Clofazimine

Details

• Internal ID: 40b50a82-79b7-4031-9810-97bdd9e17a38
• Taxonomy: Organoheterocyclic compounds > Diazanaphthalenes > Benzodiazines > Quinoxalines > Phenazines and derivatives
• IUPAC Name: N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine
• SMILES (Canonical): CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
• SMILES (Isomeric): CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
• 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
• InChI Key: WDQPAMHFFCXSNU-UHFFFAOYSA-N
• Popularity: 3,378 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₂Cl₂N₄
• Molecular Weight: 473.40 g/mol
• Exact Mass: 472.1221521 g/mol
• Topological Polar Surface Area (TPSA): 40.00 Ų
• XlogP: 7.10
• Atomic LogP (AlogP): 7.49
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 2030-63-9
• Lamprene
• Chlofazimine
• Lampren
• Clofazimina
• Clofaziminum
• NSC-141046
• B 663 (Pharmaceutical)
• Clofaziminum [INN-Latin]
• Clofazimina [INN-Spanish]
• G 30320
• B-663
• N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine
• 3-(p-Chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin
• 3-(p-Chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine
• B 663
• 3-(p-Chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine
• G-30320
• D959AE5USF
• 2-Phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-((1-methylethyl)imino)-
• CHEMBL1083384
• DTXSID7022839
• N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-(isopropylimino)phenazin-2-amine
• 2-Phenazinamine, 3,5-dihydro-N,5-bis(4-chlorophenyl)-3-((1-methylethyl)imino)-
• N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-2-phenazinamine
• MMV687800
• NSC141046
• Phenazine, 2,10-dihydro-3-(p-chloroanilino)-10-(p-chlorophenyl)-2-(isopropylimino)-
• Phenazine, 3-(p-chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-
• NCGC00016600-01
• CAS-2030-63-9
• N,5-bis(4-chlorophenyl)-3-(propan-2-ylimino)-3,5-dihydrophenazin-2-amine
• 2-Phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-
• 3-(p-Chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine
• Riminophenazine
• (E)-N,5-bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine
• N,5-bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine
• B 663 (VAN)
• (3Z)-N,5-bis(4-chlorophenyl)-3-[(1-methylethyl)imino]-3,5-dihydrophenazin-2-amine
• Lamprene (TN)
• SMR000058704
• B 663, pharmaceutical
• SR-05000001807
• EINECS 217-980-2
• UNII-D959AE5USF
• NSC 141046
• BRN 0060420
• Colfazimine
• Clofazimine (JAN/USP/INN)
• (3E)-N,5-bis(4-chlorophenyl)-3-isopropylimino-phenazin-2-amine
• Clofazimine [USAN:USP:INN:BAN]
• Prestwick_685
• MFCD00056793
• 3-(p-Chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin [German]
• SMP2_000339
• B663
• CPD000058704
• CLOFAZIMINE [MI]
• Prestwick0_000376
• Prestwick1_000376
• Prestwick2_000376
• Prestwick3_000376
• CLOFAZIMINE [INN]
• CLOFAZIMINE [JAN]
• CLOFAZIMINE [USAN]
• B. 663
• CLOFAZIMINE [VANDF]
• COLFAZIMINE [VANDF]
• cid_2794
• CHEMBL1292
• CLOFAZIMINE [MART.]
