Clofazimine (CED0003591)

Record Information

Version

1.0

Creation Date

2016-05-22 03:39:06 UTC

Update Date

2026-05-14 16:50:34 UTC

SynCED ID

CED0003591

Secondary Accession Numbers

CHEM016638

Identification

Common Name

Clofazimine

Class

Small Molecule

Description

Clofazimine is an organic compound with the formula C27H22Cl2N4 and an average molecular weight of 473.40 g/mol. Clofazimine belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. It is classified as an organoheterocyclic compound. This substance is found in or released from healthcare, pharmaceuticals, and veterinary products, specifically as antibiotics and drugs for the treatment of lepra. Recorded routes of exposure include oral and inhalation. In terms of biological activity, clofazimine has two recorded protein targets: Potassium voltage-gated channel subfamily A member 3 (KCNA3) and Peroxisome proliferator-activated receptor gamma (PPARG), for which it acts as an antagonist or modulator.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₇H₂₂Cl₂N₄

Average Molecular Mass

473.400 g/mol

Monoisotopic Mass

472.122 g/mol

CAS Registry Number

2030-63-9

IUPAC Name

(3Z)-N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine

Traditional Name

(3Z)-N,5-bis(4-chlorophenyl)-3-(isopropylimino)phenazin-2-amine

SMILES

CC(C)\N=C1\C=C2N(C3=CC=C(Cl)C=C3)C3=CC=CC=C3N=C2C=C1NC1=CC=C(Cl)C=C1

InChI Identifier

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-

InChI Key

WDQPAMHFFCXSNU-KRUMMXJUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phenazines and derivatives

Alternative Parents

Substituents

Phenazine
Aniline or substituted anilines
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Pyrazine
Heteroaromatic compound
Secondary ketimine
Azacycle
Secondary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0015 g/L	ALOGPS
logP	7.39	ALOGPS
logP	7.3	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	16.15	ChemAxon
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	39.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.55 m³·mol⁻¹	ChemAxon
Polarizability	51.52 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dj-0004900000-53aaf2e9feab733f5696	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0009300000-4e81c003ff635d972452	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000t-1009200000-1453a7404269fe261b3c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-a77f21de408c977df7c1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0000900000-6b7cc7e41f8ea912dd22	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004r-1303900000-1f018805b2b835da809b	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
1949.0 Log mg/kg [1100:3500]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000306	Antibiotics?Antibiotics are synthetic or semi-synthetic compounds used to treat bacterial infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000350	Drugs for treatment of lepra?Drugs for the treatment of leprosy, primarily consisting of antibiotics such as rifampicin, dapsone, and clofazimine, are crucial for managing this infectious disease caused by Mycobacterium leprae.	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Predicted (SEA)	Prediction Confidence Score 0.394 Applicability Domain 1.0 Statistical Significance 0.0042 Supporting Reference Compounds 126 E-value 32.8524
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	Prediction Confidence Score 0.391 Applicability Domain 1.0 Statistical Significance 0.0021 Supporting Reference Compounds 425 E-value 16.0369
Click to view 3D structure	ATP-dependent translocase ABCB1	P08183	Humans	Predicted (SEA)	Prediction Confidence Score 0.372 Applicability Domain 1.0 Statistical Significance 0.0033 Supporting Reference Compounds 139 E-value 25.4567
Click to view 3D structure	Cruzipain	P25779	Trypanosoma cruzi	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 1.0 Statistical Significance 0.0044 Supporting Reference Compounds 65 E-value 34.3315
Click to view 3D structure	Spike glycoprotein	P0DTC2	SARS-CoV-2	Predicted (SEA)	Prediction Confidence Score 0.315 Applicability Domain 1.0 Statistical Significance 2.40e-04 Supporting Reference Compounds 9 E-value 1.86838
Click to view 3D structure	Polycomb complex protein BMI-1	P35226	Humans	Predicted (SEA)	Prediction Confidence Score 0.269 Applicability Domain 0.269 Low confidence Statistical Significance 7.00e-04 Supporting Reference Compounds 1 E-value 5.44945
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.289 Low confidence Statistical Significance 0.3345 Supporting Reference Compounds 1660 E-value 2604.13
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.289 Low confidence Statistical Significance 0.2757 Supporting Reference Compounds 1103 E-value 2146.46
Click to view 3D structure	Short transient receptor potential channel 4	Q9QUQ5	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.299 Low confidence Statistical Significance 0.0706 Supporting Reference Compounds 128 E-value 549.615
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	Prediction Confidence Score 0.247 Applicability Domain 0.289 Low confidence Statistical Significance 0.3965 Supporting Reference Compounds 1017 E-value 3086.57
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase Src	P12931	Humans	Predicted (SEA)	Prediction Confidence Score 0.247 Applicability Domain 0.27 Low confidence Statistical Significance 0.4057 Supporting Reference Compounds 1158 E-value 3158.19
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.267 Low confidence Statistical Significance 0.4001 Supporting Reference Compounds 1029 E-value 3114.75
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.27 Low confidence Statistical Significance 0.4413 Supporting Reference Compounds 1130 E-value 3435.56
Click to view 3D structure	Serine/threonine-protein kinase PLK1	P53350	Humans	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.289 Low confidence Statistical Significance 0.335 Supporting Reference Compounds 705 E-value 2608.34
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.265 Low confidence Statistical Significance 0.19 Supporting Reference Compounds 487 E-value 1478.82
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.26 Low confidence Statistical Significance 0.3031 Supporting Reference Compounds 861 E-value 2360.0
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.257 Low confidence Statistical Significance 0.2387 Supporting Reference Compounds 593 E-value 1858.49
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.244 Applicability Domain 0.257 Low confidence Statistical Significance 0.2269 Supporting Reference Compounds 565 E-value 1766.4
Click to view 3D structure	Calcium-dependent protein kinase 1	P62344	Plasmodium falciparum (isolate 3D7)	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.265 Low confidence Statistical Significance 0.1289 Supporting Reference Compounds 123 E-value 1003.17
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.242 Applicability Domain 0.299 Low confidence Statistical Significance 0.6362 Supporting Reference Compounds 1498 E-value 4952.61
Click to view 3D structure	High affinity nerve growth factor receptor	P04629	Humans	Predicted (SEA)	Prediction Confidence Score 0.242 Applicability Domain 0.267 Low confidence Statistical Significance 0.4306 Supporting Reference Compounds 869 E-value 3352.42
Click to view 3D structure	Tyrosine-protein kinase ABL1	P00519	Humans	Predicted (SEA)	Prediction Confidence Score 0.241 Applicability Domain 0.267 Low confidence Statistical Significance 0.4256 Supporting Reference Compounds 927 E-value 3313.19
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	Prediction Confidence Score 0.241 Applicability Domain 0.267 Low confidence Statistical Significance 0.4905 Supporting Reference Compounds 1157 E-value 3818.66
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.241 Applicability Domain 0.265 Low confidence Statistical Significance 0.1612 Supporting Reference Compounds 386 E-value 1255.16
Click to view 3D structure	Lysine--tRNA ligase	Q8IDJ8	Plasmodium falciparum (isolate 3D7)	Predicted (SEA)	Prediction Confidence Score 0.239 Applicability Domain 0.265 Low confidence Statistical Significance 0.0465 Supporting Reference Compounds 39 E-value 362.077