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Clofazimine

Clofazimine

Synopsis, Chemistry

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Also known as: 2030-63-9, Lamprene, Chlofazimine, Lampren, Clofazimina, Clofaziminum

Molecular Formula

C₂₇H₂₂Cl₂N₄

Molecular Weight

473.4 g/mol

InChI Key

WDQPAMHFFCXSNU-UHFFFAOYSA-N

FDA UNII

D959AE5USF

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)

Clofazimine is an Antimycobacterial.

1 2D Structure

Clofazimine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine

2.1.2 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

2.1.3 InChI Key

WDQPAMHFFCXSNU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl

2.2 Other Identifiers

2.2.1 UNII

D959AE5USF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. B 663

2. B-663

3. B663

4. G 30,320

5. G-30,320

6. G30,320

7. Lamprene

8. N,5-bis(4-chlorophenyl)-3,5-dihydro-3-((1-methylethyl)imino)-2-phenazinamine

2.3.2 Depositor-Supplied Synonyms

1. 2030-63-9

2. Lamprene

3. Chlofazimine

4. Lampren

5. Clofazimina

6. Clofaziminum

7. Nsc-141046

8. B 663 (pharmaceutical)

9. Clofaziminum [inn-latin]

10. Clofazimina [inn-spanish]

11. G 30320

12. N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine

13. B-663

14. 3-(p-chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin

15. 3-(p-chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine

16. B 663

17. 3-(p-chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-phenazine

18. G-30320

19. D959ae5usf

20. 2-phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-((1-methylethyl)imino)-

21. Chembl1083384

22. N,5-bis(4-chlorophenyl)-3,5-dihydro-3-(isopropylimino)phenazin-2-amine

23. 2-phenazinamine, 3,5-dihydro-n,5-bis(4-chlorophenyl)-3-((1-methylethyl)imino)-

24. N,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-2-phenazinamine

25. Mmv687800

26. Nsc141046

27. Phenazine, 2,10-dihydro-3-(p-chloroanilino)-10-(p-chlorophenyl)-2-(isopropylimino)-

28. Phenazine, 3-(p-chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)-

29. Ncgc00016600-01

30. Cas-2030-63-9

31. N,5-bis(4-chlorophenyl)-3-(propan-2-ylimino)-3,5-dihydrophenazin-2-amine

32. 2-phenazinamine, N,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-

33. 3-(p-chloranilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine

34. Riminophenazine

35. (e)-n,5-bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine

36. N,5-bis(4-chlorophenyl)-3,5-dihydro-3-(isopropyliaino)phenazin-2-amine

37. B 663 (van)

38. (3z)-n,5-bis(4-chlorophenyl)-3-[(1-methylethyl)imino]-3,5-dihydrophenazin-2-amine

39. Lamprene (tn)

40. Smr000058704

41. B 663, Pharmaceutical

42. Sr-05000001807

43. Einecs 217-980-2

44. Unii-d959ae5usf

45. Nsc 141046

46. Brn 0060420

47. Colfazimine

48. Clofazimine (jan/usp/inn)

49. (3e)-n,5-bis(4-chlorophenyl)-3-isopropylimino-phenazin-2-amine

50. Liposome-encapsulated Clofazimine

51. Clofazimine [usan:usp:inn:ban]

52. Prestwick_685

53. Mfcd00056793

54. 3-(p-chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin [german]

55. Smp2_000339

56. (non-d)clofazimine-d7

57. B663

58. Cpd000058704

59. Clofazimine [mi]

60. Prestwick0_000376

61. Prestwick1_000376

62. Prestwick2_000376

63. Prestwick3_000376

64. Clofazimine [inn]

65. Clofazimine [jan]

66. Dsstox_cid_2839

67. Clofazimine [usan]

68. B. 663

69. Clofazimine [vandf]

70. Colfazimine [vandf]

71. Cid_2794

72. Chembl1292

73. Clofazimine [mart.]

74. Dsstox_rid_76752

75. Bidd:pxr0147

76. Dsstox_gsid_22839

77. Schembl26757

78. Schembl26758

79. Bspbio_000531

80. Clofazimine [usp-rs]

81. Clofazimine [who-dd]

82. Clofazimine [who-ip]

83. 4-25-00-03033 (beilstein Handbook Reference)

