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Chemistry

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Also known as: 90-89-1, N,n-diethyl-4-methylpiperazine-1-carboxamide, Carbamazine, Diethyl carbamazine, Carbilazine, Ethodryl

Molecular Formula

C₁₀H₂₁N₃O

Molecular Weight

199.29 g/mol

InChI Key

RCKMWOKWVGPNJF-UHFFFAOYSA-N

FDA UNII

V867Q8X3ZD

An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.

Diethylcarbamazine is an Anthelmintic.

1 2D Structure

Diethylcarbamazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-diethyl-4-methylpiperazine-1-carboxamide

2.1.2 InChI

InChI=1S/C10H21N3O/c1-4-12(5-2)10(14)13-8-6-11(3)7-9-13/h4-9H2,1-3H3

2.1.3 InChI Key

RCKMWOKWVGPNJF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CC)C(=O)N1CCN(CC1)C

2.2 Other Identifiers

2.2.1 UNII

V867Q8X3ZD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbamazine

2. Citrate, Diethylcarbamazine

3. Diethylcarbamazine Citrate

4. Diethylcarbamazine Citrate (1:1)

5. Diethylcarbamazine Citrate (1:2)

6. Diethylcarbamazine L-tartrate (1:1)

7. Diethylcarbamazine Maleate

8. Diethylcarbamazine Monohydrochloride

9. Diethylcarbamazine Phosphate (1:1)

10. Hetrazan

11. Loxuran

12. Maleate, Diethylcarbamazine

13. Monohydrochloride, Diethylcarbamazine

14. Notezine

2.3.2 Depositor-Supplied Synonyms

1. 90-89-1

2. N,n-diethyl-4-methylpiperazine-1-carboxamide

3. Carbamazine

4. Diethyl Carbamazine

5. Carbilazine

6. Ethodryl

7. Notezine

8. Cypip

9. Bitirazine

10. Caricide

11. Ditrazine Base

12. Caracide

13. Spatonin

14. N,n-diethyl-4-methyl-1-piperazinecarboxamide

15. N,n-diethylcarbamazine

16. 1-piperazinecarboxamide, N,n-diethyl-4-methyl-

17. Camin

18. Rp 3799

19. Diethylcarbamazine (inn)

20. 84l

21. Chebi:4527

22. V867q8x3zd

23. Bitirazine; Caracide;carbamazine

24. Mmv002816

25. Diaethylcarbamazinum

26. Dietilcarbamazina

27. Diethylcarbamazinum

28. Diethylcarbamazine [inn]

29. Diethylcarbamazine [inn:ban]

30. Diethylcarbamazinum [inn-latin]

31. Dietilcarbamazina [inn-spanish]

32. Nsc1364

33. Camin (tn)

34. Einecs 202-023-3

35. 1-diethylcarbamoyl-4-methylpiperazine

36. Brn 0143029

37. Unii-v867q8x3zd

38. Ai3-19612

39. 1-diethylcarbamyl-4-methylpiperazine

40. 1-methyl-4-diethylcarbamoylpiperazine

41. Banocide (salt/mix)

42. Caritrol (salt/mix)

43. Nemacide (salt/mix)

44. Spectrum_000938

45. Nn-diethyl-4-methyl-1-piperazinecarboxamide

46. Prestwick0_000284

47. Prestwick1_000284

48. Prestwick2_000284

49. Prestwick3_000284

50. Spectrum2_001022

51. Spectrum3_000390

52. Spectrum4_000511

53. Spectrum5_000877

54. Diethyl Carbamazine Citrate

55. Chembl684

56. Ec 202-023-3

57. Schembl67289

58. Bspbio_000188

59. Bspbio_002179

60. Kbiogr_001081

61. Kbioss_001418

62. 4-23-00-00225 (beilstein Handbook Reference)

63. Divk1c_000548

64. Spbio_001203

65. Spbio_002407

66. Diethylcarbamazine [mi]

67. Bpbio1_000208

68. Zinc1288

69. Dtxsid1022928

70. Kbio1_000548

71. Kbio2_001418

72. Kbio2_003986

73. Kbio2_006554

74. Kbio3_001399

75. Ninds_000548

76. Hms3604f12

77. Diethylcarbamazine [who-dd]

78. 1-diethylcarbamoyl-4-methylpiperzine

79. Hy-12642a

80. Mfcd00023288

81. Akos003268016

82. Db00711

83. Ds-9360

84. Idi1_000548

85. S10791

86. Ncgc00178778-01

87. Ncgc00178778-02

88. Ncgc00178778-07

89. Sbi-0051345.p003

90. Db-080764

91. R.p. 3799

92. 1-(n,n-diethylcarbamoyl)-4-methylpiperazine

93. Ab00053457

94. Cs-0013568

95. Ft-0624832

96. C07968

97. D07825

98. N,n-diethyl-4-methyl-piperazine-1-carboxamide

99. Ab00053457_12

100. Q409267

101. Sr-01000759234-8

102. Brd-k45542189-048-05-6

103. Brd-k45542189-048-15-5

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₁N₃O
Molecular Weight	199.29 g/mol
XLogP3	0.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	199.168462302 g/mol
Monoisotopic Mass	199.168462302 g/mol
Topological Polar Surface Area	26.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	184
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 Indication

Used for the treatment of certain filarial diseases, including tropical pulmonary eosinophilia, loiasis, and lymphatic filariasis caused by infection with Wuchereria bancrofti, Brugia malayi, or Brugia timori.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Diethylcarbamazine is an anthelmintic drug that does not resemble other antiparasitic compounds. It is a synthetic organic compound which is highly specific for several parasites and does not contain any toxic metallic elements.

5.2 MeSH Pharmacological Classification

Lipoxygenase Inhibitors

Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)

Filaricides

Pharmacological agents destructive to nematodes in the superfamily Filarioidea. (See all compounds classified as Filaricides.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

DIETHYLCARBAMAZINE

5.3.2 FDA UNII

V867Q8X3ZD

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Anthelmintic

5.4 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02C - Antinematodal agents

P02CB - Piperazine and derivatives

P02CB02 - Diethylcarbamazine

5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed following oral administration.

5.6 Metabolism/Metabolites

Partially metabolized to diethylcarbamazine N-oxide.

5.7 Biological Half-Life

Approximately 8 hours.

5.8 Mechanism of Action

The mechanism of action of diethylcarbamazine is thought to involve sensitizing the microfilariae to phagocytosis. One study showed that diethylcarbamazine's activity against Brugia malayi microfilariae is dependent on inducible nitric-oxide synthase and the cyclooxygenase pathway. It confirmed the important role of the arachidonic acid metabolic pathway in diethylcarbamazine's mechanism of action in vivo and showes that in addition to its effects on the 5-lipoxygenase pathway, it targets the cyclooxygenase pathway and COX-1.

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API Reference Price

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