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Clofazimine

Tuberculosis drug CAS# 2030-63-9

Clofazimine

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Chemical structure

Clofazimine

3D structure

Chemical Properties of Clofazimine

Cas No. 2030-63-9 SDF Download SDF
PubChem ID 2794 Appearance Powder
Formula C27H22Cl2N4 M.Wt 473.4
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 6.25 mg/mL (13.20 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine
SMILES CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
Standard InChIKey WDQPAMHFFCXSNU-UHFFFAOYSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Clofazimine

DescriptionClofazimine is a fat-soluble iminophenazine dye, has a marked anti-inflammatory effect, has been used in combination with other antimycobacterial drugs to treat AIDS and Crohn's disease.

Clofazimine Dilution Calculator

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Clofazimine Molarity Calculator

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Preparing Stock Solutions of Clofazimine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1124 mL 10.5619 mL 21.1238 mL 42.2476 mL 52.8095 mL
5 mM 0.4225 mL 2.1124 mL 4.2248 mL 8.4495 mL 10.5619 mL
10 mM 0.2112 mL 1.0562 mL 2.1124 mL 4.2248 mL 5.2809 mL
50 mM 0.0422 mL 0.2112 mL 0.4225 mL 0.845 mL 1.0562 mL
100 mM 0.0211 mL 0.1056 mL 0.2112 mL 0.4225 mL 0.5281 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Clofazimine

Clofazimine is a rhimophenazine dye, originally developed for the treatment of tuberculosis, it has both antimicrobial and antiinflammatory activity, postulated mechanisms of action include intercalation of clofazimine with bacterial DNA and increasing le

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References on Clofazimine

Effectiveness and safety of clofazimine in multidrug-resistant tuberculosis: a nationwide report from Brazil.[Pubmed:28331044]

Eur Respir J. 2017 Mar 22;49(3). pii: 49/3/1602445.

Although Clofazimine is used to treat multidrug-resistant tuberculosis (MDR-TB), there is scant information on its effectiveness and safety. The aim of this retrospective, observational study was to evaluate these factors as well as the tolerability of Clofazimine in populations in Brazil, where it was administered at a daily dose of 100 mg.day(-1) (body weight >/=45 kg) as part of a standardised MDR-TB treatment regimen until 2006 (thereafter pyrazinamide was used).All MDR-TB patients included in the Sistema de Informacao de Tratamentos Especiais da Tuberculose (SITETB) individual electronic register were analysed. The effectiveness of Clofazimine was assessed by comparing the treatment outcomes of patients undergoing Clofazimine-containing regimens against those undergoing Clofazimine-free regimens and its safety by describing Clofazimine-attributed adverse events. A total of 1446 patients were treated with Clofazimine-containing regimens and 1096 with pyrazinamide-containing regimens.Although success rates were similar in patients treated with Clofazimine versus those treated with pyrazinamide (880 out of 1446, 60.9%, versus 708 out of 1096, 64.6%; p=0.054), Clofazimine-treated cases exhibited higher death rates due to tuberculosis than pyrazinamide-treated ones (314 out of 1446, 21.7%, versus 120 out of 1096, 10.9%) but fewer failures (78 out of 1446, 5.4%, versus 95 out of 1096, 8.7%) and less loss to follow-up (144 out of 1446, 10.0%, versus 151 out of 1096, 13.8%). No relevant differences were detected when comparing adverse events in patients treated with Clofazimine-containing regimens to those treated with Clofazimine-free regimens. However, the incidence of side-effects was less than previously reported (gastro-intestinal complaints: 10.5%; hyper-pigmentation: 50.2%; neurological disturbances: 9-13%).

Primary Clofazimine and Bedaquiline Resistance among Isolates from Patients with Multidrug-Resistant Tuberculosis.[Pubmed:28320727]

Antimicrob Agents Chemother. 2017 May 24;61(6). pii: AAC.00239-17.

