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Substance Name: Clofazimine [USAN:USP:INN:BAN]
RN: 2030-63-9
UNII: D959AE5USF
InChIKey: WDQPAMHFFCXSNU-BGABXYSRSA-N

Note

  • 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. (From AMA Drug Evaluations Annual, 1993, p1619)

Molecular Formula

  • C27-H22-Cl2-N4

Molecular Weight

  • 473.4048
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antibacterial (Leprostatic)
  • Antibacterial (Tuberculostatic)
  • Antirheumatic Agents
  • Coloring Agents
  • Drug / Therapeutic Agent
  • Leprostatic Agents
  • Mutation Data
  • Peripheral Nervous System Agents
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Clofazimine
  • Clofazimine [USAN:USP:INN:BAN]

MeSH Heading

  • Clofazimine

Synonyms

  • 2-Phenazinamine, 3,5-dihydro-N,5-bis(4-chlorophenyl)-3-((1-methylethyl)imino)-
  • 2-Phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-((1-methylethyl)imino)-
  • 3-(p-Chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine
  • 3-(p-Chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin
  • 3-(p-Chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin [German]
  • 3-(p-Chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine
  • 4-25-00-03033 (Beilstein Handbook Reference)
  • B 663 (Pharmaceutical)
  • B 663 (VAN)
  • B-663
  • BRN 0060420
  • Chlofazimine
  • Clofazimina
  • Clofazimina [INN-Spanish]
  • Clofazimine
  • Clofaziminum
  • Clofaziminum [INN-Latin]
  • EINECS 217-980-2
  • G 30320
  • Lampren
  • Lamprene
  • NSC 141046
  • NSC-141046
  • UNII-D959AE5USF

Systematic Names

  • 2-Phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-((1-methylethyl)imino)-
  • Clofazimine
  • Phenazine, 2,10-dihydro-3-(p-chloroanilino)-10-(p-chlorophenyl)-2-(isopropylimino)-
  • Phenazine, 3-(p-chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-

Registry Numbers

CAS Registry Number

  • 2030-63-9

FDA UNII

  • D959AE5USF

System Generated Number

  • 0002030639

Structure Descriptors

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+

InChIKey

WDQPAMHFFCXSNU-BGABXYSRSA-N

Smiles

n1(c2ccc(Cl)cc2)c2c(nc3c1cccc3)cc(Nc1ccc(Cl)cc1)c(\c2)=N/C(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 4400mg/kg (4400mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 794, 1970.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 794, 1970.
rabbit LD50 oral 1500mg/kg (1500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 794, 1970.
rat LD50 oral 8400mg/kg (8400mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 794, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 210-212 deg C   EXP
pKa Dissociation Constant 8.51 (none)   EXP
log P (octanol-water) 7.66 (none)   EXP
Water Solubility 0.225 mg/L 25 EST
Vapor Pressure 1.45E-12 mm Hg 25 EST
Henry's Law Constant 3.60E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.36E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.