ChemFOnt: Showing chemical card for Diethylcarbamazine (CFc000009184)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:14 UTC

Chemfont ID

CFc000009184

Molecule Identification

Common Name

Diethylcarbamazine

Definition

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N,N-Diethyl-4-methyl-1-piperazinecarboxamide	Kegg
Camin	Kegg
Carbamazine	HMDB
Carbilazine	HMDB
Diethyl carbamazine	HMDB
Ditrazine base	HMDB
Ethodryl	HMDB
Diethylcarbamazine L-tartrate (1:1)	HMDB
Diethylcarbamazine phosphate (1:1)	HMDB
Maleate, diethylcarbamazine	HMDB
Monohydrochloride, diethylcarbamazine	HMDB
Citrate, diethylcarbamazine	HMDB
Diethylcarbamazine citrate (1:1)	HMDB
Diethylcarbamazine maleate	HMDB
Diethylcarbamazine citrate (1:2)	HMDB
Hetrazan	HMDB
Loxuran	HMDB
Notezine	HMDB
Aventis brand OF diethylcarbamazine citrate	HMDB
Diethylcarbamazine citrate	HMDB
Diethylcarbamazine monohydrochloride	HMDB
N,N-Diethyl-4-methylpiperazine-1-carboxamide	HMDB

Chemical Formula

C₁₀H₂₁N₃O

Average Molecular Weight

199.2932

Monoisotopic Molecular Weight

199.168462309

IUPAC Name

N,N-diethyl-4-methylpiperazine-1-carboxamide

Traditional 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

Description

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

Substituents

Piperazine-1-carboxamide
N-alkylpiperazine
N-methylpiperazine
Carbonic acid derivative
Tertiary amine
Tertiary aliphatic amine
Urea
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-methylpiperazine (CHEBI:4527 )
N-carbamoylpiperazine (CHEBI:4527 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014849)
Membrane (HMDB: HMDB0014849)

Source

Exogenous

Exogenous (HMDB: HMDB0014849)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	236 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon