description
DRUG CENTRAL
5090
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
NCI_THESAURUS
C166684
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
FDA UNII
3N1TN351VB
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
SMS_ID
100000144464
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID50985095
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
EVMPD
SUB121116
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
INN
8663
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
CHEBI
136054
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
CAS
664338-39-0
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
WIKIPEDIA
ARTEROLANE
Created by admin on Fri Dec 15 18:30:03 GMT 2023 , Edited by admin on Fri Dec 15 18:30:03 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
EC50
Related Record Type Details
ACTIVE MOIETY