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Contents

   



(Top)
  


1 Synthesis  




2 See also  




3 References  













Tiamenidine: Difference between revisions






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| IUPAC_name = ''N''-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1''H''-imidazol-2-amine

| IUPAC_name = ''N''-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1''H''-imidazol-2-amine

| image = Tiamenidine.svg

| image = Tiamenidine.svg

| width = 160

| width = 180


<!--Clinical data-->

<!--Clinical data-->
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}}

}}


'''Tiamenidine''' ([[British Approved Name|BAN]], [[United States Adopted Name|USAN]], [[International Nonproprietary Name|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 [[Alpha-1 adrenergic receptor|α1]] and [[Alpha-2 adrenergic receptor|α1 adrenergic receptor]] antagonist (with [[IC50]] 4.85μM and 0.0091μM, respectively).<ref>{{cite journal|last1=Timmermans|first1=PB|last2=de Jonge|first2=A|last3=Thoolen|first3=MJ|last4=Wilffert|first4=B|last5=Batink|first5=H|last6=van Zwieten|first6=PA|title=Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.|journal=Journal of Medicinal Chemistry|date=April 1984|volume=27|issue=4|pages=495–503|pmid=6142954|doi=10.1021/jm00370a011}}</ref> In hypertensive volunteers, like clonidine, it significantly increased sinus node recovery time and lowered [[cardiac output]].<ref>{{cite journal|last1=Roden|first1=DM|last2=Nadeau|first2=JH|last3=Primm|first3=RK|title=Electrophysiologic and Hemodynamic Effects of Chronic Oral Therapy With the Alpha 2-agonists Clonidine and Tiamenidine in Hypertensive Volunteers|journal=Clinical Pharmacology and Therapeutics|date=June 1988|volume=43|issue=6|pages=648–54|pmid=2897889|doi=10.1038/clpt.1988.90}}</ref> It was marketed (as tiamenidine hydrochloride) by [[Sanofi-Aventis]]<ref>{{cite web|title=Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride|url=http://drugs-about.com/drugs-s/sundralen.html|website=Drugs-About.com|accessdate=30 November 2015}}</ref> under the brand name '''Sundralen'''<ref>{{cite book|editor1-last=Ganten|editor1-first=D|editor2-last=Mulrow|editor2-first=Patrick J.|title=Pharmacology of Antihypertensive Therapeutics|date=2013|publisher=Springer-Verlag Berlin Heidelberg|location=[S.l.]|isbn=978-3-642-74211-8|page=880|edition=1st}}</ref> for the management of [[essential hypertension]].<ref name = "Zamboulis">{{cite journal|last1=Zamboulis|first1=C|last2=Hossmann|first2=V|last3=Dollery|first3=CT|last4=Eckert|first4=H|title=Tiamenidine, a Centrally Acting Antihypertensive Drug in Essential Hypertension [proceedings].|journal=British Journal of Clinical Pharmacology|date=October 1979|volume=8|issue=4|pages=390|pmid=508528}}</ref>

'''Tiamenidine''' ([[British Approved Name|BAN]], [[United States Adopted Name|USAN]], [[International Nonproprietary Name|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 [[Alpha-1 adrenergic receptor|α<sub>1</sub>]] and [[Alpha-2 adrenergic receptor|α<sub>2</sub> adrenergic receptor]] antagonist (with [[IC50]] 4.85 ''μ''M and 0.0091 ''μ''M, respectively).<ref>{{cite journal|last1=Timmermans|first1=PB|last2=de Jonge|first2=A|last3=Thoolen|first3=MJ|last4=Wilffert|first4=B|last5=Batink|first5=H|last6=van Zwieten|first6=PA|title=Quantitative relationships between alpha-adrenergic activity and binding affinity of alpha-adrenoceptor agonists and antagonists.|journal=Journal of Medicinal Chemistry|date=April 1984|volume=27|issue=4|pages=495–503|pmid=6142954|doi=10.1021/jm00370a011}}</ref> In hypertensive volunteers, like clonidine, it significantly increased sinus node recovery time and lowered [[cardiac output]].<ref>{{cite journal|last1=Roden|first1=DM|last2=Nadeau|first2=JH|last3=Primm|first3=RK|title=Electrophysiologic and Hemodynamic Effects of Chronic Oral Therapy With the Alpha 2-agonists Clonidine and Tiamenidine in Hypertensive Volunteers|journal=Clinical Pharmacology and Therapeutics|date=June 1988|volume=43|issue=6|pages=648–54|pmid=2897889|doi=10.1038/clpt.1988.90}}</ref> It was marketed (as tiamenidine hydrochloride) by [[Sanofi-Aventis]]<ref>{{cite web|title=Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride|url=http://drugs-about.com/drugs-s/sundralen.html|website=Drugs-About.com|accessdate=30 November 2015}}</ref> under the brand name '''Sundralen'''<ref>{{cite book|editor1-last=Ganten|editor1-first=D|editor2-last=Mulrow|editor2-first=Patrick J.|title=Pharmacology of Antihypertensive Therapeutics|date=2013|publisher=Springer-Verlag Berlin Heidelberg|location=[S.l.]|isbn=978-3-642-74211-8|page=880|edition=1st}}</ref> for the management of [[essential hypertension]].<ref name = "Zamboulis">{{cite journal|last1=Zamboulis|first1=C|last2=Hossmann|first2=V|last3=Dollery|first3=CT|last4=Eckert|first4=H|title=Tiamenidine, a Centrally Acting Antihypertensive Drug in Essential Hypertension [proceedings].|journal=British Journal of Clinical Pharmacology|date=October 1979|volume=8|issue=4|pages=390|pmid=508528}}</ref>


==Synthesis==

==Synthesis==

Revision as of 16:47, 1 September 2016

Tiamenidine
Clinical data
Trade namesSundralen, Symcorad, Symcor
ATC code
Pharmacokinetic data
Elimination half-life2.3–5 hours[1]
Identifiers

  • 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 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

  (verify)

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 α2 adrenergic receptor antagonist (with IC50 4.85 μM and 0.0091 μM, 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

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.
  • ^ 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.
  • ^ "Pharmaceutical and healthcare online databases. Tiamenidine Hydrochloride". Drugs-About.com. Retrieved 30 November 2015.
  • ^ 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.
  • ^ 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.
  • ^ Rippel, H.; Ruschig, H.; Linder, E.; Schorr, M.; 1973, U.S. patent 3,758,476

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Tiamenidine&oldid=737255204"
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    ●This page was last edited on 1 September 2016, at 16:47 (UTC).
    ●This version of the page has been revised. Besides normal editing, the reason for revision may have been that this version contains factual inaccuracies, vandalism, or material not compatible with the Creative Commons Attribution-ShareAlike License.


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