LUMEFANTRINE, (+)-

Details

Stereochemistry	UNKNOWN
Molecular Formula	C30H32Cl3NO
Molecular Weight	528.94
Optical Activity	( + )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CCCCN(CCCC)CC(O)C1=CC(Cl)=CC2=C1C3=CC=C(Cl)C=C3\C2=C\C4=CC=C(Cl)C=C4

InChI

InChIKey=DYLGFOYVTXJFJP-MYYYXRDXSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C30H32Cl3NO
Molecular Weight	528.94
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description

Lumefantrine is an antimalarial agent used to treat acute uncomplicated malaria. It is administered in combination with artemether for improved efficacy (Coartem tablets). Lumefantrine is a blood schizonticide active against erythrocytic stages of Plasmodium falciparum. The exact mechanism by which lumefantrine exerts its antimalarial effect is unknown. The most common adverse reactions of Coartem in adults are headache, anorexia, dizziness, asthenia, arthralgia and myalgia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hemin 3	Binding Agent 1,064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 95	Curative		Approved 8,429	COARTEM

C_max

Value	Dose	Co-administered	Analyte	Population
6.2 μg/mL	480 mg 1 times / day multiple, oral		LUMEFANTRINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
356 ng × h/mL	480 mg 1 times / day multiple, oral		LUMEFANTRINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.1 h	480 mg 1 times / day multiple, oral		LUMEFANTRINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.3%	480 mg 1 times / day multiple, oral		LUMEFANTRINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
240 mg 3 times / day multiple, oral Recommended	unhealthy, 2 n = 310	Disc. AE: Urticaria...
480 mg 3 times / day multiple, oral Recommended	unhealthy, 25 n = 115	Disc. AE: Abdominal pain... Other AEs: Dyspnea, Pulmonary edema...
240 mg 3 times / day multiple, oral Recommended	unhealthy, 3 n = 447	Disc. AE: Vomiting, Urticaria...

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AEs

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AE	Significance	Dose	Population
Urticaria	grade 3-4 Disc. AE	240 mg 3 times / day multiple, oral Recommended	unhealthy, 2 n = 310
Abdominal pain	grade 1-2, uncommon Disc. AE	480 mg 3 times / day multiple, oral Recommended	unhealthy, 25 n = 115
Dyspnea	grade 3-4, uncommon	480 mg 3 times / day multiple, oral Recommended	unhealthy, 25 n = 115
Pulmonary edema	grade 3-4, uncommon	480 mg 3 times / day multiple, oral Recommended	unhealthy, 25 n = 115
Vomiting	grade 3-4, most common Disc. AE	240 mg 3 times / day multiple, oral Recommended	unhealthy, 3 n = 447

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	inhibitor 1,767 inducer 389	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C19 1,478 CYP2E1 882 CYP3A4/5 278 CYP4A9/11 37		CYP1A2 701 CYP2B6 547 CYP2C8 168 CYP2C19 293 CYP3A 129 CYP1A1 108

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no [IC50 >2.0 uM]
CYP2A6 739	inhibitor 3,277	no [IC50 >2.0 uM]
CYP2C19 1,553	inhibitor 3,277	no [IC50 >2.0 uM]
CYP2C9 1,819	inhibitor 3,277	no [IC50 >2.0 uM]
CYP2E1 970	inhibitor 3,277	no [IC50 >2.0 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,737	substrate 3,367	major		yes (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626
hERG 1,647	inhibitor 1,626		DESBUYL-BENFLUMETOL 3

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-6299	http://www.3bsc.com/index/pro_info.php?id=116861
AA Blocks	AA0036I3	https://www.aablocks.com/goods/Goods/detail?id=AA0036I3
AK Scientific, Inc. (AKSCI)	65683	http://www.aksci.com/item_detail.php?cat=65683
Aaron Chemicals	AR00379V	http://www.aaronchem.com/82186-77-4
Achemo Scientific Limited	AC-74186	http://www.achemo.com/search/?Keyword= 82186-77-4

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PubMed

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Title	Date	PubMed
In vitro sensitivities of Plasmodium falciparum to different antimalarial drugs in Uganda.	2010 Mar	20065051

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Patents

Sample Use Guides

In Vivo Use Guide

Tablets should be administered over 3 days for a total of 6 doses: an initial dose, second dose after 8 hours and then twice-daily (morning and evening) for the following 2 days. The adult dosage for patients with bodyweight of 35 kg and above is 4 tablets per dose for a total of 6 doses. Tablets are scored and contain 20 mg rtemether and 120 mg lumefantrine.

Route of Administration: Oral

In Vitro Use Guide

IC90 is higher in Plasmodium falciparum strain T-996 compared with strain LS-21: for Lumefantrine 293.03 and 95.61 nmol/L (154.69 and 50.47 ng/ml of EMM).

Substance Class	Chemical
Record UNII	ZUV4B00D9P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUMEFANTRINE, (+)-

Common Name

English

9H-FLUORENE-4-METHANOL, 2,7-DICHLORO-9-((4-CHLOROPHENYL)METHYLENE)-.ALPHA.-((DIBUTYLAMINO)METHYL)-, (Z)-(+)-

Systematic Name

English

D-BENFLUMELOL

Common Name

English

9H-FLUORENE-4-METHANOL, 2,7-DICHLORO-9-((4-CHLOROPHENYL)METHYLENE)-.ALPHA.-((DIBUTYLAMINO)METHYL)-, (9Z)-(+)-

Systematic Name

English

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Code System

Code

Type

Description

CAS

120583-70-2

PRIMARY

FDA UNII

ZUV4B00D9P

PRIMARY

PUBCHEM

6437380

PRIMARY

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Related Record

Type

Details


					F38R0JR742

LUMEFANTRINE

RACEMATE -> ENANTIOMER


					01NP22J3SV

LUMEFANTRINE, (-)-

ENANTIOMER -> ENANTIOMER

Amount:

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator