DIETHYLCARBAMAZINE CITRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H21N3O.C6H8O7
Molecular Weight	391.4168
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.CCN(CC)C(=O)N1CCN(C)CC1

InChI

InChIKey=PGNKBEARDDELNB-UHFFFAOYSA-N

InChI=1S/C10H21N3O.C6H8O7/c1-4-12(5-2)10(14)13-8-6-11(3)7-9-13;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-9H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

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Description

Diethylcarbamazine is used in humans, dogs and cats for the treatment of parasitic infections, including pulmonary eosinophilia, loiasis, and lymphatic filariasis. The exact mechanism of its action is unknown, however some studies showed the involvment of inducible nitric-oxide synthase and the cyclooxygenase pathway. Although there is no information on whether the drug is marketed in the USA and Europe, it is currently used in India.

Approval Year

Conditions

Conditions

Condition	Modality	Highest Phase	Product
Tropical pulmonary eosinophilia 3	Curative	Approved 8,583	BANOCIDE
Loiasis 3	Curative	Approved 8,583	BANOCIDE
Lymphatic filariasis 3	Curative	Approved 8,583	BANOCIDE

C_max

Value	Dose	Co-administered	Analyte	Population
500 ng/mL	150 mg single, oral		DIETHYLCARBAMAZINE serum	Homo sapiens
637 ng/mL	150 mg single, oral		DIETHYLCARBAMAZINE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
5840 ng × h/mL	150 mg single, oral		DIETHYLCARBAMAZINE serum	Homo sapiens
7220 ng × h/mL	150 mg single, oral		DIETHYLCARBAMAZINE serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
14.6 h	150 mg single, oral		DIETHYLCARBAMAZINE serum	Homo sapiens
11.4 h	150 mg single, oral		DIETHYLCARBAMAZINE serum	Homo sapiens

Doses

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Dose	Population	Adverse events
6 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, 12 to 69 years	Other AEs: Fever, Pruritus...
2 mg/kg 3 times / day multiple, oral Studied dose	unhealthy, 13 to 46 years	Other AEs: Fever, Nausea...
50 mg multiple, oral Studied dose	unhealthy, 37 years	Other AEs: Lymphadenopathy, Papular urticarial eruption...
300 mg multiple, topical Studied dose	unhealthy, 40 years	Other AEs: Lymphadenopathy, Papular urticarial eruption...
6 mg/kg 1 times / day single, oral Studied dose	unhealthy, median age 35 years	Other AEs: Fatigue, Nausea...

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AEs

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AE	Significance	Dose	Population
Fever	63.6%	6 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, 12 to 69 years
Giddiness	9.1%	6 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, 12 to 69 years
Joint ache	9.1%	6 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, 12 to 69 years
Pruritus	9.1%	6 mg/kg 1 times / day multiple, oral Studied dose	unhealthy, 12 to 69 years
Fever		2 mg/kg 3 times / day multiple, oral Studied dose	unhealthy, 13 to 46 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252	inhibitor 2,438	inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2C19 2,057 OATP1B1 1,079 OATP1B3 961	CYP1A2 1,197 CYP2B6 776 P-gp 2,052	CYP1A 59

Drug as perpetrator

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Target	Modality	Activity
CYP2C19 2,141	inhibitor 4,027	no [Activation >10 uM]
CYP1A 122	inducer 1,966	no
CYP1A2 2,333	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP1A2 1,197	substrate 4,014	likely
CYP2B6 776	substrate 4,014	likely
CYP3A4 1,946	substrate 4,014	no	no (co-administration study)
P-gp 2,052	substrate 4,014	no	no (co-administration study)

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
AA Blocks	AA00IFVB	http://www.aablocks.com/goods/Goods/detail?id=AA00IFVB
Aaron Chemicals	AR00IGN3	http://www.aaronchem.com/90-89-1
abcr GmbH	AB357734	http://www.abcr.com/shop/en/AB357734
Achemo Scientific Limited	AC-89305	http://www.achemo.com/search/?Keyword= 90-89-1
AEchem Scientific Corp., USA	AE028779	http://www.aechemsc.com/info_products/AE028779.php

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PubMed

PubMed

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Title	Date	PubMed
Macrofilaricides and onchocerciasis control, mathematical modelling of the prospects for elimination.	2001	11734070
Optimising the benefits of anthelmintic treatment in children.	2001	11513281
Effectiveness of community and health services-organized drug delivery strategies for elimination of lymphatic filariasis in rural areas of Tamil Nadu, India.	2001 Dec	11737843
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.	2001 Jan	11124226
Filariasis control: ethics, economics, and good science.	2001 Jul 21	11488588

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Sample Use Guides

In Vivo Use Guide

Lymphatic filariasis: 6 mg/kg daily for 12 days administered orally, preferably in divided doses after meals (W. bancrofti infection); 3-6 mg/kg daily for 6-12 days administered orally, preferably in divided doses after meals (B. malayi and B. timori infections). Tropical pulmonary eosinophilia: a dose of 8 mg/kg daily for 14 days repeated, as necessary, if symptoms return.

Route of Administration: Oral

In Vitro Use Guide

Larvae of nocturnally subperiodic Brugia malayi was inhibited under incubation with diethylcarbamazine at concentration of 10(-5) M.

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Name

Type

Language

DIETHYLCARBAMAZINE CITRATE

Common Name

English

HETRAZAN

Preferred Name