U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H20N6O
Molecular Weight 348.4017
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMIDOCARB

SMILES

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

InChI

InChIKey=SCEVFJUWLLRELN-UHFFFAOYSA-N
InChI=1S/C19H20N6O/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/h1-6,11-12H,7-10H2,(H,20,21)(H,22,23)(H2,24,25,26)

HIDE SMILES / InChI
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

Targets

Primary TargetPharmacologyConditionPotency
590.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Imizol

Approved Use

For the treatment of babesiosis in dogs with clinical signs and/or demonstrated Babesia organisms in the blood.

Launch Date

1997
Curative
IMIDOCARB

Approved Use

For treatment of babesiosis in cattle and horses

Launch Date

2001
PubMed

PubMed

TitleDatePubMed
Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia.
1988 Jun
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Residual effect of antibabesial drugs on the live redwater blood vaccines.
2002 Oct
Effects of imidocarb dipropionate in cats with chronic haemobartonellosis.
2002 Summer
Evaluation of certain veterinary drug residues in food.
2003
Naturally acquired babesiosis in a reindeer (Rangifer tarandus tarandus) herd in Great Britain.
2003 Feb
Humoral immunity and reinfection resistance in dogs experimentally inoculated with Babesia canis and either treated or untreated with imidocarb dipropionate.
2003 Jun 25
In-vivo therapeutic efficacy trial with artemisinin derivative, buparvaquone and imidocarb dipropionate against Babesia equi infection in donkeys.
2003 Nov
Concurrent bartonellosis and babesiosis in a dog with persistent thrombocytopenia.
2003 Nov 1
Imidocarb, a potent anti-protozoan drug, up-regulates interleukin-10 production by murine macrophages.
2003 Sep 19
[Autochthonous babesiosis in dogs in the Netherlands?].
2004 May 1
Detection and molecular characterization of a novel large Babesia species in a dog.
2004 Oct 5
Autochthonous canine babesiosis in The Netherlands.
2005 Jul 15
Clinical and clinicopathological changes in 6 healthy ponies following intramuscular administration of multiple doses of imidocarb dipropionate.
2005 Mar
Pharmacokinetics and mammary elimination of imidocarb in sheep and goats.
2006 Jul
Flow cytometric evaluation of selected antimicrobial efficacy for clearance of Anaplasma marginale in short-term erythrocyte cultures.
2006 Jun
Effect of imidocarb and levamisole on the experimental infection of BALB/c mice by Leishmania (Leishmania) amazonensis.
2006 Jun 30
Clinicopathological changes and effect of imidocarb therapy in dogs experimentally infected with Babesia canis.
2006 Mar
Comparison of the efficacy of enrofloxacin, imidocarb, and oxytetracycline for clearance of persistent Anaplasma marginale infections in cattle.
2006 Winter
Pharmacokinetics and bioavailability of imidocarb dipropionate in swine.
2007 Aug
Histological and ultrastructural studies of renal lesions in Babesia canis infected dogs treated with imidocarb.
2007 Dec
Evidence of an acute phase response in dogs naturally infected with Babesia canis.
2007 Mar 31
Therapeutic and prophylactic efficacy of imidocarb dipropionate on experimental Babesia ovis infection of lambs.
2007 Oct 21
[Dogs babesiosis--still actually problem].
2008
Canine vector-borne diseases in Brazil.
2008 Aug 8
Treatment of Mycoplasma wenyonii infection in cows with imidocarb dipropionate injection-acupuncture.
2008 Dec
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
Ultrastructural and fluorochromatic changes of Anaplasma marginale exposed to oxytetracycline, imidocarb and enrofloxacin in short-term erythrocyte cultures.
2009 Apr 14
Alterations in some blood coagulation parameters in naturally occurring cases of canine babesiosis.
2009 Jun
Diagnosis and treatment of Babesia odocoilei in captive reindeer (Rangifer tarandus tarandus) and recognition of three novel host species.
2009 Mar
Babesia and its hosts: adaptation to long-lasting interactions as a way to achieve efficient transmission.
2009 Mar-Apr
Detection of a large unnamed Babesia piroplasm originally identified in dogs in North Carolina in a dog with no history of travel to that state.
2009 Oct 1
Haemotropic mycoplasmas: what's their real significance in cats?
2010 May
Detection of Babesia divergens in southern Norway by using an immunofluorescence antibody test in cow sera.
2010 Oct 6
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
INN   MART.   MI  
INN  
Official Name English
IMIZOL
Brand Name English
N,N'-BIS(3-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENYL)UREA
Systematic Name English
3,3'-DI-2-IMIDAZOLIN-2-YLCARBANILIDE
Common Name English
imidocarb [INN]
Common Name English
IMIDOCARB [MI]
Common Name English
IMIDOCARB [MART.]
Common Name English
UREA, N,N'-BIS(3-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)PHENYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
WHO-VATC QP51AE01
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
Code System Code Type Description
EVMPD
SUB08146MIG
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
WIKIPEDIA
IMIDOCARB
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
MESH
D007095
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
FDA UNII
8USS3K0VDH
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
NCI_THESAURUS
C83790
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
RXCUI
1740237
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
DRUG BANK
DB11521
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID0048345
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
DAILYMED
8USS3K0VDH
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
MERCK INDEX
m6226
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
248-711-7
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
SMS_ID
100000083918
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
PUBCHEM
21389
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
CHEBI
51804
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
CAS
27885-92-3
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
INN
2906
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL427342
Created by admin on Fri Dec 15 17:24:42 GMT 2023 , Edited by admin on Fri Dec 15 17:24:42 GMT 2023
PRIMARY