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

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24O5
Molecular Weight 284.3481
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-DIHYDROARTEMISININ

SMILES

C[C@@H]1CC[C@H]2[C@@H](C)[C@H](O)O[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO4

InChI

InChIKey=BJDCWCLMFKKGEE-KDTBHNEXSA-N
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12-,13-,14-,15-/m1/s1

HIDE SMILES / InChI
Molecular Formula C15H24O5
Molecular Weight 284.3481
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/001199/human_med_001450.jsp&mid=WC0b01ac058001d124 | https://www.hpra.ie/docs/default-source/3rd-party-documents/educational-materials/eurartesim_hcp-guide.pdf?sfvrsn=4 | https://www.ncbi.nlm.nih.gov/pubmed/20649950

Artenimol (dihydroartemisinin) is a derivate of antimalarial compound artemisinin. Artenimol (dihydroartemisinin) is able to reach high concentrations within the parasitized erythrocytes. Its endoperoxide bridge is thought to be essential for its antimalarial activity, causing free-radical damage to parasite membrane systems including: • Inhibition of falciparum sarcoplasmic-endoplasmic reticulum calcium ATPase, • Interference with mitochondrial electron transport • Interference with parasite transport proteins • Disruption of parasite mitochondrial function. Dihydroartemisinin in combination with piperaquine tetraphosphate (Eurartesim, EMA-approved in 2011) is indicated for the treatment of uncomplicated Plasmodium falciparum malaria. The formulation meets WHO recommendations, which advise combination treatment for Plasmodium falciparum malaria to reduce the risk of resistance development, with artemisinin-based preparations regarded as the ‘policy standard’. However, experimental testing demonstrates that, due to its intrinsic chemical instability, dihydroartemisinin is not suitable to be used in pharmaceutical formulations. In addition, data show that the currently available dihydroartemisinin preparations fail to meet the internationally accepted stability requirements.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Active metabolite of artesunate was detected in CSF after intravenous administration of artesunate.

Originator

Chongqing Holley|Medicines for Malaria Venture|Sigma-tau|University of Oxford
3
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8891104Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan (1982), 2, (2), 99-103.http://adisinsight.springer.com/drugs/800023198
Curator's Comment: Indicated originators are originators of Dihydroartemisinin/piperaquine formulation. Originator of Dihydroartemisinin is unknown.

Approval Year

2020
691
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Sodium/potassium-transporting ATPase subunit alpha-1
16
Target ID: P06685
Gene ID: 24211.0
Gene Symbol: Atp1a1
Target Organism: Rattus norvegicus (Rat)
Inhibitor
8504
Inhibitor
8504
 4.1 nM [IC50]
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
DNA
282
Target ID: CHEMBL2311221
Binding Agent
1076
DNA
282
Target ID: CHEMBL2366043
Binding Agent
1076
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Sodium artesunate

Approved Use

Plasmodium falciparum malaria
Curative
Approved
8583
Eurartesim

Approved Use

Eurartesim tablets (piperaquine tetraphosphate in combination with dihydroartemisinin) are indicated for the treatment of uncomplicated Plasmodium falciparum malaria in adults, children and infants aged ≥6 months and weighing ≥5kg.

Launch Date

2011
Curative
Approved
8583
Unknown

Approved Use

Although not FDA-approved for use in the United States, artesunate is used as the treatment of choice for severe malaria by the World Health Organization (WHO) over quinidine.
Curative
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.3 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTESUNATE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
3.1 μg/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTENIMOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.7 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTESUNATE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
3.5 μg × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTENIMOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.3 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTESUNATE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1.3 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTENIMOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTESUNATE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
7%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
2.4 mg/kg multiple, intravenous
dose: 2.4 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
ARTENIMOL plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Other AEs: Anemia, Transaminases increased...
Other AEs:
Anemia (65%)
Transaminases increased (27%)
Thrombocytopenia (18%)
Hyperbilirubinemia (14%)
Acute renal failure (10%)
Leukocytosis (10%)
Acute respiratory distress syndrome (8%)
Lymphopenia (7%)
Neutropenia (5%)
Disseminated intravascular coagulation (3%)
Creatinine increased (3%)
Pneumonia (3%)
Pulmonary edema (3%)
Diarrhea (3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
unhealthy, 15-35 years
Health Status: unhealthy
Age Group: 15-35 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
Other AEs: Nausea, Dizziness...
Other AEs:
Nausea (grade 1, 45%)
Dizziness (grade 1, 52%)
Vomiting (grade 1, 26%)
Convulsions (grade 1, 3%)
Bradycardia (grade 1, 23%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
2.4 mg/kg 1 times / day multiple, intravenous|oral
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous|oral
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
unhealthy, 2-87 years
Health Status: unhealthy
Age Group: 2-87 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
Other AEs: Acute renal failure, Hemoglobinuria...
Other AEs:
Acute renal failure (8.9%)
Hemoglobinuria (6.7%)
Jaundice (2.3%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
25 mg/kg 2 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 25 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
DLT: Nausea, Vomiting...
Dose limiting toxicities:
Nausea (grade 3, 1 patient)
Vomiting (grade 3, 1 patient)
ALT increased (grade 3-4, 1 patient)
Neutropenic infection (grade 3-4, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
18 mg/kg 2 times / 3 weeks multiple, intravenous
MTD
Dose: 18 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 18 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
DLT: Hypersensitivity reaction...
Dose limiting toxicities:
Hypersensitivity reaction (grade 3, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
12 mg/kg 2 times / 3 weeks multiple, intravenous
Studied dose
Dose: 12 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
DLT: Neutropenic fever...
Dose limiting toxicities:
Neutropenic fever (grade 3, 1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
AEs

