U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of Clofazimine

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

Molecular Formula C27H22Cl2N4
Molecular Weight 473.396
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002991

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

Curator's Comment: Clofazimine crosses the placenta and, albeit in very small amounts, the blood-brain barrier.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
LAMPRENE

Approved Use

Lamprene is indicated in the treatment of lepromatous leprosy, including dapsone-resistant lepromatous leprosy and lepromatous leprosy complicated by erythema nodosum leprosum. Lamprene has not been demonstrated to be effective in the treatment of other leprosy-associated inflammatory reactions.

Launch Date

1986
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.5 mg/L
300 mg 3 times / week multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
0.7 mg/L
100 mg 1 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1 mg/L
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1.4 mg/L
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
861 pmol/g
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
604 pmol/g
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
469 pmol/g
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
33900 pmol × h/g
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
29100 pmol × h/g
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
18000 pmol × h/g
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.6 day
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFAZIMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy, 30-60
Health Status: unhealthy
Age Group: 30-60
Sex: M
Sources:
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Other AEs: Gastrointestinal obstruction, Gastrointestinal bleeding...
Other AEs:
Gastrointestinal obstruction (grade 3-5)
Gastrointestinal bleeding (grade 3-5)
Splenic infarction (grade 3-5)
QT interval prolonged
Torsade de pointes
Discoloration urine
Depression
Suicidal ideation
Sources:
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Other AEs: Skin discoloration...
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Other AEs: Ichthyosis, Dry skin...
200 mg single, oral
Recommended
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
unhealthy
AEs

AEs

AESignificanceDosePopulation
Depression
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Discoloration urine
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
QT interval prolonged
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Suicidal ideation
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Torsade de pointes
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Gastrointestinal bleeding grade 3-5
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Gastrointestinal obstruction grade 3-5
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Splenic infarction grade 3-5
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Skin discoloration 75-100
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Dry skin
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Ichthyosis
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Pruritus
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
strong [IC50 1.8 uM]
strong [IC50 3.2 uM]
strong [IC50 6.8 uM]
yes [IC50 0.275 uM]
no (co-administration study)
Comment: No clinically significant differences in the pharmacokinetics of the following drugs were observed when used concomitantly with clofazimine: dapsone or rifampicin
Page: 4.0
yes [IC50 2.3 uM]
yes [IC50 4.54 uM]
no (co-administration study)
Comment: No clinically significant differences in the pharmacokinetics of the following drugs were observed when used concomitantly with clofazimine: dapsone or rifampicin
Page: 4.0
yes
PubMed

PubMed

TitleDatePubMed
10-12 years follow-up of highly bacillated BL/LL leprosy patients on combined chemotherapy and immunotherapy.
2004-09-09
Intra-abdominal, crystal-storing histiocytosis due to clofazimine in a patient with lepromatous leprosy and concurrent carcinoma of the colon.
2004-06
Shiny red-brown papules in a 21-year-old man. Histoid leprosy.
2004-06
Antimicrobial activity of clofazimine is not dependent on mycobacterial C-type phospholipases.
2004-06
Results of a standardised regimen for multidrug-resistant tuberculosis in Bangladesh.
2004-05
Regression of Novikoff rat hepatocellular carcinoma following locoregional administration of a novel formulation of clofazimine in lipiodol.
2004-04-15
Human case of lobomycosis.
2004-04
Relapses in multibacillary patients treated with multi-drug therapy until smear negativity: findings after twenty years.
2004-03
Erythema dyschromicum perstans: response to dapsone therapy.
2004-03
Anti-staphylococcal activity and mode of action of clofazimine.
2004-03
Cheilitis granulomatosa of Melkersson-Rosenthal syndrome: treatment with intralesional corticosteroid injections.
2004-02-26
Use of infliximab, an anti-tumor necrosis alpha antibody, for inflammatory dermatoses.
2004-02-20
Morbihan's disease: treatment with CO2 laser blepharoplasty.
2004-02
A microplate indicator-based method for determining the susceptibility of multidrug-resistant Mycobacterium tuberculosis to antimicrobial agents.
2004-02
[Guideline for the treatment of leprosy by new quinolones].
2004-02
Parallel assessment of 24 monthly doses of rifampin, ofloxacin, and minocycline versus two years of World Health Organization multi-drug therapy for multi-bacillary leprosy.
2004-02
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.
2004-01
Optimal management of recalcitrant disorders of hyperpigmentation in dark-skinned patients.
2004
Long-term efficacy of 2 year WHO multiple drug therapy (MDT) in multibacillary (MB) leprosy patients.
2003-12
Chronic recurrent ENL, steroid dependent: long-term treatment with high dose clofazimine.
2003-12
Invasive Mycobacterium marinum infections.
2003-11
Lepromatous leprosy and reversal reaction in a Micronesian immigrant.
2003-11
Treatment of Mycobacterium avium-intracellulare complex lung disease with a macrolide, ethambutol, and clofazimine.
2003-10
Viability and drug susceptibility testing of M. leprae using mouse footpad in 37 relapse cases of leprosy.
2003-09
Determination of clofazimine in leprosy patients by high-performance liquid chromatography.
2003-09
Along these lines...
2003-09
Dapsone induced cholangitis as a part of dapsone syndrome: a case report.
2003-08-11
[Leprosy in Brazil].
2003-08-09
[A case of lepromatous type Hansen's disease].
2003-08
[A case of Hansen's disease seen in an Indonesian resident, and tracing of the patient after coming back to Indonesia].
2003-08
Efficacy of clofazimine-modified cyclodextrin against Mycobacterium avium complex in human macrophages.
2003-07-09
Leprosy in a Mexican immigrant.
2003-07
Effectiveness of multidrug therapy in multibacillary leprosy: a long-term follow-up of 34 multibacillary leprosy patients treated with multidrug regimens till skin smear negativity.
2003-06
Disseminated Mycobacterium chelonae cutaneous infection: recalcitrant to combined antibiotic therapy.
2003-06
Pulsed corticosteroid therapy in patients with chronic recurrent ENL: a pilot study.
2003-04-24
Drug resistant-Mycobacterium leprae--results of mouse footpad studies from a laboratory in south India.
2003-03-11
[Adverse effects of multidrug therapy in leprosy patients: a five-year survey at a Health Center of the Federal University of Uberlândia].
2003-03-08
A retrospective study regarding the treatment of lupoid onychodystrophy in 30 dogs and literature review.
2003-03-06
Short report: Treatment failure in Hansen's disease.
2003-02
[Histoid leprosy with erythema nodosum leprosum].
2003
[Hansen's disease in the laboratory].
2003
Probing cell chemistry with time-of-flight secondary ion mass spectrometry: development and exploitation of instrumentation for studies of frozen-hydrated biological material.
2003
Less common methods to treat acne.
2003
Leprosy.
2002-12
[Pyoderma gangrenosum--positive effect of cyclosporin A therapy ].
2002-10
Hansen's disease mimicking palmoplantar keratoderma.
2002-09
Advances in the diagnosis and treatment of leprosy.
2002-07-22
[Systematic search for parasites among leprosy patients in Mali].
2002
Spectrum of drugs against atypical mycobacteria: how valid is the current practice of drug susceptibility testing and the choice of drugs?
1992-12
In-vivo activity of streptomycin and clofazimine against established infections of Mycobacterium avium complex in beige mice.
1992-12
Patents

Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:40:31 GMT 2025
Edited
by admin
on Mon Mar 31 23:40:31 GMT 2025
Record UNII
D959AE5USF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Clofazimine
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
LAMPRENE
Preferred Name English
G-30320
Code English
Clofazimine [WHO-IP]
Common Name English
Clofazimine [MI]
Common Name English
Clofazimine [USP IMPURITY]
Common Name English
Clofazimine [USP MONOGRAPH]
Common Name English
N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-2-phenazinamine
Systematic Name English
Clofazimine [EP MONOGRAPH]
Common Name English
Clofazimine [WHO-DD]
Common Name English
2-Phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-
Systematic Name English
CLOFAZIMINUM [WHO-IP LATIN]
Common Name English
clofazimine [INN]
Common Name English
CHLOFAZIMINE
Common Name English
Clofazimine [ORANGE BOOK]
Common Name English
3-(P-CHLOROANILINO)-10-(P-CHLOROPHENYL)-2,10-DIHYDRO-2-(ISOPROPYLIMINO)PHENAZINE
Common Name English
Clofazimine [USAN]
Common Name English
G30320
Code English
COLFAZIMINE [VANDF]
Common Name English
Clofazimine [VANDF]
Common Name English
Clofazimine [USP-RS]
Common Name English
Clofazimine [JAN]
Common Name English
NSC-141046
Code English
Clofazimine [MART.]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 770820
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
WHO-ATC J04BA01
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
FDA ORPHAN DRUG 2684
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
NCI_THESAURUS C258
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
WHO-VATC QJ04BA01
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
LIVERTOX NBK548658
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
FDA ORPHAN DRUG 646318
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
NDF-RT N0000175483
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
FDA ORPHAN DRUG 338811
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
FDA ORPHAN DRUG 436314
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
Code System Code Type Description
RXCUI
2592
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY RxNorm
FDA UNII
D959AE5USF
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
INN
2248
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
CAS
2030-63-9
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
SMS_ID
100000092385
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
NSC
141046
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
DRUG BANK
DB00845
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
RS_ITEM_NUM
1138904
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PRIMARY
EVMPD
SUB06694MIG
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PRIMARY
EPA CompTox
DTXSID7022839
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CLOFAZIMINE
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY Description: A reddish brown, fine powder; odourless or almost odourless.Solubility: Practically insoluble in water; slightly soluble in ethanol (~750 g/l) TS and in ether R.Category: Antileprosy drug.Storage: Clofazimine should be kept in a well-closed container.Additional information: Clofazimine melts at about 217 ?C.
NCI_THESAURUS
C47456
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
MESH
D002991
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
WIKIPEDIA
CLOFAZIMINE
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
LACTMED
Clofazimine
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
ECHA (EC/EINECS)
217-980-2
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
MERCK INDEX
m3637
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
692
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
CHEBI
3749
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
ChEMBL
CHEMBL1292
Created by admin on Mon Mar 31 23:40:31 GMT 2025 , Edited by admin on Mon Mar 31 23:40:31 GMT 2025
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET ORGANISM->INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY