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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-02-09 00:32:26 UTC
HMDB IDHMDB14849
Secondary Accession NumbersNone
Metabolite Identification
Common NameDiethylcarbamazine
DescriptionDiethylcarbamazine is only found in individuals that have used or taken this drug. It is an anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa. [PubChem]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.
Structure
Thumb
Synonyms
  1. Carbamazine
  2. Carbilazine
  3. Diethyl carbamazine
  4. Ditrazine base
  5. Ethodryl
Chemical FormulaC10H21N3O
Average Molecular Weight199.2932
Monoisotopic Molecular Weight199.168462309
IUPAC NameN,N-diethyl-4-methylpiperazine-1-carboxamide
Traditional IUPAC Namediethylcarbamazine
CAS Registry Number90-89-1
SMILES
CCN(CC)C(=O)N1CCN(C)CC1
InChI Identifier
InChI=1S/C10H21N3O/c1-4-12(5-2)10(14)13-8-6-11(3)7-9-13/h4-9H2,1-3H3
InChI KeyRCKMWOKWVGPNJF-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Heteromonocyclic Compounds
ClassPiperazines
Sub ClassN/A
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
Substituents
  • Tertiary Aliphatic Amine (Trialkylamine)
  • Urea
Direct ParentPiperazines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
  • Filaricides
  • Lipoxygenase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point48 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.36e+02 g/LNot Available
LogP0.1Not Available
Predicted Properties
PropertyValueSource
water solubility236 g/LALOGPS
logP0.9ALOGPS
logP0.092ChemAxon
logS0.07ALOGPS
pKa (strongest basic)6.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area26.79ChemAxon
rotatable bond count2ChemAxon
refractivity58.28ChemAxon
polarizability22.89ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00711
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00711
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00711
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2944
KEGG Compound IDC07968
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiethylcarbamazine
NuGOwiki LinkHMDB14849
Metagene LinkHMDB14849
METLIN IDNot Available
PubChem Compound3052
PDB IDNot Available
ChEBI ID129569
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
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: 2609206
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
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: 3004501
  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: 8606397
  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: 1886988
  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: 10518442
  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: 1400062
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed: 11752352
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
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: 15932636