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Identification
NameMidodrine
Accession NumberDB00211  (APRD01116)
TypeSmall Molecule
GroupsApproved
DescriptionAn ethanolamine derivative that is an adrenergic alpha agonist. It is used as a vasoconstrictor agent in the treatment of hypotension. [PubChem]
Structure
Thumb
Synonyms
(+-)-2-amino-N-(beta-hydroxy-2,5-dimethoxyphenethyl)acetamide
1-(2',5'-Dimethoxyphenyl)-2-glycinamidoethanol
2-Amino-N-(2,5-dimethoxy-beta-hydroxyphenethyl)acetamide
DL-N1-(beta-Hydroxy-2,5-dimethoxyphenethyl)glycinamid
Midodrin
Midodrina
Midodrinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmatineTablet5 mgOralShire Pharma Canada Ulc1992-12-312010-10-04Canada
AmatineTablet2.5 mgOralShire Pharma Canada Ulc1992-12-312010-09-30Canada
MidodrineTablet2.5 mgOralAa Pharma Inc2006-06-13Not applicableCanada
MidodrineTablet5.0 mgOralAa Pharma Inc2006-06-13Not applicableCanada
ProamatineTablet2.5 mg/1OralShire US Manufacturing Inc.1996-09-06Not applicableUs
ProamatineTablet5 mg/1OralShire US Manufacturing Inc.1996-09-06Not applicableUs
ProamatineTablet10 mg/1OralShire US Manufacturing Inc.2002-03-20Not applicableUs
ProamatineTablet5 mg/1OralPhysicians Total Care, Inc.2005-09-30Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Midodrine HClTablet5 mg/1OralEon Labs, Inc.2003-09-11Not applicableUs
Midodrine HClTablet5 mg/1OralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2012-11-26Not applicableUs
Midodrine HClTablet2.5 mg/1OralCardinal Health2010-05-11Not applicableUs
Midodrine HClTablet10 mg/1OralEon Labs, Inc.2002-07-02Not applicableUs
Midodrine HClTablet2.5 mg/1OralAmerican Health Packaging2010-05-11Not applicableUs
Midodrine HClTablet10 mg/1OralRebel Distributors Corp2002-07-02Not applicableUs
Midodrine HClTablet5 mg/1OralCardinal Health2004-11-03Not applicableUs
Midodrine HClTablet5 mg/1OralAmerican Health Packaging2010-05-11Not applicableUs
Midodrine HClTablet2.5 mg/1OralEon Labs, Inc.2003-09-11Not applicableUs
Midodrine HClTablet5 mg/1OralCardinal Health2004-11-03Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralApotex Corp2006-09-12Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2003-09-10Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralImpax Generics2005-12-16Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralPhysicians Total Care, Inc.2006-01-01Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralUpsher Smith Laboratories Inc.2004-11-03Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralAv Pak2011-08-17Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralAmerican Health Packaging2015-09-01Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralMylan Pharmaceuticals Inc.2003-09-11Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralCardinal Health2011-01-14Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2003-09-10Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralPhysicians Total Care, Inc.2008-08-19Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralUpsher Smith Laboratories Inc.2004-11-03Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralAv Pak2011-08-17Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralAvera Mc Kennan Hospital2015-03-01Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralMylan Pharmaceuticals Inc.2003-09-11Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralApotex Corp2006-09-12Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralCarilion Materials Management2004-05-27Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralUpsher Smith Laboratories Inc.2004-11-03Not applicableUs
Midodrine HydrochlorideTablet10 mg/1OralAv Pak2011-08-17Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralImpax Generics2004-05-27Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2003-09-10Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralApotex Corp2006-09-12Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralAv Kare, Inc.2004-05-27Not applicableUs
Midodrine HydrochlorideTablet2.5 mg/1OralMylan Pharmaceuticals Inc.2003-09-11Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralImpax Generics2004-05-27Not applicableUs
Midodrine HydrochlorideTablet5 mg/1OralMylan Institutional Inc.2006-09-11Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Midodrine hydrochloride
43218-56-0
Thumb
  • InChI Key: MGCQZNBCJBRZDT-UHFFFAOYNA-N
  • Monoisotopic Mass: 290.103334813
  • Average Mass: 290.743
DBSALT000250
Categories
UNII6YE7PBM15H
CAS number42794-76-3
WeightAverage: 254.2823
Monoisotopic: 254.126657074
Chemical FormulaC12H18N2O4
InChI KeyPTKSEFOSCHHMPD-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-amino-N-[2-(2,5-dimethoxyphenyl)-2-hydroxyethyl]acetamide
SMILES
COC1=CC(C(O)CNC(=O)CN)=C(OC)C=C1
Pharmacology
IndicationFor the treatment of symptomatic orthostatic hypotension (OH).
