Tiamenidine

Tiamenidine

Systematic (IUPAC) name
N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine
Clinical data
Trade names	Sundralen, Symcorad, Symcor
Pharmacokinetic data
Biological half-life	2.3–5 hours[1]
Identifiers
CAS Number	31428-61-2
ATC code	C02AC
PubChem	CID 39974
ChemSpider	36548
UNII	195V08O55G
KEGG	D06127
ChEMBL	CHEMBL295409
Chemical data
Formula	C8H10ClN3S
Molar mass	215.70 g/mol
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 a imidazoline compound that shares many of the pharmacological properties of clonidine. It acts as a centrally-acting α1 and α1 adrenergic receptor antagonist (with IC50 4.85μM and 0.0091μM, respectively).^[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

• Clonidine
• Tizanidine

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. 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. PMID 2897889.
4. "Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride". Drugs-About.com. Retrieved 30 November 2015.
5. Ganten, D; Mulrow, Patrick J., 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): 390. PMID 508528.
7. Rippel, H.; Ruschig, H.; Linder, E.; Schorr, M.; 1973, U.S. Patent 3,758,476