D8Z

Artemether

Created: 2018-01-10
Last modified:  2019-01-16

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Chemical Details

Formal Charge0
Atom Count47
Chiral Atom Count8
Bond Count50
Aromatic Bond Count0
2D diagram of D8Z
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Chemical Component Summary

NameArtemether
FormulaC16 H26 O5
Molecular Weight298.375
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385CO[CH]1O[CH]2O[C]3(C)CC[CH]4[CH](C)CC[CH]([CH]1C)[C]24OO3
SMILESOpenEye OEToolkits2.0.6CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C
Canonical SMILESCACTVS3.385 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
Canonical SMILESOpenEye OEToolkits2.0.6 C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC)C
InChIInChI1.03 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
InChIKeyInChI1.03 SXYIRMFQILZOAM-HVNFFKDJSA-N

Drug Info: DrugBank

DrugBank IDDB06697 
NameArtemether
Groups approved
DescriptionArtemether is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with lumefantrine for improved efficacy. This combination therapy exerts its effects against the erythrocytic stages of <i>Plasmodium spp.</i> and may be used to treat infections caused by <i>P. falciparum</i> and unidentified <i>Plasmodium</i> species, including infections acquired in chloroquine-resistant areas.
Synonyms
  • Artemetherum
  • (1R,4S,5R,8S,9R,10S,12R,13R)-10-methoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane
  • 10-methoxy-1,5,9-trimethyl-(1R,4S,5R,8S,9R,10S,12R,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
  • β-artemether
  • methyl-dihydroartemisinine
Brand NamesCoartem
IndicationArtemether and lumefantrine combination therapy is indicated for the treatment of acute uncomplicated malaria caused by <i>Plasmodium falciparum</i>, including malaria acquired in chloroquine-resistant areas. May also be used to treat uncomplicated malaria when the <i>Plasmodium</i> species has not been identified. Indicated for use in adults and children greater than 5 kg.
Categories
  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiparasitic Products, Insecticides and Repellents
  • Antiprotozoals
ATC-Code
  • P01BF01
  • P01BE02
CAS number71963-77-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inducer
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknownsubstrate,inducer
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknownsubstrate,inducer
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 68911
ChEMBL CHEMBL566534
ChEBI CHEBI:195280
CCDC/CSD COTYEP