Structured Indications
PharmacodynamicsMidodrine 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.
Mechanism of actionMidodrine 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-1A adrenergic receptorProteinyes
agonist
HumanP35348 details
Alpha-1B adrenergic receptorProteinyes
agonist
HumanP35368 details
Alpha-1D adrenergic receptorProteinunknown
agonist
HumanP25100 details
Related Articles
AbsorptionRapidly absorbed following oral administration. The absolute bioavailability of midodrine (measured as desglymidodrine) is 93% and is not affected by food.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Thorough metabolic studies have not been conducted, but it appears that deglycination of midodrine to desglymidodrine takes place in many tissues, and both compounds are metabolized in part by the liver.

SubstrateEnzymesProduct
Midodrine
Not Available
desglymidodrineDetails
Route of eliminationNot Available
Half lifeThe plasma levels of the prodrug peak after about half an hour, and decline with a half-life of approximately 25 minutes, while the metabolite reaches peak blood concentrations about 1 to 2 hours after a dose of midodrine and has a half-life of about 3 to 4 hours.
Clearance
  • Renal cl=385 mL/minute
ToxicitySymptoms of overdose could include hypertension, piloerection (goosebumps), a sensation of coldness and urinary retention. The single doses that would be associated with symptoms of overdosage or would be potentially life- threatening are unknown. The oral LD50 is approximately 30 to 50 mg/kg in rats, 675 mg/kg in mice, and 125 to 160 mg/kg in dogs. Desglymidodrine is dialyzable.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypertensive activities of Midodrine.Experimental
AcebutololAcebutolol may increase the bradycardic activities of Midodrine.Approved
AcetyldigitoxinAcetyldigitoxin may increase the bradycardic activities of Midodrine.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Midodrine.Approved, Investigational
AlprenololAlprenolol may increase the bradycardic activities of Midodrine.Approved, Withdrawn
AmineptineAmineptine may increase the vasopressor activities of Midodrine.Illicit, Withdrawn
AmitriptylineAmitriptyline may increase the vasopressor activities of Midodrine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Midodrine.Approved, Illicit
AnvirzelAnvirzel may increase the bradycardic activities of Midodrine.Investigational
Aop200704Aop200704 may increase the bradycardic activities of Midodrine.Investigational
ArotinololArotinolol may increase the bradycardic activities of Midodrine.Approved
AtenololAtenolol may increase the bradycardic activities of Midodrine.Approved
AtomoxetineAtomoxetine may increase the hypertensive activities of Midodrine.Approved
BefunololBefunolol may increase the bradycardic activities of Midodrine.Experimental
BenmoxinBenmoxin may increase the hypertensive activities of Midodrine.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Midodrine is combined with Benzphetamine.Approved, Illicit
Benzylpenicilloyl PolylysineMidodrine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetaxololBetaxolol may increase the bradycardic activities of Midodrine.Approved
BevantololBevantolol may increase the bradycardic activities of Midodrine.Approved
BisoprololBisoprolol may increase the bradycardic activities of Midodrine.Approved
BopindololBopindolol may increase the bradycardic activities of Midodrine.Approved
BromocriptineBromocriptine may increase the hypertensive activities of Midodrine.Approved, Investigational
BucindololBucindolol may increase the bradycardic activities of Midodrine.Investigational
BufuralolBufuralol may increase the bradycardic activities of Midodrine.Experimental, Investigational
BupranololBupranolol may increase the bradycardic activities of Midodrine.Approved
CabergolineCabergoline may increase the hypertensive activities of Midodrine.Approved
CaroxazoneCaroxazone may increase the hypertensive activities of Midodrine.Withdrawn
CarteololCarteolol may increase the bradycardic activities of Midodrine.Approved
CarvedilolCarvedilol may increase the bradycardic activities of Midodrine.Approved, Investigational
CeliprololCeliprolol may increase the bradycardic activities of Midodrine.Approved, Investigational
ChlorphentermineThe risk or severity of adverse effects can be increased when Midodrine is combined with Chlorphentermine.Illicit, Withdrawn
ClenbuterolThe risk or severity of adverse effects can be increased when Midodrine is combined with Clenbuterol.Approved, Vet Approved
ClomipramineClomipramine may increase the vasopressor activities of Midodrine.Approved, Vet Approved
