ARTEMETHER

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC P01BE02
UNII C7D6T3H22J
EPA CompTox DTXSID7040651

Structure

InChI Key SXYIRMFQILZOAM-HVNFFKDJSA-N
Smiles CO[C@H]1O[C@@H]2O[C@@]3(C)CC[C@H]4[C@H](C)CC[C@@H]([C@H]1C)[C@@]24OO3
InChI
InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H26O5
Molecular Weight 298.38
AlogP 2.84
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 46.15
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Ferriprotoporphyrin IX inhibitor INHIBITOR DailyMed Wikipedia Wikipedia
Assay Description Organism Bioactivity Reference
Evaluated for the neurotoxicity against NB2a Neuroblastoma cells. Mus musculus 351.0 nM
In vitro anti-protozoal activity against Plasmodium falciparum Ghana Plasmodium falciparum 25.0 nM
In vitro antimalarial activity against Plasmodium falciparum FCR3 Plasmodium falciparum 14.0 nM
In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum HB3 Plasmodium falciparum 3.42 nM
In vitro antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 Plasmodium falciparum 4.55 nM
In vitro antimalarial activity for Plasmodium falciparum W-2 Plasmodium falciparum 5.4 nM
In vitro inhibitory activity against the chloroquine-resistant Plasmodium falciparum W2 Indochina Plasmodium falciparum 5.4 nM
In vitro inhibitory concentration against chloroquine-sensitive Plasmodium falciparum HB3 Plasmodium falciparum 9.2 nM
In vitro inhibitory concentration against chloroquine-resistant Plasmodium falciparum K1 Plasmodium falciparum 6.5 nM
In vitro inhibitory concentration against chloroquine-resistant Plasmodium falciparum K1 Plasmodium falciparum 7.94 nM
In vitro inhibitory concentration against chloroquine-resistant Plasmodium falciparum FcB1 Plasmodium falciparum 3.5 nM
Inhibitory concentration against Plasmodium falciparum D6 (Sierra Leone) Plasmodium falciparum 4.49 nM
Inhibitory concentration against Plasmodium falciparum W2 Indochina Plasmodium falciparum 3.34 nM
Intrinsic equimolar activity against Plasmodium falciparum D6 (Sierra Leone) relative to QHS Plasmodium falciparum 2.34 nM
Intrinsic equimolar activity against Plasmodium falciparum W2 Indochina relative to QHS Plasmodium falciparum 1.92 nM
In vitro antimalarial activity against Plasmodium falciparum D6 (Sierra Leone I) Plasmodium falciparum 0.0008689 ug.mL-1
In vitro antimalarial activity against Plasmodium falciparum W2 Indochina Plasmodium falciparum 0.0003008 ug.mL-1
In vitro inhibition of chloroquine-resistant Plasmodium falciparum K1 Plasmodium falciparum 0.00074 ug.mL-1
In vitro inhibition of chloroquine-sensitive Plasmodium falciparum NF54 Plasmodium falciparum 0.0012 ug.mL-1
Antimalarial activity against Plasmodium falciparum K1 Plasmodium falciparum 0.00074 ug.mL-1
Antimalarial activity against Plasmodium falciparum NF54 Plasmodium falciparum 0.0012 ug.mL-1
Antimalarial activity against Plasmodium falciparum 3D7 Plasmodium falciparum 3.2 nM
Antiparasitic activity against chloroquine-sensitive Plasmodium falciparum by [3H]hypoxanthine incorporation Plasmodium falciparum 2.8 nM
Antimalarial activity against Plasmodium falciparum 3D7 Plasmodium falciparum 3.2 nM
Antimalarial activity against Plasmodium falciparum 3D7 infected human erythrocytes after 24 hrs by [3H]hypoxanthine uptake Plasmodium falciparum 3D7 1.26 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 by [3H]hypoxanthine uptake Plasmodium falciparum 3.53 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 by [3H]hypoxanthine uptake Plasmodium falciparum 3D7 2.11 nM
Antifungal activity against Cryptococcus neoformans ATCC 90113 by modified NCCLS method Cryptococcus neoformans 0.6 ug.mL-1
Antimalarial activity after 48 hrs against chloroquine-sensitive Plasmodium falciparum 3D7 by [3H]hypoxanthine uptake Plasmodium falciparum 3D7 3.53 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 infected type A+ human erythrocytes after 24 hrs by [G-3H]hypoxanthine uptake Plasmodium falciparum 3D7 3.45 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 infected type A+ human erythrocytes after 24 hrs by [G-3H]hypoxanthine uptake Plasmodium falciparum K1 1.26 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 assessed as growth inhibition by [3H]hypoxanthine incorporation assay Plasmodium falciparum 4.2 nM
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 (Thailand) assessed as growth inhibition by [3H]hypoxanthine incorporation assay Plasmodium falciparum K1 3.4 nM
Antimalarial activity against Plasmodium berghei ANKA infected Swiss CD1 mice (Mus musculus) assessed as reduction of parasitemia at 30 mg/kg, perorally administered after 3 hrs of infection for 3 days measured on day 4 relative to control Plasmodium berghei 100.0 %
