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
Molecular Formula | C15H24O5 |
Molecular Weight | 284.3481 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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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 Date1984 |
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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 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 |
---|---|---|
Gas concentration effects on secondary metabolite production by plant cell cultures. | 2001 |
|
Systematic reviews of complementary therapies - an annotated bibliography. Part 2: herbal medicine. | 2001 |
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Severe falciparum malaria in five soldiers from East Timor: a case series and literature review. | 2001 Aug |
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Artemisinin and derivatives: the future for malaria treatment? | 2001 Dec |
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Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action. | 2001 Dec |
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Redox reaction of artemisinin with ferrous and ferric ions in aqueous buffer. | 2001 Dec |
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Artemisinin antimalarials in pregnancy: a prospective treatment study of 539 episodes of multidrug-resistant Plasmodium falciparum. | 2001 Dec 15 |
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Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. | 2001 Jan |
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Antifungal activity of Artemisia annua endophyte cultures against phytopathogenic fungi. | 2001 Jul 12 |
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Rational use of drugs against Plasmodium falciparum. | 2001 Jul-Aug |
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In vitro evidence for auto-induction of artemisinin metabolism in the rat. | 2001 Jul-Sep |
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Drug resistant falciparum malaria: clinical consequences and strategies for prevention. | 2001 Jun |
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Molecular cloning and characterization of peroxiredoxin from Toxoplasma gondii. | 2001 Jun |
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Radical mechanism of action of the artemisinin-type compounds. | 2001 Jun |
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Total synthesis of (+)-arteanniun M using the tandem oxy-Cope/ene reaction. | 2001 Jun 14 |
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Possible modes of action of the artemisinin-type compounds. | 2001 Mar |
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Artemisinin and its derivatives: an important new class of antimalarial agents. | 2001 May-Jun |
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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 |
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In vitro susceptibility of Plasmodium falciparum isolates from Myanmar to antimalarial drugs. | 2001 Nov |
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In vitro beta-hematin formation assays with plasma of mice infected with Plasmodium yoelii and other parasite preparations: comparative inhibition with quinoline and endoperoxide antimalarials. | 2001 Oct 26 |
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Antimalarial activity of azithromycin, artemisinin and dihydroartemisinin in fresh isolates of Plasmodium falciparum in Thailand. | 2001 Sep 1 |
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Fourier transform infrared investigation of non-heme Fe(III) and Fe(II) decomposition of artemisinin and of a simplified trioxane alcohol. | 2001 Sep 13 |
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Deoxyartemisinin derivatives from photooxygenation of anhydrodeoxydihydroartemisinin and their cytotoxic evaluation. | 2002 Feb |
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Mechanism-based design of parasite-targeted artemisinin derivatives: synthesis and antimalarial activity of new diamine containing analogues. | 2002 Feb 28 |
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Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model. | 2002 Feb 8 |
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Transmission electron microscopic observations on ultrastructural damage in juvenile Schistosoma mansoni caused by artemether. | 2002 Jan |
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In vitro antiprotozoal effects of artemisinin on Neospora caninum. | 2002 Jan 3 |
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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 |
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Antiulcerogenic activity of some sesquiterpene lactones isolated from Artemisia annua. | 2002 Jun |
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Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement? | 2002 Mar 25 |
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Transferrin overcomes drug resistance to artemisinin in human small-cell lung carcinoma cells. | 2002 May 28 |
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Characterization of noncovalent complexes of antimalarial agents of the artemisinin-type and FE(III)-heme by electrospray mass spectrometry and collisional activation tandem mass spectrometry. | 2004 Aug |
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A histidine-rich protein 2-based malaria drug sensitivity assay for field use. | 2004 Dec |
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Clinical pharmacokinetics of the diastereomers of arteether in healthy volunteers. | 2005 |
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Drug-resistant malaria in Bangui, Central African Republic: an in vitro assessment. | 2005 Aug |
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Synthesis and immunosuppressive activity of new artemisinin derivatives. 1. [12(beta or alpha)-Dihydroartemisininoxy]phen(ox)yl aliphatic acids and esters. | 2005 Jul 14 |
|
Toxicokinetics and hydrolysis of artelinate and artesunate in malaria-infected rats. | 2005 Jul-Aug |
|
Life-saving rectal artesunate for complicated malaria in children. | 2005 May |
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In vitro interactions of Aspilia africana (Pers.) C.D. Adams, a traditional antimalarial medicinal plant, with artemisinin against Plasmodium falciparum. | 2005 Nov 14 |
|
Synergistic cytotoxicity of artemisinin and sodium butyrate on human cancer cells. | 2005 Nov-Dec |
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An open randomized clinical trial of Artekin vs artesunate-mefloquine in the treatment of acute uncomplicated falciparum malaria. | 2005 Sep |
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Association of failures of seven-day courses of artesunate in a non-immune population in Bangui, Central African Republic with decreased sensitivity of Plasmodium falciparum. | 2005 Sep |
|
From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements. | 2006 |
|
Dihydroartemisinin enhances radiosensitivity of human glioma cells in vitro. | 2006 Feb |
|
[Synthesis and immunosuppressive activity of new artemisinin derivatives containing polyethylene glycol group]. | 2006 Jan |
|
Manslaughter by fake artesunate in Asia--will Africa be next? | 2006 Jun |
|
Re-evaluation of how artemisinins work in light of emerging evidence of in vitro resistance. | 2006 May |
|
Pharmacokinetics of piperaquine after repeated oral administration of the antimalarial combination CV8 in 12 healthy male subjects. | 2006 May |
|
Pharmacokinetics of dihydroartemisinin following oral artesunate treatment of pregnant women with acute uncomplicated falciparum malaria. | 2006 May |
|
The reaction of artemisinins with hemoglobin: a unified picture. | 2006 May 1 |
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.
Substance Class |
Chemical
Created
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on
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Sat Dec 16 16:30:17 GMT 2023
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Record UNII |
6A9O50735X
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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 |
P01BF05
Created by
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NCI_THESAURUS |
C271
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WHO-ATC |
P01BE05
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FDA ORPHAN DRUG |
234006
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EU-Orphan Drug |
EU/3/07/468
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EMA ASSESSMENT REPORTS |
EURARTESIM (AUTHORIZED: MALARIA)
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SUB30709
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100000115442
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C039060
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DB11638
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DTXSID501021652
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6A9O50735X
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71939-50-9
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3000518
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ARTENIMOL
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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. | ||
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1200520
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7777
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DIHYDROARTEMISININ
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m2077
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PRIMARY | Merck Index | ||
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4194
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C87432
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CHEMBL252518
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PRIMARY |
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