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Details

Stereochemistry RACEMIC
Molecular Formula C12H18N2O4
Molecular Weight 254.2823
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDODRINE

SMILES

COC1=CC=C(OC)C(=C1)C(O)CNC(=O)CN

InChI

InChIKey=PTKSEFOSCHHMPD-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C12H18N2O4
Molecular Weight 254.2823
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/midodrine.html

Midodrine is a prodrug, i.e., the therapeutic effect of orally administered midodrine is due to the major metabolite desglymidodrine formed by deglycination of midodrine. Desglymidodrine diffuses poorly across the blood-brain barrier, and is therefore not associated with effects on the central nervous system. Administration of midodrine results in a rise in standing, sitting, and supine systolic and diastolic blood pressure in patients with orthostatic hypotension of various etiologies. Standing systolic blood pressure is elevated by approximately 15 to 30 mmHg at 1 hour after a 10-mg dose of midodrine, with some effect persisting for 2 to 3 hours. Midodrine has no clinically significant effect on standing or supine pulse rates in patients with autonomic failure. Midodrine forms an active metabolite, desglymidodrine, that is an alpha1-agonist, and exerts its actions via activation of the alpha-adrenergic receptors of the arteriolar and venous vasculature, producing an increase in vascular tone and elevation of blood pressure. Desglymidodrine does not stimulate cardiac beta-adrenergic receptors. Midodrine is used for the treatment of symptomatic orthostatic hypotension (OH). Midodrine is marketed under the brand names Amatine, ProAmatine, Gutron.

CNS Activity

CNS Non-penetrant
1040
Curator's Comment: does not cross the blood-brain barrier

Originator

Approval Year

1996
224
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ORVATEN

Approved Use

indicated for the treatment of symptomatic orthostatic hypotension

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.2 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
21 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2.5 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
18.5 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
0.54 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26597181
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MIDODRINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
350 mg single, oral
Overdose
Dose: 350 mg
Route: oral
Route: single
Dose: 350 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
unhealthy, 20 years
Health Status: unhealthy
Age Group: 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
Other AEs: Hypertension, Bradycardia...
Other AEs:
Hypertension (severe, 1 patient)
Bradycardia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
90 mg 1 times / day steady, oral
Highest studied dose
Dose: 90 mg, 1 times / day
Route: oral
Route: steady
Dose: 90 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/31381098
unhealthy, 49 years
Health Status: unhealthy
Age Group: 49 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/31381098
Sources:
https://pubmed.ncbi.nlm.nih.gov/31381098
2.5 mg single, intravenous
Dose: 2.5 mg
Route: intravenous
Route: single
Dose: 2.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7690382
healthy, adult
Health Status: healthy
Age Group: adult
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/7690382
Sources:
https://pubmed.ncbi.nlm.nih.gov/7690382
205 mg single, oral
Overdose
Dose: 205 mg
Route: oral
Route: single
Dose: 205 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
unknown
Health Status: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Other AEs: Lethargic...
Other AEs:
Lethargic (1 patient)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
unknown
Health Status: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Other AEs: Blood pressure systolic increased...
Other AEs:
Blood pressure systolic increased (1 patient)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
10 mg 3 times / day steady, oral
Recommended
Dose: 10 mg, 3 times / day
Route: oral
Route: steady
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Disc. AE: Supine hypertension...
AEs leading to
discontinuation/dose reduction:
Supine hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
7.5 mg 1 times / day steady, oral
Dose: 7.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 7.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11007859
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/11007859
Other AEs: Pancytopenia...
Other AEs:
Pancytopenia (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11007859
AEs

AEs

AESignificanceDosePopulation
Bradycardia 1 patient
350 mg single, oral
Overdose
Dose: 350 mg
Route: oral
Route: single
Dose: 350 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
unhealthy, 20 years
Health Status: unhealthy
Age Group: 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
Hypertension severe, 1 patient
350 mg single, oral
Overdose
Dose: 350 mg
Route: oral
Route: single
Dose: 350 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
unhealthy, 20 years
Health Status: unhealthy
Age Group: 20 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/27417951
Lethargic 1 patient
205 mg single, oral
Overdose
Dose: 205 mg
Route: oral
Route: single
Dose: 205 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
unknown
Health Status: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Blood pressure systolic increased 1 patient
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
unknown
Health Status: unknown
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Supine hypertension Disc. AE
10 mg 3 times / day steady, oral
Recommended
Dose: 10 mg, 3 times / day
Route: oral
Route: steady
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Pancytopenia 2 patients
7.5 mg 1 times / day steady, oral
Dose: 7.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 7.5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/11007859
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/11007859
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6933
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6933
ChemicalBook
CB4297224
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4297224
MolPort
MolPort-003-849-221
https://www.molport.com/shop/molecule-link/MolPort-003-849-221
PubMed

