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 |
---|---|---|
Acute dystonia induced by adding midodrine, a selective alpha 1 agonist, to risperidone in a patient with catatonic schizophrenia. | 2000 Spring |
|
Treatment of Severe Intradialytic Hypotension With the Addition of High Dialysate Calcium Concentration to Midodrine and/or Cool Dialysate. | 2001 Feb |
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Midodrine for the management of orthostatic hypotension in patients with spinal cord injury: A case report. | 2001 May |
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Clinical case-based approach to understanding intradialytic hypotension. | 2001 Oct |
|
[Lipothymia and syncope in adolescents]. | 2002 Dec |
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[Syncope - a systematic overview of classification, pathogenesis, diagnosis and management]. | 2002 Feb |
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Orthostatic hypotension. | 2002 May |
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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 |
|
Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent. | 2004 Jul |
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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 |
|
[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 |
|
[Treatment of ejaculation disorders]. | 2005 Feb |
|
Consequences of cardiovascular adaptation to spaceflight: implications for the use of pharmacological countermeasures. | 2005 Jun |
|
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 Nov |
|
Effect of mineralocorticoids on interdialytic weight gain in hemodialysis patients with perdialytic hypotension. | 2005 Oct |
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
Thu Jul 06 23:00:35 UTC 2023
by
admin
on
Thu Jul 06 23:00:35 UTC 2023
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Record UNII |
6YE7PBM15H
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Record Status |
Validated (UNII)
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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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255-945-3
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1803
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Midodrine
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DTXSID0023321
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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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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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Biological Half-life |
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Elimination PHARMACOKINETIC |
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