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
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)
| 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 | ( + / - ) |
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL229 Sources: http://www.drugbank.ca/drugs/DB00211 |
|||
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 |
|---|---|---|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 05:29:10 UTC 2021
by
admin
on
Sat Jun 26 05:29:10 UTC 2021
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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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WHO-VATC |
QC01CA17
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7240
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DB00211
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C61846
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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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42794-76-3
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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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ENANTIOMER -> RACEMATE | |||
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TARGET -> AGONIST | |||
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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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