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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O8
Molecular Weight 384.4216
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTESUNATE

SMILES

C[C@]1([H])CC[C@@]2([H])[C@@]([H])(C)[C@]([H])(OC(=O)CCC(=O)O)O[C@@]3([H])[C@]42[C@@]1([H])CC[C@](C)(O3)OO4

InChI

InChIKey=FIHJKUPKCHIPAT-AHIGJZGOSA-N
InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1

HIDE SMILES / InChI
Molecular Formula C19H28O8
Molecular Weight 384.4216
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/8891104

treatment of falciparum malaria since 1990. It is a potent antimalarial drug that can reduce parasitaemia by 90% within 24 h of administration. Sodium artesunate was first isolated in China, it is a water soluble antimalaria used clinically in China.

CNS Activity

CNS Penetrant
2415
Curator's Comment:: Active metabolite of artesunate was detected in CSF after intravenous administration of artesunate.

Originator

Egyesult Gyogyszer es Tapszergyar
12
Sources: http://adisinsight.springer.com/drugs/800023198https://www.ncbi.nlm.nih.gov/pubmed/8891104Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan (1982), 2, (2), 99-103.
Curator's Comment:: Indicated originators are originators of Dihydroartemisinin/piperaquine formulation. Originator of Dihydroartemisinin is unknown.

Approval Year

2020
91
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7701
Sodium/potassium-transporting ATPase subunit alpha-1
16
Target ID: P06685
Gene ID: 24211
Gene Symbol: Atp1a1
Target Organism: Rattus norvegicus (Rat)
Inhibitor
7701
Inhibitor
7701
Plasmodium falciparum malaria
 4.09999999999999964 nM [IC50]
Inhibitor
7701
Inhibitor
7701
Inhibitor
7701
Plasmodium falciparum malaria
DNA
229
Target ID: CHEMBL2311221
Binding Agent
994
Colorectal cancer
Cervical cancer
Hepatocellular carcinoma
Breast cancer
DNA
229
Target ID: CHEMBL2366043
Binding Agent
994
Schistosoma mansoni infection
Binding Agent
994
Malaria
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Plasmodium falciparum
Approved
7997
Sodium artesunate

Approved Use

Plasmodium falciparum malaria
Curative
Plasmodium falciparum
Approved
7997
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

1319587200000
Curative
Plasmodium falciparum
Approved
7997

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
DNA
Phase III
650
Primary
DNA
Phase II
Primary
DNA
Phase I
593
Primary
DNA
Phase I
593
Primary
DNA
Phase I
593
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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 unknown
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
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 unknown
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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 unknown
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
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 unknown
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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 unknown
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
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 unknown
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:
ARTENIMOL unknown
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:
ARTESUNATE unknown
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1318
inhibitor
1421
inhibitor
1360

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
679

CYP2C19
1215

CYP3A4/5
225

CYP1A2
1268
UGT1A9
327

UGT2B7
329

P-gp
1223
CYP2A6
74

CYP3A
102
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1406
 no [IC50 >100 uM]
CYP2B6
845
 no [IC50 >100 uM]
CYP2B6
845
 no [IC50 >100 uM]
DHA
3
CYP2C19
1277
 no [IC50 >100 uM]
CYP2C9
1362
 no [IC50 >100 uM]
CYP2C9
1362
 no [IC50 >100 uM]
DHA
3
CYP2D6
1455
 no [IC50 >100 uM]
CYP2D6
1455
 no [IC50 >100 uM]
DHA
3
CYP3A4/5
277
 no [IC50 >100 uM]
CYP3A4/5
277
 no [IC50 >100 uM]
DHA
3
CYP1A2
1406
 weak [IC50 32.3 uM]
DHA
3
CYP2C19
1277
 weak [IC50 75.4 uM]
DHA
3
CYP2A6
625
 yes
DHA
3
CYP3A
244
 yes
DHA
3
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1223
 no
DHA
3
UGT1A9
327
 yes
DHA
3
UGT2B7
329
 yes
DHA
3
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1392
DHA
3
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:63918
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:63918
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
Penetration of dihydroartemisinin into cerebrospinal fluid after administration of intravenous artesunate in severe falciparum malaria.
2003 Jan
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 Sep
Mechanistic perspectives for 1,2,4-trioxanes in anti-cancer therapy.
2005 Feb-Apr
Glutathione-related enzymes contribute to resistance of tumor cells and low toxicity in normal organs to artesunate.
2005 Jan-Feb
Adding artesunate to sulphadoxine-pyrimethamine greatly improves the treatment efficacy in children with uncomplicated falciparum malaria on the coast of Benin, West Africa.
2007 Dec 21
Treatment of experimental nephrotic syndrome with artesunate.
2007 Jul-Aug
Auditory assessment of patients with acute uncomplicated Plasmodium falciparum malaria treated with three-day mefloquine-artesunate on the north-western border of Thailand.
2008 Nov 6
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 Jun
Patents

Patents

20070275244
8
20090192216
3
20100184846
3
4791135
3
7678828
3
7790905
103
7914893
7
7927613
115
7956086
3
WO2002026226A1
3
WO2003075912A1
3
WO2004028476A3
3
WO2007017646A2
3
WO2007146288A2
3
WO2013167743A1
13

