Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H24O5 |
Molecular Weight | 284.3481 |
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](O)[C@@H]2C)O4
InChI
InChIKey=BJDCWCLMFKKGEE-ISOSDAIHSA-N
InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
DescriptionSources: http://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.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022268s012lbl.pdfCurator'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
Sources: http://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.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022268s012lbl.pdf
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: https://www.springboard4health.com/notebook/nutrients_artemisinin.html https://www.drlam.com/blog/artemisinin-cancer-research/19627/https://www.ncbi.nlm.nih.gov/pubmed/12499215http://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
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21989013Kexue Tongbao (Chinese Edition) (1979), 24, (14), 667-9.
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. |
|||
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. |
|||
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 Date1984 |
|||
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 Date2009 |
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 |
---|---|---|
Pharmacokinetics of artesunate after single oral administration to rats. | 2001 |
|
Demonstrating the validity of natural products as anti-infective drugs. | 2001 |
|
Antiparasitic properties of medicinal plants and other naturally occurring products. | 2001 |
|
Artemisinin and derivatives: the future for malaria treatment? | 2001 Dec |
|
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 |
|
Authentication of artemether, artesunate and dihydroartemisinin antimalarial tablets using a simple colorimetric method. | 2001 Dec |
|
A comparison of oral artesunate and artemether antimalarial bioactivities in acute falciparum malaria. | 2001 Dec |
|
The potential of artemether for the control of schistosomiasis. | 2001 Dec |
|
C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene. | 2001 Dec 20 |
|
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 |
|
Selective toxicity of dihydroartemisinin and holotransferrin toward human breast cancer cells. | 2001 Nov 21 |
|
'To search and studdy out the secrett of tropical diseases by way of experiment'. | 2001 Nov-Dec |
|
[Prevention and treatment of malaria: in vitro evaluation of new compounds]. | 2001 Sep |
|
Combination therapy for malaria: the way forward? | 2002 |
|
Effect of antimalarial drugs on plasmodia cell-free protein synthesis. | 2002 Apr |
|
Epidemiology of drug-resistant malaria. | 2002 Apr |
|
Efficacy of artesunate and praziquantel in Schistosoma haematobium infected schoolchildren. | 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 |
|
Anhydrodihydroartemisinin and its 10-trifluoromethyl analogue: access to novel d-ring-contracted artemisinin trifluoromethyl ketones. | 2002 Feb 22 |
|
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 |
|
New chemical and biological aspects of artemisinin-derived trioxane dimers. | 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 |
|
In vitro antiprotozoal effects of artemisinin on Neospora caninum. | 2002 Jan 3 |
|
Simple and rapid physico-chemical methods to examine action of antimalarial drugs with hemin: its application to Artemisia annua constituents. | 2002 Jan 4 |
|
Assessment of the neurotoxicity of oral dihydroartemisinin in mice. | 2002 Jan-Feb |
|
Development and validation of a high-performance liquid chromatography-mass spectrometry assay for the determination of artemether and its metabolite dihydroartemisinin in human plasma. | 2002 Jul 15 |
|
Antiulcerogenic activity of some sesquiterpene lactones isolated from Artemisia annua. | 2002 Jun |
|
Management of malaria in Thailand. | 2002 Mar |
|
Heme-artemisinin adducts are crucial mediators of the ability of artemisinin to inhibit heme polymerization. | 2002 Mar |
|
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 |
|
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement? | 2002 Mar 25 |
|
First synthesis of 10 alpha-(trifluoromethyl)deoxoartemisinin. | 2002 Mar 7 |
|
Activity of drugs from traditional Chinese medicine toward sensitive and MDR1- or MRP1-overexpressing multidrug-resistant human CCRF-CEM leukemia cells. | 2002 Mar-Apr |
|
Recent investigations of artemether, a novel agent for the prevention of schistosomiasis japonica, mansoni and haematobia. | 2002 May |
|
How might qinghaosu (artemisinin) and related compounds kill the intraerythrocytic malaria parasite? A chemist's view. | 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 |
Sample Use Guides
Adults and children: 25 mg/kg on the first day followed by 12.5 mg/kg on the second and third days in combination with mefloquine (15 mg/kg) in a single dose on the second day. In some areas, a higher dose (25 mg/kg) of mefloquine may be required for a cure to be obtained.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1440803
Artemisinine was active against 3 chloroquine-resistant strains of Plasmodium falciparum, strains K1 and T996 from Thailand and LS21 from India, with complete growth inhibition at 10(-7) M.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
P01BF05
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
||
|
NCI_THESAURUS |
C271
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
||
|
WHO-ATC |
P01BE05
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
||
|
FDA ORPHAN DRUG |
234006
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
||
|
EU-Orphan Drug |
EU/3/07/468
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
EURARTESIM (AUTHORIZED: MALARIA)
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB30709
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
100000115442
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
C039060
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
DB11638
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
DTXSID501021652
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
6A9O50735X
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
71939-50-9
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
3000518
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
ARTENIMOL
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | Description: Colourless needles or a white or almost white, crystalline powder. Solubility: Practically insoluble in water; slightly soluble in acetonitrile R, ethanol (~750 g/l) TS and dichloromethane R. Category: Antimalarial. Storage: Artenimol should be kept in a well-closed container, protected from light. Definition: Artenimol contains not less than 97.0% and not more than the equivalent of 102.0% of C15H24O5 using Assay method A, and not less than 98.0% and not more than the equivalent of 102.0% of C15H24O5 using Assay method B, both calculated with reference to the dried substance. | ||
|
1200520
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
7777
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
DIHYDROARTEMISININ
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
m2077
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | Merck Index | ||
|
4194
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
C87432
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY | |||
|
CHEMBL252518
Created by
admin on Sat Dec 16 16:30:19 GMT 2023 , Edited by admin on Sat Dec 16 16:30:19 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)
PARENT (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)