Midodrine hydrochloride

First approved in 1996

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H18N2O4.ClH
Molecular Weight	290.743
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.COC1=CC=C(OC)C(=C1)C(O)CNC(=O)CN

InChI

InChIKey=MGCQZNBCJBRZDT-UHFFFAOYSA-N

InChI=1S/C12H18N2O4.ClH/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);1H

HIDE SMILES / InChI

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	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-1a adrenergic receptor 67 Target ID: CHEMBL229 Sources: http://www.drugbank.ca/drugs/DB00211	Agonist 2752
Alpha-1b adrenergic receptor 45 Target ID: CHEMBL232 Sources: http://www.drugbank.ca/drugs/DB00211	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Orthostatic hypotension 4 Sources: https://www.drugs.com/pro/midodrine.html	Primary		Approved 8583	ORVATEN Approved Use indicated for the treatment of symptomatic orthostatic hypotension Launch Date 2004

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

F_unbound

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 Dose: 350 mg Route: oral Route: single Dose: 350 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27417951	unhealthy, 20 years Health Status: unhealthy Age Group: 20 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/27417951	Other AEs: Hypertension, Bradycardia... Other AEs: Hypertension (severe, 1 patient) Bradycardia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/27417951
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: https://pubmed.ncbi.nlm.nih.gov/31381098	unhealthy, 49 years Health Status: unhealthy Age Group: 49 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/31381098	Sources: https://pubmed.ncbi.nlm.nih.gov/31381098
2.5 mg single, intravenous Dose: 2.5 mg Route: intravenous Route: single Dose: 2.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7690382	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/7690382	Sources: https://pubmed.ncbi.nlm.nih.gov/7690382
205 mg single, oral Overdose Dose: 205 mg Route: oral Route: single Dose: 205 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	unknown Health Status: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	Other AEs: Lethargic... Other AEs: Lethargic (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	unknown Health Status: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	Other AEs: Blood pressure systolic increased... Other AEs: Blood pressure systolic increased (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	Disc. AE: Supine hypertension... AEs leading to discontinuation/dose reduction: Supine hypertension Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/11007859	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/11007859	Other AEs: Pancytopenia... Other AEs: Pancytopenia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/11007859

AEs

AE	Significance	Dose	Population
Bradycardia	1 patient	350 mg single, oral Overdose Dose: 350 mg Route: oral Route: single Dose: 350 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27417951	unhealthy, 20 years Health Status: unhealthy Age Group: 20 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/27417951
Hypertension	severe, 1 patient	350 mg single, oral Overdose Dose: 350 mg Route: oral Route: single Dose: 350 mg Sources: https://pubmed.ncbi.nlm.nih.gov/27417951	unhealthy, 20 years Health Status: unhealthy Age Group: 20 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/27417951
Lethargic	1 patient	205 mg single, oral Overdose Dose: 205 mg Route: oral Route: single Dose: 205 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	unknown Health Status: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
Blood pressure systolic increased	1 patient	250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	unknown Health Status: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/019815s010lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/11007859	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/11007859

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6933	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6933
ChemicalBook	CB4297224	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4297224
MolPort	MolPort-003-849-221	https://www.molport.com/shop/molecule-link/MolPort-003-849-221

