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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H26O5
Molecular Weight 298.3746
Optical Activity ( + )
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARTEMETHER

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

InChIKey=SXYIRMFQILZOAM-HVNFFKDJSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H26O5
Molecular Weight 298.3746
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Artemether is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with lumefantrine for improved efficacy against malaria. Artemether is rapidly metabolized into an active metabolite dihydroartemisinin (DHA). The antimalarial activity of artemether and DHA has been attributed to endoperoxide moiety. Artemethe involves an interaction with ferriprotoporphyrin IX (“heme”), or ferrous ions, in the acidic parasite food vacuole, which results in the generation of cytotoxic radical species. The generally accepted mechanism of action of peroxide antimalarials involves interaction of the peroxide-containing drug with heme, a hemoglobin degradation byproduct, derived from proteolysis of hemoglobin. This interaction is believed to result in the formation of a range of potentially toxic oxygen and carbon-centered radicals. Other mechanisms of action for artemether include their ability to reduce fever by production of signals to hypothalamus thermoregulatory center. Now, recent research has shown the presence of a new, previously unknown cyclooxygenase enzyme COX-3, found in the brain and spinal cord, which is selectively inhibited by artemether, and is distinct from the two already known cyclooxygenase enzymes COX-1 and COX-2. It is now believed that this selective inhibition of the enzyme COX-3 in the brain and spinal cord explains the ability of artemether in relieving pain and reducing fever which is produced by malaria. The most common adverse reactions in adults (>30%) are headache, anorexia, dizziness, asthenia, arthralgia and myalgia.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COARTEM
PubMed

PubMed

TitleDatePubMed
Antimalarial drugs: QT prolongation and cardiac arrhythmias.
2005 May
In vitro inhibition of Toxoplasma gondii by four new derivatives of artemisinin.
2006 Dec
Artemisinin-derived dimers have greatly improved anti-cytomegalovirus activity compared to artemisinin monomers.
2010 Apr 28
Thiazole, oxadiazole, and carboxamide derivatives of artemisinin are highly selective and potent inhibitors of Toxoplasma gondii.
2010 May 13
A SYBR Green 1-based in vitro test of susceptibility of Ghanaian Plasmodium falciparum clinical isolates to a panel of anti-malarial drugs.
2013 Dec 17
Antimalarial activity of 10-alkyl/aryl esters and -aminoethylethers of artemisinin.
2013 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Tablets should be administered over 3 days for a total of 6 doses: an initial dose, second dose after 8 hours and then twice-daily (morning and evening) for the following 2 days. The adult dosage for patients with bodyweight of 35 kg and above is 4 tablets per dose for a total of 6 doses. Tablets are scored and contain 20 mg rtemether and 120 mg lumefantrine.
Route of Administration: Oral
In Vitro Use Guide
IC90 is higher in Plasmodium falciparum strain T-996 compared with strain LS-21: for artemether, 34.45 and 7.11 nmol/L (10.28 and 2.12 ng/ml of erythrocyte-medium mixture [EMM]).
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:27:04 UTC 2019
Edited
by admin
on Mon Oct 21 20:27:04 UTC 2019
Record UNII
C7D6T3H22J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARTEMETHER
DASH   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RC   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
DIHYDROARTEMISININ IMPURITY G [USP-RC]
Common Name English
.BETA.-ARTEMETHER
Common Name English
NSC-665970
Code English
GVITHER
Common Name English
(+)-ARTEMETHER
Common Name English
ARTEMETHER [JAN]
Common Name English
COARTEM COMPONENT ARTEMETHER
Brand Name English
SM 224
Code English
ARTEMETHER [MART.]
Common Name English
(3R,5AS,6R,8AS,9R,10S,12R,12AR)-10-METHOXY-3,6,9-TRIMETHYLDECAHYDRO-3,12-EPOXYPYRANO(4,3-J)-1,2-BENZODIOXEPINE
Common Name English
ARTEMETHERUM [WHO-IP LATIN]
Common Name English
MALARTEM
Common Name English
(3R,5AS,6R,8AS,9R,10S,12R,12AR)-DECAHYDRO-10-METHOXY-3,6,9-TRIMETHYL-3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN
Systematic Name English
ARTEMETHER [HSDB]
Common Name English
ARTESAPH
Common Name English
ARTEMETHER [WHO-DD]
Common Name English
LARITHER
Common Name English
ARTEMETHER [USAN]
Common Name English
FALCIDOL
Common Name English
PALUTHER
Common Name English
3,12-EPOXY-12H-PYRANO(4,3-J)-1,2-BENZODIOXEPIN, DECAHYDRO-10-METHOXY-3,6,9-TRIMETHYL-, (3R,5AS,6R,8AS,9R,10S,12R,12AR)-
Common Name English
ARTEMETHER [USP-RS]
Common Name English
ARTEMETHER [INN]
Common Name English
.BETA.-DIHYDROARTEMISININ METHYL ETHER
Common Name English
ARTEMETHER [MI]
Common Name English
ARTEMETHER [VANDF]
Common Name English
ARTEMETHER [WHO-IP]
Common Name English
ARTEMETHER COMPONENT OF COARTEM
Brand Name English
ARTEMETHER [USP-RC]
Common Name English
ARTEMETHER [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-ATC P01BF01
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
NDF-RT N0000175482
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
FDA ORPHAN DRUG 245507
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
WHO-ATC P01BE02
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (ART/LUM)
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
EU-Orphan Drug EU/3/09/702
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
NCI_THESAURUS C271
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
Code System Code Type Description
WIKIPEDIA
ARTEMETHER
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
PUBCHEM
68911
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
ChEMBL
CHEMBL566534
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
MESH
C032942
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
RXCUI
18343
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY RxNorm
EVMPD
SUB05574MIG
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
MERCK INDEX
M2075
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C73001
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
EPA CompTox
71963-77-4
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
DRUG BANK
DB06697
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
HSDB
71963-77-4
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ARTEMETHER
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY Description: White crystals or a white, crystalline powder. Solubility: Practically insoluble in water; very soluble in dichloromethane R and acetone R; freely soluble in ethyl acetate R and dehydrated ethanol R. Category: Antimalarial drug. Storage: Artemether should be kept in a tightly closed container and protected from light. Labelling: The designation Artemether for parenteral use indicates that the substance complies with the additional requirements and may be used for parenteral administration. Additional information: The parenteral form is normally intended for intramuscular administration. Requirement: Artemether contains not less than 97.0% and not more than the equivalent of 102.0% of C16H26O5 using ?Assay?, method A, andnot less than 98.0% and not more than the equivalent of 102.0% of C16H26O5 using ?Assay?, method B, both calculated with reference to the dried substance.
INN
6458
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
CAS
71963-77-4
Created by admin on Mon Oct 21 20:27:04 UTC 2019 , Edited by admin on Mon Oct 21 20:27:04 UTC 2019
PRIMARY
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