Clofazimine has been repurposed for the treatment of tuberculosis, especially for multidrug-resistant tuberculosis (MDR-TB). To test the susceptibility to Clofazimine of Mycobacterium tuberculosis clinical isolates, MICs of Clofazimine were determined using the microplate alamarBlue assay (MABA) method for 80 drug-resistant isolates and 10 drug-susceptible isolates for comparison. For five Clofazimine-resistant strains isolated from previously treated pre-extensively drug-resistant TB (pre-XDR-TB) and XDR-TB patients without prior exposure to Clofazimine or bedaquiline, Clofazimine MICs were >/=1.2 mug/ml. Four isolates with cross-resistance to bedaquiline had Rv0678 mutations. The other isolate with no resistance to bedaquiline had an Rv1979c mutation. This study adds to a recent study showing that 6.3% of MDR-TB patients without prior Clofazimine or bedaquiline exposure harbored isolates with Rv0678 mutations, which raises concern that preexisting resistance to these drugs may be associated with prior TB treatment. Furthermore, we propose a tentative breakpoint of 1.2 mug/ml for Clofazimine resistance using the MABA method. More-widespread surveillance and individualized testing for Clofazimine and bedaquiline resistance, together with assessment of their clinical usage, especially among previously treated and MDR-TB patients, are warranted.

Clofazimine-Containing Regimen for the Treatment of Mycobacterium abscessus Lung Disease.[Pubmed:28348153]

Antimicrob Agents Chemother. 2017 May 24;61(6). pii: AAC.02052-16.

Patients with lung disease caused by Mycobacterium abscessus subsp. abscessus (here M. abscessus) typically have poor treatment outcomes. Although Clofazimine (CFZ) has been increasingly used in the treatment of M. abscessus lung disease in clinical practice, there are no reported data on its effectiveness for this disease. This study sought to evaluate the clinical efficacy of a CFZ-containing regimen for the treatment of M. abscessus lung disease. We performed a retrospective review of the medical records of 42 patients with M. abscessus lung disease who were treated with CFZ-containing regimens between November 2013 and January 2015. CFZ was administered in combination with other antibiotics as an initial antibiotic regimen in 15 (36%) patients (initial treatment group), and it was added to an existing antibiotic regimen for refractory M. abscessus lung disease in 27 (64%) patients (salvage treatment group). Overall, there was an 81% treatment response rate based on symptoms and a 31% response rate based on radiographic findings. Conversion to culture-negative sputum samples was achieved in 10 (24%) patients after CFZ-containing antibiotic treatment, and during treatment, there were significant decreases in the positivity of semiquantitative sputum cultures for acid-fast bacilli in both the initial (P = 0.018) and salvage (P = 0.001) treatment groups. Our study suggests that CFZ-containing regimens may improve treatment outcomes in patients with M. abscessus lung disease and that a prospective evaluation of CFZ in M. abscessus lung disease is warranted.

Clofazimine encapsulation in nanoporous silica particles for the oral treatment of antibiotic-resistant Mycobacterium tuberculosis infections.[Pubmed:28338408]

Nanomedicine (Lond). 2017 Apr;12(8):831-844.

AIM: First extensive reformulation of Clofazimine (CLZ) in nanoporous silica particles (NSPs) for tackling antibiotic-resistant tuberculosis (TB) infections. MATERIALS & METHODS: Solid-state characterization of several CLZ-encapsulated NSP formulations was followed by in vitro drug solubility, Caco-2 intestinal cells drug permeability and TB antibacterial activity. RESULTS: NSPs stabilize the amorphous state of CLZ (shelf stability >6 months) and dramatically increase the drug solubility in simulated gastric fluid (up to 20-fold) with different dissolution kinetics depending on the NSPs used. CLZ encapsulation in NSP substantially enhances the permeation through model intestinal cell layer, achieving effective antimicrobial concentrations in TB-infected macrophages. CONCLUSION: Promising results toward refurbishment of an approved marketed drug for a different indication suitable for oral anti-TB formulation.

Description

Clofazimine is a fat-soluble iminophenazine dye, has a marked anti-inflammatory effect, has been used in combination with other antimycobacterial drugs to treat AIDS and Crohn's disease.

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