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 Date1.09935362E12 |
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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Caudate hemorrhage as a possible complication of midodrine-induced supine hypertension. | 2001 Dec |
|
Treatment of erectile dysfunction with sildenafil citrate (Viagra) in parkinsonism due to Parkinson's disease or multiple system atrophy with observations on orthostatic hypotension. | 2001 Sep |
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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 |
|
[Vasoconstrictors in the treatment of hepatorenal syndrome]. | 2002 |
|
Strategy for the management of vasovagal syncope. | 2002 |
|
Unusual causes of severe orthostatic hypotension. | 2002 Apr |
|
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 |
|
[Syncope - a systematic overview of classification, pathogenesis, diagnosis and management]. | 2002 Feb |
|
Hemodynamics in patients with intradialytic hypotension treated with cool dialysate or midodrine. | 2002 Jan |
|
Chronic hypotension in the dialysis patient. | 2002 Jul-Aug |
|
Recurrent syncope in a 31-year-old army staff sergeant. | 2002 Mar |
|
Orthostatic hypotension. | 2002 May |
|
Supine hypertension during general anesthesia in a patient taking midodrine. | 2002 Nov |
|
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 |
|
Adrenergic drugs for urinary incontinence in adults. | 2003 |
|
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 |
|
Usefulness of intravenous metoprolol during positive isoproterenol tilt-table test in the choice of treatment for neurocardiogenic syncope. | 2003 Jan-Feb |
|
Drug treatment of orthostatic hypotension and vasovagal syncope. | 2003 Jan-Feb |
|
Hepatorenal syndrome. | 2003 Jan-Mar |
|
Successful treatment of chronic fatigue syndrome with midodrine: a pilot study. | 2003 May-Jun |
|
Effects of fatty acids and iontophoresis on the delivery of midodrine hydrochloride and the structure of human skin. | 2003 Oct |
|
Randomized clinical trials of neurally mediated syncope. | 2003 Sep |
|
[Successful midodrin treatment for vasovagal syncopes accompanied by asystole]. | 2004 |
|
[Results of midodrin treatment of vasovagal syncope]. | 2004 |
|
Dysautonomia in chronic fatigue syndrome: facts, hypotheses, implications. | 2004 |
|
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 |
|
Diabetic neuropathy: an intensive review. | 2004 Jan 15 |
|
Midodrine, octreotide, albumin, and TIPS in selected patients with cirrhosis and type 1 hepatorenal syndrome. | 2004 Jul |
|
Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent. | 2004 Jul |
|
The in vitro metabolism of desglymidodrine, an active metabolite of prodrug midodrine by human liver microsomes. | 2004 Jul-Sep |
|
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 |
|
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 |
|
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 |
|
[Treatment of ejaculation disorders by midodrine (Gutron) per os. Retrospective study of about 16 subjects]. | 2005 Feb |
|
Consequences of cardiovascular adaptation to spaceflight: implications for the use of pharmacological countermeasures. | 2005 Jun |
|
Pregnancy in postural orthostatic tachycardia syndrome. | 2005 Jun |
|
Successful treatment of hypotension associated with stunned myocardium with oral midodrine therapy. | 2005 Mar |
|
[Pharmacotherapy of stress incontinence]. | 2005 Oct 14 |
|
Heat-related morbidity in patients with orthostatic hypotension and primary autonomic failure. | 2005 Sep |
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
Sun Dec 18 20:37:08 UTC 2022
by
admin
on
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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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WHO-ATC |
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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6YE7PBM15H
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42794-76-3
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SUB08954MIG
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6963
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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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3186
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7854
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> AGONIST |
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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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