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Tiamenidine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tiamenidine
Clinical data
Trade namesSundralen, Symcorad, Symcor
ATC code
Pharmacokinetic data
Eliminationhalf-life2.3–5 hours[1]
Identifiers
  • N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC8H10ClN3S
Molar mass215.70 g·mol−1
3D model (JSmol)
  • Clc2scc(c2N/C1=N/CCN1)C
  • 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) checkY
  • Key:CVWILQHZFWRYPB-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tiamenidine (BAN,USAN,INN, also known asthiamenidine,Hoe 440) is animidazoline compound that shares many of the pharmacological properties ofclonidine. It is acentrally-actingα2 adrenergic receptoragonist (IC50 = 9.1 nM).[2] It also acts as anα1-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 loweredcardiac output.[3] It was marketed (as tiamenidine hydrochloride) bySanofi-Aventis[4] under the brand nameSundralen[5] for the management ofessential hypertension.[6]

Synthesis

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

Reaction of thiourea1 withmethyl iodide gives the corresponding S-methyl analogue (2), followed by heating withethylenediamine, completes the synthesis of tiamenidine (3).

See also

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References

[edit]
  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. ^abTimmermans 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. Retrieved30 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 
Sympatholytic (and closely related)antihypertensives (C02)
Sympatholytics
(antagonizeα-adrenergic
vasoconstriction)
Central
α2-Adrenergic receptor agonists
Adrenergic release inhibitors
Imidazoline receptor agonists
Ganglion-blocking/nicotinic antagonists
Peripheral
Indirect
Monoamine oxidase inhibitors
VMAT inhibitors
Tyrosine hydroxylase inhibitors
Direct
α1-Adrenergic receptor blockers
Non-selective α-adrenergic receptor blockers
Otherantagonists
Serotonin receptor antagonists
Endothelin receptor antagonists (forPHTooltip Pulmonary hypertension)
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
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