Identification
- Summary
Diethylcarbamazine is an anthelmintic used to treat filarial infections like Wuchereria bancrofti and Loa loa.
- Generic Name
- Diethylcarbamazine
- DrugBank Accession Number
- DB00711
- Background
An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Diethylcarbamazine (DB00711)
- Weight
- Average: 199.2932
Monoisotopic: 199.168462309 - Chemical Formula
- C10H21N3O
- Synonyms
- Diethylcarbamazin
- Diéthylcarbamazine
- Diethylcarbamazine
- Diethylcarbamazinum
- Dietilcarbamazina
- External IDs
- L 84
- RP 3799
- RP-3799
Pharmacology
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Filarial infection •••••••••••• •••••• Treatment of Onchocerciasis •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
- 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.
Target Actions Organism AArachidonate 5-lipoxygenase inhibitorHumans UProstaglandin G/H synthase 1 inhibitorHumans - Absorption
Readily absorbed following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Partially metabolized to diethylcarbamazine N-oxide.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Approximately 8 hours.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Oral LD50 in rat and mouse is 1400 mg/kg and 660 mg/kg, respectively.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Diethylcarbamazine may increase the bradycardic activities of Acebutolol. Acetylcholine The risk or severity of adverse effects can be increased when Diethylcarbamazine is combined with Acetylcholine. Aclidinium Diethylcarbamazine may increase the neuromuscular blocking activities of Aclidinium. Amantadine The therapeutic efficacy of Amantadine can be decreased when used in combination with Diethylcarbamazine. Amifampridine The risk or severity of adverse effects can be increased when Diethylcarbamazine is combined with Amifampridine. - Food Interactions
- Take after a meal.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Diethylcarbamazine citrate OS1Z389K8S 1642-54-2 PGNKBEARDDELNB-UHFFFAOYSA-N - International/Other Brands
- Banocide (GlaxoSmithKline) / Banocide Forte (GlaxoSmithKline) / Camin / Carbilazine / Caricide / Cypip / Decet (RND Labs) / Dicarb (Inga) / Diethizine (Pond's Chemical) / Eofil / Ethodryl / Hetrazan (Wyeth) / Notezine (Sanofi-Aventis) / Spatonin / Supatonin (Tanabe Mitsubishi Pharma)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Hetrazan Tab 50mg Tablet 50 mg / tab Oral Lederle Cyanamid Canada Inc. 1982-05-31 2000-08-02 Canada 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ฟีลาตั้น Tablet 100 mg Oral บริษัท พอนด์ เคมีคอล จำกัด 2015-12-23 2020-09-01 Thailand 
Categories
- ATC Codes
- P02CB02 — Diethylcarbamazine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as piperazine carboxamides. These are heterocyclic compounds containing a piperazine ring substituted by one or more carboxamide group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- Piperazine carboxamides
- Alternative Parents
- N-methylpiperazines / Ureas / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic heteromonocyclic compound / Amine / Azacycle / Carbonic acid derivative / Carbonyl group / Hydrocarbon derivative / N-alkylpiperazine / N-methylpiperazine / Organic nitrogen compound / Organic oxide
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- N-methylpiperazine, N-carbamoylpiperazine (CHEBI:4527)
- Affected organisms
- Humans and other mammals
- Parasitic nematodes and other roundworms
Chemical Identifiers
- UNII
- V867Q8X3ZD
- CAS number
- 90-89-1
- InChI Key
- 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
- IUPAC Name
- N,N-diethyl-4-methylpiperazine-1-carboxamide
- SMILES
- CCN(CC)C(=O)N1CCN(C)CC1
References
- Synthesis Reference
Kushner, S. and Brancone, L.; US. Patent 2,467,893; April 19,1949; assigned to American Cyanamid Company. Kushner, S. and Brancone, L.; US. Patent 2,467,895; April 19, 1949; assigned to American Cyanamid Company.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014849
- KEGG Drug
- D07825
- KEGG Compound
- C07968
- PubChem Compound
- 3052
- PubChem Substance
- 46506830
- ChemSpider
- 2944
- BindingDB
- 50024883
- 3384
- ChEBI
- 4527
- ChEMBL
- CHEMBL684
- ZINC
- ZINC000000001288
- Therapeutic Targets Database
- DAP000914
- PharmGKB
- PA164748883
- Wikipedia
- Diethylcarbamazine
- MSDS
- Download (65.5 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Loiasis 1 4 Completed Treatment Filarial; Infestation 1 3 Active Not Recruiting Treatment Filariasis, Lymphatic 1 3 Completed Treatment Lymphatic Filariases / Scabies / Strongyloidiasis / Trachoma / Yaws 1 2 Completed Treatment Filariasis, Lymphatic 2
Pharmacoeconomics
- Manufacturers
- Lederle laboratories div american cyanamid co
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet Oral 300 mg Tablet Oral 50 mg / tab Tablet Oral 100 mg Tablet Oral 50 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 150-155 Kushner, S. and Brancone, L.; US. Patent 2,467,893; April 19,1949; assigned to American Cyanamid Company. Kushner, S. and Brancone, L.; US. Patent 2,467,895; April 19, 1949; assigned to American Cyanamid Company. 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 236.0 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 58.28 m3·mol-1 Chemaxon Polarizability 22.89 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9746 Blood Brain Barrier + 0.9851 Caco-2 permeable + 0.5947 P-glycoprotein substrate Substrate 0.7326 P-glycoprotein inhibitor I Non-inhibitor 0.6368 P-glycoprotein inhibitor II Non-inhibitor 0.9745 Renal organic cation transporter Non-inhibitor 0.6243 CYP450 2C9 substrate Non-substrate 0.8563 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.595 CYP450 1A2 substrate Non-inhibitor 0.8168 CYP450 2C9 inhibitor Non-inhibitor 0.882 CYP450 2D6 inhibitor Non-inhibitor 0.8952 CYP450 2C19 inhibitor Non-inhibitor 0.9141 CYP450 3A4 inhibitor Non-inhibitor 0.9891 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9614 Ames test Non AMES toxic 0.8203 Carcinogenicity Non-carcinogens 0.9183 Biodegradation Not ready biodegradable 0.85 Rat acute toxicity 2.2639 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5 hERG inhibition (predictor II) Non-inhibitor 0.7766
Spectra
- Mass Spec (NIST)
- Download (11 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00fs-9300000000-f87d8f7a7093cd53de37 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0980000000-1821938d687395d17dee Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-1900000000-f325d6ce1e9daf363293 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0un9-9710000000-85ac265d59a4989fd258 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-9400000000-936c4bc2d0140d6824e8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9100000000-ef503663ef71cf1a5ee0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-9100000000-6f146ed4b7526301e3a5 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 154.5364108 predictedDarkChem Lite v0.1.0 [M-H]- 154.8688108 predictedDarkChem Lite v0.1.0 [M-H]- 143.59453 predictedDeepCCS 1.0 (2019) [M+H]+ 154.0275108 predictedDarkChem Lite v0.1.0 [M+H]+ 155.5425108 predictedDarkChem Lite v0.1.0 [M+H]+ 146.82225 predictedDeepCCS 1.0 (2019) [M+Na]+ 154.8802108 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.1035108 predictedDarkChem Lite v0.1.0 [M+Na]+ 155.82008 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Iron 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
- Uniprot Name
- Arachidonate 5-lipoxygenase
- Molecular Weight
- 77982.595 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Davidson D, Drafta D: Prolonged pulmonary hypertension caused by platelet-activating factor and leukotriene C4 in the rat lung. J Appl Physiol (1985). 1992 Sep;73(3):955-61. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Identical protein binding
- 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
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:59