Lumefantrine CAS 82186-77-4
Introduction：Basic information about Lumefantrine CAS 82186-77-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Lumefantrine Basic informationAntimalarial drug Physical and Chemical Properties Pharmacokinetics Dosage Adverse reactions Precautions
| Product Name: | Lumefantrine |
| Synonyms: | (9Z)-2,7-Dichloro-9-[(4-chlorophenyl)methylene]-α-[(dibutylamino)methyl]-9H-fluorene-4-methanol;CPG-56695;Benwuchun;Benflumentol;benflumetol;Lumefantrine;BENFLUMETOL (OR LUMEFANTRINE);(9Z)-2,7-Dichloro-9-[(4-chlorophenyl)methylene]-a-[(dibutylamino)methyl]-9H-fluorene-4-methanol |
| CAS: | 82186-77-4 |
| MF: | C30H32Cl3NO |
| MW: | 528.94 |
| EINECS: | 617-303-4 |
| Product Categories: | Pharmaceutical intermediates;Antibiotics;API;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;82186-77-4 |
| Mol File: | 82186-77-4.mol |
Lumefantrine Chemical Properties
| Melting point | 129-131°C |
| Boiling point | 642.5±55.0 °C(Predicted) |
| density | 1.252 |
| storage temp. | 15-25°C |
| solubility | DMSO: ≥20mg/mL |
| pka | 13.44±0.20(Predicted) |
| form | powder |
| color | yellow |
| Merck | 14,5597 |
| Major Application | pharmaceutical (small molecule) |
| InChIKey | DYLGFOYVTXJFJP-MYYYXRDXSA-N |
| SMILES | C12C(C(CN(CCCC)CCCC)O)=CC(Cl)=CC=1/C(=C\C1C=CC(Cl)=CC=1)/C1C=C(Cl)C=CC2=1 |
| CAS DataBase Reference | 82186-77-4(CAS DataBase Reference) |
Safety Information
| WGK Germany | 3 |
| HS Code | 29221950 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 82186-77-4(Hazardous Substances Data) |
| Antimalarial drug | Benflumetol and artemether are the widely used antimalarial drugs currently in clinical , they are the main ingredients of the well-known anti-malarial drugs called Compound artemether of Novartis ,which can kill plasmodia asexual, insecticidal rate is high, the cure rate is about 95%, but it is invalid in the pre-erythrocytic stage and gametophyte . Animal experiments suggest it is drug with micro toxicity,but the mutagenic and teratogenic tests are negative. It is mainly used for the treatment of falciparum malaria in clinical, especially for the chloroquine-resistant falciparum malaria treatment. |
| Physical and Chemical Properties | Yellow crystalline powder, bitter almond smell, tasteless. Soluble in chloroform, slightly soluble in acetone, almost insoluble in alcohol, melting point of 125~131 ℃. |
| Pharmacokinetics | Oral absorption is slow, elimination is also slow,it can stay a long time in the body . Tmax after administration is 4~5h, t1/2 is 24~72h. |
| Dosage | 4d therapy: Adults eat 800mg at draught on the first day ,on day 2, 3, 4, each 400mg at draught; children daily take 8mg/kg at draught, and continue for 4d, the first dose is doubled, but the first dose does not exceed the maximum dose of 0.6g. The above information is edited by the chemicalbook of Tian Ye. |
| Adverse reactions | There are no significant adverse reactions, a small number of patients suffer with electrocardiographic Q~T interval transient mild extending. |
| Precautions | Patients with heart, kidney dysfunction,should use with caution. After symptoms are controlled in patients with malignant malaria and the parasite is killed in the pre-erythrocytic stage ,primaquine can be used to kill gametocytes. It is saved in the dark, sealed, cool and dry place. |
| Description | Lumefantrine is an antimalarial drug that is used in combination with artemether . The pairing of lumefantrine and artemether is a major form of oral artemisinin combination therapy used against uncomplicated P. falciparum malaria. Lumefantrine also blocks the rapidly activating delayed-rectifier potassium channel (IKr; IC50 = 8.1 μM). |
| Chemical Properties | Yellow Solid |
| Uses | A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. |
| Application | Lumefantrine has been used: to study its effect on ex-vivo Plasmodium falciparum sensitivity using the tritiated hypoxanthine-based assay as a standard in the quantification of combined tablet formulation using HPTLC as a drug molecule in in vitro growth inhibition assay for in vitro B. caballi growth inhibition studies |
| Definition | ChEBI: Lumefantrine is an antimalarial drug used in combination with artemether for the treatment of multi-drug resistant strains of falciparum malaria. |
| Antimicrobial activity | Lumefantrine has marked blood schizonticidal activity against a wide range of plasmodia, including chloroquineresistant P. falciparum. The 50% and 90% effective concentrations (EC50 and EC90) in vitro are similar: <10 and 40 nmol/L, respectively. The racemate and the two enantiomers exhibit similar activities. Blood schizonticidal activity of desbutylbenflumetol is four to five times greater than benflumetol in vitro. |
| Acquired resistance | Treatment with artemether–lumefantrine can select for polymorphismsin the P. falciparum pfmdr1 gene. Resistance hasbeen selected experimentally in murine malaria. |
| General Description | Lumefantrine was developed in China. Itsmechanism of action is poorly understood. There is some evidencethat it inhibits the formation of β-hematin by forming acomplex with hemin. Lumefantrine is very lipophilic and is marketed in combination with the lipophilic artemesininderivedartemether. |
| Pharmaceutical Applications | A dichlorobenzylidene derivative given orally in combinationwith artemether. |
| Biochem/physiol Actions | Lumefantrine is is an antimalarial for the treatment of multi-drug resistant strains of falciparum malaria. |
| Pharmacokinetics | Bioavailability after oral administration is variable; absorptionis substantially increased by co-administration with food,particularlywith a high fat content. Peak plasma concentrationsoccur after 6–8 h. The elimination half-life is 4–6 days. Itis almost completely protein bound and metabolized mainlyin the liver by CYP3A4. |
| Clinical Use | Treatment of P. falciparum infections (including mixed infections)in a fixed-dose combination treatment with artemether. |
| Side effects | The most common adverse effects in combination with artemetherinclude headache, dizziness and gastrointestinal disturbances. |
| Metabolism | Primaquine is almost totally metabolized by CYP3A4 (99%), with the primary metabolite beingcarboxyprimaquine. Trace amounts of N-acetylprimaquine plus aromatichydroxylation and conjugation metabolites also have been reported. |
| References | [1] AURéLIE PASCUAL. Ex vivo activity of the ACT new components pyronaridine and piperaquine in comparison with conventional ACT drugs against isolates of Plasmodium falciparum.[J]. Malaria Journal, 2012, 11: 45. DOI: 10.1186/1475-2875-11-45 [2] HELENA H ASKLING. Management of imported malaria in Europe.[J]. Malaria Journal, 2012, 11: 328. DOI: 10.1186/1475-2875-11-328 [3] MAYFONG MAYXAY. Efficacy of artemether-lumefantrine, the nationally-recommended artemisinin combination for the treatment of uncomplicated falciparum malaria, in southern Laos.[J]. Malaria Journal, 2012, 11: 184. DOI: 10.1186/1475-2875-11-184 [4] Lü-PEI DU . The pharmacophore hypotheses of IKr potassium channel blockers: novel class III antiarrhythmic agents[J]. Bioorganic & Medicinal Chemistry Letters, 2004, 14 18: Pages 4771-4777. DOI: 10.1016/j.bmcl.2004.06.070 |
Lumefantrine Preparation Products And Raw materials