• BIDD:PXR0147
• SCHEMBL26757
• SCHEMBL26758
• BSPBio_000531
• CLOFAZIMINE [USP-RS]
• CLOFAZIMINE [WHO-DD]
• CLOFAZIMINE [WHO-IP]
• 4-25-00-03033 (Beilstein Handbook Reference)
• MLS000028617
• MLS001424318
• MLS006010789
• SPBio_002452
• BPBio1_000585
• CHEBI:3749
• DTXCID302839
• GTPL9184
• SCHEMBL5663361
• CLOFAZIMINE [ORANGE BOOK]
• WDQPAMHFFCXSNU-KRUMMXJUSA-N
• CLOFAZIMINE [EP MONOGRAPH]
• CLOFAZIMINE [USP IMPURITY]
• HMS1569K13
• HMS2052B05
• HMS2093J10
• HMS2096K13
• HMS2231B04
• HMS3370N05
• HMS3394B05
• HMS3652A16
• HMS3713K13
• KUC109573N
• Pharmakon1600-01505974
• CLOFAZIMINE [USP MONOGRAPH]
• AMY22515
• BCP07792
• CLOFAZIMINUM [WHO-IP LATIN]
• HY-B1046
• KSC-27-052A
• Tox21_110516
• BDBM50318909
• BDBM50378783
• NSC759283
• s4107
• AKOS015896438
• AKOS026749881
• N,5-Bis(4-chlorophenyl)-3,5-dihydro-3-(isopropyliaino)phenazin-2-amine
• CCG-101159
• CCG-269477
• CS-4567
• DB00845
• KS-1412
• NC00409
• NSC-759283
• NCGC00016600-02
• NCGC00016600-03
• NCGC00016600-04
• NCGC00016600-05
• NCGC00016600-07
• NCGC00016600-08
• NCGC00016600-09
• NCGC00179529-01
• SMR004701474
• Clofazimine 100 microg/mL in Acetonitrile
• Phenazine,10-dihydro-2-(isopropylimino)-
• SBI-0206865.P001
• C2866
• FT-0657414
• SW196840-4
• C06915
• D00278
• EN300-267815
• A814428
• EN300-21680301
• Q418611
• SR-01000000259
• J-013203
• SR-01000000259-6
• SR-05000001807-1
• SR-05000001807-2
• BRD-K56614220-001-10-9
• Z2037279473
• Clofazimine, European Pharmacopoeia (EP) Reference Standard
• N,5-bis(4-chlorophenyl)-3-propan-2-ylimino-2-phenazinamine
• N,5-bis(4-chlorophenyl)-3-propan-2-ylimino-phenazin-2-amine
• Clofazimine, United States Pharmacopeia (USP) Reference Standard
• 2-p-Chloranilino-5-p-chlorphenyl-3,5-dihydro-3-isopropylimino-phenazin
• (3E)-N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine
• (4-Chloro-phenyl)-[5-(4-chloro-phenyl)-3-isopropylimino-3,5-dihydro-phenazin-2-yl]-amine
• 2-Phenazinamine,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-
• 2-Phenazinamine,5-dihydro-N,5-bis(4-chlorophenyl)-3-[(1-methylethyl)imino]-
• 2-Phenazinamine,N,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-
• Clofazimine for system suitability, European Pharmacopoeia (EP) Reference Standard
• N,5-Bis(4-chlorophenyl)-3-([1-methylethyl]imino)-3,5-dihydro-2-phenazinamine #
• N,5-bis(4-chlorophenyl)-3-[(propan-2-yl)imino]-3,5-dihydrophenazin-2-amine
• Phenazine,10-dihydro-3-(p-chloroanilino)-10-(p-chlorophenyl)-2-(isopropylimino)-
• 2458811-14-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9796	97.96%
Caco-2	-	0.5827	58.27%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5091	50.91%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.9030	90.30%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5569	55.69%
BSEP inhibitior	+	0.9873	98.73%
P-glycoprotein inhibitior	+	0.7535	75.35%
P-glycoprotein substrate	+	0.8190	81.90%
CYP3A4 substrate	-	0.5502	55.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8234	82.34%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.8731	87.31%
CYP inhibitory promiscuity	+	0.9292	92.92%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7800	78.00%
Carcinogenicity (trinary)	Non-required	0.6023	60.23%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9542	95.42%
Skin irritation	-	0.6215	62.15%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9404	94.04%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.7550	75.50%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.4814	48.14%
Acute Oral Toxicity (c)	IV	0.6240	62.40%
Estrogen receptor binding	+	0.8670	86.70%
Androgen receptor binding	-	0.7273	72.73%
Thyroid receptor binding	+	0.8065	80.65%
Glucocorticoid receptor binding	+	0.7744	77.44%
Aromatase binding	+	0.6687	66.87%
PPAR gamma	+	0.8180	81.80%
Honey bee toxicity	-	0.8551	85.51%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.7573	75.73%
Fish aquatic toxicity	+	0.9709	97.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL230	P35354	Cyclooxygenase-2	97.57%	89.63%
CHEMBL3401	O75469	Pregnane X receptor	96.93%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.35%	86.33%
CHEMBL240	Q12809	HERG	95.24%	89.76%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	93.57%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.21%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.57%	95.56%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	89.01%	91.43%
CHEMBL221	P23219	Cyclooxygenase-1	88.31%	90.17%
CHEMBL2581	P07339	Cathepsin D	85.98%	98.95%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.81%	93.81%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.52%	96.67%
CHEMBL1936	P10721	Stem cell growth factor receptor	84.42%	84.17%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.13%	93.03%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	83.90%	97.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.80%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.39%	94.00%
CHEMBL1293289	P25440	Bromodomain-containing protein 2	82.96%	86.19%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.13%	89.62%
CHEMBL2069	P21731	Thromboxane A2 receptor	81.81%	92.62%
CHEMBL2535	P11166	Glucose transporter	80.39%	98.75%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 2794
• LOTUS: LTS0067857
• wikiData: Q418611