| Common Name |
Lumefantrine
| Description |
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.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(+-)-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, (+)-isomerMeSH
Benflumetol, (+-)-isomerMeSH
Benflumetol, (-)-isomerMeSH
| Chemical Formlia |
C30H32Cl3NO
| Average Molecliar Weight |
528.94
| Monoisotopic Molecliar Weight |
527.154947772
| IUPAC Name |
2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol
| Traditional Name |
lumefantrine
| CAS Registry Number |
82186-77-4
| 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 Key |
DYLGFOYVTXJFJP-MYYYXRDXSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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 |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Fluorenes
| Direct Parent |
Fluorenes
| Alternative Parents |
Chlorobenzenes
Aralkylamines
Aryl chlorides
Trialkylamines
Secondary alcohols
1,2-aminoalcohols
Organopnictogen compounds
Organochlorides
Hydrocarbon derivatives
Aromatic alcohols
| 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
| Molecliar Framework |
Aromatic homopolycyclic compounds
| External Descriptors |
tertiary amine (CHEBI:156095 )
secondary alcohol (CHEBI:156095 )
monochlorobenzenes (CHEBI:156095 )
fluorenes (CHEBI:156095 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Antimalarial Agents
Antimalarials
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06708
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06708
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB06708
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
4941944
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Lumefantrine
| NuGOwiki Link |
HMDB15653
| Metagene Link |
HMDB15653
| METLIN ID |
Not Available
| PubChem Compound |
6437380
| PDB ID |
Not Available
| ChEBI ID |
156095
Product: Niflumic acid
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Artemether and Lumefantrine (2010). AHFS Drug Information [Electronic versionb]. Retrieved October 24, 2010.. .
- (). Artemether/Lumefantrine (2010). DrugPoints® System [Electronic version]. Retrieved October 24, 2010.. .
- (). 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
PMID: 15911692
