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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
    Diethylcarbamazine Citrate
    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 Weight 391.42 g/mol
    Molecular Formula C16H29N3O8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count7
    Exact Mass391.19546489 g/mol
    Monoisotopic Mass391.19546489 g/mol
    Topological Polar Surface Area159 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity411
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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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    ABOUT THIS PAGE

    Diethylcarbamazine Citrate Manufacturers

    A Diethylcarbamazine Citrate manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Diethylcarbamazine Citrate, including repackagers and relabelers. The FDA regulates Diethylcarbamazine Citrate manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Diethylcarbamazine Citrate API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Diethylcarbamazine Citrate manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Diethylcarbamazine Citrate Suppliers

    A Diethylcarbamazine Citrate supplier is an individual or a company that provides Diethylcarbamazine Citrate active pharmaceutical ingredient (API) or Diethylcarbamazine Citrate finished formulations upon request. The Diethylcarbamazine Citrate suppliers may include Diethylcarbamazine Citrate API manufacturers, exporters, distributors and traders.

    click here to find a list of Diethylcarbamazine Citrate suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Diethylcarbamazine Citrate USDMF

    A Diethylcarbamazine Citrate DMF (Drug Master File) is a document detailing the whole manufacturing process of Diethylcarbamazine Citrate active pharmaceutical ingredient (API) in detail. Different forms of Diethylcarbamazine Citrate DMFs exist exist since differing nations have different regulations, such as Diethylcarbamazine Citrate USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Diethylcarbamazine Citrate DMF submitted to regulatory agencies in the US is known as a USDMF. Diethylcarbamazine Citrate USDMF includes data on Diethylcarbamazine Citrate's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Diethylcarbamazine Citrate USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Diethylcarbamazine Citrate suppliers with USDMF on PharmaCompass.

    Diethylcarbamazine Citrate WC

    A Diethylcarbamazine Citrate written confirmation (Diethylcarbamazine Citrate WC) is an official document issued by a regulatory agency to a Diethylcarbamazine Citrate manufacturer, verifying that the manufacturing facility of a Diethylcarbamazine Citrate active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Diethylcarbamazine Citrate APIs or Diethylcarbamazine Citrate finished pharmaceutical products to another nation, regulatory agencies frequently require a Diethylcarbamazine Citrate WC (written confirmation) as part of the regulatory process.

    click here to find a list of Diethylcarbamazine Citrate suppliers with Written Confirmation (WC) on PharmaCompass.

    Diethylcarbamazine Citrate GMP

    Diethylcarbamazine Citrate Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Diethylcarbamazine Citrate GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Diethylcarbamazine Citrate GMP manufacturer or Diethylcarbamazine Citrate GMP API supplier for your needs.

    Diethylcarbamazine Citrate CoA

    A Diethylcarbamazine Citrate CoA (Certificate of Analysis) is a formal document that attests to Diethylcarbamazine Citrate's compliance with Diethylcarbamazine Citrate specifications and serves as a tool for batch-level quality control.

    Diethylcarbamazine Citrate CoA mostly includes findings from lab analyses of a specific batch. For each Diethylcarbamazine Citrate CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Diethylcarbamazine Citrate may be tested according to a variety of international standards, such as European Pharmacopoeia (Diethylcarbamazine Citrate EP), Diethylcarbamazine Citrate JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Diethylcarbamazine Citrate USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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