Basic information
- CAS
90-89-1- Standard SMILES
CCN(CC)C(=O)N1CCN(C)CC1- InChIKey
RCKMWOKWVGPNJF-UHFFFAOYSA-N- Molecular formula
- C10H21N3O
- Average molar mass
- 199.29 g/mol
- Monoisotopic mass
- 199.1684623
Overview
Diethylcarbamazine is a N-carbamoylpiperazine and a N-methylpiperazine.
Names & identifiers
- Preferred name
- Diethylcarbamazine
- IUPAC
- N,N-diethyl-4-methylpiperazine-1-carboxamide
- English name
- Diethylcarbamazine
- Molecular formula
- C10H21N3O
- Molecular weight
- 199.29
Names & synonyms
diethylcarbamazine90-89-1CarbamazineN,N-Diethyl-4-methyl-1-piperazinecarboxamide1-Piperazinecarboxamide, N,N-diethyl-4-methyl-DietilcarbamazinaDiaethylcarbamazinumCaminDiethylcarbamazinumV867Q8X3ZDCHEBI:4527DTXSID1022928
Show more names
DIETHYL CARBAMAZINE84LCypiprp3799RP 3799patoninBanocideCaracideCaricideEthodryl
RefChem:587348Maleate, Diethylcarbamazineditrazinum (for the citrate)DTXCID802928P02CB02Monohydrochloride, Diethylcarbamazine202-023-3N,N-diethyl-4-methylpiperazine-1-carboxamide
Database identifiers
- CAS
90-89-1- PubChem CID
- 3052
- DTXSID
DTXSID1022928- ChEMBL
CHEMBL684- ChEBI
CHEBI:4527
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 26.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 184
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP0.1
Solubility2.36e+02 g/L
Human DrugsAntifilarials
Melting Point
150-155
48 °C
Physical DescriptionSolid
Collision Cross Section143.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 65 · 65-67℃
- Boiling point
- 127 · 127-129℃ (10 Torr)
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: Diethylcarbamazine (EC: 202-023-3)
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
diethylcarbamazine
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Safety data
- tsca
- TSCA listed
- hs_code
- 2933599590
- Toxicity
- LD50 intraperitoneal in mouse: 240mg/kg
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H319
- REACH Registrations
- Active
- Precautionary statements
- P264-P270-P280-P301+P312+P330-P305+P351+P338-P337+P313-P501
Chemistry & industry
Pharmacology
ATC Code
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
P02CB02
PharmacodynamicsDiethylcarbamazine 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 <i>Brugia malayi</i> 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 <i>in vivo</i> and showes that in addition to its effects on the 5-lipoxygenase pathway, it targets the cyclooxygenase pathway and COX-1.
Biological Half-LifeApproximately 8 hours.
Metabolism/MetabolitesPartially metabolized to diethylcarbamazine N-oxide.
FDA Pharmacological Classification
V867Q8X3ZD
DIETHYLCARBAMAZINE
Established Pharmacologic Class [EPC] - Anthelmintic
Diethylcarbamazine is an Anthelmintic.
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.
Absorption, Distribution and ExcretionReadily absorbed following oral administration.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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