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

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 of IMIDOCARB DIPROPIONATE

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

Molecular Formula C19H20N6O
Molecular Weight 348.4017
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C3H6O2
Molecular Weight 74.0785
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Electron microscopic investigations on stages of dog piroplasms cultured in vitro: Asian isolates of Babesia gibsoni and strains of B. canis from France and Hungary.
2002 Jan
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
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
First isolation and molecular characterization of Ehrlichia canis in Spain.
2004 Nov 10
Detection and molecular characterization of a novel large Babesia species in a dog.
2004 Oct 5
[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
Autochthonous canine babesiosis in The Netherlands.
2005 Jul 15
Identification of anti-babesial activity for four ethnoveterinary plants in vitro.
2005 Jun 10
Pharmacokinetics and mammary elimination of imidocarb in sheep and goats.
2006 Jul
Failure of imidocarb dipropionate to clear experimentally induced Ehrlichia canis infection in dogs.
2006 Jul-Aug
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
Chemotherapy against babesiosis.
2006 May 31
Clinical manifestations of canine babesiosis in Hungary (63 cases).
2006 Sep
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
Molecular characterisation of Babesia gibsoni infection from a pit-bull terrier pup recently imported into South Africa.
2007 Mar
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
Detection of persistent Cytauxzoon felis infection by polymerase chain reaction in three asymptomatic domestic cats.
2008 Jul
An unusual form of canine babesiosis.
2008 Mar
The clinical course of babesiosis in 76 dogs infected with protozoan parasites Babesia canis canis.
2009
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
Rocky Mountain spotted fever in dogs, Brazil.
2009 Mar
Residue depletion of imidocarb in Swine tissue.
2009 Mar 25
Canine babesiosis: from molecular taxonomy to control.
2009 Mar 26
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:56:29 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:29 GMT 2023
Record UNII
ZSM1M03SHC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IMIDOCARB DIPROPIONATE
GREEN BOOK   MART.  
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
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
CFR 21 CFR 522.1155
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4046604
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
WIKIPEDIA
Imidocarb dipropionate
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
RXCUI
1740238
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
DAILYMED
ZSM1M03SHC
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
PUBCHEM
9983292
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
259-791-8
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
NCI_THESAURUS
C76007
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
CAS
55750-06-6
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
SMS_ID
300000023751
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
FDA UNII
ZSM1M03SHC
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
MESH
C031719
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
DRUG BANK
DBSALT001684
Created by admin on Fri Dec 15 15:56:29 GMT 2023 , Edited by admin on Fri Dec 15 15:56:29 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY