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Details

Stereochemistry RACEMIC
Molecular Formula C12H18N2O4
Molecular Weight 254.2828
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDODRINE

SMILES

COc1ccc(c(c1)C(CN=C(CN)O)O)OC

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 254.2828
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

Curator's Comment:: does not cross the blood-brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ORVATEN

Approved Use

indicated for the treatment of symptomatic orthostatic hypotension

Launch Date

1.09935362E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21 ng/mL
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
2.2 ng/mL
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
18.5 ng × h/mL
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
2.5 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.54 h
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
0.6 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
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:
unhealthy, 20 years
n = 1
Health Status: unhealthy
Age Group: 20 years
Sex: F
Population Size: 1
Sources:
Other AEs: Hypertension, Bradycardia...
Other AEs:
Hypertension (severe, 1 patient)
Bradycardia (1 patient)
Sources:
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:
unhealthy, 49 years
n = 1
Health Status: unhealthy
Condition: hypotension
Age Group: 49 years
Sex: M
Population Size: 1
Sources:
2.5 mg single, intravenous
Dose: 2.5 mg
Route: intravenous
Route: single
Dose: 2.5 mg
Sources:
healthy, adult
n = 12
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 12
Sources:
205 mg single, oral
Overdose
Dose: 205 mg
Route: oral
Route: single
Dose: 205 mg
Sources:
unknown
n = 1
Other AEs: Lethargic...
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
unknown
n = 1
Other AEs: Blood pressure systolic increased...
Other AEs:
Blood pressure systolic increased (1 patient)
Sources:
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:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
Disc. AE: Supine hypertension...
AEs leading to
discontinuation/dose reduction:
Supine hypertension
Sources:
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:
unhealthy
n = 2
Health Status: unhealthy
Population Size: 2
Sources:
Other AEs: Pancytopenia...
Other AEs:
Pancytopenia (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Bradycardia 1 patient
350 mg single, oral
Overdose
Dose: 350 mg
Route: oral
Route: single
Dose: 350 mg
Sources:
unhealthy, 20 years
n = 1
Health Status: unhealthy
Age Group: 20 years
Sex: F
Population Size: 1
Sources:
Hypertension severe, 1 patient
350 mg single, oral
Overdose
Dose: 350 mg
Route: oral
Route: single
Dose: 350 mg
Sources:
unhealthy, 20 years
n = 1
Health Status: unhealthy
Age Group: 20 years
Sex: F
Population Size: 1
Sources:
Lethargic 1 patient
205 mg single, oral
Overdose
Dose: 205 mg
Route: oral
Route: single
Dose: 205 mg
Sources:
unknown
n = 1
Blood pressure systolic increased 1 patient
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
unknown
n = 1
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:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
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:
unhealthy
n = 2
Health Status: unhealthy
Population Size: 2
Sources:
PubMed