84. Mls000028617

85. Mls001424318

86. Mls006010789

87. Spbio_002452

88. Bpbio1_000585

89. Chebi:3749

90. Gtpl9184

91. Schembl5663361

92. Dtxsid7022839

93. Clofazimine [orange Book]

94. Clofazimine [ep Monograph]

95. Clofazimine [usp Impurity]

96. Hms1569k13

97. Hms2052b05

98. Hms2093j10

99. Hms2096k13

100. Hms2231b04

101. Hms3370n05

102. Hms3394b05

103. Hms3652a16

104. Hms3713k13

105. Kuc109573n

106. Pharmakon1600-01505974

107. Clofazimine [usp Monograph]

108. Amy22515

109. Bcp07792

110. Clofaziminum [who-ip Latin]

111. Hy-b1046

112. Ksc-27-052a

113. Tox21_110516

114. Bdbm50318909

115. Bdbm50378783

116. Nsc759283

117. S4107

118. Zinc17953024

119. Akos015896438

120. Akos026749881

121. Zinc100037101

122. Zinc253916263

123. Ccg-101159

124. Ccg-269477

125. Cs-4567

126. Db00845

127. Ks-1412

128. Nc00409

129. Nsc-759283

130. Ncgc00016600-02

131. Ncgc00016600-03

132. Ncgc00016600-04

133. Ncgc00016600-05

134. Ncgc00016600-07

135. Ncgc00016600-08

136. Ncgc00016600-09

137. Ncgc00179529-01

138. Smr004701474

139. Clofazimine 100 Microg/ml In Acetonitrile

140. Phenazine,10-dihydro-2-(isopropylimino)-

141. Sbi-0206865.p001

142. Ft-0657414

143. Sw196840-4

144. A16462

145. C06915

146. D00278

147. 030c639

148. A814428

149. Q418611

150. Sr-01000000259

151. J-013203

152. Sr-01000000259-6

153. Sr-05000001807-1

154. Sr-05000001807-2

155. Brd-k56614220-001-10-9

156. Z2037279473

157. Clofazimine, European Pharmacopoeia (ep) Reference Standard

158. N,5-bis(4-chlorophenyl)-3-propan-2-ylimino-2-phenazinamine

159. N,5-bis(4-chlorophenyl)-3-propan-2-ylimino-phenazin-2-amine

160. Clofazimine, United States Pharmacopeia (usp) Reference Standard

161. 2-p-chloranilino-5-p-chlorphenyl-3,5-dihydro-3-isopropylimino-phenazin

162. N,5-bis(4-chlorophenyl)-3-(isopropylimino)-3,5-dihydrophenazin-2-amine

163. (4-chloro-phenyl)-[5-(4-chloro-phenyl)-3-isopropylimino-3,5-dihydro-phenazin-2-yl]-amine

164. 2-phenazinamine,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-

165. 2-phenazinamine,5-dihydro-n,5-bis(4-chlorophenyl)-3-[(1-methylethyl)imino]-

166. 2-phenazinamine,n,5-bis(4-chlorophenyl)-3,5-dihydro-3-[(1-methylethyl)imino]-

167. Clofazimine For System Suitability, European Pharmacopoeia (ep) Reference Standard

168. N,5-bis(4-chlorophenyl)-3-([1-methylethyl]imino)-3,5-dihydro-2-phenazinamine #

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

170. Phenazine,10-dihydro-3-(p-chloroanilino)-10-(p-chlorophenyl)-2-(isopropylimino)-

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₂Cl₂N₄
Molecular Weight	473.4 g/mol
XLogP3	7.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	472.1221521 g/mol
Monoisotopic Mass	472.1221521 g/mol
Topological Polar Surface Area	40 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	829
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Lamprene
PubMed Health	Clofazimine (By mouth)
Drug Classes	Leprostatic
Active Ingredient	Clofazimine
Dosage Form	Capsule
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Novartis

2 of 2
Drug Name	Lamprene
PubMed Health	Clofazimine (By mouth)
Drug Classes	Leprostatic
Active Ingredient	Clofazimine
Dosage Form	Capsule
Route	Oral
Strength	50mg
Market Status	Prescription
Company	Novartis

