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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
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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 APolyunsaturated fatty acid 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
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Oral LD50 in rat and mouse is 1400 mg/kg and 660 mg/kg, respectively.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Recruiting Not Available Filariasis / Helminthiasis / Mansonelliasis / Onchocerciasis / Parasitic infection NOS 1 somestatus stop reason just information to hide 4 Completed Basic Science Loiasis 1 somestatus stop reason just information to hide 4 Completed Treatment Filarial; Infestation 1 somestatus stop reason just information to hide 3 Active Not Recruiting Treatment Filariasis, Lymphatic 1 somestatus stop reason just information to hide 3 Completed Treatment Lymphatic Filariases / Scabies / Strongyloidiasis / Trachoma / Yaws 1 somestatus stop reason just information to hide
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
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxygenation of arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate) to 5-hydroperoxyeicosatetraenoate (5-HPETE) followed by the dehydration to 5,6- epoxyeicosatetraenoate (Leukotriene A4/LTA4), the first two steps in the biosynthesis of leukotrienes, which are potent mediators of inflammation (PubMed:19022417, PubMed:21233389, PubMed:22516296, PubMed:23246375, PubMed:24282679, PubMed:24893149, PubMed:31664810, PubMed:8615788, PubMed:8631361). Also catalyzes the oxygenation of arachidonate into 8-hydroperoxyicosatetraenoate (8-HPETE) and 12-hydroperoxyicosatetraenoate (12-HPETE) (PubMed:23246375). Displays lipoxin synthase activity being able to convert (15S)-HETE into a conjugate tetraene (PubMed:31664810). Although arachidonate is the preferred substrate, this enzyme can also metabolize oxidized fatty acids derived from arachidonate such as (15S)-HETE, eicosapentaenoate (EPA) such as (18R)- and (18S)-HEPE or docosahexaenoate (DHA) which lead to the formation of specialized pro-resolving mediators (SPM) lipoxin and resolvins E and D respectively, therefore it participates in anti-inflammatory responses (PubMed:17114001, PubMed:21206090, PubMed:31664810, PubMed:32404334, PubMed:8615788). Oxidation of DHA directly inhibits endothelial cell proliferation and sprouting angiogenesis via peroxisome proliferator-activated receptor gamma (PPARgamma) (By similarity). It does not catalyze the oxygenation of linoleic acid and does not convert (5S)-HETE to lipoxin isomers (PubMed:31664810). In addition to inflammatory processes, it participates in dendritic cell migration, wound healing through an antioxidant mechanism based on heme oxygenase-1 (HO-1) regulation expression, monocyte adhesion to the endothelium via ITGAM expression on monocytes (By similarity). Moreover, it helps establish an adaptive humoral immunity by regulating primary resting B cells and follicular helper T cells and participates in the CD40-induced production of reactive oxygen species (ROS) after CD40 ligation in B cells through interaction with PIK3R1 that bridges ALOX5 with CD40 (PubMed:21200133). May also play a role in glucose homeostasis, regulation of insulin secretion and palmitic acid-induced insulin resistance via AMPK (By similarity). Can regulate bone mineralization and fat cell differentiation increases in induced pluripotent stem cells (By similarity)
- Specific Function
- Arachidonate 12(s)-lipoxygenase activity
- Gene Name
- ALOX5
- Uniprot ID
- P09917
- Uniprot Name
- Polyunsaturated fatty acid 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- Heme binding
- 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
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- Acetylcholinesterase activity
- 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 May 03, 2024 10:11