CLOFAZIMINE

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Search structure


Trade Names	LAMPRENE
Synonyms	Chlofazimine Clofazimine Clofaziminum Colfazimine G 30320 G-30320 Lamprene NSC-141046
Status
Molecule Category	UNKNOWN
ATC	J04BA01
UNII	D959AE5USF


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	WDQPAMHFFCXSNU-BGABXYSRSA-N
Smiles	CC(C)/N=c1\cc2n(-c3ccc(Cl)cc3)c3ccccc3nc-2cc1Nc1ccc(Cl)cc1
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/b30-24+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C27H22Cl2N4
Molecular Weight	473.41
AlogP	7.49
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	4.0
Polar Surface Area	42.21
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	33.0

Bioactivity

Mechanism of Action	Action	Reference
DNA inhibitor	INHIBITOR	FDA ISBN

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family	-	6000-40000	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	12900-12900	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	10400	-	-	-

Assay Description	Organism	Bioactivity	Reference
PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium tuberculosis H37Rv. (Class of assay: confirmatory)	None	391.0 nM
TP_TRANSPORTER: inhibition of Daunorubicin efflux in NIH-3T3-G185 cells	None	600.0 nM
Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay	Chlorocebus sabaeus	68.6 ug.mL-1
DNDI: Leish (macro) in Vitro, 96 hour	Leishmania donovani	950.0 nM
Trypanocidal activity against GFP expressing Trypanosoma cruzi Y C57BL/6J mouse acute model of trypanosomal infection assessed as reduction in parasitemia at 20 mg/kg/day, ip measured at 10,14 and 20 days post infection	Trypanosoma cruzi	40.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	59.44 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	9.66 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	13.39 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	6.99 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	-0.68 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	5.63 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-11.17 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	4.74 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	21.09 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	15.66 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.37 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.51 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.51 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.37 %
Growth inhibiting activity of Naegleria gruberi in vitro	Naegleria gruberi	67.9 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 2 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control	Mycobacterium leprae	94.0 %
Inhibition of PGL1 synthesis in Mycobacterium leprae infected Swiss Webster mouse macrophages assessed as decrease in [U-14C]PA incorporation at 0.2 uM preincubated for 4 days post infection followed by [U-14C]PA addition and measured after 7 days by liquid scintillation counter analysis relative to control	Mycobacterium leprae	70.0 %

Cross References

Resources	Reference
ChEBI	3749
ChEMBL	CHEMBL1292
DrugBank	DB00845
DrugCentral	692
FDA SRS	D959AE5USF
Guide to Pharmacology	9184
KEGG	C06915
SureChEMBL	SCHEMBL26757
ZINC	ZINC000100037101

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).