Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H26O5 |
Molecular Weight | 298.3746 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@H](C)[C@]3([H])CC[C@]4(C)OO[C@@]13[C@]([H])(O[C@H](OC)[C@@H]2C)O4
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 | 298.3746 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022268s012lbl.pdfhttp://apps.who.int/medicinedocs/en/d/Jh2922e/2.5.12.html#Jh2922e.2.5.12http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/001199/WC500118113.pdfCurator's Comment: Description was created based on several sources, including
http://nutritionaloncology.org/Artemisinin.html
http://www.druginfosys.com/drug.aspx?drugcode=1429&type=1
https://www.ncbi.nlm.nih.gov/pubmed/27006895
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022268s012lbl.pdfhttp://apps.who.int/medicinedocs/en/d/Jh2922e/2.5.12.html#Jh2922e.2.5.12http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/001199/WC500118113.pdf
Curator's Comment: Description was created based on several sources, including
http://nutritionaloncology.org/Artemisinin.html
http://www.druginfosys.com/drug.aspx?drugcode=1429&type=1
https://www.ncbi.nlm.nih.gov/pubmed/27006895
Artenimol (also known as dihydroqinghaosu, dihydroartemisinin or DHA) is the active metabolite of all artemisinin compounds (artemisinin, artesunate, artemether, etc.) and is also available as a drug used to treat malaria. The proposed mechanism of action of artemisinin involves cleavage of endoperoxide bridges by iron, producing free radicals (hypervalent iron-oxo species, epoxides, aldehydes, and dicarbonyl compounds) which damage biological macromolecules causing oxidative stress in the cells of the parasite. Malaria is caused by apicomplexans, primarily Plasmodium falciparum, which largely reside in red blood cells and itself contains iron-rich heme-groups (in the form of hemozoin). Recent mechanism research discovered that artemisinin targets a broad spectrum of proteins in the human cancer cell proteome through heme-activated radical alkylation. Dihydroartemisinin is used to treat malaria, generally as a combination drug with piperaquine. In a systematic review of randomized controlled trials, both dihydroartemisinin-piperaquine and artemether-lumefantrine are very effective at treating malaria (high-quality evidence). However, dihydroartemisinin-piperaquine cures slightly more patients than artemether-lumefantrine, and it also prevents further malaria infections for longer after treatment (high-quality evidence). Dihydroartemisinin-piperaquine and artemether-lumefantrine probably have similar side effects (moderate-quality evidence). The studies were all conducted in Africa. In studies of people living in Asia, dihydroartemisinin-piperaquine is as effective as artesunate plus mefloquine at treating malaria (moderate-quality evidence). Artesunate plus mefloquine probably causes more nausea, vomiting, dizziness, sleeplessness, and palpitations than dihydroartemisinin-piperaquine (moderate-quality evidence).
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/12499215https://www.springboard4health.com/notebook/nutrients_artemisinin.html https://www.drlam.com/blog/artemisinin-cancer-research/19627/https://www.ncbi.nlm.nih.gov/pubmed/12499215
Curator's Comment: Dihydroartemisinin might accumulate in CSF during frequent artesunate dosing.
Originator
Sources: Kexue Tongbao (Chinese Edition) (1979), 24, (14), 667-9.https://www.ncbi.nlm.nih.gov/pubmed/21989013
Curator's Comment: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2778258/
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25148516 |
5.5 nM [EC50] | ||
Target ID: CHEMBL612653 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11141088 |
|||
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18823976 |
24.0 nM [IC50] | ||
Target ID: PfATP6, Plasmodium falciparum Sources: https://www.ncbi.nlm.nih.gov/pubmed/17145800 |
79.0 nM [IC50] | ||
Target ID: CHEMBL612888 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27380994 |
|||
Target ID: CHEMBL613897 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Eurartesim Approved UseEurartesim is indicated for the treatment of uncomplicated Plasmodium falciparum malaria in adults, adolescents, children and infants 6 months and over and weighing 5 kg or more. |
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Curative | Eurartesim Approved UseEurartesim is indicated for the treatment of uncomplicated Plasmodium falciparum malaria in adults, adolescents, children and infants 6 months and over and weighing 5 kg or more. |
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Curative | Artemisinin Approved UseTreatment of uncomplicated falciparum malaria in areas where there is evidence that chloroquine, pyrimethamine/sulfadoxine, mefloquine and quinine are ineffective. It should always be administered together with mefloquine in full therapeutic dose. Launch Date4.7329919E11 |
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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 |
|
Demonstrating the validity of natural products as anti-infective drugs. | 2001 |
|
Gas concentration effects on secondary metabolite production by plant cell cultures. | 2001 |
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Dodgy malaria drugs. | 2001 Aug |
|
In vivo-in vitro model for the assessment of clinically relevant antimalarial cross-resistance. | 2001 Dec |
|
Artemisinin for treatment of uncomplicated falciparum malaria: is there a place for monotherapy? | 2001 Dec |
