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

Details

Stereochemistry ACHIRAL
Molecular Formula C27H22Cl2N4
Molecular Weight 473.3973
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLOFAZIMINE

SMILES

CC(C)/N=c/1\cc2-c(cc1Nc3ccc(cc3)Cl)nc4ccccc4n2-c5ccc(cc5)Cl

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
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

5.34988784E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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: Page: p.1986
unhealthy, 30-60
n = 6
Health Status: unhealthy
Condition: Lepromatous leprosy
Age Group: 30-60
Sex: M
Population Size: 6
Sources: Page: p.1986
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
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: Page: p.1, p.3
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1, p.3
Other AEs: Skin discoloration...
Other AEs:
Skin discoloration (75-100)
Sources: Page: p.1, p.3
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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.3
Other AEs: Ichthyosis, Dry skin...
Other AEs:
Ichthyosis
Dry skin
Pruritus
Sources: Page: p.3
200 mg single, oral
Recommended
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.4
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1
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: Page: p.1, p.3
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.1, p.3
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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.3
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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.3
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: Page: p.3
unhealthy
Health Status: unhealthy
Condition: Lepromatous leprosy
Sources: Page: p.3
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
Activities of eighteen antimicrobial regimens against Mycobacterium avium infection in beige mice.
1999 Fall
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.
2000 Feb 1
Tetramethylpiperidine-substituted phenazines inhibit the proliferation of intrinsically multidrug resistant carcinoma cell lines.
2001
[Pyoderma gangrenosum. 15 cases].
2001 Feb
[Late reversal leprous reaction appearing 18 months after the termination of treatment].
2001 Mar 3
Pyoderma gangrenosum associated with sclerosing cholangitis, type 1 diabetes mellitus and ulcerative colitis.
2001 May
Leprosy.
2001 May
Nodular rash in an Indonesian girl.
2001 Nov
Sweet's syndrome in association with generalized granuloma annulare in a patient with previous breast carcinoma.
2001 Nov
Bilateral conjunctival lesions in Melkersson-Rosenthal syndrome.
2001 Oct
[A 50-year history of new drugs in Japan: the developments of antileprosy drugs and their epidemiological aspects].
2002
[What is your diagnosis? Sensory motor polyneuropathy in borderline leprosy. Trophic skin disorders with ulcerations, local superinfection on the right foot with right inguinal lymphadenopathy].
2002 Jan 16
[Leprosy in Brazil].
2003 May-Jun
Lepromatous leprosy and reversal reaction in a Micronesian immigrant.
2003 Nov
Determination of clofazimine in leprosy patients by high-performance liquid chromatography.
2003 Sep
Optimal management of recalcitrant disorders of hyperpigmentation in dark-skinned patients.
2004
Cheilitis granulomatosa of Melkersson-Rosenthal syndrome: treatment with intralesional corticosteroid injections.
2004 Jan-Feb
Relapses in multibacillary patients treated with multi-drug therapy until smear negativity: findings after twenty years.
2004 Mar
10-12 years follow-up of highly bacillated BL/LL leprosy patients on combined chemotherapy and immunotherapy.
2004 Sep 9
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.
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
G-30320
Code English
CLOFAZIMINE [WHO-IP]
Common Name English
CLOFAZIMINE [MI]
Common Name English
CLOFAZIMINE [USP MONOGRAPH]
Common Name English
CLOFAZIMINE [EP MONOGRAPH]
Common Name English
2-PHENAZINAMINE, N,5-BIS(4-CHLOROPHENYL)-3,5-DIHYDRO-3-((1-METHYLETHYL)IMINO)-
Systematic Name English
CLOFAZIMINE [WHO-DD]
Common 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 [USP]
Common Name English
CLOFAZIMINE [USAN]
Common Name English
G 30320
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
LAMPRENE
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 770820
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
WHO-ATC J04BA01
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
FDA ORPHAN DRUG 2684
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
NCI_THESAURUS C258
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
WHO-VATC QJ04BA01
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
LIVERTOX 220
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
FDA ORPHAN DRUG 646318
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
NDF-RT N0000175483
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
FDA ORPHAN DRUG 436314
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
FDA ORPHAN DRUG 338811
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
Code System Code Type Description
RXCUI
2592
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY RxNorm
FDA UNII
D959AE5USF
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
INN
2248
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
CAS
2030-63-9
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
DRUG BANK
DB00845
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
USP_CATALOG
1138904
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY USP-RS
EVMPD
SUB06694MIG
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
EPA CompTox
2030-63-9
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CLOFAZIMINE
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
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 Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
MESH
D002991
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
WIKIPEDIA
CLOFAZIMINE
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
LACTMED
Clofazimine
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
217-980-2
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
MERCK INDEX
M3637
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
692
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL1292
Created by admin on Fri Jun 25 20:58:57 UTC 2021 , Edited by admin on Fri Jun 25 20:58:57 UTC 2021
PRIMARY