Human Metabolome Database Version 3.5

Showing metabocard for Diethylcarbamazine (HMDB14849)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:26 -0700
HMDB ID HMDB14849
Secondary Accession Numbers None
Metabolite Identification
Common Name Diethylcarbamazine
Description Diethylcarbamazine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Carbamazine
  2. Carbilazine
  3. Diethyl carbamazine
  4. Ditrazine base
  5. Ethodryl
Chemical Formula C10H21N3O
Average Molecular Weight 199.2932
Monoisotopic Molecular Weight 199.168462309
IUPAC Name N,N-diethyl-4-methylpiperazine-1-carboxamide
Traditional IUPAC Name diethylcarbamazine
CAS Registry Number 90-89-1
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 Key RCKMWOKWVGPNJF-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Piperazines
Sub Class N/A
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
Substituents
  • Tertiary Aliphatic Amine (Trialkylamine)
  • Urea
Direct Parent Piperazines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
  • Filaricides
  • Lipoxygenase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 48 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.36e+02 g/L Not Available
LogP 0.1 Not Available
Predicted Properties
Property Value Source
LogP 0.90 ALOGPS
LogP 0.092 ChemAxon
LogS 0.07 ALOGPS
pKa (strongest basic) 6.9 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 26.79 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 58.28 ChemAxon
Polarizability 22.89 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00711
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00711
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00711 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 2944 Link_out
KEGG Compound ID C07968 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Diethylcarbamazine Link_out
NuGOwiki Link HMDB14849 Link_out
Metagene Link HMDB14849 Link_out
METLIN ID Not Available
PubChem Compound 3052 Link_out
PDB ID Not Available
ChEBI ID 129569 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Cholinesterase
Reactions: Not Available
Gene Name: BCHE
Uniprot ID: P06276 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Arachidonate 5-lipoxygenase
Reactions: Not Available
Gene Name: ALOX5
Uniprot ID: P09917 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 1
Reactions: Not Available
Gene Name: PTGS1
Uniprot ID: P23219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA