Midodrine

Midodrine
	Above: molecular structure of midodrine Below: 3D representation of a midodrine molecule
Clinical data
Trade names	Amatine, Gutron, Orvaten, ProAmatine, others
Other names	ST-1085; TS-701; 3,6-Dimethoxy-β-hydroxy-N-aminoethanonyl-2-phenylethylamine; 2-Amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide; 1-2',5'-Dimethoxyphenyl-1)-2 glycinamidoethanol
AHFS/Drugs.com	Monograph
MedlinePlus	a616030
License data	US DailyMed: Midodrine;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
Drug class	α1-Adrenergic receptor agonist; Antihypotensive agent
ATC code	C01CA17 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	93% (as desglymidodrine)
Metabolism	Deglycination
Metabolites	• Desglymidodrine
Onset of action	≤1 hour
Elimination half-life	Midodrine: 0.5 hours; Desglymidodrine: 2–4 hours
Duration of action	2–6 hours
Identifiers
	IUPAC name (RS)-N-[2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl]glycinamide;
CAS Number	42794-76-3 ;
PubChem CID	4195;
IUPHAR/BPS	7240;
DrugBank	DB00211 ;
ChemSpider	4050 ;
UNII	6YE7PBM15H;
KEGG	D08220 ;
ChEBI	CHEBI:6933 ;
ChEMBL	ChEMBL1201212 ;
CompTox Dashboard (EPA)	DTXSID0023321 ;
ECHA InfoCard	100.151.349 100.050.842, 100.151.349
Chemical and physical data
Formula	C12H18N2O4
Molar mass	254.286 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=C(NCC(O)c1cc(OC)ccc1OC)CN;
	InChI InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16) ; Key:PTKSEFOSCHHMPD-UHFFFAOYSA-N ;
	(verify)

Midodrine, sold under the brand names ProAmatine and Orvaten among others, is an antihypotensive medication used to treat orthostatic hypotension (low blood pressure when standing) and urinary incontinence. It is taken by mouth.

Side effects of midodrine include hypertension (high blood pressure), paresthesia, itching, goosebumps, chills, urinary urgency, urinary retention, and urinary frequency. Midodrine is a prodrug of its active metabolite desglymidodrine. This metabolite acts as a selective agonist of the α₁-adrenergic receptor. This in turn results in vasoconstriction and increased blood pressure.

Midodrine was discovered by 1971 and was introduced for medical use in the United States in 1996.

Clinical data

Above: molecular structure of midodrine Below: 3D representation of a midodrine molecule
Trade names	Amatine, Gutron, Orvaten, ProAmatine, others
Other names	ST-1085; TS-701; 3,6-Dimethoxy-β-hydroxy-N-aminoethanonyl-2-phenylethylamine; 2-Amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide; 1-2',5'-Dimethoxyphenyl-1)-2 glycinamidoethanol
AHFS/Drugs.com	Monograph
MedlinePlus	a616030
License data	US DailyMed: Midodrine
Pregnancy category	AU: C
Routes of administration	By mouth
Drug class	α₁-Adrenergic receptor agonist; Antihypotensive agent
ATC code	C01CA17 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	93% (as desglymidodrine)
Metabolism	Deglycination
Metabolites	• Desglymidodrine
Onset of action	≤1 hour
Elimination half-life	Midodrine: 0.5 hours Desglymidodrine: 2–4 hours
Duration of action	2–6 hours
Identifiers
IUPAC name (RS)-N-[2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl]glycinamide
CAS Number	42794-76-3^Y
PubChem CID	4195
IUPHAR/BPS	7240
DrugBank	DB00211^Y
ChemSpider	4050^Y
UNII	6YE7PBM15H
KEGG	D08220^Y
ChEBI	CHEBI:6933^Y
ChEMBL	ChEMBL1201212^Y
CompTox Dashboard (EPA)	DTXSID0023321
ECHA InfoCard	100.151.349 100.050.842, 100.151.349
Chemical and physical data
Formula	C₁₂H₁₈N₂O₄
Molar mass	254.286 g·mol⁻¹
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES O=C(NCC(O)c1cc(OC)ccc1OC)CN
InChI InChI=1S/C12H18N2O4/c1-17-8-3-4-11(18-2)9(5-8)10(15)7-14-12(16)6-13/h3-5,10,15H,6-7,13H2,1-2H3,(H,14,16)^Y Key:PTKSEFOSCHHMPD-UHFFFAOYSA-N^Y
(verify)