4.2 Drug Indication

Clofazimine is indicated for the treatment of lepromatous leprosy, including dapsone-resistant lepromatous leprosy and lepromatous leprosy complicated by erythema nodosum leprosum. To prevent the development of drug resistance, it should be used only in combination with other antimycobacterial leprosy treatments.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Clofazimine exerts a slow bactericidal effect on Mycobacterium leprae (Hansen's bacillus) due primarily to its action on the bacterial outer membrane, though there is some evidence that activity on the bacterial respiratory chain and ion transporters may play a role. It also exerts anti-inflammatory properties due to the suppression of T-lymphocyte activity. Clofazimine has a relatively long duration of action owing to its long residence time in the body, but is still administered daily. Approximately 75-100% of patients receiving clofazimine will experience an orange-pink to brownish-black discoloration of the skin, conjunctivae, and bodily fluids. Skin discoloration may take several months or years to reverse following the cessation of therapy. Clofazimine has also been implicated in abdominal obstruction, in some cases fatal, due to the deposition of drug and formation of crystals in the intestinal mucosa - complaints of abdominal pain and nausea/vomiting should be investigated promptly, and the doses of clofazimine should be lowered or discontinued if it is found to be the culprit. Its use should be avoided in patients with hepatic dysfunction.

5.2 MeSH Pharmacological Classification

Leprostatic Agents

Substances that suppress Mycobacterium leprae, ameliorate the clinical manifestations of leprosy, and/or reduce the incidence and severity of leprous reactions. (See all compounds classified as Leprostatic Agents.)

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CLOFAZIMINE

5.3.2 FDA UNII

D959AE5USF

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Antimycobacterial

5.4 ATC Code

J - Antiinfectives for systemic use

J04 - Antimycobacterials

J04B - Drugs for treatment of lepra

J04BA - Drugs for treatment of lepra

J04BA01 - Clofazimine

5.5 Absorption, Distribution and Excretion

Absorption

Absorption varies from 45 to 62% following oral administration in leprosy patients. Co-administration of a 200mg dose of clofazimine with food resulted in a C_max of 0.41 mg/L with a T_max of 8 h; administered in a fasting state, the corresponding C_max was 30% lower while the time to Cmax was 12 h.

Route of Elimination

Part of an ingested dose of clofazimine is found in the feces, which may represent excretion in the bile, and a small amount is also eliminated in the sputum, sebum, and sweat. Excretion of unchanged drug and metabolites in a 24-hour urine collection was negligible.

Volume of Distribution

Clofazimine is highly lipophilic and therefore deposits primarily in fatty tissues and cells of the reticuloendothelial system, where it is taken up by macrophages and further distributed throughout the body. Crystalized deposits have been found in the mesenteric lymph nodes, adrenals, subcutaneous fat, liver, bile, gall bladder, spleen, small intestine, muscles, bones, and skin.

5.6 Metabolism/Metabolites

Three metabolites have been identified in the urine following repeated oral doses of clofazimine. It is unclear whether these metabolites are pharmacologically active. Metabolite I may be the result of the hydrolytic dehalogenation of clofazimine and metabolite II presumably is formed by a hydrolytic deamination reaction followed by glucuronidation.

5.7 Biological Half-Life

The mean elimination half-life is approximately 25 days.

5.8 Mechanism of Action

Although the precise mechanism(s) of action of clofazimine have not been elucidated, its antimicrobial activity appears to be membrane-directed. It was previously thought that, due to its lipophilicity, clofazimine participated in the generation of intracellular reactive oxygen species (ROS) via redox cycling, specifically H₂O₂ and superoxide, which then exerted an antimicrobial effect. A more recent and compelling theory involves clofazimine interacting with bacterial membrane phospholipids to generate antimicrobial lysophospholipids - bactericidal efficacy may, then, arise from the combined membrane-destabilizing effects of both clofazimine and lysophospholipids, which interfere with K+ uptake and, ultimately, ATP production. The anti-inflammatory activity of clofazimine is the result of its inhibition of T-lymphocyte activation and proliferation. Several mechanisms have been proposed, including direct antagonism of T-cell Kv 1.3 potassium channels and indirect action by promoting the release of E-series prostaglandins and reactive oxygen species from bystander neutrophils and monocytes.