Isometamidium chloride

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 571127

CAS#: 34301-55-8 (chloride)

Description: Isometamidium chloride is an antiprotozoal agent used in veterinary medicine.

Chemical Structure

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Isometamidium chloride
CAS# 34301-55-8 (chloride)
Instruction

Theoretical Analysis

MedKoo Cat#: 571127
Name: Isometamidium chloride
CAS#: 34301-55-8 (chloride)
Chemical Formula: C28H26ClN7
Exact Mass: 495.19
Molecular Weight: 496.020
Elemental Analysis: C, 67.80; H, 5.28; Cl, 7.15; N, 19.77

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 20438-03-3 (cation)   34301-55-8 (chloride)    

Synonym: Isometamidium chloride; A-4180; A4180; A 4180

IUPAC/Chemical Name: Phenanthridinium, 3-amino-8-(3-(3-(aminoiminomethyl)phenyl)-1-triazenyl)-5-ethyl-6-phenyl-, chloride

InChi Key: QNZJTSGALAVCLH-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H25N7.ClH/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);1H

SMILES Code: CC[N+]1=C(C2=CC=CC=C2)C3=CC(/N=N/NC4=CC=CC(C(N)=N)=C4)=CC=C3C5=C1C=C(N)C=C5.[Cl-]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 496.02 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Sahin A, Asencio C, Izotte J, Pillay D, Coustou V, Karembe H, Baltz T. The susceptibility of Trypanosoma congolense and Trypanosoma brucei to isometamidium chloride and its synthetic impurities. Vet Parasitol. 2014 Jul 14;203(3-4):270-5. doi: 10.1016/j.vetpar.2014.04.002. Epub 2014 Apr 13. PubMed PMID: 24836423.

2: Tchamdja E, Kulo AE, Akoda K, Teko-Agbo A, Assoumy AM, Niang EM, Batawui K, Adomefa K, Bankolé AA, Kombiagou K, Hoppenheit A, Clausen PH, Mattioli RC, Peter R, Napier GB, De Deken R, Marcotty T, Van Den Abbeele J, Delespaux V. Drug quality analysis through high performance liquid chromatography of isometamidium chloride hydrochloride and diminazene diaceturate purchased from official and unofficial sources in Northern Togo. Prev Vet Med. 2016 Apr 1;126:151-8. doi: 10.1016/j.prevetmed.2016.02.001. Epub 2016 Feb 4. PubMed PMID: 26907208.

3: Van Den Bossche P, Akoda K, Djagmah B, Marcotty T, De Deken R, Kubi C, Parker A, Van Den Abbeele J. Effect of isometamidium chloride treatment on susceptibility of tsetse flies (Diptera: Glossinidae) to trypanosome infections. J Med Entomol. 2006 May;43(3):564-7. PubMed PMID: 16739416.

4: Sow A, Sidibé I, Bengaly Z, Marcotty T, Séré M, Diallo A, Vitouley HS, Nebié RL, Ouédraogo M, Akoda GK, Van den Bossche P, Van Den Abbeele J, De Deken R, Delespaux V. Field detection of resistance to isometamidium chloride and diminazene aceturate in Trypanosoma vivax from the region of the Boucle du Mouhoun in Burkina Faso. Vet Parasitol. 2012 Jun 8;187(1-2):105-11. doi: 10.1016/j.vetpar.2011.12.019. Epub 2011 Dec 23. PubMed PMID: 22264748.

5: Peregrine AS, Knowles G, Ibitayo AI, Scott JR, Moloo SK, Murphy NB. Variation in resistance to isometamidium chloride and diminazene aceturate by clones derived from a stock of Trypanosoma congolense. Parasitology. 1991 Feb;102 Pt 1:93-100. PubMed PMID: 2038504.

6: Sutherland IA, Codjia V, Moloo SK, Holmes PH, Peregrine AS. Therapeutic activity of isometamidium chloride in Boran cattle against a tsetse-transmitted clone of Trypanosoma congolense with a low level of drug resistance. Trop Anim Health Prod. 1992 Aug;24(3):157-63. PubMed PMID: 1304663.

7: Jamal S, Sigauque I, Macuamule C, Neves L, Penzhorn BL, Marcotty T, Van Den Bossche P. The susceptibility of Trypanosoma congolense isolated in Zambézia Province, Mozambique, to isometamidium chloride, diminazene aceturate and homidium chloride. Onderstepoort J Vet Res. 2005 Dec;72(4):333-8. PubMed PMID: 16562737.

