artesunate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antimalarial agents, artemisinin related compounds 247 88495-63-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • artesunate
  • arinate
  • arsuamoon
  • arsumax
  • artesunic acid
  • cosunate
  • dihydroqinghasu hemsuccinate
  • artesunate amivas
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.
  • Molecular weight: 384.43
  • Formula: C19H28O8
  • CLOGP: 2.93
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 1
  • TPSA: 100.52
  • ALOGS: -2.75
  • ROTB: 5
  • Status: ONP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.28 g O
0.28 g P
0.28 g R

ADMET properties:

PropertyValueReference
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

Approvals:

DateAgencyCompanyOrphan
Nov. 22, 2021 EMA AMIVAS IRELAND LTD
May 26, 2020 FDA AMIVAS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Haemolytic anaemia 102.21 94.12 20 269 10105 63478628

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Haemolytic anaemia 113.15 77.74 20 76 10459 34946376

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Haemolytic anaemia 207.91 77.33 40 345 17780 79726223

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
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:35610 antineoplastic agents
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:173085 ferroptosis inducers

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (acidic/basic)
pKa1 8.0 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
110MG/VIAL ARTESUNATE AMIVAS N213036 May 26, 2020 RX POWDER INTRAVENOUS May 26, 2025 NEW CHEMICAL ENTITY
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:

IDSource
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
C111789 MESH_SUPPLEMENTAL_RECORD_UI
6917864 PUBCHEM_CID
9956 IUPHAR_LIGAND_ID
6459 INN_ID
60W3249T9M UNII
228453 MMSL
27009 MMSL
d07559 MMSL
432410005 SNOMEDCT_US
432555000 SNOMEDCT_US
4025235 VANDF
009953 NDDF

Pharmaceutical products:

None