Clofazimine

Structural formula
General
Non-proprietary name	Clofazimine
other names	2- (4-chloroanilino) -5- (4-chlorophenyl) -3-isopropylimino-3,5-dihydrophenazine ( IUPAC ); Clofaziminum ( Latin );
Molecular formula	C 27 H 22 Cl 2 N 4
Brief description	reddish brown, fine powder, shows polymorphism
External identifiers / databases
EC number	217-980-2
ECHA InfoCard	100.016.347
PubChem	2794
DrugBank	DB00845
Wikidata	Q418611
Drug information
ATC code	J04 BA01
Drug class	Leprosy drugs
properties
Molar mass	473.3964 g · mol -1
Physical state	firmly
Melting point	210-212 ° C
pK s value	8.51
solubility	practically insoluble in water (0.225 mg l −1 at 25 ° C); soluble in dichloromethane , very sparingly soluble in ethanol ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	8400 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Clofazimin is a red dye that can be used as a drug against leprosy because of its bacteriostatic effect on mycobacterium leprae . The commercial preparation Lampren (e) ^® is currently only available in France.

The drug is used in leprosy in a three-way combination with rifampicin and dapsone . In this way, resistance can largely be avoided. Clofazimin is hydrophobic and can be absorbed orally. In terms of its chemical structure, it belongs to the group of cationic amphiphilic drugs (CAD).

Mechanism of action

The mechanism of action is not yet fully understood. Clofazimin works u. a. as FIASMA (functional inhibitor of acid sphingomyelinase ).

Web links

FDA label from Lamprene (PDF; 165 kB)

Individual evidence

↑ ^a ^b European Pharmacopoeia Commission (ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.8 , 2006.
↑ ^a ^b ^c ^d Entry on clofazimine in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b Data sheet clofazimine from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
↑ ABDA database (as of April 1, 2016).
↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .

[Ph._Eur._5-1] European Pharmacopoeia Commission (ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.8 , 2006.

[ChemIDplus-2] Entry on clofazimine in the ChemIDplus database of the United States National Library of Medicine (NLM)

[Sigma-3] Data sheet clofazimine from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).

[4] ABDA database (as of April 1, 2016).

[pmid18504571-5] Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .