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

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
Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia.	1988 Jun	3137861
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.	1992 Sep	1416885
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995 Nov 24	7490723
The in vitro effects of isometamidium chloride (Samorin) on the piscine hemoflagellate Cryptobia salmositica (Kinetoplastida, Bodonina).	2001 Feb	11227891
Therapeutic and prophylactic effects of isometamidium chloride (Samorin) against the hemoflagellate Cryptobia salmositica in chinook salmon (Oncorhynchus tshawytscha) and the effects of the drug on uninfected rainbow trout (O. mykiss).	2001 Jan	11199844
Cryptobiosis and its control in North American fishes.	2001 May 1	11334944
Transporters in African trypanosomes: role in drug action and resistance.	2001 May 1	11334936
Monitoring the correct use of isometamidium by farmers and veterinary assistants in Eastern Province of Zambia using the isometamidium-ELISA.	2002 Dec 11	12446096
Financial implications of rearing sheep and goats under natural trypanosomosis challenge at Galana ranch, Kenya.	2002 Nov	12537388
Drug sensitivity of trypanosome populations from cattle in a peri-urban dairy production system in Uganda.	2002 Oct	12387907
Field studies of drug-resistant cattle trypanosomes in Kénédougou Province, Burkina Faso.	2003 Apr	12711108
Application of field methods to assess isometamidium resistance of trypanosomes in cattle in western Ethiopia.	2004 Apr	15177142
RNA-interference silencing of the adenosine transporter-1 gene in Trypanosoma evansi confers resistance to diminazene aceturate.	2004 May-Jun	15208037
Evaluation of isometamidium levels in the serum of sheep and goats after prophylactic treatment against trypanosomosis.	2004 Sep	15580765
Trypanocidal failure suggested by PCR results in cattle field samples.	2004 Sep	15301970
The susceptibility of Trypanosoma congolense isolated in Zambézia Province, Mozambique, to isometamidium chloride, diminazene aceturate and homidium chloride.	2005 Dec	16562737
Detection of trypanosomes in small ruminants and pigs in western Kenya: important reservoirs in the epidemiology of sleeping sickness?	2005 Jul 14	16018802
Rapid identification of isometamidium-resistant stocks of Trypanosoma b. brucei by PCR-RFLP.	2006 Aug	16541260
Drug-resistance of Trypanosoma b. rhodesiense isolates from Tanzania.	2006 Feb	16451338
The transmissibility of Trypanosoma congolense seems to be associated with its level of resistance to isometamidium chloride.	2006 Feb 18	16303254
Effect of isometamidium chloride treatment on susceptibility of tsetse flies (Diptera: Glossinidae) to trypanosome infections.	2006 May	16739416
Response of Trypanosoma vivax and Trypanosoma congolense in zebu cattle in North Cameroon to prophylactic treatment with two formulations of isometamidium.	2006 Sep 15	16777250
Point mutations in mitochondrial topoisomerase enzymes of Trypanosoma congolense are not involved in isometamidium resistance.	2007 Jan	17123643
Absence of correlation between karyotype profiles of Trypanosoma congolense and resistance to isometamidium chloride.	2007 Jul 20	17537578
Occurrence of multiple drug resistance in Trypanosoma brucei rhodesiense isolated from sleeping sickness patients.	2007 Mar	17708149
The history of African trypanosomiasis.	2008 Feb 12	18275594
Health management of horses under high challenge from trypanosomes: a case study from Serengeti, Tanzania.	2008 Jul 4	18450381
Prevalence of bovine trypanosomosis and trypanocidal drug sensitivity studies on Trypanosoma congolense in Wolyta and Dawero zones of southern Ethiopia.	2008 Mar 25	18207329
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 May	18355771
Genotypic status of the TbAT1/P2 adenosine transporter of Trypanosoma brucei gambiense isolates from Northwestern Uganda following melarsoprol withdrawal.	2009 Sep 29	19787038
Immunology and cell biology of parasitic diseases.	2010	21547254
Immunobiology of African trypanosomes: need of alternative interventions.	2010	20182644
Diverse effects on mitochondrial and nuclear functions elicited by drugs and genetic knockdowns in bloodstream stage Trypanosoma brucei.	2010 May 4	20454560
Chemosensitization of Trypanosoma congolense strains resistant to isometamidium chloride by tetracyclines and enrofloxacin.	2010 Sep 28	20927189

Sample Use Guides

In Vivo Use Guide

0.5 or 1.0 mg/kg bw.

Route of Administration: Intramuscular

Name

Type

Language

ISOMETAMIDIUM

Common Name

English

ISOMETAMIDIUM CATION

Common 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