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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H36N2O4.C4H4O4
Molecular Weight 508.6044
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ARTEROLANE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC(C)(N)CNC(=O)C[C@H]1CC[C@]2(CC1)OOC3(O2)C4CC5CC(C4)CC3C5

InChI

InChIKey=SVDSPJJUJMMDFX-CXCXETQFSA-N
InChI=1S/C22H36N2O4.C4H4O4/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;5-3(6)1-2-4(7)8/h14-18H,3-13,23H2,1-2H3,(H,24,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15?,16?,17?,18?,21+,22?;

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Identification of an antimalarial synthetic trioxolane drug development candidate.
2004 Aug 19
[Artemisinin and successors].
2005
In vitro susceptibility of P. falciparum populations from Colombia and Tanzania to a new synthetic peroxide (OZ277).
2007 Jun
Development and validation of a headspace gas chromatographic method for the determination of residual solvents in arterolane (RBx11160) maleate bulk drug.
2010 Jan
The structure-activity relationship of the antimalarial ozonide arterolane (OZ277).
2010 Jan 14
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:04:37 GMT 2023
Edited
by admin
on Sat Dec 16 15:04:37 GMT 2023
Record UNII
1C86ZU1OEN
Record Status Validated (UNII)
Record Version
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Name Type Language
ARTEROLANE MALEATE
Common Name English
Arterolane maleate [WHO-DD]
Common Name 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-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
959520-73-1
Created by admin on Sat Dec 16 15:04:37 GMT 2023 , Edited by admin on Sat Dec 16 15:04:37 GMT 2023
PRIMARY
FDA UNII
1C86ZU1OEN
Created by admin on Sat Dec 16 15:04:37 GMT 2023 , Edited by admin on Sat Dec 16 15:04:37 GMT 2023
PRIMARY
SMS_ID
300000039291
Created by admin on Sat Dec 16 15:04:37 GMT 2023 , Edited by admin on Sat Dec 16 15:04:37 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY