NAV

Lumefantrine

Identification

Summary

Lumefantrine is an antimalarial agent used in combination with artemether for the treatment of acute uncomplicated malaria caused by Plasmodium falciparum.

Brand Names
Coartem
Generic Name
Lumefantrine
DrugBank Accession Number
DB06708
Background

Lumefantrine is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with artemether for improved efficacy. This combination therapy exerts its effects against the erythrocytic stages of Plasmodium spp. and may be used to treat infections caused by P. falciparum and unidentified Plasmodium species, including infections acquired in chloroquine-resistant areas.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 528.94
Monoisotopic: 527.154947772
Chemical Formula
C30H32Cl3NO
Synonyms
  • (±)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-α-((dibutylamino)methyl)fluorene-4-methanol
  • 2-Dibutylamino-1-[2,7-dichloro-9-(4-chloro-benzylidene)-9H-fluoren-4-yl]-ethanol
  • 2-Dibutylamino-1-{2,7-dichloro-9-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-9H-fluoren-4-yl}-ethanol
  • Benflumetol
  • dl-Benflumelol
  • Lumefantrine
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Pharmacology

Indication

Lumefantrine and artemether combination therapy is indicated for the treatment of acute uncomplicated malaria caused by Plasmodium falciparum, including malaria acquired in chloroquine-resistant areas. May also be used to treat uncomplicated malaria when the Plasmodium species has not been identified. Indicated for use in adults and children greater than 5 kg.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatUncomplicated malaria caused by plasmodium falciparumCombination Product in combination with: Artemether (DB06697)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Lumefantrine is a blood schizonticide active against erythrocytic stages of Plasmodium falciparum. It is thought that administration of lumefantrine with artemether results in cooperate antimalarial clearing effects. Artemether has a rapid onset of action and is rapidly cleared from the body. It is thus thought to provide rapid symptomatic relief by reducing the number of malarial parasites. Lumefantrine has a much longer half life and is believed to clear residual parasites.

Mechanism of action

The exact mechanism by which lumefantrine exerts its antimalarial effect is unknown. However, available data suggest that lumefantrine inhibits the formation of β-hematin by forming a complex with hemin and inhibits nucleic acid and protein synthesis.

Absorption

Food increases absorption.

Volume of distribution

Not Available

Protein binding

99.7% bound

Metabolism

Extensively metabolized in the liver primarily by cytochrome P450 3A4. The major metabolite found in plasma is desbutyl-lumefantrine.

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Route of elimination

Not Available

Half-life

~ 4.5 days

Clearance

Not Available

Adverse Effects
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Toxicity

Common side effects of combination artemether/lumefantrine therapy in adults include headache, anorexia, dizziness, and asthenia. Common side effects in children include pyrexia, cough, vomiting, anorexia, and headache. Possible serious adverse effects include QT prolongation, bullous eruption, urticaria, splenomegaly (9%), hepatomegaly (adults, 9%; children, 6%), hypersensitivty reaction, and angioedema.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbametapirThe serum concentration of Lumefantrine can be increased when it is combined with Abametapir.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Lumefantrine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Lumefantrine.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Lumefantrine is combined with Acetophenazine.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Lumefantrine.
Food Interactions
  • Avoid grapefruit products.
  • Take with food. Food increases absorption.

Products

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Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
CoartemLumefantrine (120 mg/1) + Artemether (20 mg/1)TabletOralCentral Texas Community Health Centers2009-04-07Not applicableUS flag
CoartemLumefantrine (120 mg/1) + Artemether (20 mg/1)TabletOralNovartis Pharmaceuticals Corporation2009-04-07Not applicableUS flag
CoartemLumefantrine (120 mg/1) + Artemether (20 mg/1)TabletOralDepartment Of State Health Services, Pharmacy Branch2009-04-072018-02-28US flag
COARTEM 20/120Lumefantrine (120 mg) + Artemether (20 mg)Tablet, orally disintegratingOralบริษัท โนวาร์ตีส (ประเทศไทย) จำกัด2017-10-28Not applicableThailand flag
COARTEM DISPERSIBLE (20/120 MG TABLETS)Lumefantrine (120 MG) + Artemether (20 MG)Tablet, solubleOralบริษัท โนวาร์ตีส (ประเทศไทย) จำกัด2017-10-28Not applicableThailand flag

