Tiamenidine

Tiamenidine
Clinical data
Trade names	Sundralen, Symcorad, Symcor
ATC code	C02AC (WHO) ;
Pharmacokinetic data
Elimination half-life	2.3–5 hours
Identifiers
	IUPAC name N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine;
CAS Number	31428-61-2 ;
PubChem CID	39974;
ChemSpider	36548 ;
UNII	195V08O55G;
KEGG	D06127 ;
ChEMBL	ChEMBL295409 ;
CompTox Dashboard (EPA)	DTXSID80185349 ;
Chemical and physical data
Formula	C8H10ClN3S
Molar mass	215.70 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc2scc(c2N/C1=N/CCN1)C;
	InChI InChI=1S/C8H10ClN3S/c1-5-4-13-7(9)6(5)12-8-10-2-3-11-8/h4H,2-3H2,1H3,(H2,10,11,12) ; Key:CVWILQHZFWRYPB-UHFFFAOYSA-N ;
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Tiamenidine (BAN, USAN, INN, also known as thiamenidine, Hoe 440) is an imidazoline compound that shares many of the pharmacological properties of clonidine. It is a centrally-acting α₂ adrenergic receptor agonist (IC₅₀ = 9.1 nM).^[2] It also acts as an α₁-adrenergic receptor agonist to a far lesser extent (IC₅₀ = 4.85 μM).^[2] In hypertensive volunteers, like clonidine, it significantly increased sinus node recovery time and lowered cardiac output.^[3] It was marketed (as tiamenidine hydrochloride) by Sanofi-Aventis^[4] under the brand name Sundralen^[5] for the management of essential hypertension.^[6]

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ChemDrug Synthesis:^[7] Patent:^[8]

Reaction of thiourea 1 with methyl iodide gives the corresponding S-methyl analogue (2), followed by heating with ethylenediamine, completes the synthesis of tiamenidine (3).

[1]
Eckert HG, Baudner S, Weimer KE, Wissmann H (1981). "Determination of tiamenidine in biological specimens by radioimmunoassay". Arzneimittel-Forschung. 31 (3): 419–24. PMID 7194666.
[2]
Timmermans PB, de Jonge A, Thoolen MJ, Wilffert B, Batink H, van Zwieten PA (April 1984). "Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists". Journal of Medicinal Chemistry. 27 (4): 495–503. doi:10.1021/jm00370a011. PMID 6142954.
[3]
Roden DM, Nadeau JH, Primm RK (June 1988). "Electrophysiologic and hemodynamic effects of chronic oral therapy with the alpha 2-agonists clonidine and tiamenidine in hypertensive volunteers". Clinical Pharmacology and Therapeutics. 43 (6): 648–54. doi:10.1038/clpt.1988.90. PMID 2897889. S2CID 44263714.
[4]
"Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride". Drugs-About.com. Retrieved 30 November 2015.
[5]
Ganten D, Mulrow PJ, eds. (2013). Pharmacology of Antihypertensive Therapeutics (1st ed.). [S.l.]: Springer-Verlag Berlin Heidelberg. p. 880. ISBN 978-3-642-74211-8.
[6]
Zamboulis C, Hossmann V, Dollery CT, Eckert H (October 1979). "Tiamenidine, a centrally acting antihypertensive drug in essential hypertension [proceedings]". British Journal of Clinical Pharmacology. 8 (4): 390P. doi:10.1111/j.1365-2125.1979.tb04737.x. PMID 508528.
[7]
Castaer, J.; Thorpe, P.; Tiamenidine. Drugs Fut 1976, 1, 10, 502.
[8]
US 3758476, 0 Rippel H, Ruschig H, Linder E, Schorr M, issued 1973

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[1] [1]
Eckert HG, Baudner S, Weimer KE, Wissmann H (1981). "Determination of tiamenidine in biological specimens by radioimmunoassay". Arzneimittel-Forschung. 31 (3): 419–24. PMID 7194666.

[pmid6142954-2] [2]
Timmermans PB, de Jonge A, Thoolen MJ, Wilffert B, Batink H, van Zwieten PA (April 1984). "Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists". Journal of Medicinal Chemistry. 27 (4): 495–503. doi:10.1021/jm00370a011. PMID 6142954.

[3] [3]
Roden DM, Nadeau JH, Primm RK (June 1988). "Electrophysiologic and hemodynamic effects of chronic oral therapy with the alpha 2-agonists clonidine and tiamenidine in hypertensive volunteers". Clinical Pharmacology and Therapeutics. 43 (6): 648–54. doi:10.1038/clpt.1988.90. PMID 2897889. S2CID 44263714.

[4] [4]
"Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride". Drugs-About.com. Retrieved 30 November 2015.

[5] [5]
Ganten D, Mulrow PJ, eds. (2013). Pharmacology of Antihypertensive Therapeutics (1st ed.). [S.l.]: Springer-Verlag Berlin Heidelberg. p. 880. ISBN 978-3-642-74211-8.

[Zamboulis-6] [6]
Zamboulis C, Hossmann V, Dollery CT, Eckert H (October 1979). "Tiamenidine, a centrally acting antihypertensive drug in essential hypertension [proceedings]". British Journal of Clinical Pharmacology. 8 (4): 390P. doi:10.1111/j.1365-2125.1979.tb04737.x. PMID 508528.

[7] [7]
Castaer, J.; Thorpe, P.; Tiamenidine. Drugs Fut 1976, 1, 10, 502.

[8] [8]
US 3758476, 0 Rippel H, Ruschig H, Linder E, Schorr M, issued 1973

[2]

[3]

[4]

[5]

[6]

[1]

[7]

[8]

Tiamenidine

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Synthesis

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References