Basic information
- CAS
16354-46-4- Standard SMILES
CCN(CC)C(=O)N1CCN(C)CC1.O=C(O)CC(O)(CC(=O)O)C(=O)O- InChIKey
PGNKBEARDDELNB-UHFFFAOYSA-N- Molecular formula
- C10H21N3O.C6H8O7
- Average molar mass
- 391.42 g/mol
- Monoisotopic mass
- 391.19546489
Overview
Diethylcarbamazine citrate is a crystalline solid, scored white tablets. Used against filariasis in man and animals. (EPA, 1998)
Names & identifiers
- Preferred name
- Diethylcarbamazine Citrate
- IUPAC
- N,N-diethyl-4-methylpiperazine-1-carboxamide;2-hydroxypropane-1,2,3-tricarboxylic acid
Names & synonyms
DIETHYLCARBAMAZINE CITRATE1642-54-2LoxuranDicarocideCaritrolFilazineFranocideFranozanCarbam PalatabsDitrazin citrateEthodryl citrateDirocide
Show more names
DitrazineDitrazinumFilarabitsLongicidDitrazini citrasDiethylcarbamazane citrateDiethylcarbamazine acid citrateDiethylcarbamazini citras
Database identifiers
- CAS
16354-46-4、1642-54-2- PubChem CID
- 15432
- DTXSID
DTXSID4045555- ChEMBL
CHEMBL937- ChEBI
CHEBI:4528- UNII
- OS1Z389K8S
- EC Number
- 216-696-6
Properties
Computed structural properties
- Topological polar surface area
- 159 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 7
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 411
Experimental & physicochemical properties
OdorOdorless or slight odor
TasteBitter acid taste
Color/FormWhite, crystalline powder
Solubility
> 75% in water @ 20 °C
Freely sol in hot alcohol
Sparingly sol in cold alcohol
Practically insoluble in acetone, benzene, chloroform and ether
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
DecompositionWhen heated to decomposition it emits ... fumes of nitrogen oxides.
Melting Point
286 to 289 °F (EPA, 1998)
141-143 °C
Physical DescriptionDiethylcarbamazine citrate is a crystalline solid, scored white tablets. Used against filariasis in man and animals. (EPA, 1998)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P271, P284, P301+P317, P304+P340, P316, P320, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1-Piperazinecarboxamide, N,N-diethyl-4-methyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)
Diethylcarbamazine citrate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 1-Piperazinecarboxamide, N,N-diethyl-4-methyl-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1): Environment tier I assessment
DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of nitrogen oxides. Avoid decomposing heat. (EPA, 1998)
Health Hazards
(Non-Specific -- Drugs, n.o.s.) May be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating or poisonous gases. Runoff from fire control or dilution water may cause pollution. The average adult man tolerates a single dose of 1.5 gm without ill effects. (EPA, 1998)
Reactive GroupAlcohols and Polyols
Air and Water Reactions
Chemistry & industry
Pharmacology
Mechanism of Action
The drug has two types of action on susceptible microfilariae. The first is to decrease the muscular activity and eventually immobilize the organisms; this may result from a hyerpolarizing effect of the piperazine moiety, and it causes dislocation of the parasites from their normal habitat in the host. The second action is to produce alterations in the microfilarial surface membranes, thereby rendering them more susceptible to destruction by host defense mechanisms. There is definite evidence that diethylcarbamazine kills adult worms of Loa loa and presumptive evidence that it kills adult Wuchereria bancrofti and Wuchereria malayi. However, it has little action against adult Onchocerca volvulus. The mechanism of the filaricidal action of diethylcarbamazine is unknown. /Diethylcarbamazine/
It is postulated that in naturally infected animals, diethylcarbamazine somehow promotes the combination of antigen and antibody on the surface of serotonin-rich platelets. Serotonin is released from damaged platelets, which dramatically increases vascular permeability and leads to shock. This generally but not always occurs in dogs with a high microfilaremia.
Diethylcarbamazine causes rapid disappearance of microfilariae of Wuchereriia bancrofti, Wuchereria malayi, and Loa loa from the blood of man. The drug causes microfilariae of Onchlcerca volvulus to disappear from the skin but does not kill microfilariae in nodules that contain the adult (female) worms. It does not affect the microfilariae of Wuchereria bancrofti in a hydrocele, despite penetration into the fluid.
Biological Half-Life... the plasma half-life /in man/ is about 8 hr after a 200 mg dose and 12 hr after an 800 mg dose.
Metabolism/MetabolitesOnly 10-25% of the drug is excreted unchanged; the remainder is excreted as one of four known metabolites, all of which contain the intact piperazine ring.
MeSH Pharmacological Classification
Pharmacological agents destructive to nematodes in the superfamily Filarioidea.
Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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