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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H39NO5
Molecular Weight 469.613
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTEFENOMEL

SMILES

C(CN1CCOCC1)OC2=CC=C(C=C2)[C@H]3CC[C@@]4(CC3)OO[C@@]5(O4)C6CC7CC(C6)CC5C7

InChI

InChIKey=XLCNVWUKICLURR-WMORPJFDSA-N
InChI=1S/C28H39NO5/c1-3-26(31-14-11-29-9-12-30-13-10-29)4-2-22(1)23-5-7-27(8-6-23)32-28(34-33-27)24-16-20-15-21(18-24)19-25(28)17-20/h1-4,20-21,23-25H,5-19H2/t20?,21?,23-,24?,25?,27-,28-

HIDE SMILES / InChI

Molecular Formula C28H39NO5
Molecular Weight 469.613
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Artefenomel, a novel trioxolane, is a lead candidate for inclusion in a new antimalarial combination, specifically formulated for children. Artefenomel has been demonstrated curative in as little as one dose.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1710 ng/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1500 ng/mL
1200 mg single, oral
dose: 1200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
339 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
732 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19700 ng × h/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
25100 ng × h/mL
1200 mg single, oral
dose: 1200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3180 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6450 ng × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
58 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
57 h
1200 mg single, oral
dose: 1200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
46.3 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
62.3 h
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARTEFENOMEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
PubMed

PubMed

TitleDatePubMed
Synthetic ozonide drug candidate OZ439 offers new hope for a single-dose cure of uncomplicated malaria.
2011 Mar 15
Patents

Sample Use Guides

In clinical trials, Artefenomel is administered in 800 mg doses in loose combination with Piperaquine phosphate doses of either 640, 960, 1440 mg
Route of Administration: Oral
Asexual parasites were seeded at a density of 0.5% parasitemia in 3% hematocrit in a black 384-well plate in 30 μL of culture medium, and 30 μL of diluted compound was added. Following a 72 h incubation at 37°C, 98% humidity, 93% N2, 4% CO2 and 3% O2, the increase in parasitemia was assessed using the modified Plasmodium lactate dehydrogenase assay. Artefenomel was diluted in DMSO and subsequently in culture medium to reach a final DMSO concentration of 0.1%.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:49:07 GMT 2023
Edited
by admin
on Sat Dec 16 02:49:07 GMT 2023
Record UNII
RIK029813G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEFENOMEL
INN   WHO-DD  
INN  
Official Name English
MORPHOLINE, 4-(2-(4-CIS-DISPIRO(CYCLOHEXANE-1,3'-(1,2,4)TRIOXOLANE-5',2''-TRICYCLO(3.3.1.13,7)DECAN)-4-YLPHENOXY)ETHYL)-
Systematic Name English
OZ439
Code English
4-(2-(4-(CIS-DISPIRO(ADAMANTANE-2,3'-(1,2,4)TRIOXOLANE-5',1''-CYCLOHEXANE)-4''-YL)PHENOXY)ETHYL)MORPHOLINE
Systematic Name English
OZ-439
Code English
artefenomel [INN]
Common Name English
CIS-ADAMANTANE-2-SPIRO-3'-8'-(4'-(2'-(4'-MORPHOLINYL)ETHOXY)PHENYL)-1',2,'4'-TRIOXASPIRO(4.5)DECANE
Common Name English
Artefenomel [WHO-DD]
Common Name English
Code System Code Type Description
EVMPD
SUB181577
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
INN
9766
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
NCI_THESAURUS
C169787
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
CAS
1029940-24-6
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
ALTERNATIVE
PUBCHEM
24999143
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
SMS_ID
100000167370
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
FDA UNII
RIK029813G
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
DRUG BANK
DB11809
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
CAS
1029939-86-3
Created by admin on Sat Dec 16 02:49:08 GMT 2023 , Edited by admin on Sat Dec 16 02:49:08 GMT 2023
PRIMARY
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