Tiamenidine

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]

Tiamenidine
Clinical data
Trade namesSundralen, Symcorad, Symcor
ATC code
Pharmacokinetic data
Elimination half-life2.3–5 hours[1]
Identifiers
IUPAC name
  • N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC8H10ClN3S
Molar mass215.70 g·mol−1
3D model (JSmol)
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) Y
  • Key:CVWILQHZFWRYPB-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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
  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. US 3758476, 0 Rippel H, Ruschig H, Linder E, Schorr M, issued 1973
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