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.
Eurartesim (piperaquine tetraphosphate (PQP)/
Route of Administration: Oral
In Vitro Use Guide
dihydroartemisinin at micromolar dose levels exhibits a dose- and time-dependent cytotoxicity in ovarian cancer cell lines.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:32:58 UTC 2021
Edited
by admin
on Sat Jun 26 13:32:58 UTC 2021
Record UNII
60W3249T9M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTESUNATE
DASH   HSDB   INN   MART.   MI   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
ARTESUNATE [USP-RS]
Common Name English
4-OXO-4-(3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXYPYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE
Common Name English
LJPC-0118
Code English
BUTANEDIOIC ACID, MONO(DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER, (3R-(3.ALPHA.,5A.BETA.,6.BETA.,8A.BETA.,9.ALPHA.,10.BETA.,12.BETA.,12AR*))-
Systematic Name English
ARTESUNATE [WHO-IP]
Common Name English
ZYSUNATE
Brand Name English
ARTESUNATE [USAN]
Common Name English
SAPHNATE
Common Name English
ARTESUNATE [HSDB]
Common Name English
ARTESUNATE [WHO-DD]
Common Name English
ARTESUNATE [VANDF]
Common Name English
.ALPHA.-ARTESUNIC ACID
Common Name English
ARTESUNATE [MI]
Common Name English
ARTESUNATE [MART.]
Common Name English
ARTESUNATUM [WHO-IP LATIN]
Common Name English
NSC-712571
Code English
DIHYDROQINGHAOSU HEMISUCCINATE
Common Name English
3R,5AS,6R,8AS,9R,10S,12R,12AR)-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL HYDROGEN BUTANEDIOATE
Systematic Name English
DIHYDROARTEMISININE-12.ALPHA.-SUCCINATE
Common Name English
BUTANEDIOIC ACID, MONO((3R,5AS,6R,8AS,9R,10S,12R,12AR)-DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-YL) ESTER
Common Name English
QINGHAOZHI
Common Name English
ARTESUNATE [INN]
Common Name English
ARTESUNIC ACID
Common Name English
PLASMOTRIN
Brand Name English
(3R,5AS,6R,8AS,9R,10S,12R,12AR)-DECAHYDRO-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN-10-OL, HYDROGEN SUCCINATE
Systematic Name English
ARSUMAX
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 651218
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
FDA ORPHAN DRUG 598517
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
FDA ORPHAN DRUG 221206
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ATC P01BE03
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
FDA ORPHAN DRUG 693719
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (ART/AMO)
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ATC P01BF03
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ATC P01BF02
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ATC P01BF04
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
WHO-ATC P01BF06
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
EU-Orphan Drug EU/3/15/1521
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
FDA ORPHAN DRUG 125599
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
NCI_THESAURUS C277
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
Code System Code Type Description
DRUG CENTRAL
247
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
LACTMED
Artesunate
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
CAS
88495-63-0
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL361497
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
INN
6459
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
RXCUI
18346
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY RxNorm
EPA CompTox
88495-63-0
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
DRUG BANK
DB09274
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
MERCK INDEX
M2078
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY Merck Index
FDA UNII
60W3249T9M
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
PUBCHEM
6917864
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
NCI_THESAURUS
C73005
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
HSDB
7458
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ARTESUNATE
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY Description: A fine, white crystalline powder. Solubility: Very slightly soluble in water; very soluble in dichloromethane R; freely soluble in ethanol (~750 g/l) TS and acetone R. Category: Antimalarial. Storage: Artesunate should be kept in a well-closed container or, if sterile, in a hermetically closed container. It should be protected from light. Labelling: The label states where applicable:? that the substance is free from bacterial endotoxins;? that the substance is sterile. Definition: Artesunate contains not less than 96.0% and not more than 102.0% of artesunate (C19H28O8) using Assay method A, and not less than 98.0% and not more than 102.0% of artesunate (C19H28O8) using Assay method B, both calculated with reference to the anhydrous substance.
MESH
C039726
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
USP_CATALOG
1042850
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY USP-RS
EVMPD
SUB05576MIG
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
WIKIPEDIA
ARTESUNATE
Created by admin on Sat Jun 26 13:32:59 UTC 2021 , Edited by admin on Sat Jun 26 13:32:59 UTC 2021
PRIMARY
Related Record Type Details
OATP1B1
TRANSPORTER -> INHIBITOR
WEAK
IC50
PLASMODIUM FALCIPARUM
TARGET ORGANISM->INHIBITOR
IC50
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
Structure of SODIUM ARTESUNATE
SALT/SOLVATE -> PARENT
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
OAT-3
TRANSPORTER -> INHIBITOR
WEAK
Related Record Type Details
Structure of ARTENIMOL
METABOLITE ACTIVE -> PARENT
Structure of .ALPHA.-DIHYDROARTEMISININ
METABOLITE ACTIVE -> PRODRUG
ratio of alpha to beta DIHYDROARTEMISININ is 3.5
PLASMA
Related Record Type Details
Structure of ARTEMISININ
IMPURITY -> PARENT
In the chromatogram obtained with solution (1): the area of any peak corresponding to impurity B (artemisinin) is not greater than 0.5 times the area of the principal peak obtained with solution (4) (0.5%).
Structure of ANHYDRODIHYDROARTEMISNIN
IMPURITY -> PARENT
In the chromatogram obtained with solution (1): the area of any peak corresponding to impurity C, when multiplied by a correction factor of 0.07, is not greater than 0.2 times the area of the principal peak obtained with solution (4) (0.2%) the sum of the corrected area of any peak corresponding to impurity C and the areas of all other peaks, other than the principal peak, is not greater than twice the area of the principal peak obtained with solution (4) (2.0%).
Related Record Type Details
Structure of .ALPHA.-DIHYDROARTEMISININ
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC INTRAVENOUS ADMINISTRATION

IN PATIENTS WITH SEVERE MALARIA

Biological Half-life PHARMACOKINETIC IN PATIENTS WITH SEVERE MALARIA

INTRAVENOUS ADMINISTRATION

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