PubMed

TitleDatePubMed
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.
2000 Dec
Syncope in pharmacologically unmasked Brugada syndrome: indication for an implantable defibrillator or an unresolved dilemma?
2001 Apr
Use of midodrine (Gutron) to treat permanent hypotension in a chronic hemodialysis patient.
2001 Aug
[Orthostatic intolerance syndromes].
2001 Jan-Mar
Clinical case-based approach to understanding intradialytic hypotension.
2001 Oct
[Vasoconstrictors in the treatment of hepatorenal syndrome].
2002
Pandysautonomia associated with impaired ganglionic neurotransmission and circulating antibody to the neuronal nicotinic receptor.
2002 Aug
ABT-866, a novel alpha(1A)-adrenoceptor agonist with antagonist properties at the alpha(1B)- and alpha(1D)-adrenoceptor subtypes.
2002 Aug 2
Treatment of orthostatic hypotension.
2002 Dec
[Lipothymia and syncope in adolescents].
2002 Dec
Determination of midodrine in human plasma by high-performance liquid chromatography with fluorescence detection.
2003 Feb
Acute renal failure in patients with cirrhosis: perspectives in the age of MELD.
2003 Feb
Efficacy and safety of midodrine in the treatment of dialysis-associated hypotension.
2003 Jan
Hepatorenal syndrome.
2003 Jan-Mar
Midodrine improves chronic hypotension in hemodialysis patients.
2003 May
Randomized clinical trials of neurally mediated syncope.
2003 Sep
Dysautonomia in chronic fatigue syndrome: facts, hypotheses, implications.
2004
Midodrine treatment for chronic fatigue syndrome.
2004 Apr
Postprandial hypotension treated with acarbose in a patient with type 1 diabetes mellitus.
2004 Dec
Reconsidering hepatorenal syndrome. Throw in the towel? Not so fast!
2004 Dec
Clinical history.
2004 Feb
Midodrine, octreotide, albumin, and TIPS in selected patients with cirrhosis and type 1 hepatorenal syndrome.
2004 Jul
The in vitro metabolism of desglymidodrine, an active metabolite of prodrug midodrine by human liver microsomes.
2004 Jul-Sep
Intestinal obstruction associated with oral midodrine.
2004 Jun
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 Jun 3
Pharmacology of orthostatic hypotension in Parkinson's disease: from pathophysiology to management.
2004 May
[Orthostatic hypotension and supine hypertension in pure autonomic failure].
2004 Nov
Management of vasovagal syncope: 2004.
2004 Nov
Taste and smell disturbance with the alpha-adrenoceptor agonist midodrine.
2004 Nov
Effects of midodrine on exercise-induced hypotension and blood pressure recovery in autonomic failure.
2004 Nov
Midodrine appears to be safe and effective for dialysis-induced hypotension: a systematic review.
2004 Oct
A patient responding to combined therapy with pirmenol and midodrine for refractory neurally mediated syncope complicated by prostatic hypertrophy.
2004 Sep
New approaches to the treatment and prevention of neurally mediated reflex (neurocardiogenic) syncope.
2004 Sep
[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
Fludrocortisone in patients with familial dysautonomia--assessing effect on clinical parameters and gene expression.
2005 Aug
[Pure autonomic failure. Bradbury Eggleston Syndrome. Case report].
2005 Feb
Hepatorenal syndrome: a dreaded complication of end-stage liver disease.
2005 Feb
[Treatment of ejaculation disorders by midodrine (Gutron) per os. Retrospective study of about 16 subjects].
2005 Feb
Treatment of vasodepressor carotid sinus syndrome with midodrine: a randomized, controlled pilot study.
2005 Jan
Effects of therapy based on tilt testing results on the long-term outcome in patients with syncope.
2005 Jul
Adverse drug reactions related to drugs used in orthostatic hypotension: a prospective and systematic pharmacovigilance study in France.
2005 Jul
Adrenergic drugs for urinary incontinence in adults.
2005 Jul 20
[Diabetes mellitus and orthostatic intolerance].
2005 Jun
Pregnancy in postural orthostatic tachycardia syndrome.
2005 Jun
Successful treatment of hypotension associated with stunned myocardium with oral midodrine therapy.
2005 Mar
Effect of mineralocorticoids on interdialytic weight gain in hemodialysis patients with perdialytic hypotension.
2005 Oct
L-DOPS therapy for refractory orthostatic hypotension in autoimmune autonomic neuropathy.
2005 Oct 11
[Pharmacotherapy of stress incontinence].
2005 Oct 14
Patents

Sample Use Guides

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 Sat Jun 26 05:29:10 UTC 2021
Edited
by admin
on Sat Jun 26 05:29:10 UTC 2021
Record UNII
6YE7PBM15H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
ST 1085
Code 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 Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
NCI_THESAURUS C29709
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
NDF-RT N0000000209
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
WHO-ATC C01CA17
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
WHO-VATC QC01CA17
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
Code System Code Type Description
IUPHAR
7240
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
DRUG BANK
DB00211
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
NCI_THESAURUS
C61846
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
MERCK INDEX
M7533
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1201212
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
MESH
D008879
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
FDA UNII
6YE7PBM15H
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
CAS
42794-76-3
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
EVMPD
SUB08954MIG
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
RXCUI
6963
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
255-945-3
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
DRUG CENTRAL
1803
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
WIKIPEDIA
Midodrine
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
EPA CompTox
42794-76-3
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
PUBCHEM
4195
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
INN
3186
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
HSDB
7854
Created by admin on Sat Jun 26 05:29:10 UTC 2021 , Edited by admin on Sat Jun 26 05:29:10 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
TARGET -> AGONIST
TARGET -> AGONIST
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
MAJOR
PLASMA
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life Elimination
PHARMACOKINETIC