ISOMETAMIDIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H26N7
Molecular Weight	460.5529
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CC[N+]1=C(C2=CC=CC=C2)C3=C(C=CC(N\N=N\C4=CC(=CC=C4)C(N)=N)=C3)C5=CC=C(N)C=C15

InChI

InChIKey=UGKOYGZYLRKTJH-UHFFFAOYSA-O

InChI=1S/C28H25N7/c1-2-35-26-16-20(29)11-13-24(26)23-14-12-22(17-25(23)27(35)18-7-4-3-5-8-18)33-34-32-21-10-6-9-19(15-21)28(30)31/h3-17,29H,2H2,1H3,(H4,30,31,32,33)/p+1

HIDE SMILES / InChI

Molecular Formula	C28H25N7
Molecular Weight	459.545
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.drugs.com/international/isometamidium-chloride.html | http://www.inchem.org/documents/jecfa/jecmono/v25je10.htm

ISOMETAMIDIUM (as a chloride salt) is widely used in tropical countries as an antiprotozoal agent to control animal trypanosomiasis. It is used principally in cattle but also in sheep, goats, buffalos, donkeys, horses, camels and dogs.

Approval Year

PubMed

Title	Date	PubMed
The killing of African trypanosomes by ethidium bromide.	2010-12-16	21187912
Dyes, trypanosomiasis and DNA: a historical and critical review.	2010-12	21080764
Chemosensitization of Trypanosoma congolense strains resistant to isometamidium chloride by tetracyclines and enrofloxacin.	2010-09-28	20927189
Diverse effects on mitochondrial and nuclear functions elicited by drugs and genetic knockdowns in bloodstream stage Trypanosoma brucei.	2010-05-04	20454560
Immunology and cell biology of parasitic diseases.	2010	21547254
Immunobiology of African trypanosomes: need of alternative interventions.	2010	20182644
Immunological and therapeutic strategies against salmonid cryptobiosis.	2010	20052385
Genotypic status of the TbAT1/P2 adenosine transporter of Trypanosoma brucei gambiense isolates from Northwestern Uganda following melarsoprol withdrawal.	2009-09-29	19787038
Advancing drug innovation for neglected diseases-criteria for lead progression.	2009-08-25	19707561
Health management of horses under high challenge from trypanosomes: a case study from Serengeti, Tanzania.	2008-07-04	18450381
Does isometamidium chloride treatment protect tsetse flies from trypanosome infections during SIT campaigns?	2008-06	18498613
Molecular tools for the rapid detection of drug resistance in animal trypanosomes.	2008-05	18420457
Assessment of the occurrence of trypanocidal drug resistance in trypanosomes of naturally infected cattle in the Adamaoua region of Cameroon using the standard mouse test and molecular tools.	2008-05	18355771
Prevalence of bovine trypanosomosis and trypanocidal drug sensitivity studies on Trypanosoma congolense in Wolyta and Dawero zones of southern Ethiopia.	2008-03-25	18207329
The history of African trypanosomiasis.	2008-02-12	18275594
Development and validation of an improved HPLC method for the control of potentially counterfeit isometamidium products.	2008-01-07	17931814
Absence of correlation between karyotype profiles of Trypanosoma congolense and resistance to isometamidium chloride.	2007-07-20	17537578
Occurrence of multiple drug resistance in Trypanosoma brucei rhodesiense isolated from sleeping sickness patients.	2007-03	17708149
Point mutations in mitochondrial topoisomerase enzymes of Trypanosoma congolense are not involved in isometamidium resistance.	2007-01	17123643
Metabolism of isometamidium in hepatocytes isolated from control and inducer-treated rats.	2006-12	17083459
Response of Trypanosoma vivax and Trypanosoma congolense in zebu cattle in North Cameroon to prophylactic treatment with two formulations of isometamidium.	2006-09-15	16777250
Rapid identification of isometamidium-resistant stocks of Trypanosoma b. brucei by PCR-RFLP.	2006-08	16541260
Effect of isometamidium chloride treatment on susceptibility of tsetse flies (Diptera: Glossinidae) to trypanosome infections.	2006-05	16739416
