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artesunate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| antimalarial agents, artemisinin related compounds | 247 | 88495-63-0 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
A water-soluble, semi-synthetic derivative of the sesquiterpene lactone artemisinin with anti-malarial, anti-schistosomiasis, antiviral, and potential anti-neoplastic activities. Artesunate (AS) contains an endoperoxide bridge that is activated by heme iron, resulting in the generation of free radicals that alkylate parasite proteins and ultimately lead to cell death. Dihydroartemisinin (DHA, also known as artenimol), the active metabolite of artesunate, was found to specifically increase oxidative stress in P. falciparum-infected erythrocytes but not uninfected cells, by reduction of antioxidants.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.28 | g | O |
| 0.28 | g | P |
| 0.28 | g | R |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 9.36 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| Vd (Volume of distribution) | 15 L/kg | Lombardo F, Berellini G, Obach RS |
| CL (Clearance) | 1070 mL/min/kg | Lombardo F, Berellini G, Obach RS |
| fu (Fraction unbound in plasma) | 0.25 % | Lombardo F, Berellini G, Obach RS |
| t_half (Half-life) | 0.22 hours | Lombardo F, Berellini G, Obach RS |
| S (Water solubility) | 0.06 mg/mL | Bocci G, Oprea TI, Benet LZ |
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 2 | Bocci G, Oprea TI, Benet LZ |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| kinase-safety-class | ACVR2B,AXL,BTK,CAMK2D,CDK5,CDK9,DYRK1B,EIF2AK3,ERBB2,GRK2,ITK,MAP2K6,MAPK7,MAPKAPK2,NTRK2,PDK1,PDK2,PRKDC,TEK | 19 | |||
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pld-class | Phospholipidosis risk class (1 = positive, 0 = negative) | 0 | Moderate | 0.66 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| May 26, 2020 | FDA | AMIVAS | |
| Nov. 22, 2021 | EMA | AMIVAS IRELAND LTD |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Haemolytic anaemia | 138.20 | 74.20 | 26 | 352 | 11671 | 90616398 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Haemolytic anaemia | 115.65 | 80.49 | 21 | 100 | 12106 | 42609108 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Haemolytic anaemia | 240.10 | 71.98 | 46 | 462 | 20874 | 110567917 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | P01BE03 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, plain |
| ATC | P01BF02 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations |
| ATC | P01BF03 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations |
| ATC | P01BF04 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations |
| ATC | P01BF06 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations |
| ATC | P01BF09 | ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations |
| MeSH PA | D000871 | Anthelmintics |
| MeSH PA | D000890 | Anti-Infective Agents |
| MeSH PA | D000962 | Antimalarials |
| MeSH PA | D000970 | Antineoplastic Agents |
| MeSH PA | D000977 | Antiparasitic Agents |
| MeSH PA | D000980 | Antiplatyhelmintic Agents |
| MeSH PA | D000981 | Antiprotozoal Agents |
| MeSH PA | D000998 | Antiviral Agents |
| MeSH PA | D012556 | Schistosomicides |
| CHEBI has role | CHEBI:22587 | antiviral agent |
| CHEBI has role | CHEBI:35610 | antineoplastic agent |
| CHEBI has role | CHEBI:38068 | antimalarial |
| CHEBI has role | CHEBI:66981 | ophthalmology drug |
| CHEBI has role | CHEBI:173085 | ferroptosis inducer |
| CHEBI has role | CHEBI:233423 | antifibrotic agent |
Related Drugs by ATC class:
P01BE Artemisinin and derivatives, plain 4 drugs
P01BF Artemisinin and derivatives, combinations 11 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Vivax malaria | indication | 27052006 | DOID:12978 |
| Falciparum malaria | indication | 62676009 | DOID:14067 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 8.0 | acidic |
Orange Book patent data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Patent number | Patent expiration date | Patent use |
|---|---|---|---|---|---|---|---|---|---|---|
| 110MG/VIAL | ARTESUNATE | AMIVAS | N213036 | May 26, 2020 | RX | POWDER | INTRAVENOUS | 12390442 | Feb. 16, 2044 | A METHOD OF TREATING MALARIA USING MICRONIZED POWDER OF CRYSTALLINE ARTESUNATE PREPARED BY STERILIZING AND FILLING THE POWDER INTO A CONTAINER AT A RELATIVE HUMIDITY OF 30 TO 40%, MIXING THE POWDER WITH A BUFFER AND ADMINISTERING THE COMPOSITION |
Orange Book exclusivity data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Exclusivity date | Description |
|---|---|---|---|---|---|---|---|---|---|
| 110MG/VIAL | ARTESUNATE | AMIVAS | N213036 | May 26, 2020 | RX | POWDER | INTRAVENOUS | May 26, 2027 | INDICATED FOR THE INITIAL TREATMENT OF SEVERE MALARIA IN ADULT AND PEDIATRIC PATIENTS TO ALWAYS BE FOLLOWED BY A COMPLETE TREATMENT COURSE OF AN APPROPRIATE ORAL ANTIMALARIAL REGIMEN |
Bioactivity Summary:
None
External reference:
| ID | Source |
|---|---|
| 4025235 | VUID |
| N0000179045 | NUI |
| D02482 | KEGG_DRUG |
| 18346 | RXNORM |
| C0052432 | UMLSCUI |
| CHEBI:63918 | CHEBI |
| D95 | PDB_CHEM_ID |
| CHEMBL361497 | ChEMBL_ID |
| DB09274 | DRUGBANK_ID |
| D000077332 | MESH_DESCRIPTOR_UI |
| 6917864 | PUBCHEM_CID |
| 9956 | IUPHAR_LIGAND_ID |
| C111789 | MESH_SUPPLEMENTAL_RECORD_UI |
| 6459 | INN_ID |
| 60W3249T9M | UNII |
| 228453 | MMSL |
| 27009 | MMSL |
| d07559 | MMSL |
| 4025235 | VANDF |
| 009953 | NDDF |
| 432410005 | SNOMEDCT_US |
| 432555000 | SNOMEDCT_US |
| 60W3249T9M | INXIGHT DRUGS |
Pharmaceutical products:
None