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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H31NO6S
Molecular Weight 401.518
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTEMISONE

SMILES

[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@@]4(C)OO[C@@]13[C@]([H])(O[C@H]([C@@H]2C)N5CCS(=O)(=O)CC5)O4

InChI

InChIKey=FDMUNKXWYMSZIR-NQWKWHCYSA-N
InChI=1S/C19H31NO6S/c1-12-4-5-15-13(2)16(20-8-10-27(21,22)11-9-20)23-17-19(15)14(12)6-7-18(3,24-17)25-26-19/h12-17H,4-11H2,1-3H3/t12-,13-,14+,15+,16-,17-,18-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H31NO6S
Molecular Weight 401.518
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Artemisone (also known as BAY-44-9585; BAY-449585) is a 10-amino-artemisinin derivative that is markedly superior in vitro and in vivo to current artemisinins against malaria and also possesses antitumor activity. Nonetheless, its low water solubility and bioavailability has limited its clinical use, that is why was studied the encapsulated artemisone against human melanoma A-375. In addition, artemisone has the potential to be efficacious for the treatment of H. pylori infection, especially in combination with antibiotics.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
95 ng/mL
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARTEMISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
130.3 ng/mL
80 mg 1 times / day multiple, oral
dose: 80 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARTEMISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
190.7 ng × h/mL
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARTEMISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
337.3 ng × h/mL
80 mg 1 times / day multiple, oral
dose: 80 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARTEMISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.37 h
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARTEMISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.07 h
80 mg 1 times / day multiple, oral
dose: 80 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARTEMISONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Artemisone--a highly active antimalarial drug of the artemisinin class.
2006 Mar 20
In vitro activity of artemisone and artemisinin derivatives against extracellular and intracellular Helicobacter pylori.
2016 Jul
Patents

Patents

Sample Use Guides

Artemisone 4 mg/kg/day for 3 days plus mefloquine 15mg/kg on day 3 and 10mg/kg on day 4
Route of Administration: Oral
The in vitro activity of the new artemisinin derivative artemisone as well as other molecules of the same class against Helicobacter pylori and their effects when combined with standard antibiotics were evaluated. Artemisone showed MIC50 and MIC90 values of 0.25 mg/L and 0.5 mg/L, respectively, and an MBC50 value of 0.5 mg/L. Artemisone was synergistic with amoxicillin in 60% of strains, with clarithromycin in 40% and with metronidazole in 20%.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:26:36 GMT 2023
Edited
by admin
on Fri Dec 15 17:26:36 GMT 2023
Record UNII
796LMW5BUZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEMISONE
INN  
INN  
Official Name English
4-((3R,5AS,6R,8AS,9R,10R,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-12H-3,12-EPOXYPYRANO(4,3-J)(1,2)BENZODIOXEPIN-10-YL)THIOMORPHOLINE-1,1-DIONE
Common Name English
BAY 44-9585
Code English
BAY-449585
Code English
ARTEMIFONE
Common Name English
artemisone [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 590117
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
NCI_THESAURUS C271
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
Code System Code Type Description
FDA UNII
796LMW5BUZ
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
INN
8344
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID201037214
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
MESH
C514498
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
CAS
255730-18-8
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
SMS_ID
300000034160
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL516268
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
PUBCHEM
11531457
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
NCI_THESAURUS
C87431
Created by admin on Fri Dec 15 17:26:36 GMT 2023 , Edited by admin on Fri Dec 15 17:26:36 GMT 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
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