midodrine

Also known as A-4020 Linz, Proamatine®, ST-1085, DL-N1-(beta-Hydroxy-2,5-dimethoxyphenethyl)glycinamid, 2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamide, 1-(2',5'-Dimethoxyphenyl)-2-glycinamidoethanol, (+-)-2-amino-N-(beta-hydroxy-2,5-dimethoxyphenethyl)acetamide

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

Key facts

Drug.KEGG: D08220
Drug.ChEBI: 6933
Drug.ChEMBL: 1201212
Drug.image: Midodrine structure.svg
Drug.image_class: skin-invert-image
Drug.width: 250px
Drug.caption: Above: molecular structure of midodrineBelow: 3D representation of midodrine
Drug.image2: Midodrine 3D.png
Drug.image_class2: bg-transparent
Drug.width2: 250px
Drug.tradename: Proamatine, others
Drug.MedlinePlus: a616030
Drug.DailyMedID: Midodrine
Drug.pregnancy_AU: C
Drug.routes_of_administration: By mouth
Drug.class: α1-Adrenergic receptor agonist; Antihypotensive agent
Drug.ATC_prefix: C01
Drug.ATC_suffix: CA17

via Wikipedia infobox

Chemical data

Formula: C12H18N2O4
Molecular weight: 254.28 g/mol
IUPAC name: 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
SMILES: COC1=CC(=C(C=C1)OC)C(CNC(=O)CN)O
InChIKey: PTKSEFOSCHHMPD-UHFFFAOYSA-N
XLogP: -0.6
Polar surface area: 93.8 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1996
Admin. routes: oral
Indications: cardiovascular disease, hypotension, orthostatic hypotension, septic shock

via ChEMBL · EBI

Research

990 papers

Effect of midodrine versus placebo on time to vasopressor discontinuation in patients with persistent hypotension in the intensive care unit (MIDAS): an international randomised clinical trial.Intensive care medicine · 2020
Midodrine for the prevention of vasovagal syncope: a systematic review and meta-analysis.Europace : European pacing, arrhythmias, and cardiac electrophysiology : journal of the working groups on cardiac pacing, arrhythmias, and cardiac cellular electrophysiology of the European Society of Cardiology · 2022
Terlipressin plus albumin versus midodrine and octreotide plus albumin in the treatment of hepatorenal syndrome: A randomized trial.Hepatology (Baltimore, Md.) · 2015
Efficacy of adjuvant use of midodrine in patients with septic shock: An open label randomized controlled trial.Pharmacotherapy · 2025
Midodrine for severe orthostatic hypotension.Drug and therapeutics bulletin · 2016

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 254.126657
Has use: medication

Show 7 more facts

chemical formula: C₁₂H₁₈N₂O₄
medical condition treated: urinary incontinence
canonical SMILES: COC1=CC(=C(C=C1)OC)C(CNC(=O)CN)O
World Health Organisation international non-proprietary name: midodrine
defined daily dose: 30
Commons category: Midodrine
significant drug interaction: phenelzine

Sources (4)

via Wikidata · CC0

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Encyclopedic overview

16 sections

Contents

Medical uses
Available forms
Contraindications
Side effects
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
Stereochemistry
Synthesis
History
Society and culture
Names
See also
References
External links

Side effects of midodrine include hypertension (high blood pressure), paresthesia, itching (pruritus), goose bumps, 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.

Excerpted from Wikipedia’s “midodrine” article, available under the CC BY-SA 4.0 licence.