Categories

ATC Codes
P01BF01 — Artemether and lumefantrine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fluorenes. These are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Fluorenes
Sub Class
Not Available
Direct Parent
Fluorenes
Alternative Parents
Chlorobenzenes / Aralkylamines / Aryl chlorides / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homopolycyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Fluorene
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
tertiary amine, secondary alcohol, monochlorobenzenes, fluorenes (CHEBI:156095)
Affected organisms
  • Plasmodium

Chemical Identifiers

UNII
F38R0JR742
CAS number
82186-77-4
InChI Key
DYLGFOYVTXJFJP-MYYYXRDXSA-N
InChI
InChI=1S/C30H32Cl3NO/c1-3-5-13-34(14-6-4-2)19-29(35)28-18-23(33)17-27-25(15-20-7-9-21(31)10-8-20)26-16-22(32)11-12-24(26)30(27)28/h7-12,15-18,29,35H,3-6,13-14,19H2,1-2H3/b25-15-
IUPAC Name
2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol
SMILES
CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1

References

General References
Not Available
Human Metabolome Database
HMDB0015653
KEGG Drug
D03821
PubChem Compound
6437380
PubChem Substance
99443260
ChemSpider
4941944
BindingDB
50238630
RxNav
847728
ChEBI
156095
ChEMBL
CHEMBL38827
PharmGKB
PA165111722
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lumefantrine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentUncomplicated Malaria caused by Plasmodium falciparum1
4CompletedNot AvailableMalaria1
4CompletedBasic ScienceDrug Drug Interaction (DDI)1
4CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
4CompletedBasic SciencePlasmodium Falciparum Clinical Episode / Plasmodium Falciparum Infection / Plasmodium Vivax Clinical Episode / Plasmodium Vivax Infection1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
Tablet, orally disintegratingOral
Tablet, solubleOral
Tablet, film coatedOral
TabletOral20 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.09e-05 mg/mLALOGPS
logP8.34ALOGPS
logP9.19Chemaxon
logS-7.2ALOGPS
pKa (Strongest Acidic)14.1Chemaxon
pKa (Strongest Basic)9.78Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area23.47 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity160.81 m3·mol-1Chemaxon
Polarizability60.69 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9363
Caco-2 permeable+0.6319
P-glycoprotein substrateSubstrate0.8389
P-glycoprotein inhibitor IInhibitor0.6854
P-glycoprotein inhibitor IINon-inhibitor0.5475
Renal organic cation transporterInhibitor0.5792
CYP450 2C9 substrateNon-substrate0.7971
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.7076
CYP450 1A2 substrateInhibitor0.6872
CYP450 2C9 inhibitorNon-inhibitor0.7112
CYP450 2D6 inhibitorInhibitor0.7727
CYP450 2C19 inhibitorNon-inhibitor0.6525
CYP450 3A4 inhibitorNon-inhibitor0.6983
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7168
Ames testNon AMES toxic0.6424
CarcinogenicityNon-carcinogens0.7629
BiodegradationNot ready biodegradable0.9924
Rat acute toxicity2.4077 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7654
hERG inhibition (predictor II)Inhibitor0.776
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000l-5908110000-30364837a4164a8491be
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0100290000-5e9edc410e52f9ba0d8b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0200090000-2089a0cc55acd9123904
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0059-7602890000-8aeb7bc5641f33034f58
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-9700020000-c538369b95430a2b5140
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002k-7309310000-a0c0eab9876e8c118bb1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100400000-35bde6e2c15f6a467f51
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-223.8673454
predicted
DarkChem Lite v0.1.0
[M-H]-222.5257
predicted
DeepCCS 1.0 (2019)
[M+H]+223.8309454
predicted
DarkChem Lite v0.1.0
[M+H]+224.92125
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.0939454
predicted
DarkChem Lite v0.1.0
[M+Na]+230.83379
predicted
DeepCCS 1.0 (2019)

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. FDA Approved Drug Products: COARTEM (artemether and lumefantrine) tablets, for oral use [Link]
Details2. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Lumefantrine inhibits CYP2D6 in vitro.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. FDA Approved Drug Products: COARTEM (artemether and lumefantrine) tablets, for oral use [Link]

Drug created at May 16, 2010 01:04 / Updated at January 24, 2021 06:02