Dimetofrine

Dimetofrine (INNTooltip 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]

Dimetofrine

Clinical data
Trade names	Dovida, Pressamina, Superten
Other names	Dimethophrine; 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	C01CA12 (WHO)
Identifiers
IUPAC name (RS)-4-[1-Hydroxy-2-(methylamino)ethyl]-2,6-dimethoxyphenol
CAS Number	22950-29-4 Y
PubChem CID	31513
DrugBank	DB13494 Y
ChemSpider	29227 Y
UNII	BOM1J10QQM
KEGG	D07149 Y
ChEBI	CHEBI:134932
ChEMBL	ChEMBL2105040
CompTox Dashboard (EPA)	DTXSID60865076
ECHA InfoCard	100.041.210
Chemical and physical data
Formula	C11H17NO4
Molar mass	227.260 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1cc(cc(OC)c1O)C(O)CNC)C
InChI 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 Y Key:ZKGDBJAHIIXDDW-UHFFFAOYSA-N Y
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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]

References

1. 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. 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. 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. 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.