Antiparasitic activity against Toxoplasma gondii 2F infected in HFF cells assessed as beta galactosidase activity after 5 days Toxoplasma gondii 310.0 nM
Antimalarial activity against Plasmodium falciparum 3D7 assessed as parasite growth inhibition at 8 nM after 6 hrs by [3H]hypoxanthin incorporation assay Plasmodium falciparum 90.0 %
Induction of heme alkylation of Fe(II) heme assessed as loss of heme at 10 uM in presence of 50% ACN-H2O with excess sodium dithionite under argon at 20 degC by spectrophotometry None 24.0 %
Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 Plasmodium falciparum K1 2.5 nM
Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 after 72 hrs by MSF assay Plasmodium falciparum 0.0004 ug.mL-1
Antimalarial activity against mature gametocytic stage of Plasmodium falciparum assessed as inhibition of mature gamete exflagellation at 10 uM incubated for 24 hrs prior to exflagellation induction at 21 degC measured after 20 mins by microscopic analysis relative to control Plasmodium falciparum 50.0 %
Antiplasmodial activity against Plasmodium berghei ANKA early trophozoite stage by parasite LDH assay Plasmodium berghei ANKA 3.0 nM
Antimalarial activity against chloroquine-sensitive asexual Plasmodium falciparum NF54 infected in human erythrocytes assessed as inhibition of parasite proliferation after 96 hrs by SYBR Green I fluorescence based assay Plasmodium falciparum NF54 5.77 nM
Antimalarial activity against multidrug resistant Plasmodium falciparum K1 infected in human erythrocytes assessed as inhibition of parasite proliferation after 96 hrs by SYBR Green I fluorescence based assay Plasmodium falciparum K1 7.26 nM
Antimalarial activity against multidrug resistant Plasmodium falciparum W2 infected in human erythrocytes assessed as inhibition of parasite proliferation after 96 hrs by SYBR Green I fluorescence based assay Plasmodium falciparum 4.5 nM
Antiplasmodial activity against chloroquine-sensitive asexual erythrocyte stage form Plasmodium falciparum NF54 measured after 48 hrs by pLDH assay Plasmodium falciparum NF54 3.8 nM
Antiplasmodial activity against chloroquine-resistant asexual erythrocyte stage form Plasmodium falciparum Dd2 measured after 48 hrs by pLDH assay Plasmodium falciparum Dd2 2.3 nM
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K1 infected in human O-positive erythrocytes assessed as decrease in parasitaemia after 72 hrs by NBT dye-based spectrophotometric method Plasmodium falciparum K1 20.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 8.78 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 13.66 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 9.17 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 12.03 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 30.63 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 19.11 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 6.04 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 8.42 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.43 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 23.59 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.09 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.34 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.09 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.34 %
Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum NF54 by LDH assay Plasmodium falciparum 3.8 nM
Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum Dd2 by LDH assay Plasmodium falciparum 2.3 nM
Antifungal activity against Candida albicans SC5314 assessed as inhibition of fungal growth by measuring decrease in OD600 at 100 microM measured after 24 hrs by absorbance based analysis Candida albicans 10.1 %
Antifungal activity against Saccharomyces cerevisiae BY4742 assessed as inhibition of fungal growth at 100 uM measured after 24 hrs by absorbance based analysis relative to vehicle-treated control Saccharomyces cerevisiae 45.8 %
Potentiation of fluconazole-induced antifungal activity against Saccharomyces cerevisiae BY4742 assessed as inhibition of fungal growth at 100 uM measured after 24 hrs in presence of fluconazole by absorbance based analysis relative to fluconazole-treated control Saccharomyces cerevisiae 68.8 %

Related Entries

Cross References

Resources Reference
ChEBI 195280
ChEMBL CHEMBL566534
DrugBank DB06697
DrugCentral 245
FDA SRS C7D6T3H22J
Human Metabolome Database HMDB0015643
Guide to Pharmacology 9955
PDB D8Z
PubChem 68911
SureChEMBL SCHEMBL1650501
ZINC ZINC000014263142
CONTENTS