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    Diethylcarbamazine

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    PharmaCompass
    $ API Ref.Price (USD/KG) : 28Xls

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    2D Structure
    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

    2D Structure

    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 Weight 199.29 g/mol
    Molecular Formula C10H21N3O
    XLogP30.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass199.168462302 g/mol
    Monoisotopic Mass199.168462302 g/mol
    Topological Polar Surface Area26.8 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity184
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.