Desglymidodrine

Desglymidodrine
Clinical data
Other names	Deglymidodrine; ST-1059; 3,6-Dimethoxy-β-hydroxy-2-phenylethylamine
Drug class	α1-Adrenergic receptor agonist; Antihypotensive agent; Vasopressor
Identifiers
	IUPAC name 2-amino-1-(2,5-dimethoxyphenyl)ethanol;
CAS Number	3600-87-1 ;
PubChem CID	43260;
DrugBank	DBMET00829;
UNII	S57K35I2FV;
KEGG	C21521;
ChEBI	CHEBI:73248;
ChEMBL	ChEMBL1076;
CompTox Dashboard (EPA)	DTXSID00957424 ;
ECHA InfoCard	100.322.299
Chemical and physical data
Formula	C10H15NO3
Molar mass	197.234 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C=C1)OC)C(CN)O;
	InChI InChI=1S/C10H15NO3/c1-13-7-3-4-10(14-2)8(5-7)9(12)6-11/h3-5,9,12H,6,11H2,1-2H3; Key:VFRCNXKYZVQYLX-UHFFFAOYSA-N;

Desglymidodrine (developmental code name ST-1059) is the active metabolite of the prodrug antihypotensive agent midodrine.^[1]^[2]^[3] It acts as a selective α₁-adrenergic receptor agonist.^[1]^[2]^[3] Desglymidodrine is formed from midodrine via deglycination.^[1]^[2]^[3]

Chemistry

Desglymidodrine, also known as 3,6-dimethoxy-β-hydroxy-2-phenylethylamine, is a substituted phenethylamine derivative.^[4]^[5]

Midodrine's experimental log P is -0.5 and its predicted log P ranges from -0.49 to -0.95.^[6]^[7] The predicted log P of desglymidodrine ranges from -0.01 to 0.15.^[4]^[5]

An analogue of desglymidodrine is dimetofrine (3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine).

References

^ ^a ^b ^c 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.
^ ^a ^b ^c Cruz DN (May 2000). "Midodrine: a selective alpha-adrenergic agonist for orthostatic hypotension and dialysis hypotension". Expert Opinion on Pharmacotherapy. 1 (4): 835–840. doi:10.1517/14656566.1.4.835. PMID 11249519.
^ ^a ^b ^c Gutman LB, Wilson BJ (August 2017). "The Role of Midodrine for Hypotension Outside of the Intensive Care Unit". Journal of Population Therapeutics and Clinical Pharmacology = Journal De La Therapeutique Des Populations Et De La Pharmacologie Clinique. 24 (3): e45–e50. doi:10.22374/1710-6222.24.3.4 (inactive 2024-08-29). PMID 28873293.{{cite journal}}: CS1 maint: DOI inactive as of August 2024 (link)
^ ^a ^b "Desglymidodrine". PubChem. U.S. National Library of Medicine. Retrieved 1 August 2024.
^ ^a ^b "Metabolite desglymidodrine". DrugBank Online. Retrieved 1 August 2024.
^ "Midodrine". PubChem. U.S. National Library of Medicine. Retrieved 1 August 2024.
^ "Midodrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 December 1992. Retrieved 1 August 2024.

[McClellanWisemanWilde1998-1] 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.

[Cruz2000-2] Cruz DN (May 2000). "Midodrine: a selective alpha-adrenergic agonist for orthostatic hypotension and dialysis hypotension". Expert Opinion on Pharmacotherapy. 1 (4): 835–840. doi:10.1517/14656566.1.4.835. PMID 11249519.

[GutmanWilson2017-3] Gutman LB, Wilson BJ (August 2017). "The Role of Midodrine for Hypotension Outside of the Intensive Care Unit". Journal of Population Therapeutics and Clinical Pharmacology = Journal De La Therapeutique Des Populations Et De La Pharmacologie Clinique. 24 (3): e45–e50. doi:10.22374/1710-6222.24.3.4 (inactive 2024-08-29). PMID 28873293.{{cite journal}}: CS1 maint: DOI inactive as of August 2024 (link)

[PubChem-Desglymidodrine-4] "Desglymidodrine". PubChem. U.S. National Library of Medicine. Retrieved 1 August 2024.

[DrugBank-Desglymidodrine-5] "Metabolite desglymidodrine". DrugBank Online. Retrieved 1 August 2024.

[PubChem-Midodrine-6] "Midodrine". PubChem. U.S. National Library of Medicine. Retrieved 1 August 2024.

[DrugBank-Midodrine-7] "Midodrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 December 1992. Retrieved 1 August 2024.

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