|
Current progress in the development and use of artemether for chemoprophylaxis of major human schistosome parasites. | 2001 Dec |
|
New trends in extraction, identification and quantification of artemisinin and its derivatives. | 2001 Dec |
|
Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. | 2001 Dec |
|
The genetics of artemisinin content in Artemisia annua L. and the breeding of high yielding cultivars. | 2001 Dec |
|
Redox reaction of artemisinin with ferrous and ferric ions in aqueous buffer. | 2001 Dec |
|
A comparison of the in vivo kinetics of Plasmodium falciparum ring-infected erythrocyte surface antigen-positive and -negative erythrocytes. | 2001 Jul 15 |
|
In vitro evidence for auto-induction of artemisinin metabolism in the rat. | 2001 Jul-Sep |
|
Drug resistant falciparum malaria: clinical consequences and strategies for prevention. | 2001 Jun |
|
Effects of matrine, artemisinin, tetrandrine on cytosolic [Ca2+]i in guinea pig ventricular myocytes. | 2001 Jun |
|
Frequency of early rising parasitemia in falciparum malaria treated with artemisinin derivatives. | 2001 Mar |
|
Effects of arteether on an auditory radial-arm maze task in rats. | 2001 May |
|
Artemisinin and its derivatives: an important new class of antimalarial agents. | 2001 May-Jun |
|
Resistance of Plasmodium falciparum to antimalarial drugs in a highly endemic area of southern Viet Nam: a study in vivo and in vitro. | 2001 May-Jun |
|
Artesunate and praziquantel for the treatment of Schistosoma haematobium infections: a double-blind, randomized, placebo-controlled study. | 2001 Nov 15 |
|
'To search and studdy out the secrett of tropical diseases by way of experiment'. | 2001 Nov-Dec |
|
Proposed reductive metabolism of artemisinin by glutathione transferases in vitro. | 2001 Oct |
|
Improved oral bioavailability of artemisinin through inclusion complexation with beta- and gamma-cyclodextrins. | 2001 Oct 4 |
|
[Prevention and treatment of malaria: in vitro evaluation of new compounds]. | 2001 Sep |
|
Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand. | 2001 Sep 1 |
|
Epidemiology of drug-resistant malaria. | 2002 Apr |
|
Clinical status and implications of antimalarial drug resistance. | 2002 Feb |
|
Deoxyartemisinin derivatives from photooxygenation of anhydrodeoxydihydroartemisinin and their cytotoxic evaluation. | 2002 Feb |
|
Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance. | 2002 Feb 10 |
|
Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues. | 2002 Feb 28 |
|
Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model. | 2002 Feb 8 |
|
Plasmodium falciparum: in vitro interactions of artemisinin with amodiaquine, pyronaridine, and chloroquine. | 2002 Jan |
|
Transmission electron microscopic observations on ultrastructural damage in juvenile Schistosoma mansoni caused by artemether. | 2002 Jan |
|
Structure-activity relationships of the antimalarial agent artemisinin. 6. The development of predictive in vitro potency models using CoMFA and HQSAR methodologies. | 2002 Jan 17 |
|
From mechanistic studies on artemisinin derivatives to new modular antimalarial drugs. | 2002 Mar |
|
Inhibition of nitric oxide-dependent activation of soluble guanylyl cyclase by the antimalarial drug, artemisinin. | 2002 Mar 1 |
|
First synthesis of 10 alpha-(trifluoromethyl)deoxoartemisinin. | 2002 Mar 7 |
|
Recent investigations of artemether, a novel agent for the prevention of schistosomiasis japonica, mansoni and haematobia. | 2002 May |
|
Central role of the spleen in malaria parasite clearance. | 2002 May 15 |
|
Transferrin overcomes drug resistance to artemisinin in human small-cell lung carcinoma cells. | 2002 May 28 |
|
Antimalarial drugs: QT prolongation and cardiac arrhythmias. | 2005 May |
|
In vitro inhibition of Toxoplasma gondii by four new derivatives of artemisinin. | 2006 Dec |
|
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 |
|
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 |
|
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 |
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
Wed Jul 05 23:09:13 UTC 2023
by
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on
Wed Jul 05 23:09:13 UTC 2023
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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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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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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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665970
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18343
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Artemether and Lumefantrine
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SUB05574MIG
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195280
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C7D6T3H22J
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M2075
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C73001
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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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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 |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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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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