Clofazimine

  • CAT Number: A000925
  • CAS Number: 2030-63-9
  • Molecular Formula: C27H22Cl2N4
  • Molecular Weight: 473.4
  • Purity: ≥95%
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Clofazimine 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 also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. Clofazimine works by binding to the guanine bases of bacterial DNA, thereby blocking the template function of the DNA and inhibiting bacterial proliferation.

Catalog Number A000925
CAS Number 2030-63-9
Synonyms

2030-63-9; Lamprene; Lampren; Chlofazimine; Clofazimina

Molecular Formula

C27H22Cl2N4

Purity 95%
Storage -20°C
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
InChIKey WDQPAMHFFCXSNU-BGABXYSRSA-N
SMILES CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
Reference

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peak/ of clofazimine: A solution degradation product of clofazimine via
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[Epub ahead of print] PubMed PMID: 29245088.
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2: Maartens G, Brill MJE, Pandie M, Svensson EM. Pharmacokinetic interaction
between bedaquiline and clofazimine in patients with drug-resistant tuberculosis.
Int J Tuberc Lung Dis. 2018 Jan 1;22(1):26-29. doi: 10.5588/ijtld.17.0615. Epub
2017 Nov 16. PubMed PMID: 29145924.

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3: Chaves LL, Costa Lima SA, Vieira ACC, Barreiros L, Segundo MA, Ferreira D,
Sarmento B, Reis S. Development of PLGA nanoparticles loaded with clofazimine for
oral delivery: Assessment of formulation variables and intestinal permeability.
Eur J Pharm Sci. 2018 Jan 15;112:28-37. doi: 10.1016/j.ejps.2017.11.004. Epub
2017 Nov 6. PubMed PMID: 29122712.
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4: Yew WW, Liang D, Chan DP, Shi W, Zhang Y. Molecular mechanisms of clofazimine
resistance in Mycobacterium tuberculosis. J Antimicrob Chemother. 2017 Oct
1;72(10):2943-2944. doi: 10.1093/jac/dkx227. PubMed PMID: 29091204.
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5: Tuvshintulga B, AbouLaila M, Sivakumar T, Tayebwa DS, Gantuya S, Naranbaatar
K, Ishiyama A, Iwatsuki M, Otoguro K, ōmura S, Terkawi MA, Guswanto A, Rizk MA,
Yokoyama N, Igarashi I. Chemotherapeutic efficacies of a clofazimine and
diminazene aceturate combination against piroplasm parasites and their AT-rich
DNA-binding activity on Babesia bovis. Sci Rep. 2017 Oct 24;7(1):13888. doi:
10.1038/s41598-017-14304-0. PubMed PMID: 29066849; PubMed Central PMCID:
PMC5654833.
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6: Brunaugh AD, Jan SU, Ferrati S, Smyth HDC. Excipient-Free Pulmonary Delivery
and Macrophage Targeting of Clofazimine via Air Jet Micronization. Mol Pharm.
2017 Nov 6;14(11):4019-4031. doi: 10.1021/acs.molpharmaceut.7b00690. Epub 2017
Oct 19. PubMed PMID: 29047275.
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7: Murashov MD, LaLone V, Rzeczycki PM, Keswani RK, Yoon GS, Sud S, Rajeswaran W,
Larsen S, Stringer KA, Rosania GR. The Physicochemical Basis of
Clofazimine-Induced Skin Pigmentation. J Invest Dermatol. 2017 Oct 16. pii:
S0022-202X(17)33040-3. doi: 10.1016/j.jid.2017.09.031. [Epub ahead of print]
PubMed PMID: 29042210.
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8: Xu J, Tasneen R, Peloquin CA, Almeida DV, Li SY, Barnes-Boyle K, Lu Y,
Nuermberger E. Verapamil Increases the Bioavailability and Efficacy of
Bedaquiline but Not Clofazimine in a Murine Model of Tuberculosis. Antimicrob
Agents Chemother. 2017 Dec 21;62(1). pii: e01692-17. doi: 10.1128/AAC.01692-17.
Print 2018 Jan. PubMed PMID: 29038265; PubMed Central PMCID: PMC5740328.
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9: Sangana R, Gu H, Chun DY, Einolf HJ. Evaluation of Clinical Drug Interaction
Potential of Clofazimine Using Static and Dynamic Modeling Approaches. Drug Metab
Dispos. 2018 Jan;46(1):26-32. doi: 10.1124/dmd.117.077834. Epub 2017 Oct 16.
PubMed PMID: 29038231.
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10: Makgatho EM, Mbajiorgu EF. In vitro investigation of clofazimine analogues
for antiplasmodial, cytotoxic and pro-oxidative activities. Afr Health Sci. 2017
Mar;17(1):191-198. doi: 10.4314/ahs.v17i1.24. PubMed PMID: 29026393; PubMed
Central PMCID: PMC5636247.

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