The transmissibility of Trypanosoma congolense seems to be associated with its level of resistance to isometamidium chloride.	2006-02-18	16303254
Drug-resistance of Trypanosoma b. rhodesiense isolates from Tanzania.	2006-02	16451338
Isometamidium sensitivity of Trypanosoma congolense stocks from cattle in West Africa tested in mice and the drug incubation infectivity test.	2006-01	16256933
RNA aptamers as potential pharmaceuticals against infections with African trypanosomes.	2006	16594626
The susceptibility of Trypanosoma congolense isolated in Zambézia Province, Mozambique, to isometamidium chloride, diminazene aceturate and homidium chloride.	2005-12	16562737
Detection of trypanosomes in small ruminants and pigs in western Kenya: important reservoirs in the epidemiology of sleeping sickness?	2005-07-14	16018802
Identification of a genetic marker for isometamidium chloride resistance in Trypanosoma congolense.	2005-02	15710444
Knowledge and attitudes of cattle owners regarding trypanosomosis control in tsetse-infested areas of Uganda.	2004-12	15830601
Protective efficacy of isometamidium chloride and diminazene aceturate against natural Trypanosoma brucei, Trypanosoma congolense and Trypanosoma vivax infections in cattle under a suppressed tsetse population in Uganda.	2004-09	15580773
Evaluation of isometamidium levels in the serum of sheep and goats after prophylactic treatment against trypanosomosis.	2004-09	15580765
Trypanocidal failure suggested by PCR results in cattle field samples.	2004-09	15301970
Application of field methods to assess isometamidium resistance of trypanosomes in cattle in western Ethiopia.	2004-04	15177142
Trypanocidal drug resistance in eastern province of Zambia.	2004-01-30	14746972
Cryptobia (Trypanoplasma) salmositica and salmonid cryptobiosis.	2004-01-09	14710756
RNA-interference silencing of the adenosine transporter-1 gene in Trypanosoma evansi confers resistance to diminazene aceturate.	2003-10-22	15208037
Field studies of drug-resistant cattle trypanosomes in Kénédougou Province, Burkina Faso.	2003-04	12711108
Monitoring the correct use of isometamidium by farmers and veterinary assistants in Eastern Province of Zambia using the isometamidium-ELISA.	2002-12-11	12446096
Financial implications of rearing sheep and goats under natural trypanosomosis challenge at Galana ranch, Kenya.	2002-11	12537388
Growth and mortality in sheep and goats under high tsetse challenge in Kenya.	2002-11	12537387
A competitive enzyme-linked immunosorbent assay for diminazene.	2002-11	12429424
Drug sensitivity of trypanosome populations from cattle in a peri-urban dairy production system in Uganda.	2002-10	12387907
Drug-resistant Trypanosoma congolense in naturally infected donkeys in north Omo Zone, southern Ethiopia.	2001-08-31	11511413
Cryptobiosis and its control in North American fishes.	2001-05-01	11334944
Transporters in African trypanosomes: role in drug action and resistance.	2001-05-01	11334936
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995-11-24	7490723
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992-09	1416885
Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia.	1988-06	3137861

Sample Use Guides

In Vivo Use Guide

0.5 or 1.0 mg/kg bw.

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:56 GMT 2025`
Record UNII	S9HA0WUW3H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOMETAMIDIUM

Common Name

English

ISOMETAMIDIUM CATION

Preferred Name

English

ISOMETAMIDIUM ION

Common Name

English

PHENANTHRIDINIUM, 3-AMINO-8-(3-(3-(AMINOIMINOMETHYL)PHENYL)-1-TRIAZENYL)-5-ETHYL-6-PHENYL-

Systematic Name

English

8-(3-(M-AMIDINOPHENYL)-2-TRIAZENO)-3-AMINO-5-ETHYL-6-PHENYLPHENANTHRIDINIUM

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QP51AX19