IMIDOCARB DIPROPIONATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H20N6O.2C3H6O2
Molecular Weight	496.5588
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(O)=O.CCC(O)=O.O=C(NC1=CC=CC(=C1)C2=NCCN2)NC3=CC=CC(=C3)C4=NCCN4

InChI

InChIKey=AFGQXWSHYUHHNV-UHFFFAOYSA-N

InChI=1S/C19H20N6O.2C3H6O2/c26-19(24-15-5-1-3-13(11-15)17-20-7-8-21-17)25-16-6-2-4-14(12-16)18-22-9-10-23-18;2*1-2-3(4)5/h1-6,11-12H,7-10H2,(H,20,21)(H,22,23)(H2,24,25,26);2*2H2,1H3,(H,4,5)

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/vet/imizol.html | http://www.adwia.com/index.php?option=com_content&view=article&id=135&Itemid=148&lang=en | https://www.vetinfo.com/treating-canine-ehrlichiosis-with-imidocarb-imizol.html

Imidocarb is a carbanilide derivative with antiprotozoal activity. It is usually administered as the dipropionate salt. Imidocarb is a drug sold under the brand name Imizol and is used to treat canine ehrlichiosis. wo mechanisms of action have been proposed: As the effect of imidocarb on Trypanosoma brucei is antagonized by excess polyamines, it is has been suggested that imidocarb interferes with their production and/or use. Imidocarb blocks the entry of inositol into erythrocytes containing Babesia, resulting in starvation of the parasite. It is generally accepted in that imidocarb has anticholinesterase activity.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Acetylcholinesterase 207 Target ID: CHEMBL4768 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27301742	Inhibitor 8297
Adenosine deaminase 13 Target ID: CHEMBL2966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27301742	Inhibitor 8297
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20053484	Inhibitor 8297	590.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Babesiosis 7 Sources: https://www.drugs.com/vet/imizol.html http://www.fao.org/fileadmin/user_upload/vetdrug/docs/41-11-imidocarb_dipropionate.pdf	Curative		Approved 8429	Imizol Approved Use For the treatment of babesiosis in dogs with clinical signs and/or demonstrated Babesia organisms in the blood. Launch Date 1997
Babesiosis 7 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500014474.pdf http://www.adwia.com/index.php?option=com_content&view=article&id=135&Itemid=148&lang=en	Curative		Approved 8429	IMIDOCARB Approved Use For treatment of babesiosis in cattle and horses Launch Date 2001

PubMed

Title	Date	PubMed
Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia.	1988 Jun	3137861
Evaluation of certain veterinary drug residues in food.	2003	12970947
Concurrent bartonellosis and babesiosis in a dog with persistent thrombocytopenia.	2003 Nov 1	14621218
Imidocarb, a potent anti-protozoan drug, up-regulates interleukin-10 production by murine macrophages.	2003 Sep 19	12951065
First isolation and molecular characterization of Ehrlichia canis in Spain.	2004 Nov 10	15482892
[A literature review of equine piroplasmosis after an episode of acute babesiosis in a Dutch Standardbred foal after a stay in Normandy].	2005 Dec 1	16363205
Autochthonous canine babesiosis in The Netherlands.	2005 Jul 15	15923085
Identification of anti-babesial activity for four ethnoveterinary plants in vitro.	2005 Jun 10	15893064
Clinical manifestations of canine babesiosis in Hungary (63 cases).	2006 Sep	17020140
Comparison of the efficacy of enrofloxacin, imidocarb, and oxytetracycline for clearance of persistent Anaplasma marginale infections in cattle.	2006 Winter	17216590
Pharmacokinetics and bioavailability of imidocarb dipropionate in swine.	2007 Aug	17610411
Molecular characterisation of Babesia gibsoni infection from a pit-bull terrier pup recently imported into South Africa.	2007 Mar	17665757
Therapeutic and prophylactic efficacy of imidocarb dipropionate on experimental Babesia ovis infection of lambs.	2007 Oct 21	17709209
Treatment of Mycoplasma wenyonii infection in cows with imidocarb dipropionate injection-acupuncture.	2008 Dec	20633467
Repeated high dose imidocarb dipropionate treatment did not eliminate Babesia caballi from naturally infected horses as determined by PCR-reverse line blot hybridization.	2008 Feb 14	18160222
Alterations in some blood coagulation parameters in naturally occurring cases of canine babesiosis.	2009 Jun	19584042
Rocky Mountain spotted fever in dogs, Brazil.	2009 Mar	19239764
Canine babesiosis: from molecular taxonomy to control.	2009 Mar 26	19426443
Canine babesiosis in northern Portugal and molecular characterization of vector-borne co-infections.	2010 Apr 8	20377861
Detection of Babesia divergens in southern Norway by using an immunofluorescence antibody test in cow sera.	2010 Oct 6	20925923

Patents

Sample Use Guides

In Vivo Use Guide

Use intramuscularly or subcutaneously at a rate of 6.6 mg/kg (3 mg/lb) body weight. Repeat the dose in two (2) weeks, for a total of two (2) treatments.

Route of Administration: Other

In Vitro Use Guide

The concentration of Imidocarb causing 50% inhibition of [3H]hypoxanthine incorporation (ID50 value) by Babesia bovis (Lismore and Samford isolates) cultured in vitro for Imidocarb was determined to be 3 ng/ml (8.6 nM).

Name

Type

Language

IMIDOCARB DIPROPIONATE

Common Name

English

N,N'-BIS(3-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENYL)UREA DIPROPIONATE

Systematic Name

English

3,3'-DI-2-IMIDAZOLIN-2-YLCARBANILIDE DIPROPIONATE

Common Name

English

IMIDOCARB DIPROPIONATE [GREEN BOOK]

Common Name

English

IMIDOCARB DIPROPIONATE [MART.]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.1156