AEs

AESignificanceDosePopulation
Acute renal failure 10%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Leukocytosis 10%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Hyperbilirubinemia 14%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Thrombocytopenia 18%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Transaminases increased 27%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Creatinine increased 3%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Diarrhea 3%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Disseminated intravascular coagulation 3%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Pneumonia 3%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Pulmonary edema 3%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Neutropenia 5%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Anemia 65%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Lymphopenia 7%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Acute respiratory distress syndrome 8%
2.4 mg/kg 1 times / day multiple, intravenous
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
unhealthy, 1-72 years
Health Status: unhealthy
Age Group: 1-72 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
Bradycardia grade 1, 23%
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
unhealthy, 15-35 years
Health Status: unhealthy
Age Group: 15-35 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
Vomiting grade 1, 26%
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
unhealthy, 15-35 years
Health Status: unhealthy
Age Group: 15-35 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
Convulsions grade 1, 3%
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
unhealthy, 15-35 years
Health Status: unhealthy
Age Group: 15-35 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
Nausea grade 1, 45%
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
unhealthy, 15-35 years
Health Status: unhealthy
Age Group: 15-35 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
Dizziness grade 1, 52%
100 mg 1 times / day multiple, oral
Studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
unhealthy, 15-35 years
Health Status: unhealthy
Age Group: 15-35 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/8205643/
Jaundice 2.3%
2.4 mg/kg 1 times / day multiple, intravenous|oral
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous|oral
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
unhealthy, 2-87 years
Health Status: unhealthy
Age Group: 2-87 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
Hemoglobinuria 6.7%
2.4 mg/kg 1 times / day multiple, intravenous|oral
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous|oral
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
unhealthy, 2-87 years
Health Status: unhealthy
Age Group: 2-87 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
Acute renal failure 8.9%
2.4 mg/kg 1 times / day multiple, intravenous|oral
Recommended
Dose: 2.4 mg/kg, 1 times / day
Route: intravenous|oral
Route: multiple
Dose: 2.4 mg/kg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
unhealthy, 2-87 years
Health Status: unhealthy
Age Group: 2-87 years
Sex: M+F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/213036s000lbl.pdf
https://pubmed.ncbi.nlm.nih.gov/16125588/
Nausea grade 3, 1 patient
DLT
25 mg/kg 2 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 25 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
Vomiting grade 3, 1 patient
DLT
25 mg/kg 2 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 25 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
ALT increased grade 3-4, 1 patient
DLT
25 mg/kg 2 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 25 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
Neutropenic infection grade 3-4, 1 patient
DLT
25 mg/kg 2 times / 3 weeks multiple, intravenous
Highest studied dose
Dose: 25 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 25 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
Hypersensitivity reaction grade 3, 1 patient
DLT
18 mg/kg 2 times / 3 weeks multiple, intravenous
MTD
Dose: 18 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 18 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
Neutropenic fever grade 3, 1 patient
DLT
12 mg/kg 2 times / 3 weeks multiple, intravenous
Studied dose
Dose: 12 mg/kg, 2 times / 3 weeks
Route: intravenous
Route: multiple
Dose: 12 mg/kg, 2 times / 3 weeks
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/29392450
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:63918
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63918
eMolecules
1935656
https://www.emolecules.com/cgi-bin/more?vid=1935656
eMolecules
29933844
https://www.emolecules.com/cgi-bin/more?vid=29933844
eMolecules
31224737
https://www.emolecules.com/cgi-bin/more?vid=31224737
MolPort
MolPort-006-392-384
https://www.molport.com/shop/molecule-link/MolPort-006-392-384
ZINC
ZINC000014096305
http://zinc15.docking.org/substances/ZINC000014096305
PubMed

