Isometamidium chloride

Isometamidium chloride
Clinical data
ATCvet code	QP51DX04 (WHO) ;
Identifiers
	IUPAC name 3-[N'-[(3-amino-5-ethyl-6-phenyl-8-phenanthridin-5-iumyl)imino]hydrazino]benzamidine chloride;
CAS Number	34301-55-8;
PubChem CID	92295;
ChemSpider	83326;
UNII	7NH28I651F;
CompTox Dashboard (EPA)	DTXSID10955855 ;
ECHA InfoCard	100.047.191
Chemical and physical data
Formula	C28H26ClN7
Molar mass	496.02 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [Cl-].[N@H]=C(N)c1cc(ccc1)N/N=N/c4ccc3c2ccc(N)cc2[n ](c(c3c4)c5ccccc5)CC;
	InChI 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; Key:QNZJTSGALAVCLH-UHFFFAOYSA-N;

Isometamidium chloride is a triazene trypanocidal agent used in veterinary medicine.^[1]^[2]

It consists of a single ethidium bromide like subunit linked to a fragment of the diminazene molecule.^{[citation needed]}

Resistance

The Gibe River Valley in southwest Ethiopia showed universal resistance between July 1989 and February 1993.^[3] This likely indicates a permanent loss of function in this area against the tested target, T. congolense isolated from Boran cattle.^[3]

References

^ Whitelaw DD, Bell IR, Holmes PH, Moloo SK, Hirumi H, Urquhart GM, Murray M (June 1986). "Isometamidium chloride prophylaxis against Trypanosoma congolense challenge and the development of immune responses in Boran cattle". The Veterinary Record. 118 (26): 722–6. doi:10.1136/vr.118.26.722 (inactive 1 November 2024). PMID 3739193. S2CID 39168151.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)
^ Peregrine AS, Ogunyemi O, Whitelaw DD, Holmes PH, Moloo SK, Hirumi H, et al. (April 1988). "Factors influencing the duration of isometamidium chloride (Samorin) prophylaxis against experimental challenge with metacyclic forms of Trypanosoma congolense". Veterinary Parasitology. 28 (1–2): 53–64. doi:10.1016/0304-4017(88)90018-0. PMID 3388736.
^ ^a ^b Mulugeta W, Wilkes J, Mulatu W, Majiwa PA, Masake R, Peregrine AS (April 1997). "Long-term occurrence of Trypanosoma congolense resistant to diminazene, isometamidium and homidium in cattle at Ghibe, Ethiopia". Acta Tropica. 64 (3–4). Elsevier BV: 205–17. doi:10.1016/s0001-706x(96)00645-6. PMID 9107367. S2CID 23878484.

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[Whitelaw-1] Whitelaw DD, Bell IR, Holmes PH, Moloo SK, Hirumi H, Urquhart GM, Murray M (June 1986). "Isometamidium chloride prophylaxis against Trypanosoma congolense challenge and the development of immune responses in Boran cattle". The Veterinary Record. 118 (26): 722–6. doi:10.1136/vr.118.26.722 (inactive 1 November 2024). PMID 3739193. S2CID 39168151.{{cite journal}}: CS1 maint: DOI inactive as of November 2024 (link)

[Peregrine-2] Peregrine AS, Ogunyemi O, Whitelaw DD, Holmes PH, Moloo SK, Hirumi H, et al. (April 1988). "Factors influencing the duration of isometamidium chloride (Samorin) prophylaxis against experimental challenge with metacyclic forms of Trypanosoma congolense". Veterinary Parasitology. 28 (1–2): 53–64. doi:10.1016/0304-4017(88)90018-0. PMID 3388736.

[Mulugeta-et-al-1997-3] Mulugeta W, Wilkes J, Mulatu W, Majiwa PA, Masake R, Peregrine AS (April 1997). "Long-term occurrence of Trypanosoma congolense resistant to diminazene, isometamidium and homidium in cattle at Ghibe, Ethiopia". Acta Tropica. 64 (3–4). Elsevier BV: 205–17. doi:10.1016/s0001-706x(96)00645-6. PMID 9107367. S2CID 23878484.

[1]

[2]

[3]

Clinical data

ATCvet code	QP51DX04 (WHO)
Identifiers
IUPAC name 3-[N'-[(3-amino-5-ethyl-6-phenyl-8-phenanthridin-5-iumyl)imino]hydrazino]benzamidine chloride
CAS Number	34301-55-8
PubChem CID	92295
ChemSpider	83326
UNII	7NH28I651F
CompTox Dashboard (EPA)	DTXSID10955855
ECHA InfoCard	100.047.191
Chemical and physical data
Formula	C₂₈H₂₆ClN₇
Molar mass	496.02 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [Cl-].[N@H]=C(N)c1cc(ccc1)N/N=N/c4ccc3c2ccc(N)cc2[n ](c(c3c4)c5ccccc5)CC
InChI 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 Key:QNZJTSGALAVCLH-UHFFFAOYSA-N