Clofazimine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H22Cl2N4
Molecular Weight	473.396
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)\N=C1/C=C2N(C3=CC=C(Cl)C=C3)C4=C(C=CC=C4)N=C2C=C1NC5=CC=C(Cl)C=C5

InChI

InChIKey=WDQPAMHFFCXSNU-BGABXYSRSA-N

InChI=1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3/b30-24+

HIDE SMILES / InChI

Description

Clofazimine (Lamprene®) is a fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine (Lamprene®) exerts a slow bactericidal effect on Mycobacterium leprae (Hansen’s bacillus). It inhibits mycobacterial growth and binds preferentially to mycobacterial DNA. It also exerts anti-inflammatory properties in controlling erythema nodosum leprosum reactions. However, its precise mechanisms of action are unknown.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282	Binding Agent 1,076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Lepromatous leprosy 3	Curative		Approved 8,583	LAMPRENE

C_max

Value	Dose	Analyte	Population
0.5 mg/L	300 mg 3 times / week multiple, oral	CLOFAZIMINE plasma	Homo sapiens
0.7 mg/L	100 mg 1 times / day multiple, oral	CLOFAZIMINE plasma	Homo sapiens
1 mg/L	300 mg 1 times / day multiple, oral	CLOFAZIMINE plasma	Homo sapiens
1.4 mg/L	400 mg 1 times / day multiple, oral	CLOFAZIMINE plasma	Homo sapiens
861 pmol/g	200 mg single, oral	CLOFAZIMINE plasma	Homo sapiens
604 pmol/g	200 mg single, oral	CLOFAZIMINE plasma	Homo sapiens
469 pmol/g	200 mg single, oral	CLOFAZIMINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
33900 pmol × h/g	200 mg single, oral	CLOFAZIMINE plasma	Homo sapiens
29100 pmol × h/g	200 mg single, oral	CLOFAZIMINE plasma	Homo sapiens
18000 pmol × h/g	200 mg single, oral	CLOFAZIMINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.6 day	200 mg single, oral		CLOFAZIMINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
200 mg single, oral Highest studied dose	unhealthy, 30-60
100 mg 1 times / day steady, oral Recommended	unhealthy	Other AEs: Gastrointestinal obstruction, Gastrointestinal bleeding...
100 mg 1 times / day steady, oral Recommended	unhealthy	Other AEs: Skin discoloration...
100 mg 1 times / day steady, oral Recommended	unhealthy	Other AEs: Ichthyosis, Dry skin...
200 mg single, oral Recommended	unhealthy

Showing 1 to 5 of 5 entries

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AEs

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AE	Dose	Population
Depression	100 mg 1 times / day steady, oral Recommended	unhealthy
Discoloration urine	100 mg 1 times / day steady, oral Recommended	unhealthy
QT interval prolonged	100 mg 1 times / day steady, oral Recommended	unhealthy
Suicidal ideation	100 mg 1 times / day steady, oral Recommended	unhealthy
Torsade de pointes	100 mg 1 times / day steady, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1,087 inhibitor 2,252		inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,741 BCRP 910 MRP1 116 BSEP 550

Drug as perpetrator

Show entries

Target	Modality	Activity	Clinical evidence
P-gp 1,932	inhibitor 4,027	strong [IC50 1.8 uM]
BCRP 985	inhibitor 4,027	strong [IC50 3.2 uM]
MRP1 232	inhibitor 4,027	strong [IC50 6.8 uM]
CYP3A4 2,633	inhibitor 4,027	yes [IC50 0.275 uM]	no (co-administration study)
BSEP 554	inhibitor 4,027	yes [IC50 2.3 uM]

Showing 1 to 5 of 7 entries

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3749	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3749
MolPort	MolPort-042-621-745	https://www.molport.com/shop/molecule-link/MolPort-042-621-745
ZINC	ZINC000253916263	http://zinc15.docking.org/substances/ZINC000253916263

Showing 1 to 3 of 3 entries

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PubMed

Show entries

Title	Date	PubMed
In-vivo activity of streptomycin and clofazimine against established infections of Mycobacterium avium complex in beige mice.	1992 Dec	1289358
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.	2000 Feb 1	10609550
Clofazimine enteropathy in a pediatric bone marrow transplant recipient.	2001 Apr	11295724
Pyodera gangrenosum after aortic valve replacement.	2001 Jan	11216779
Cutaneous lupus erythematosus.	2001 Mar	11308132

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Patents

Sample Use Guides

In Vivo Use Guide

Lamprene® should be given at a dosage of 100 mg daily in combination with one or more other antileprosy drugs for 3 years, followed by monotherapy with 100 mg of Lamprene® daily. It should be taken with meals.

Route of Administration: Oral

In Vitro Use Guide

The following in vitro data are available, but their clinical significance is unknown. Lamprene® has been shown in vitro to inhibit M. avium and M. bovis at concentrations of approximately 0.1-1.0 ug/mL. The MIC for M. avium-intracellulare isolated from patients with acquired immunodeficiency syndrome (AIDS) ranged from 1.0 to 5.0 ug/mL.

Show entries

Name

Type

Language

Clofazimine

Official Name

English

LAMPRENE

Preferred Name

English

G-30320

Code

English

Clofazimine [WHO-IP]

Common Name

English

Clofazimine [MI]

Common Name

English

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

770820

Drugs for treatment of lepra

WHO-ATC

J04BA01

Designated/Approved

FDA ORPHAN DRUG

2684

Anti-Infective Agent

NCI_THESAURUS

C258

Drugs for treatment of lepra

WHO-VATC

QJ04BA01

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Code System

Code

Type

Description

RXCUI

2592

PRIMARY

RxNorm

FDA UNII

D959AE5USF

PRIMARY

INN

2248

PRIMARY

CAS

2030-63-9

PRIMARY

SMS_ID

100000092385

PRIMARY

Showing 1 to 5 of 20 entries

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ACTIVE MOIETY


					D959AE5USF

Clofazimine

METABOLITE (PARENT)


					C1WZJ4W2OH

1-HYDROXY-CLOFAZIMINE

METABOLITE (PARENT)


					G9ZDT91MJ9

CLOFAZIMINE HYDROGEN-SULFATE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator