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Chemistry

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Also known as: 1642-54-2, Hetrazan, Loxuran, Dicarocide, Caritrol, Diethylcarbamazine (citrate)

Molecular Formula

C₁₆H₂₉N₃O₈

Molecular Weight

391.42 g/mol

InChI Key

PGNKBEARDDELNB-UHFFFAOYSA-N

FDA UNII

OS1Z389K8S

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

1 2D Structure

Diethylcarbamazine Citrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-diethyl-4-methylpiperazine-1-carboxamide;2-hydroxypropane-1,2,3-tricarboxylic acid

2.1.2 InChI

InChI=1S/C10H21N3O.C6H8O7/c1-4-12(5-2)10(14)13-8-6-11(3)7-9-13;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-9H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

2.1.3 InChI Key

PGNKBEARDDELNB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

OS1Z389K8S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbamazine

2. Citrate, Diethylcarbamazine

3. Diethylcarbamazine

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. 1642-54-2

2. Hetrazan

3. Loxuran

4. Dicarocide

5. Caritrol

6. Diethylcarbamazine (citrate)

7. Eosinopin

8. Filazine

9. Franocide

10. Franozan

11. Carbam Palatabs

12. Ditrazin Citrate

13. Ethodryl Citrate

14. Diro-form

15. Dec Chewable

16. Dek-tabs

17. Diethylcarbamazine Dihydrogen Citrate

18. Diethylcarbamazane Citrate

19. D.e.c. Sol

20. Diethylcarbamazine Acid Citrate

21. Diethylcarbamazine Citrate Salt

22. Diethylcarbamazine Hydrogen Citrate

23. Ethylaminoazine Citrate

24. 1-methyl-4-diethylcarbamoylpiperazine Citrate

25. Nsc-80513

26. N,n-diethyl-4-methyl-1-piperazinecarboxamide Citrate

27. 1-diethylcarbamoyl-4-methylpiperazine Dihydrogen Citrate

28. Mls000069762

29. Mls001074102

30. Os1z389k8s

31. N,n-diethyl-4-methyl-1-piperazinecarboxamide Citrate (1:1)

32. N,n-diethyl-4-methyl-1-piperazinecarboxamide Dihydrogen Citrate

33. 1-piperazinecarboxamide, N,n-diethyl-4-methyl-, 2-hydroxy-1,2,3-propanetricarboxylate

34. N,n-diethyl-4-methylpiperazine-1-carboxamide 2-hydroxypropane-1,2,3-tricarboxylate

35. Ncgc00017034-01

36. Dirocide

37. Ditrazine

38. Ditrazinum

39. Filarabits

40. Longicid

41. Smr000058650

42. Cas-1642-54-2

43. Ditrazini Citras

44. Carricide Citrate

45. Ditrazine Citrate

46. Dsstox_cid_25555

47. Dsstox_rid_80952

48. N,n-diethyl-4-methylpiperazine-1-carboxamide;2-hydroxypropane-1,2,3-tricarboxylic Acid

49. 1642-54-1(citrate); 90-89-1(free Base)

50. Dsstox_gsid_45555

51. N,n-diethyl-4-methylpiperazine-1-carboxamide Citrate

52. Diethylcarbamazini Citras

53. Hsdb 6421

54. Sr-01000759234

55. Einecs 216-696-6

56. Mfcd00039124

57. Nsc 80513

58. Unii-os1z389k8s

59. Hetrazan (tn)

60. Prestwick_166

61. Diethylcarbamazine Citrate [usp:jan]

62. N,n-diethyl-4-methyl-1-piperazine Carboxamide Citrate

63. 1-piperazinecarboxamide, N,n-diethyl-4-methyl-, Citrate

64. Opera_id_558

65. 1-piperazinecarboxamide, N,n-diethyl-4-methyl-, Citrate (1:1)

66. N,n-diethyl-4-methyl-1-piperazinecarboxamide Dihydrogen Citrate (1:1)

67. Chembl937

68. 1-piperazinecarboxamide, N,n-diethyl-4-methyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

69. Schembl37736

70. Mls002207116

71. Mls004773909

72. Spectrum1500242

73. Chebi:4528

74. Dtxsid4045555

75. Hms501l10

76. Hms1568j10

77. Hms1920g06

78. Hms2091m16

79. Hms2095j10

80. Hms2234d17

81. Hms3370g20

82. Hms3712j10

83. Pharmakon1600-01500242

84. Tox21_110748

85. Ccg-40067

86. Nsc152050

87. Nsc756735

88. S4564

89. Akos003390253

90. Tox21_110748_1

91. Cs-3871

92. Diethylcarbamazine Citrate (jp17/usp)

93. Diethylcarbamazine Citrate [mi]

94. Nsc-152050

95. Nsc-756735

96. 2-hydroxypropane-1,2,3-tricarboxylic Acid; N,n-diethyl-4-methylpiperazine-1-carboxamide

97. Diethylcarbamazine Citrate [jan]

98. Diethylcarbamazine Citrate [hsdb]

99. Ncgc00017034-02

100. Ncgc00017034-03

101. Ncgc00090954-07

102. Ncgc00094651-01

103. Ncgc00094651-02

104. Bs-15595

105. Diethylcarbamazine Citrate [mart.]

106. Hy-12642

107. Diethylcarbamazine Citrate [usp-rs]

108. Diethylcarbamazine Citrate [who-dd]

109. Db-043586

110. D1898

111. Ft-0624487

112. C73172

113. D00803

114. Diethylcarbamazine Citrate [green Book]

115. Diethylcarbamazine Citrate [orange Book]

116. Diethylcarbamazine Citrate [usp Impurity]

117. A810546

118. Diethylcarbamazine Citrate [usp Monograph]

119. Wln: T6n Dntj Avn2&2 D1 &ov1xqvo&1vo

120. Sr-01000759234-2

121. Sr-01000759234-4

122. W-107945

123. Diethylcarbamazine Dihydrogen Citrate [who-ip]

124. Q27285812

125. Diethylcarbamazini Dihydrogenocitras [who-ip Latin]

126. 1-piperazinecarboxamide,n-diethyl-4-methyl-, Citrate (1:1)

