Banner
targets (2) enzymes (1)
for drugs
Identification
Name Diethylcarbamazine
Accession Number DB00711 (APRD00918)
Type small molecule
Groups approved
Description

An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Carbamazine
Carbilazine
Diethyl carbamazine
Ditrazine base
Ethodryl
Salts Not Available
Brand names
Name Company
Bitirazine
Caracide
Caricide
Cypip
Decacide
Hetrazan
Notezine
Spatonin
Brand mixtures
Brand Name Ingredients
Filaribits Plus 180/136mg Chewable Tablet Diethylcarbamazine citrate + Oxibendazole
Categories
  • Lipoxygenase Inhibitors
  • Anthelmintics
  • Filaricides
CAS number 90-89-1
Weight Average: 199.2932
Monoisotopic: 199.168462309
Chemical Formula C10H21N3O
InChI Key InChIKey=RCKMWOKWVGPNJF-UHFFFAOYSA-N
InChI
InChI=1S/C10H21N3O/c1-4-12(5-2)10(14)13-8-6-11(3)7-9-13/h4-9H2,1-3H3
Plain Text
IUPAC Name
N,N-diethyl-4-methylpiperazine-1-carboxamide
SMILES
CCN(CC)C(=O)N1CCN(C)CC1
Plain Text
Mass Spec show (11 KB)
Taxonomy
Kingdom Organic
Classes
  • Piperazines
Substructures
  • Piperazines
  • Ureas and Derivatives
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
Pharmacology
Indication Used for the treatment of individual patients with certain filarial diseases including tropical pulmonary eosinophilia, loiasis, and lymphatic filariasis caused by infection with Wuchereria bancrofti, Brugia malayi, or Brugia timori.
Pharmacodynamics 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. Diethylcarbamazine continues to be the mainstay for treatment of patients with lymphatic filariasis and loiasis.
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.
Absorption Readily absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Partially metabolized to diethylcarbamazine N-oxide.

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Diethylcarbamazine
    		diethylcarbamazine N-oxide Details
    Route of elimination Not Available
    Half life Approximately 8 hours.
    Clearance Not Available
    Toxicity Oral LD50 in rat and mouse is 1400 mg/kg and 660 mg/kg, respectively.
    Affected organisms
    • Humans and other mammals
    • Parasitic nematodes and other roundworms
    Pathways Not Available
    Pharmacoeconomics
    Manufacturers
    • Lederle laboratories div american cyanamid co
    Packagers Not Available
    Dosage forms Not Available
    Prices Not Available
    Patents Not Available
    Properties
    State solid
    Experimental Properties
    Property Value Source
    melting point 48 °C PhysProp
    water solubility 63.7 mg/mL at 25 °C MEYLAN,WM et al. (1996)
    logP 0.1 Not Available
    Predicted Properties
    Property Value Source
    water solubility 2.36e+02 g/l ALOGPS
    logP 0.9 ALOGPS
    logP 0.092 ChemAxon
    logS 0.07 ALOGPS
    pKa (strongest basic) 6.9 ChemAxon
    physiological charge 0 ChemAxon
    hydrogen acceptor count 2 ChemAxon
    hydrogen donor count 0 ChemAxon
    polar surface area 26.79 ChemAxon
    rotatable bond count 2 ChemAxon
    refractivity 58.28 ChemAxon
    polarizability 22.89 ChemAxon
    References
    Synthesis Reference Not Available
    General Reference Not Available
    External Links
    Resource Link
    KEGG Drug D00803 Link_out
    KEGG Compound C07968 Link_out
    PubChem Compound 3052 Link_out
    PubChem Substance 46506830 Link_out
    ChemSpider 2944 Link_out
    BindingDB 50024883 Link_out
    Therapeutic Targets Database DAP000914 Link_out
    PharmGKB PA164748883 Link_out
    Drug Product Database 346667 Link_out
    Wikipedia http://en.wikipedia.org/wiki/Diethylcarbamazine Link_out
    ATC Codes
    • P02CB02
    AHFS Codes Not Available
    PDB Entries Not Available
    FDA label Not Available
    MSDS show (65.5 KB)
    Interactions
    Drug Interactions Not Available
    Food Interactions Not Available
    Targets

    1. Arachidonate 5-lipoxygenase

    Pharmacological action: yes
    Actions: inhibitor
    Organism class: human
    UniProt ID: P09917 Link_out
    Gene: ALOX5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    References:
    1. Bach MK, Brashler JR: Inhibition of the leukotriene synthetase of rat basophil leukemia cells by diethylcarbamazine, and synergism between diethylcarbamazine and piriprost, a 5-lipoxygenase inhibitor. Biochem Pharmacol. 1986 Feb 1;35(3):425-33. Pubmed
    2. Cernak I, Savic J, Malicevic Z, Zunic G, Radosevic P, Ivanovic I: Leukotrienes in the pathogenesis of pulmonary blast injury. J Trauma. 1996 Mar;40(3 Suppl):S148-51. Pubmed
    3. Gross NJ, Holloway NO, Narine KR: Effects of some nonsteroidal anti-inflammatory agents on experimental radiation pneumonitis. Radiat Res. 1991 Sep;127(3):317-24. Pubmed
    4. Zunic G, Cernak I, Malicevic Z, Savic J: Inhibition of leukotriene formation by diethylcarbamazine modifies the acid-base balance in the rabbits with blast injuries of the lungs. Vojnosanit Pregl. 1999 May-Jun;56(3):243-7. Pubmed
    5. Davidson D, Drafta D: Prolonged pulmonary hypertension caused by platelet-activating factor and leukotriene C4 in the rat lung. J Appl Physiol. 1992 Sep;73(3):955-61. Pubmed
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

    2. Prostaglandin G/H synthase 1

    Pharmacological action: unknown
    Actions: inhibitor

    May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

    Organism class: human
    UniProt ID: P23219 Link_out
    Gene: PTGS1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    References:
    1. McGarry HF, Plant LD, Taylor MJ: Diethylcarbamazine activity against Brugia malayi microfilariae is dependent on inducible nitric-oxide synthase and the cyclooxygenase pathway. Filaria J. 2005 Jun 2;4:4. Pubmed
    Enzymes

    1. Cholinesterase

    Actions: inhibitor

    An acylcholine + H(2)O = choline + a carboxylate

    UniProt ID: P06276 Link_out
    Gene: BCHE Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    SNPs: SNPJam Report Link_out

    References:
    1. Fujimaki Y, Sakamoto M, Shimada M, Kimura E, Aoki Y: Diethylcarbamazine: inhibitory effect on acetylcholinesterase of Dirofilaria immitis and Brugia pahangi. Southeast Asian J Trop Med Public Health. 1989 Jun;20(2):179-82. Pubmed
    Comments
    Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19