PubMed

TitleDatePubMed
Beneficial haemodynamic and renal sodium handling effects of combined midodrine and octreotide treatment in a cirrhotic patient with large hepatic hydrothorax and mild ascites.
2005-11
[Pharmacotherapy of stress incontinence].
2005-10-14
L-DOPS therapy for refractory orthostatic hypotension in autoimmune autonomic neuropathy.
2005-10-11
Effect of mineralocorticoids on interdialytic weight gain in hemodialysis patients with perdialytic hypotension.
2005-10
Heat-related morbidity in patients with orthostatic hypotension and primary autonomic failure.
2005-09
Fludrocortisone in patients with familial dysautonomia--assessing effect on clinical parameters and gene expression.
2005-08
Adrenergic drugs for urinary incontinence in adults.
2005-07-20
Effects of therapy based on tilt testing results on the long-term outcome in patients with syncope.
2005-07
Adverse drug reactions related to drugs used in orthostatic hypotension: a prospective and systematic pharmacovigilance study in France.
2005-07
Consequences of cardiovascular adaptation to spaceflight: implications for the use of pharmacological countermeasures.
2005-06
[Diabetes mellitus and orthostatic intolerance].
2005-06
Pregnancy in postural orthostatic tachycardia syndrome.
2005-06
Familial dysautonomia: a review of the current pharmacological treatments.
2005-04
The effects of chronic treatment with octreotide versus octreotide plus midodrine on systemic hemodynamics and renal hemodynamics and function in nonazotemic cirrhotic patients with ascites.
2005-04
Successful treatment of hypotension associated with stunned myocardium with oral midodrine therapy.
2005-03
[Pure autonomic failure. Bradbury Eggleston Syndrome. Case report].
2005-02
[Sjögren's syndrome with autonomic failure and epilepsy].
2005-02
Hepatorenal syndrome: a dreaded complication of end-stage liver disease.
2005-02
[Treatment of ejaculation disorders].
2005-02
[Treatment of ejaculation disorders by midodrine (Gutron) per os. Retrospective study of about 16 subjects].
2005-02
Treatment of vasodepressor carotid sinus syndrome with midodrine: a randomized, controlled pilot study.
2005-01
[Efficacy and safety of a herbal drug containing hawthorn berries and D-camphor in hypotension and orthostatic circulatory disorders/results of a retrospective epidemiologic cohort study].
2005
Postprandial hypotension treated with acarbose in a patient with type 1 diabetes mellitus.
2004-12
Reconsidering hepatorenal syndrome. Throw in the towel? Not so fast!
2004-12
The in vitro metabolism of desglymidodrine, an active metabolite of prodrug midodrine by human liver microsomes.
2004-11-13
[Orthostatic hypotension and supine hypertension in pure autonomic failure].
2004-11
Management of vasovagal syncope: 2004.
2004-11
Taste and smell disturbance with the alpha-adrenoceptor agonist midodrine.
2004-11
Effects of midodrine on exercise-induced hypotension and blood pressure recovery in autonomic failure.
2004-11
Midodrine appears to be safe and effective for dialysis-induced hypotension: a systematic review.
2004-10
A patient responding to combined therapy with pirmenol and midodrine for refractory neurally mediated syncope complicated by prostatic hypertrophy.
2004-09
New approaches to the treatment and prevention of neurally mediated reflex (neurocardiogenic) syncope.
2004-09
Midodrine, octreotide, albumin, and TIPS in selected patients with cirrhosis and type 1 hepatorenal syndrome.
2004-07
Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent.
2004-07
Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist.
2004-06-03
Intestinal obstruction associated with oral midodrine.
2004-06
Midodrine prescribed to improve recurrent post-spaceflight orthostatic hypotension.
2004-06
Pharmacology of orthostatic hypotension in Parkinson's disease: from pathophysiology to management.
2004-05
Midodrine treatment for chronic fatigue syndrome.
2004-04
Clinical history.
2004-02
Diabetic neuropathy: an intensive review.
2004-01-15
[Successful midodrin treatment for vasovagal syncopes accompanied by asystole].
2004
Double-blinded, placebo-controlled trial of midodrine for exercise performance enhancement in tetraplegia: a pilot study.
2004
[Results of midodrin treatment of vasovagal syncope].
2004
Dysautonomia in chronic fatigue syndrome: facts, hypotheses, implications.
2004
Effects of fatty acids and iontophoresis on the delivery of midodrine hydrochloride and the structure of human skin.
2003-10
[Blood pressure disorders during idiopathic Parkinson's disease].
2003-08-09
Hepatorenal syndrome.
2003-01-02
Drug treatment of orthostatic hypotension because of autonomic failure or neurocardiogenic syncope.
2002
Computer systems analysis of the cardiovascular mechanisms of reentry orthostasis in astronauts.
2002
Patents

