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Diethylcarbamazine

Diethylcarbamazine structure

CAS No:
90-89-1
Formula:
C10H21N3O
Chemical Name:
Diethylcarbamazine
Synonyms:
1-Piperazinecarboxamide,N,N-diethyl-4-methyl-;N,N-Diethyl-4-methyl-1-piperazinecarboxamide;84L;RP 3799;Caracide;Carbamazine;Carbilazine;Caricide;Diethylcarbamazine;1-Diethylcarbamoyl-4-methylpiperazine;Ethodryl;1-Methyl-4-diethylcarbamylpiperazine;Notezine;Spatonin;1-Methyl-4-diethylcarbamoylpiperazine;Cypip;Ditrazine base;Bitirazine;1-(N,N-Diethylcarbamoyl)-4-methylpiperazine;8028-18-0;12672-34-3
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Solid

Diethylcarbamazine is a N-methylpiperazine and a N-carbamoylpiperazine.|An anthelmintic used primarily as the citrate in the treatment of filariasis, particularly infestations with Wucheria bancrofti or Loa loa.|Diethylcarbamazine is an Anthelmintic.

Diethylcarbamazine Basic Attributes

Molecular Weight：

199.29

Exact Mass：

199.29

EC Number：

202-023-3

UNII：

V867Q8X3ZD

DSSTox ID：

DTXSID1022928

ATC Code：

P - Antiparasitic products, insecticides and repellents

Characteristics

PSA：

26.8

XLogP3：

0.3

Appearance：

Solid

Density：

1.013g/cm3

Melting Point：

48 °C

Boiling Point：

108.5-111 °C @ Press: 3 Torr

Flash Point：

98ºC

Refractive Index：

1.492

Water Solubility：

2.36e+02 g/L

Toxicity：

LD50 intraperitoneal in mouse: 240mg/kg

Safety Information

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity Summary：

Oral LD50 in rat and mouse is 1400 mg/kg and 660 mg/kg, respectively.

Drug Information

Drug 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.

Pharmacology：

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.

MeSH：

Pharmacological agents destructive to nematodes in the superfamily Filarioidea. (See all compounds classified as Filaricides.)|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. (See all compounds classified as Lipoxygenase Inhibitors.)

Absorption：

Readily absorbed following oral administration.

Metabolism/Metabolites：

Partially metabolized to diethylcarbamazine N-oxide.

Biological Half-Life：

Approximately 8 hours.

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.

MeSH Entry Terms：

Carbamazine

Diethylcarbamazine Use and Manufacturing

Methods of Manufacturing

Thus, another embodiment of the present invention is a salt of one or these four compounds with an anthelmintic base selected from the group consisting ofbephenium, diethylcarbamazine, levamisole, morantel, nicotine, piperazine, andpyrantel.

Uses

This product is an anti-filariasis, and ethylamine is formed into a salt with citric acid to obtain ethylamine citrate, that is, sea group. As the antifilaria drug, ethylamine salts also include hydrochloride and phosphate. Filariasis is caused by filariasis parasitic on the human lymph or connective tissue. Ethamazine is used clinically for the treatment and prevention of filariasis. The anti-insect effect is not ideal, and there are certain adverse reactions, but compared with the existing anti-filariasis drugs, it is still the first choice.

Manufacturing Info：

1-Piperazinecarboxamide, N,N-diethyl-4-methyl-: INACTIVE

Computed Properties

Molecular Weight:199.29
XLogP3:0.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:199.168462302
Monoisotopic Mass:199.168462302
Topological Polar Surface Area:26.8
Heavy Atom Count:14
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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