PubMed

TitleDatePubMed
Untargeted Proteomics and Systems-Based Mechanistic Investigation of Artesunate in Human Bronchial Epithelial Cells.
2015-10-19
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs.
2015-06
Delayed anemia after treatment with injectable artesunate in the Democratic Republic of the Congo: a manageable issue.
2014-10
Artesunate induces apoptosis through caspase-dependent and -independent mitochondrial pathways in human myelodysplastic syndrome SKM-1 cells.
2014-08-05
Dihydroartemisinin-piperaquine for treating uncomplicated Plasmodium falciparum malaria.
2014-01-20
Artesunate-mefloquine combination therapy in acute Plasmodium falciparum malaria in young children: a field study regarding neurological and neuropsychiatric safety.
2010-10-21
In Tanzania, hemolysis after a single dose of primaquine coadministered with an artemisinin is not restricted to glucose-6-phosphate dehydrogenase-deficient (G6PD A-) individuals.
2010-05
Factors determining sensitivity or resistance of tumor cell lines towards artesunate.
2010-04-15
The neurological assessment in young children treated with artesunate monotherapy or artesunate-mefloquine combination therapy for uncomplicated Plasmodium falciparum malaria.
2009-09-02
Combination treatment of malignant B cells using the anti-CD20 antibody rituximab and the anti-malarial artesunate.
2009-07
Auditory assessment of patients with acute uncomplicated Plasmodium falciparum malaria treated with three-day mefloquine-artesunate on the north-western border of Thailand.
2008-11-06
Adding artesunate to sulphadoxine-pyrimethamine greatly improves the treatment efficacy in children with uncomplicated falciparum malaria on the coast of Benin, West Africa.
2007-12-21
Treatment of experimental nephrotic syndrome with artesunate.
2007-07-31
Artesunate in the treatment of metastatic uveal melanoma--first experiences.
2005-12
Glutathione-related enzymes contribute to resistance of tumor cells and low toxicity in normal organs to artesunate.
2005-03-31
Mechanistic perspectives for 1,2,4-trioxanes in anti-cancer therapy.
2005-03-29
Randomized control trial of quinine and artesunate in complicated malaria.
2004-04
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.
2003-09
Penetration of dihydroartemisinin into cerebrospinal fluid after administration of intravenous artesunate in severe falciparum malaria.
2003-01
Artesunate and mefloquine given simultaneously for three days via a prepacked blister is equally effective and tolerated as a standard sequential treatment of uncomplicated acute Plasmodium falciparum malaria: randomized, double-blind study in Thailand.
2002-11
Diuretic effect of sodium artesunate in patients with malaria.
2002-11
Effects of sodium artesunate, a new antimalarial drug, on renal function.
2001-03
Monotherapy with sodium artesunate for uncomplicated falciparum malaria in Thailand: a comparison of 5- and 7-day regimens.
1997-09-30
[Effects of sodium artesunate on electrical properties and Na+,K(+)-ATPase activities of mouse small intestine].
1990-07
Antimalarial agents, 2. Artesunate, an inhibitor of cytochrome oxidase activity in Plasmodium berghei.
1986-01-01
Patents

Patents

20070275244
8
20090192216
3
20100184846
3
4791135
3
7678828
3
7790905
107
7914893
7
7927613
119
7956086
3
WO2002026226A1
3
WO2003075912A1
3
WO2004028476A3
3
WO2007017646A2
3
WO2007146288A2
3
WO2013167743A1
14

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Oral route is possible: One group of 45 patients received 400 mg of Sodium artesunate on the first day of treatment and then 200 mg daily for 4 days for a total of 1200 mg (group I: 5-day treatment). A second group of 46 patients received 400 mg of Sodium artesunate on the first day of treatment and then 200 mg daily for 6 days for a total of 1600 mg (group II: 7-day treatment). 5- or 7-day regimens of sodium artesunate with a total dose of 1200-1600 mg are effective and safe in treating falciparum malaria acquired in Thailand. https://www.ncbi.nlm.nih.gov/pubmed/9241384
Artesunate can be used orally, by intravenous or intramuscular injection or as a suppository. As an injection, artesunate 2.4mg/kg bw i.v or i.m. given on admission (time =0), then at 12hr and 24hr, then once a day.
Route of Administration: Other
In Vitro Use Guide
An artemisinin concentration of 100-300 nM in vitro caused swelling of the endoplasmic reticulum and mitochondria, as well as injuries both to the limiting and to the nuclear membranes of chloroquine-resistant P. falciparum (ItG2 strain) within 2 h.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:36:20 GMT 2025
Edited
by admin
on Mon Mar 31 21:36:20 GMT 2025
Record UNII
X0UIV26ABX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-OL, DECAHYDRO-3,6,9-TRIMETHYL-, (3R,5AS,6R,8AS,9R,10R,12R,12AR)-
Preferred Name English
.ALPHA.-DIHYDROARTEMISININ
Common Name English
DIHYDROARTIMISININ
Common Name English
3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-OL, DECAHYDRO-3,6,9-TRIMETHYL-, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-
Common Name English
NSC-758682
Code English
Code System Code Type Description
CAS
81496-81-3
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
DRUG BANK
DBMET00793
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
PUBCHEM
11358077
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
FDA UNII
X0UIV26ABX
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
RXCUI
2584841
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
NSC
758682
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID5045962
Created by admin on Mon Mar 31 21:36:20 GMT 2025 , Edited by admin on Mon Mar 31 21:36:20 GMT 2025
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
Related Record Type Details
Structure of ARTESUNATE
PRODRUG -> METABOLITE ACTIVE
ratio of alpha to beta DIHYDROARTEMISININ is 3.5
PLASMA
Structure of ARTEMETHER
PARENT -> METABOLITE
NIH
NCATS
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