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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 UTC
HMDB IDHMDB0015653
Secondary Accession Numbers
  • HMDB15653
Metabolite Identification
Common NameLumefantrine
DescriptionLumefantrine, also known as benflumetol, belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. Lumefantrine is a blood schizonticide active against erythrocytic stages of Plasmodium falciparum. Lumefantrine is a very strong basic compound (based on its pKa). 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. and may be used to treat infections caused by P. falciparum and unidentified Plasmodium species, including infections acquired in chloroquine-resistant areas. Lumefantrine is an antimalarial agent used to treat acute uncomplicated malaria.
Structure
Data?1582753320
Synonyms
ValueSource
(+-)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-alpha-((dibutylamino)methyl)fluorene-4-methanolChEBI
2-Dibutylamino-1-[2,7-dichloro-9-(4-chloro-benzylidene)-9H-fluoren-4-yl]-ethanolChEBI
2-Dibutylamino-1-{2,7-dichloro-9-[1-(4-chloro-phenyl)-meth-(Z)-ylidene]-9H-fluoren-4-yl}-ethanolChEBI
BenflumetolChEBI
DL-BenflumelolChEBI
(+-)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-a-((dibutylamino)methyl)fluorene-4-methanolGenerator
(+-)-2,7-Dichloro-9-((Z)-p-chlorobenzylidene)-α-((dibutylamino)methyl)fluorene-4-methanolGenerator
Benflumetol, (+)-isomerHMDB
Benflumetol, (+-)-isomerHMDB
Benflumetol, (-)-isomerHMDB
Chemical FormulaC30H32Cl3NO
Average Molecular Weight528.94
Monoisotopic Molecular Weight527.154947772
IUPAC Name2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol
Traditional Namelumefantrine
CAS Registry Number82186-77-4
SMILES
CCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C1
InChI Identifier
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-
InChI KeyDYLGFOYVTXJFJP-MYYYXRDXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassFluorenes
Sub ClassNot Available
Direct ParentFluorenes
Alternative Parents
Substituents
  • Fluorene
  • Chlorobenzene
  • Aralkylamine
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Secondary alcohol
  • Tertiary amine
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.1e-05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity160.81 m³·mol⁻¹ChemAxon
Polarizability60.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+226.65330932474
DeepCCS[M-H]-224.25830932474
DeepCCS[M-2H]-257.14130932474
DeepCCS[M+Na]+232.56630932474
AllCCS[M+H]+223.832859911
AllCCS[M+H-H2O]+222.232859911
AllCCS[M+NH4]+225.332859911
AllCCS[M+Na]+225.732859911
AllCCS[M-H]-215.332859911
AllCCS[M+Na-2H]-216.332859911
AllCCS[M+HCOO]-217.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LumefantrineCCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C15379.9Standard polar33892256
LumefantrineCCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C13739.5Standard non polar33892256
LumefantrineCCCCN(CCCC)CC(O)C1=C2C(=CC(Cl)=C1)\C(=C/C1=CC=C(Cl)C=C1)C1=C2C=CC(Cl)=C13889.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lumefantrine,1TMS,isomer #1CCCCN(CCCC)CC(O[Si](C)(C)C)C1=CC(Cl)=CC2=C1C1=CC=C(Cl)C=C1/C2=C/C1=CC=C(Cl)C=C13840.0Semi standard non polar33892256
Lumefantrine,1TBDMS,isomer #1CCCCN(CCCC)CC(O[Si](C)(C)C(C)(C)C)C1=CC(Cl)=CC2=C1C1=CC=C(Cl)C=C1/C2=C/C1=CC=C(Cl)C=C14035.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lumefantrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-5908110000-30364837a4164a8491be2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lumefantrine GC-MS (1 TMS) - 70eV, Positivesplash10-0bt9-5300960000-f57d30fd0683000ba1df2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lumefantrine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lumefantrine GC-MS ("Lumefantrine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 10V, Positive-QTOFsplash10-03fr-0000190000-2026e5ba94f08f73450d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 20V, Positive-QTOFsplash10-03e9-3309470000-dd7cd2616b9942c35f6d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 40V, Positive-QTOFsplash10-0a4i-9214100000-82786f2daa0ffb34e5932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 10V, Negative-QTOFsplash10-004i-0000090000-75a6769f5d87d37f65312016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 20V, Negative-QTOFsplash10-004i-0602290000-621f19a6f82ad39466a42016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 40V, Negative-QTOFsplash10-0ul1-5209000000-229aedab58de48c7d7fa2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 10V, Positive-QTOFsplash10-004i-0000090000-f3e5f6566ad7bc0d69312021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 20V, Positive-QTOFsplash10-004i-3100290000-5859b739d14324e74b772021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 40V, Positive-QTOFsplash10-01q1-9301010000-442ed46841c5606394762021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 10V, Negative-QTOFsplash10-004i-0000090000-6f1797933f6c478c462e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 20V, Negative-QTOFsplash10-004i-0205690000-b150da224a2d334104c32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lumefantrine 40V, Negative-QTOFsplash10-0f89-7509400000-ffd74bf582f10032d9042021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06708 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06708 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06708
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4941944
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLumefantrine
METLIN IDNot Available
PubChem Compound6437380
PDB IDNot Available
ChEBI ID156095
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Artemether and Lumefantrine (2010). AHFS Drug Information [Electronic versionb]. Retrieved October 24, 2010.. .
  2. (). Artemether/Lumefantrine (2010). DrugPoints® System [Electronic version]. Retrieved October 24, 2010.. .
  3. (). Novartis. Coartem (artemether/lumefantrine) tablets prescribing information. East Hanover, NJ; 2010 Feb.. .

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94