8: Ardelli BF, Woo PT. The in vitro effects of isometamidium chloride (Samorin) on the piscine hemoflagellate Cryptobia salmositica (Kinetoplastida, Bodonina). J Parasitol. 2001 Feb;87(1):194-202. PubMed PMID: 11227891.

9: Li YG, Zou Y, Zhang L, Xi CX, Wang GM, Li XL, Zhang JZ, Li ZG. Determination of isometamidium residues in animal-derived foods by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Apr 15;879(13-14):1008-12. doi: 10.1016/j.jchromb.2011.02.040. Epub 2011 Mar 3. PubMed PMID: 21419723.

10: Sutherland IA, Moloo SK, Holmes PH, Peregrine AS. Therapeutic and prophylactic activity of isometamidium chloride against a tsetse-transmitted drug-resistant clone of Trypanosoma congolense in Boran cattle. Acta Trop. 1991 Apr;49(1):57-64. PubMed PMID: 1678576.

11: Ali BH, Hassan T. Preliminary pharmacokinetic study of isometamidium chloride in camels. Res Vet Sci. 1984 Nov;37(3):376-7. PubMed PMID: 6522836.

12: Ardelli BF, Woo PT. An antigen-capture enzyme-linked immunosorbent assay (ELISA) to detect isometamidium chloride in Oncorhynchus spp. Dis Aquat Organ. 2000 Feb 9;39(3):231-6. PubMed PMID: 10768291.

13: Delespaux V, Geysen D, Majiwa PA, Geerts S. Identification of a genetic marker for isometamidium chloride resistance in Trypanosoma congolense. Int J Parasitol. 2005 Feb;35(2):235-43. Epub 2004 Dec 25. PubMed PMID: 15710444.

14: Schad GJ, Euerby MR, Skellern GG, Tettey JN. Chromatographic retention behaviour, modelling and separation optimisation of the quaternary ammonium salt isometamidium chloride and related compounds on a range of reversed-phase liquid chromatographic stationary phases. Anal Bioanal Chem. 2012 Jul;404(1):239-55. doi: 10.1007/s00216-012-6105-5. Epub 2012 May 23. PubMed PMID: 22618328.

15: Münstermann S, Mbura RJ, Maloo SH, Löhr KF. Trypanosomiasis control in Boran cattle in Kenya: a comparison between chemoprophylaxis and a parasite detection and intravenous treatment method using isometamidium chloride. Trop Anim Health Prod. 1992 Feb;24(1):17-27. PubMed PMID: 1306914.

16: Eze AA, Gould MK, Munday JC, Tagoe DN, Stelmanis V, Schnaufer A, De Koning HP. Reduced Mitochondrial Membrane Potential Is a Late Adaptation of Trypanosoma brucei brucei to Isometamidium Preceded by Mutations in the γ Subunit of the F1Fo-ATPase. PLoS Negl Trop Dis. 2016 Aug 12;10(8):e0004791. doi: 10.1371/journal.pntd.0004791. eCollection 2016 Aug. PubMed PMID: 27518185; PubMed Central PMCID: PMC4982688.

17: Delespaux V, Vitouley HS, Marcotty T, Speybroeck N, Berkvens D, Roy K, Geerts S, Van den Bossche P. Chemosensitization of Trypanosoma congolense strains resistant to isometamidium chloride by tetracyclines and enrofloxacin. PLoS Negl Trop Dis. 2010 Sep 28;4(9):e828. doi: 10.1371/journal.pntd.0000828. PubMed PMID: 20927189; PubMed Central PMCID: PMC2946901.

18: Peregrine AS, Moloo SK, Whitelaw DD. Differences in sensitivity of Kenyan Trypanosoma vivax populations to the prophylactic and therapeutic actions of isometamidium chloride in Boran cattle. Trop Anim Health Prod. 1991 Feb;23(1):29-38. PubMed PMID: 2038768.

19: Peregrine AS, Moloo SK, Whitelaw DD. Therapeutic and prophylactic activity of isometamidium chloride in Boran cattle against Trypanosoma vivax transmitted by Glossina morsitans centralis. Res Vet Sci. 1987 Sep;43(2):268-70. Erratum in: Res Vet Sci 1987 Nov;43(3):268. PubMed PMID: 3685643.

20: Elrayah IE, Kaminsky R. The effect of diminazene aceturate and isometamidium chloride on cultured procyclic forms of susceptible and drug-resistant Trypanosoma congolense. Acta Trop. 1991 Aug;49(3):201-13. PubMed PMID: 1685301.