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Nifurtimox

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Chemistry

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Also known as: Lampit, Bayer 2502, 23256-30-6, Nifurtimoxum, Bay 2502, Bayer-2502

Molecular Formula

C₁₀H₁₃N₃O₅S

Molecular Weight

287.29 g/mol

InChI Key

ARFHIAQFJWUCFH-IZZDOVSWSA-N

FDA UNII

M84I3K7C2O

A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.

1 2D Structure

Nifurtimox

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine

2.1.2 InChI

InChI=1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+

2.1.3 InChI Key

ARFHIAQFJWUCFH-IZZDOVSWSA-N

2.1.4 Canonical SMILES

CC1CS(=O)(=O)CCN1N=CC2=CC=C(O2)[N+](=O)[O-]

2.1.5 Isomeric SMILES

CC1CS(=O)(=O)CCN1/N=C/C2=CC=C(O2)[N+](=O)[O-]

2.2 Other Identifiers

2.2.1 UNII

M84I3K7C2O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bayer 2502

2. Lampit

2.3.2 Depositor-Supplied Synonyms

1. Lampit

2. Bayer 2502

3. 23256-30-6

4. Nifurtimoxum

5. Bay 2502

6. Bayer-2502

7. Chebi:7566

8. Bay-a2502

9. Bay-2502

10. Dndi1613515

11. 4-thiomorpholinamine, 3-methyl-n-((5-nitro-2-furanyl)methylene)-, 1,1-dioxide

12. M84i3k7c2o

13. 4-((5-nitrofurfurylidene)amino)-3-methylthiomorpholine 1,1-dioxide

14. Thiomorpholine, 3-methyl-4-((5-nitrofurfurylidene)amino)-, 1,1-dioxide

15. 4-thiomorpholinamine, 3-methyl-n-[(5-nitro-2-furanyl)methylene]-, 1,1-dioxide

16. Nifurtimox [inn:ban]

17. Nifurtimoxum [inn-latin]

18. Ccris 2201

19. (+/-)-nifurtimox

20. X4kcv4zi9m

21. Sr-01000838852

22. Einecs 245-531-0

23. 1g5dd3p35c

24. Unii-m84i3k7c2o

25. 4-[(5-nitrofurfurylidene)amino]-3-methylthiomorpholine 1,1-dioxide

26. Bay A2502

27. (+)-nifurtimox

28. (-)-nifurtimox

29. Lampit (tn)

30. Nifurtimox, (+)-

31. Nifurtimox, (-)-

32. Nifurtimox [mi]

33. Nifurtimox [inn]

34. 4-((5-nitrofurfurylidene)amino)-3-methylthiomorpholine-1,1-dioxide

35. Nifurtimox (usan/inn)

36. Prestwick2_001024

37. Prestwick3_001024

38. Unii-x4kcv4zi9m

39. Nifurtimox [usan]

40. 1-((5-nitrofurfurylidene)amino)-2-methyltetrahydro-1,4-thiazine-4,4-dioxide

41. 3-methyl-n-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine 1,1-dioxide

42. Nifurtimox [mart.]

43. Nifurtimox [who-dd]

44. Nifurtimox [who-ip]

45. Tetrahydro-3-methyl-4-((5-nitrofurfurylidene)amino)-2h-1,4-thiazine 1,1-dioxide

46. Unii-1g5dd3p35c

47. Bspbio_001207

48. Bpbio1_001329

49. Chembl290960

50. Schembl1650162

51. Nifurtimox [orange Book]

52. Nifurtimox, >=98% (hplc)

53. Chebi:91472

54. Bay2502

55. Kuc114565n

56. 39072-15-6

57. 39072-16-7

58. Ex-a4624

59. Nifurtimoxum [who-ip Latin]

60. Bdbm50259708

61. S6459

62. Cs-w020813

63. Db11820

64. Hy-w040073

65. Ksc-427-39-1

66. C08002

67. D00833

68. A912676

69. J-015055

70. Sr-01000838852-2

71. Sr-01000838852-3

72. Brd-a84020532-001-03-5

73. Brd-a84020532-001-04-3

74. (e)-3-methyl-4-(((5-nitrofuran-2-yl)methylene)amino)thiomorpholine 1,1-dioxide

