Dimetofrine

Last updated
Dimetofrine
Dimetofrine.png
Clinical data
Trade names Dovida, Pressamina, Superten
Other namesDimethophrine; Dimetrophine; Dimethofrine; DMP; SM-14; 3,5-Dimethoxy-4,β-dihydroxy-N-methylphenethylamine; 3,5-Dimethoxy-4,β-dihydroxy-N-methyl-β-phenylethylamine
Routes of
administration
Oral [1]
Drug class α1-Adrenergic receptor agonist; Antihypotensive agent; Vasopressor
ATC code
Identifiers
  • (RS)-4-[1-Hydroxy-2-(methylamino)ethyl]-2,6-dimethoxyphenol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.041.210 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H17NO4
Molar mass 227.260 g·mol−1
3D model (JSmol)
  • O(c1cc(cc(OC)c1O)C(O)CNC)C
  • InChI=1S/C11H17NO4/c1-12-6-8(13)7-4-9(15-2)11(14)10(5-7)16-3/h4-5,8,12-14H,6H2,1-3H3 Yes check.svgY
  • Key:ZKGDBJAHIIXDDW-UHFFFAOYSA-N Yes check.svgY
   (verify)

Dimetofrine (INN Tooltip International Nonproprietary Name), also known as dimethophrine or dimetophrine and sold under the brand names Dovida, Pressamina, and Superten, is a medication described as a sympathomimetic, vasoconstrictor, and cardiac stimulant. [2] [3] [4] It is said to be similarly or less effective than midodrine in the treatment of orthostatic hypotension and shows substantially lower potency. [5] [1]

The drug is a selective α1-adrenergic receptor agonist [6] but is also said to have β-adrenergic receptor agonist activity. [1] It is a substituted phenethylamine and is also known as 3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine. [2] Its chemical structure is similar to that of desglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), the active metabolite of midodrine. [5]

Dimetofrine remained marketed only in Italy in 2000. [3]

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References

  1. 1 2 3 McTavish D, Goa KL (November 1989). "Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders". Drugs. 38 (5): 757–777. doi:10.2165/00003495-198938050-00004. PMID   2480881.
  2. 1 2 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 443. ISBN   978-1-4757-2085-3 . Retrieved 31 August 2024.
  3. 1 2 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 352. ISBN   978-3-88763-075-1 . Retrieved 31 August 2024.
  4. Baldrighi V, Aiazzi L, Castelli C, Seveso G (1984). "Double-blind clinical evaluation of dimetophrine in chronically reduced arterial tension". Curr Med Res Opin. 9 (2): 78–85. doi:10.1185/03007998409109563. PMID   6399891.
  5. 1 2 McClellan KJ, Wiseman LR, Wilde MI (January 1998). "Midodrine. A review of its therapeutic use in the management of orthostatic hypotension". Drugs Aging. 12 (1): 76–86. doi:10.2165/00002512-199812010-00007. PMID   9467688.
  6. Marini U, Cecchi A, Venturini M (1984). "Controlled clinical investigation of dimetophrine versus midodrine in the management of moderately decreased arterial blood pressure". Curr Med Res Opin. 9 (4): 265–274. doi:10.1185/03007998409109590. PMID   6210180.