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
SMILES
COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1
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)
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 | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00211Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/midodrine.html
Sources: http://www.drugbank.ca/drugs/DB00211
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2452997
Curator's Comment: does not cross the blood-brain barrier
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL229 Sources: http://www.drugbank.ca/drugs/DB00211 |
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Target ID: CHEMBL232 Sources: http://www.drugbank.ca/drugs/DB00211 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ORVATEN Approved Useindicated for the treatment of symptomatic orthostatic hypotension Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
350 mg single, oral Overdose |
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) Sources: Bradycardia (1 patient) |
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 Health Status: unknown Population Size: 1 Sources: |
Other AEs: Lethargic... Other AEs: Lethargic (1 patient) Sources: |
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: |
unknown n = 1 Health Status: unknown Population Size: 1 Sources: |
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 |
Other AEs: Pancytopenia... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bradycardia | 1 patient | 350 mg single, oral Overdose |
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 |
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 Health Status: unknown Population Size: 1 Sources: |
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 Health Status: unknown Population Size: 1 Sources: |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Diagnosis and treatment of diabetic autonomic neuropathy. | 2001 Dec |
|
[Pharmacologic stimulation of ejaculation with midodrine hydrochloride (Gutron) for medically assisted reproduction in spinal injury]. | 2001 Dec |
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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 |
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[Vasoconstrictors in the treatment of hepatorenal syndrome]. | 2002 |
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Strategy for the management of vasovagal syncope. | 2002 |
|
Unusual causes of severe orthostatic hypotension. | 2002 Apr |
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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 |
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[Lipothymia and syncope in adolescents]. | 2002 Dec |
|
Recurrent syncope in a 31-year-old army staff sergeant. | 2002 Mar |
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Orthostatic hypotension. | 2002 May |
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Midodrine, an alternative to intravenous vasopressor therapy after spinal surgery. | 2002 Nov |
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Supine hypertension during general anesthesia in a patient taking midodrine. | 2002 Nov |
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Midodrine in neurally mediated syncope: a double-blind, randomized, crossover study. | 2002 Sep |
|
N-[3-(1H-imidazol-4-ylmethyl)phenyl]ethanesulfonamide (ABT-866, 1),(1) a novel alpha(1)-adrenoceptor ligand with an enhanced in vitro and in vivo profile relative to phenylpropanolamine and midodrine. | 2002 Sep 26 |
|
A pilot randomized trial of induced blood pressure elevation: effects on function and focal perfusion in acute and subacute stroke. | 2003 |
|
Adrenergic drugs for urinary incontinence in adults. | 2003 |
|
Neurocardiogenic syncope in children : current concepts in diagnosis and management. | 2003 |
|
Atrial septal aneurysm with right-to-left interatrial shunting. | 2003 |
|
Recurrent syncope in a patient after myocardial infarction. | 2003 Apr |
|
[Blood pressure disorders during idiopathic Parkinson's disease]. | 2003 Aug 9 |
|
Determination of midodrine in human plasma by high-performance liquid chromatography with fluorescence detection. | 2003 Feb |
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Efficacy and safety of midodrine in the treatment of dialysis-associated hypotension. | 2003 Jan |
|
Usefulness of intravenous metoprolol during positive isoproterenol tilt-table test in the choice of treatment for neurocardiogenic syncope. | 2003 Jan-Feb |
|
Hepatorenal syndrome. | 2003 Jan-Mar |
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Midodrine improves chronic hypotension in hemodialysis patients. | 2003 May |
|
Successful treatment of chronic fatigue syndrome with midodrine: a pilot study. | 2003 May-Jun |
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Effects of fatty acids and iontophoresis on the delivery of midodrine hydrochloride and the structure of human skin. | 2003 Oct |
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Randomized clinical trials of neurally mediated syncope. | 2003 Sep |
|
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 |
|
Midodrine treatment for chronic fatigue syndrome. | 2004 Apr |
|
Diabetic neuropathy: an intensive review. | 2004 Jan 15 |
|
Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent. | 2004 Jul |
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Intestinal obstruction associated with oral midodrine. | 2004 Jun |
|
Midodrine prescribed to improve recurrent post-spaceflight orthostatic hypotension. | 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 |
|
[Orthostatic hypotension and supine hypertension in pure autonomic failure]. | 2004 Nov |
|
Management of vasovagal syncope: 2004. | 2004 Nov |
|
Effects of midodrine on exercise-induced hypotension and blood pressure recovery in autonomic failure. | 2004 Nov |
|
New approaches to the treatment and prevention of neurally mediated reflex (neurocardiogenic) syncope. | 2004 Sep |
|
[Sjögren's syndrome with autonomic failure and epilepsy]. | 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 |
|
[Diabetes mellitus and orthostatic intolerance]. | 2005 Jun |
|
[Pharmacotherapy of stress incontinence]. | 2005 Oct 14 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/midodrine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/61715
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
Edited
Sat Dec 16 17:38:25 GMT 2023
by
admin
on
Sat Dec 16 17:38:25 GMT 2023
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Record UNII |
6YE7PBM15H
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175552
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NCI_THESAURUS |
C29709
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NDF-RT |
N0000000209
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C01CA17
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QC01CA17
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7240
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DB00211
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6933
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C61846
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6YE7PBM15H
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m7533
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CHEMBL1201212
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D008879
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42794-76-3
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255-945-3
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1803
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Midodrine
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DTXSID0023321
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4195
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100000080628
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3186
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7854
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> AGONIST |
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TARGET -> AGONIST |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
MAJOR
PLASMA
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Elimination PHARMACOKINETIC |
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