From Wikipedia, the free encyclopedia
Chemical compound
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]
Synthesis
Tiamenidine synthesis:
[7]
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 ).
See also
References
^ 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 .
^
a
b 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 .
^ 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 .
^
"Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride" . Drugs-About.com . Retrieved 30 November 2015 .
^ 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 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 .
^
US 3758476 , 0 Rippel H, Ruschig H, Linder E, Schorr M, issued 1973
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β