PubMed

Title	Date	PubMed
Beneficial haemodynamic and renal sodium handling effects of combined midodrine and octreotide treatment in a cirrhotic patient with large hepatic hydrothorax and mild ascites.	2005-11	16105868
[Pharmacotherapy of stress incontinence].	2005-10-14	16231235
L-DOPS therapy for refractory orthostatic hypotension in autoimmune autonomic neuropathy.	2005-10-11	16217067
Effect of mineralocorticoids on interdialytic weight gain in hemodialysis patients with perdialytic hypotension.	2005-10	16219052
Heat-related morbidity in patients with orthostatic hypotension and primary autonomic failure.	2005-09	15954131
Fludrocortisone in patients with familial dysautonomia--assessing effect on clinical parameters and gene expression.	2005-08	16032383
Adrenergic drugs for urinary incontinence in adults.	2005-07-20	16034867
Effects of therapy based on tilt testing results on the long-term outcome in patients with syncope.	2005-07	16136424
Adverse drug reactions related to drugs used in orthostatic hypotension: a prospective and systematic pharmacovigilance study in France.	2005-07	15991040
Consequences of cardiovascular adaptation to spaceflight: implications for the use of pharmacological countermeasures.	2005-06	16038093
[Diabetes mellitus and orthostatic intolerance].	2005-06	15999765
Pregnancy in postural orthostatic tachycardia syndrome.	2005-06	15955196
Familial dysautonomia: a review of the current pharmacological treatments.	2005-04	15934882
The effects of chronic treatment with octreotide versus octreotide plus midodrine on systemic hemodynamics and renal hemodynamics and function in nonazotemic cirrhotic patients with ascites.	2005-04	15784036
Successful treatment of hypotension associated with stunned myocardium with oral midodrine therapy.	2005-03	15821841
[Pure autonomic failure. Bradbury Eggleston Syndrome. Case report].	2005-02	15824832
[Sjögren's syndrome with autonomic failure and epilepsy].	2005-02	15710261
Hepatorenal syndrome: a dreaded complication of end-stage liver disease.	2005-02	15667508
[Treatment of ejaculation disorders].	2005-02	15664683
[Treatment of ejaculation disorders by midodrine (Gutron) per os. Retrospective study of about 16 subjects].	2005-02	15664682
Treatment of vasodepressor carotid sinus syndrome with midodrine: a randomized, controlled pilot study.	2005-01	15667387
[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	16149711
Postprandial hypotension treated with acarbose in a patient with type 1 diabetes mellitus.	2004-12	15666070
Reconsidering hepatorenal syndrome. Throw in the towel? Not so fast!	2004-12	15620124
The in vitro metabolism of desglymidodrine, an active metabolite of prodrug midodrine by human liver microsomes.	2004-11-13	15537169
[Orthostatic hypotension and supine hypertension in pure autonomic failure].	2004-11	15633433
Management of vasovagal syncope: 2004.	2004-11	15500436
Taste and smell disturbance with the alpha-adrenoceptor agonist midodrine.	2004-11	15466905
Effects of midodrine on exercise-induced hypotension and blood pressure recovery in autonomic failure.	2004-11	15273244
Midodrine appears to be safe and effective for dialysis-induced hypotension: a systematic review.	2004-10	15280522
A patient responding to combined therapy with pirmenol and midodrine for refractory neurally mediated syncope complicated by prostatic hypertrophy.	2004-09	15717144
New approaches to the treatment and prevention of neurally mediated reflex (neurocardiogenic) syncope.	2004-09	15306096
Midodrine, octreotide, albumin, and TIPS in selected patients with cirrhosis and type 1 hepatorenal syndrome.	2004-07	15239086
Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent.	2004-07	15190580
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.	2004-06-03	15163201
Intestinal obstruction associated with oral midodrine.	2004-06	15241651
Midodrine prescribed to improve recurrent post-spaceflight orthostatic hypotension.	2004-06	15198285
Pharmacology of orthostatic hypotension in Parkinson's disease: from pathophysiology to management.	2004-05	15151485
Midodrine treatment for chronic fatigue syndrome.	2004-04	15082846
Clinical history.	2004-02	15045601
Diabetic neuropathy: an intensive review.	2004-01-15	14750401
[Successful midodrin treatment for vasovagal syncopes accompanied by asystole].	2004	15540425
Double-blinded, placebo-controlled trial of midodrine for exercise performance enhancement in tetraplegia: a pilot study.	2004	15478524
[Results of midodrin treatment of vasovagal syncope].	2004	15471395
Dysautonomia in chronic fatigue syndrome: facts, hypotheses, implications.	2004	14962627
Effects of fatty acids and iontophoresis on the delivery of midodrine hydrochloride and the structure of human skin.	2003-10	14620516
[Blood pressure disorders during idiopathic Parkinson's disease].	2003-08-09	14506467
Hepatorenal syndrome.	2003-01-02	15094702
Drug treatment of orthostatic hypotension because of autonomic failure or neurocardiogenic syncope.	2002	14727996
Computer systems analysis of the cardiovascular mechanisms of reentry orthostasis in astronauts.	2002	14686452

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 17:59:45 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:45 GMT 2025`
Record UNII	59JV96YTXV
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PRO-AMATINE

Preferred Name

English

Midodrine hydrochloride

Official Name

English

Midodrine HCL

Common Name

English

METLIGINE

Brand Name

English

(±)-Midodrine hydrochloride

Common Name

English

ST-1085 BASE

Code

English

ST-PETER-224

Code

English

ST1085 HYDROCHLORIDE

Code

English

Midodrine hydrochloride [MI]

Common Name

English

Amatine

Brand Name

English

GUTRON

Brand Name

English

Midodrine hydrochloride [ORANGE BOOK]

Common Name

English

Midodrine monohydrochloride

Common Name

English

ST-1085 HYDROCHLORIDE

Code

English

ST. PETER 224

Code

English

ORVATEN

Brand Name

English

Midodrine hydrochloride [USAN]

Common Name

English

Midodrine hydrochloride [USP-RS]

Common Name

English

Acetamide, 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-, hydrochloride (1:1)

Systematic Name

English

PROAMATINE

Brand Name

English

NSC-758429

Code

English

(±)-Midodrin hydrochloride

Common Name

English

Midodrine hydrochloride [VANDF]

Common Name

English

Acetamide, 2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]-, monohydrochloride, (±)-

Systematic Name

English

(±)-2-Amino-N-(.beta.-hydroxy-2,5-dimethoxyphenethyl)acetamide monohydrochloride

Systematic Name

English

Midodrine hydrochloride [USP MONOGRAPH]

Common Name

English

A-4020 LINZ

Code

English

HIPERTAN

Brand Name

English

Midodrine hydrochloride [MART.]

Common Name

English

Midodrine hydrochloride [JAN]

Common Name

English

Midodrine hydrochloride [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709