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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H18F6O3
Molecular Weight 408.3348
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ARTEFLENE

SMILES

C[C@H]1[C@@H]2C[C@H](CC1=O)[C@@](C)(OO2)\C=C/C3=C(C=C(C=C3)C(F)(F)F)C(F)(F)F

InChI

InChIKey=LRTRTVPZZJAADL-DAHZFVMQSA-N
InChI=1S/C19H18F6O3/c1-10-15(26)8-13-9-16(10)27-28-17(13,2)6-5-11-3-4-12(18(20,21)22)7-14(11)19(23,24)25/h3-7,10,13,16H,8-9H2,1-2H3/b6-5-/t10-,13+,16+,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H18F6O3
Molecular Weight 408.3348
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Arteflene is the sesquiterpene peroxide. It is a synthetic derivative of yingzhaosuwas. Arteflene found negative in a battery of mutagenicity tests. It had low acute toxicity after oral or subcutaneous administration in pre-clinical studies. Experimentally arteflene proved to be a highly effective antimalarial drug. An open, non-comparative clinical trial was carried out in Nigeria and Burkina Faso to investigate the safety and efficacy of the arteflene in patients with mild malaria. The lower than expected effect was thought to be due to inadequate storage of the arteflene suspension. There were no withdrawals due to adverse events and no deaths. Arteflene had no major effect on TNF, IL-alpha or IL-6 cytokine release from mononuclear cells stimulated with malaria antigens or lipopolysaccharide and it did not affect cell viability. Arteflene only slightly suppressed cytoadherence of infected erythrocytes to melanoma cells. The therapeutic effect of Arteflene appears to be confined to its parasite killing activity. Single dose monotherapy with arteflene was not effective in curing children suffering from uncomplicated P. falciparum malaria in Gabon. Arteflene is reported to be more cytotoxic to primary rat hepatocytes than some non-endoperoxide antimalarials.

Approval Year

Sample Use Guides

Single dose 25 mg/kg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:10 GMT 2023
Record UNII
5PE5HV9NF0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEFLENE
INN   MI   USAN  
INN   USAN  
Official Name English
2,3-DIOXABICYCLO(3.3.1)NONAN-7-ONE, 4-(2-(2,4-BIS(TRIFLUOROMETHYL)PHENYL)ETHENYL)-4,8-DIMETHYL-(1S-(1.ALPHA.,4.BETA.(Z),5.ALPHA.,8.BETA.))-
Common Name English
(1S,4R,5R,8S)-4-[(Z)-2,4-Bis(trifluoromethyl)styryl]-4,8-dimethyl-2,3-dioxabicyclo[3.3.1]nonan-7-one
Systematic Name English
arteflene [INN]
Common Name English
ARTEFLENE [MI]
Common Name English
RO-421611
Code English
RO-42-1611
Code English
RO421611
Code English
RO 42-1611
Code English
ARTEFLENE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
Code System Code Type Description
INN
7168
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
CAS
123407-36-3
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
MERCK INDEX
m2074
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY Merck Index
USAN
GG-86
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
EVMPD
SUB05573MIG
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
NCI_THESAURUS
C75263
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL380230
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
FDA UNII
5PE5HV9NF0
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
PUBCHEM
6436134
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID001318573
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
SMS_ID
100000086604
Created by admin on Fri Dec 15 15:40:10 GMT 2023 , Edited by admin on Fri Dec 15 15:40:10 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY