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+
| 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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68002991
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4429181
Curator's Comment: Clofazimine crosses the placenta and, albeit in very small amounts, the blood-brain barrier.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2366041 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | LAMPRENE Approved UseLamprene 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 Date1986 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
33900 pmol × h/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10.6 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3559339/ |
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
| Dose | Population | Adverse events |
|---|---|---|
200 mg single, oral Highest studied dose |
unhealthy, 30-60 |
|
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 Health Status: unhealthy Sources: |
Other AEs: Gastrointestinal obstruction, Gastrointestinal bleeding... Other AEs: Gastrointestinal obstruction (grade 3-5) Sources: Gastrointestinal bleeding (grade 3-5) Splenic infarction (grade 3-5) QT interval prolonged Torsade de pointes Discoloration urine Depression 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 Health Status: unhealthy Sources: |
Other AEs: Skin discoloration... Other AEs: Skin discoloration (75-100) 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 Health Status: unhealthy Sources: |
Other AEs: Ichthyosis, Dry skin... Other AEs: Ichthyosis Sources: Dry skin Pruritus |
200 mg single, oral Recommended Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
|
| 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 Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical 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 |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/19520776/ Page: 7.0 |
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
| Title | Date | PubMed |
|---|---|---|
| 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
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
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Mon Mar 31 23:40:31 GMT 2025
by
admin
on
Mon Mar 31 23:40:31 GMT 2025
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| Record UNII |
D959AE5USF
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
770820
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WHO-ATC |
J04BA01
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FDA ORPHAN DRUG |
2684
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NCI_THESAURUS |
C258
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WHO-VATC |
QJ04BA01
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LIVERTOX |
NBK548658
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FDA ORPHAN DRUG |
646318
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NDF-RT |
N0000175483
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FDA ORPHAN DRUG |
338811
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FDA ORPHAN DRUG |
436314
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WHO-ESSENTIAL MEDICINES LIST |
6.2.3
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| Code System | Code | Type | Description | ||
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2592
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D959AE5USF
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2248
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2030-63-9
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100000092385
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141046
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DB00845
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1138904
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SUB06694MIG
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DTXSID7022839
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CLOFAZIMINE
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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. | ||
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C47456
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D002991
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CLOFAZIMINE
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Clofazimine
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217-980-2
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m3637
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PRIMARY | Merck Index | ||
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692
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3749
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CHEMBL1292
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TRANSPORTER -> INHIBITOR | |||
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METABOLITE -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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