Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H26O5 |
Molecular Weight | 298.3753 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]1([H])CC[C@@]2([H])[C@@]([H])(C)[C@@]([H])(OC)O[C@@]3([H])[C@]42[C@@]1([H])CC[C@](C)(O3)OO4
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
Molecular Formula | C16H26O5 |
Molecular Weight | 298.3753 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment:: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB06697
http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7866ec19-dfac-47d4-a53f-511a12643cbf
Curator's Comment:: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB06697
http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7866ec19-dfac-47d4-a53f-511a12643cbf
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/12499215
Curator's Comment:: Meningeal inflammation increases artemether concentrations in cerebrospinal fluid in сhildrens treated with intramuscular artemether.
http://aac.asm.org/content/55/11/5027.full
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL613897 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | COARTEM Approved UseCoartem (artemether/lumefantrine) Tablets are indicated for treatment of acute, uncomplicated malaria infections due to Plasmodium falciparum in patients of 5 kg bodyweight and above. Coartem Tablets have been shown to be effective in geographical regions where resistance to chloroquine has been reported [see Clinical Studies (14.1) Launch Date1.23906241E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60 ng/mL |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARTEMETHER plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
146 ng × h/mL |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARTEMETHER plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.6 h |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARTEMETHER plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.6% |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
ARTEMETHER plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
80 mg 3 times / day multiple, oral Recommended Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Co-administed with:: lumefantrine, p.o(480 mg, b.i.d) Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Plasmodium falciparum malaria Sources: Page: p.3 |
Disc. AE: QT interval prolonged... AEs leading to discontinuation/dose reduction: QT interval prolonged Sources: Page: p.3 |
80 mg 3 times / day multiple, oral Recommended Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Co-administed with:: lumefantrine, p.o(480 mg, b.i.d) Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Plasmodium falciparum malaria Sources: Page: p.1 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
QT interval prolonged | Disc. AE | 80 mg 3 times / day multiple, oral Recommended Dose: 80 mg, 3 times / day Route: oral Route: multiple Dose: 80 mg, 3 times / day Co-administed with:: lumefantrine, p.o(480 mg, b.i.d) Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Plasmodium falciparum malaria Sources: Page: p.3 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 14.0 |
major | yes (co-administration study) Comment: administration of ketoconazole le to an increase in artemether (2.3-fold), dihydroartemisinin (1.5 fold), and lumefantrine (1.6-fold) exposure in healthy subjects; Page: 14.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022268s000_ClinPharmR.pdf#page=21 Page: 21.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022268s000_ClinPharmR.pdf#page=21 Page: 21.0 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022268s000_ClinPharmR.pdf#page=21 Page: 21.0 |
minor |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of growth of Toxoplasma gondii by qinghaosu and derivatives. | 1990 Oct |
|
Extraction of artemisinin and artemisinic acid: preparation of artemether and new analogues. | 1994 Jun |
|
Antifungal activity of artemisinin derivatives. | 2005 Aug |
|
Antimalarial drugs: QT prolongation and cardiac arrhythmias. | 2005 May |
|
In vitro inhibition of Toxoplasma gondii by four new derivatives of artemisinin. | 2006 Dec |
|
Two-step synthesis of achiral dispiro-1,2,4,5-tetraoxanes with outstanding antimalarial activity, low toxicity, and high-stability profiles. | 2008 Apr 10 |
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The clinical efficacy of artemether/lumefantrine (Coartem). | 2009 Oct 12 |
|
Evaluation of drug effects on Toxoplasma gondii nuclear and plastid DNA replication using real-time PCR. | 2010 Apr |
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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 |
|
Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols. | 2010 May 7 |
|
Schistosoma mansoni: N-acetylcysteine downregulates oxidative stress and enhances the antischistosomal activity of artemether in mice. | 2011 Jul |
|
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 |
|
Use of artemether-lumefantrine to treat malaria during pregnancy: what do we know and need to know? | 2013 Feb |
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Antimalarial activity of 10-alkyl/aryl esters and -aminoethylethers of artemisinin. | 2013 Feb |
|
Fetal bovine serum and human constitutive androstane receptor: evidence for activation of the SV23 splice variant by artemisinin, artemether, and arteether in a serum-free cell culture system. | 2014 Jun 1 |
Patents
Sample Use Guides
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10497987
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
Edited
Fri Jun 25 22:01:24 UTC 2021
by
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on
Fri Jun 25 22:01:24 UTC 2021
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Record UNII |
C7D6T3H22J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
P01BF01
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.1
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NDF-RT |
N0000175482
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FDA ORPHAN DRUG |
245507
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WHO-ATC |
P01BE02
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.1 (ART/LUM)
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EU-Orphan Drug |
EU/3/09/702
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NCI_THESAURUS |
C271
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Code System | Code | Type | Description | ||
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C7D6T3H22J
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ARTEMETHER
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68911
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CHEMBL566534
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C032942
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18343
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PRIMARY | RxNorm | ||
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Artemether and Lumefantrine
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SUB05574MIG
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1042780
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M2075
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C73001
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71963-77-4
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DB06697
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7456
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ARTEMETHER
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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. | ||
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6458
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245
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71963-77-4
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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METABOLITE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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