75. 4-thiomorpholinamine, 3-methyl-n-((5-nitro-2-furanyl)methylene)-, 1,1-dioxide, (+)-

76. 4-thiomorpholinamine, 3-methyl-n-((5-nitro-2-furanyl)methylene)-, 1,1-dioxide, (-)-

77. N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitro-2-furyl)methanimine

78. Tetrahydro-3-methyl-4-((5-nitrofurfurylidene)amino)-4h-1,4-thiazine 1,1-dioxide

79. (rs)-3-methyl-n-((1e)-(5-nitro-2-furyl)methylene)thiomorpholin-4-amine 1,1-dioxide

2.4 Create Date

2006-06-06

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₃N₃O₅S
Molecular Weight	287.29 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	287.05759170 g/mol
Monoisotopic Mass	287.05759170 g/mol
Topological Polar Surface Area	117 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	467
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Nifurtimox is indicated in pediatric patients under 18 weighing at least 2.5 kg. Continued approval of this drug for this indication is dependent upon confirmatory clinical trial results.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nifurtimox exerts trypanosomal activity against Trypanosoma cruzi, treating Chagas disease. One study reports that nifurtimox and other benzofuran derivatives reduce parasite dehydrogenase activity. Results of a recent phase III clinical trial have shown that a significant number of pediatric patients with acute or chronic Chagas disease treated with nifurtimox were immunoglobulin G (IgG) antibody negative and demonstrated at least a 20% decrease in optical density on two IgG antibody tests for T. cruzi antigens.

5.2 MeSH Pharmacological Classification

Trypanocidal Agents

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)

5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01C - Agents against leishmaniasis and trypanosomiasis

P01CC - Nitrofuran derivatives

P01CC01 - Nifurtimox

5.4 Absorption, Distribution and Excretion

Absorption

The average AUC of nifurtimox is estimated between 1676-2670 gh/L. One pharmacokinetic study of healthy volunteers revealed an AUC of 5430 ngml^-1h. Cmax ranges between 425-568 g/L (2650%) after a single dose of 20 mg with food in adults. Tmax is 4 hours, ranging from 2 to 8 hours post-dose in the fed state. In a pharmacokinetic study of healthy volunteers, serum concentration was low, likely due to the first-pass effect.

Route of Elimination

In the fed state, 44% of the dose was mainly recovered in the urine as metabolites. Fecal and biliary excretion of nifurtimox have not been studied.

Volume of Distribution

Nifurtimox crosses the blood-brain barrier and the placenta.

Clearance

One pharmacokinetic study of nifurtimox revealed a clearance of 193.4 lh^-1. In patients without renal failure; clearance was 99.7 lh^-1.

5.5 Metabolism/Metabolites

Nifurtimox is largely metabolized via nitroreductase enzymes. Two major inactive metabolites have been identified: M-4 and M-6. The M-4 metabolite is a cysteine conjugate of nifurtimox, while M-6 is likely formed by hydrolytic cleavage of the hydrazone moiety of nifurtimox. Other minor metabolites have also been identified in human plasma.

5.6 Biological Half-Life

The elimination half-life of nifurtimox ranges from 2.43.6 hours. A pharmacokinetic study of healthy volunteers and patients with renal failure revealed respective mean half-lives of 2.95 h and 3.95 h.

5.7 Mechanism of Action

The mechanism of action of nifurtimox has not been fully elucidated, however, is believed to occur by the activation of nitroreductase enzymes that produce reactive metabolites with a series of deleterious effects on Trypanosoma cruzi, the parasite causing Chagas disease. The antiprotozoal actions of nifurtimox occur both intracellularly and extracellularly. Inhibition of parasite dehydrogenase activity is another purported mode of action of nifurtimox that warrants further research.

Drugs in Development