127. Diethylcarbamazine Citrate Salt, Vetranal(tm), Analytical Standard

128. Diethylcarbamazine Citrate, British Pharmacopoeia (bp) Reference Standard

129. Diethylcarbamazine Citrate, European Pharmacopoeia (ep) Reference Standard

130. 1-piperazinecarboxamide,n-diethyl-4-methyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

131. Diethylcarbamazine Citrate, United States Pharmacopeia (usp) Reference Standard

132. N,n-diethyl-4-methyl-1-piperazinecarboxamide; 2-hydroxypropane-1,2,3-tricarboxylic Acid

133. 16354-46-4

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₉N₃O₈
Molecular Weight	391.42 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	391.19546489 g/mol
Monoisotopic Mass	391.19546489 g/mol
Topological Polar Surface Area	159 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	411
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	2

4 Drug and Medication Information

4.1 Therapeutic Uses

Filaricides; Lipoxygenase Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Dietylcarbamazine citrate is usually admin by mouth as tablets. ... It has also been given by intramuscular injection.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 91

For mass treatment /against microfilariae of Wucereria bancrofti and Wuchereria malayi/ with the objective of reducing microfilaremia to subinfective levels for mosquitoes, the dose is 2 mg/kg, three times daily after meals, for 7 days for treatment directed toward possible cure, this dosage regimen is carried out for 10 to 30 days. ... For practical purposes, an adequate amount seems to be a total dose of about 72 mg/kg of the citrate salt.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1010

For /treatment against Loa loa microfilariae/ a dose of 2 mg/kg should be given 3 times daily after meals for 2 to 3 weeks. If repeated courses are required to produce cure, they should be separated by periods of 3 to 4 weeks.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1011

For more Therapeutic Uses (Complete) data for DIETHYLCARBAMAZINE CITRATE (16 total), please visit the HSDB record page.

4.2 Drug Warning

There are no contraindications to the use of diethylcarbamazine, other than the fact that low doses should be used for initial therapy, especially in onchocerciasis and infection due to Loa loa (to minimize adverse reactions to destruction of the parasites).

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1011

Special care should be taken in using diethylcarbamazine in areas where both onchocerciasis and loaiasis occur. /Diethylcarbamazine/

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 91

In patients infected with Onchocerca volvulus or Wuchereria malayi, and to a lesser extent in those infected with Wuchereria bancrofti and Loa loa, the initial systemic reactions provoked by the massive destruction of microfilariae, or both during treatment may be severs. In such cases the dosage should be lowered or the drug stopped temporarily. Relief of these symptoms in heavily infected individuals may be afforded by pretreatment with corticosteroids, for example, dexamethasone (2 to 4 mg twice daily).

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1011

... use of diethylcarbamazine in microfilariae-positive dogs, is strictly contraindicated. ... The AVMA Council on Veterinary Services advises that all previously treated heartworm cases should be checked 3 months after the dog is started on diethylcarbamazine. If microfilariae are detected, the prophylactic program must be stopped until existing microfilariae are eliminated.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 849

For more Drug Warnings (Complete) data for DIETHYLCARBAMAZINE CITRATE (6 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Filaricides

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

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.)

5.2 Absorption, Distribution and Excretion

Diethylcarbamazine is readily absorbed from the gastrointestinal tract. After a single oral dose of 200 to 400 mg, the concentration in plasma peaks in 1 to 2 hours ... Excretion is nearly all urinary, & more than 70% of the drug appears as metabolites. The compound is distributed almost completely throughout all body compartments with the exception of fat. Little accumulation occurs when repeated doses are given. /Diethylcarbamazine/

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1010

5.3 Metabolism/Metabolites

Only 10-25% of the drug is excreted unchanged; the remainder is excreted as one of four known metabolites, all of which contain the intact piperazine ring.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 849

5.4 Biological Half-Life

... the plasma half-life /in man/ is about 8 hr after a 200 mg dose and 12 hr after an 800 mg dose.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1010

5.5 Mechanism of Action

The drug has two types of action on susceptible microfilariae. The first is to decrease the muscular activity and eventually immobilize the organisms; this may result from a hyerpolarizing effect of the piperazine moiety, and it causes dislocation of the parasites from their normal habitat in the host. The second action is to produce alterations in the microfilarial surface membranes, thereby rendering them more susceptible to destruction by host defense mechanisms. There is definite evidence that diethylcarbamazine kills adult worms of Loa loa and presumptive evidence that it kills adult Wuchereria bancrofti and Wuchereria malayi. However, it has little action against adult Onchocerca volvulus. The mechanism of the filaricidal action of diethylcarbamazine is unknown. /Diethylcarbamazine/

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1010

It is postulated that in naturally infected animals, diethylcarbamazine somehow promotes the combination of antigen and antibody on the surface of serotonin-rich platelets. Serotonin is released from damaged platelets, which dramatically increases vascular permeability and leads to shock. This generally but not always occurs in dogs with a high microfilaremia.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 848

Diethylcarbamazine causes rapid disappearance of microfilariae of Wuchereriia bancrofti, Wuchereria malayi, and Loa loa from the blood of man. The drug causes microfilariae of Onchlcerca volvulus to disappear from the skin but does not kill microfilariae in nodules that contain the adult (female) worms. It does not affect the microfilariae of Wuchereria bancrofti in a hydrocele, despite penetration into the fluid.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 1010

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