Patents

JPH09136831A
2
JPH09136843A
2

Sample Use Guides

In Vivo Use Guide
10 mg orally three times a day. Do not give more frequently than every 3 hours, after the evening meal, or less than 4 hours before bedtime.
Route of Administration: Oral
In Vitro Use Guide
A decrease in atrial rate was elicited by high concentrations (above 10(-4) to 10(-3) M) of the sympathomimetic agent midodrine in guinea-pig right atrial preparation
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:24:06 GMT 2025
Edited
by admin
on Wed Apr 02 09:24:06 GMT 2025
Record UNII
6YE7PBM15H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ST 1085
Preferred Name English
MIDODRINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Midodrine [WHO-DD]
Common Name English
MIDODRINE [VANDF]
Common Name English
ACETAMIDE, 2-AMINO-N-(2-(2,5-DIMETHOXYPHENYL)-2-HYDROXYETHYL)-, (±)-
Systematic Name English
(±)-2-AMINO-N-(.BETA.-HYDROXY-2,5-DIMETHOXYPHENETHYL)ACETAMIDE
Systematic Name English
midodrine [INN]
Common Name English
MIDODRINE [MI]
Common Name English
MIDODRINE [HSDB]
Common Name English
ST-1085
Code English
Classification Tree Code System Code
NDF-RT N0000175552
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
NCI_THESAURUS C29709
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
NDF-RT N0000000209
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
WHO-ATC C01CA17
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
WHO-VATC QC01CA17
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
Code System Code Type Description
IUPHAR
7240
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
DRUG BANK
DB00211
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
CHEBI
6933
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
NCI_THESAURUS
C61846
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
DAILYMED
6YE7PBM15H
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
MERCK INDEX
m7533
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1201212
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
MESH
D008879
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
FDA UNII
6YE7PBM15H
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
CAS
42794-76-3
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
EVMPD
SUB08954MIG
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
RXCUI
6963
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
255-945-3
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
DRUG CENTRAL
1803
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
WIKIPEDIA
Midodrine
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
EPA CompTox
DTXSID0023321
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
PUBCHEM
4195
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
SMS_ID
100000080628
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
INN
3186
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
HSDB
7854
Created by admin on Wed Apr 02 09:24:06 GMT 2025 , Edited by admin on Wed Apr 02 09:24:06 GMT 2025
PRIMARY
Related Record Type Details
Structure of MIDODRINE, (R)-
ENANTIOMER -> RACEMATE
Structure of Midodrine hydrochloride
SALT/SOLVATE -> PARENT
Structure of MIDODRINE, (S)-
ENANTIOMER -> RACEMATE
ALPHA-1A ADRENERGIC RECEPTOR
TARGET -> AGONIST
Structure of Midodrine hydrochloride
SALT/SOLVATE -> PARENT
ALPHA-1B ADRENERGIC RECEPTOR
TARGET -> AGONIST
Related Record Type Details
Structure of DESGLYMIDODRINE
METABOLITE ACTIVE -> PRODRUG
MAJOR
PLASMA
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life Elimination
PHARMACOKINETIC
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