CyclobenzaprineCyclobenzaprine may increase the vasopressor activities of Midodrine.Approved
DesipramineDesipramine may increase the vasopressor activities of Midodrine.Approved
DeslanosideDeslanoside may increase the bradycardic activities of Midodrine.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Midodrine.Approved
DigitoxinDigitoxin may increase the bradycardic activities of Midodrine.Approved
DigoxinDigoxin may increase the bradycardic activities of Midodrine.Approved
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Midodrine.Approved
DiltiazemDiltiazem may increase the bradycardic activities of Midodrine.Approved
DobutamineThe risk or severity of adverse effects can be increased when Midodrine is combined with Dobutamine.Approved
DopamineThe risk or severity of adverse effects can be increased when Midodrine is combined with Dopamine.Approved
DosulepinDosulepin may increase the vasopressor activities of Midodrine.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Midodrine.Approved
DoxepinDoxepin may increase the vasopressor activities of Midodrine.Approved
DoxofyllineThe risk or severity of adverse effects can be increased when Midodrine is combined with Doxofylline.Approved
DronabinolDronabinol may increase the tachycardic activities of Midodrine.Approved, Illicit
DroxidopaMidodrine may increase the hypertensive activities of Droxidopa.Approved, Investigational
DuloxetineDuloxetine may increase the tachycardic activities of Midodrine.Approved
EphedrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Ephedrine.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Epinephrine.Approved, Vet Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Midodrine.Approved
ErgonovineErgonovine may increase the hypertensive activities of Midodrine.Approved
ErgotamineErgotamine may increase the hypertensive activities of Midodrine.Approved
EsmirtazapineEsmirtazapine may increase the vasopressor activities of Midodrine.Investigational
EsmololEsmolol may increase the bradycardic activities of Midodrine.Approved
EtilefrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Etilefrine.Withdrawn
FenoterolThe risk or severity of adverse effects can be increased when Midodrine is combined with Fenoterol.Approved
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Midodrine.Approved, Illicit, Investigational, Vet Approved
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Midodrine.Approved
FurazolidoneFurazolidone may increase the hypertensive activities of Midodrine.Approved, Vet Approved
HyaluronidaseHyaluronidase may increase the vasoconstricting activities of Midodrine.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypertensive activities of Midodrine.Approved
Hydroxyamphetamine hydrobromideThe risk or severity of adverse effects can be increased when Midodrine is combined with Hydroxyamphetamine hydrobromide.Approved
ImipramineImipramine may increase the vasopressor activities of Midodrine.Approved
IndenololIndenolol may increase the bradycardic activities of Midodrine.Withdrawn
IndoraminIndoramin may decrease the vasoconstricting activities of Midodrine.Withdrawn
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Midodrine.Approved
IproclozideIproclozide may increase the hypertensive activities of Midodrine.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Midodrine.Withdrawn
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Midodrine.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Midodrine is combined with Isoprenaline.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Midodrine is combined with Isoxsuprine.Approved, Withdrawn
LabetalolLabetalol may increase the bradycardic activities of Midodrine.Approved
LevobunololLevobunolol may increase the bradycardic activities of Midodrine.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Midodrine.Approved
LinezolidLinezolid may increase the hypertensive activities of Midodrine.Approved, Investigational
MebanazineMebanazine may increase the hypertensive activities of Midodrine.Withdrawn
MephentermineThe risk or severity of adverse effects can be increased when Midodrine is combined with Mephentermine.Approved
MetaraminolThe risk or severity of adverse effects can be increased when Midodrine is combined with Metaraminol.Approved, Investigational
MethamphetamineThe risk or severity of adverse effects can be increased when Midodrine is combined with Methamphetamine.Approved, Illicit
MethoxamineThe risk or severity of adverse effects can be increased when Midodrine is combined with Methoxamine.Approved
Methylene blueMethylene blue may increase the hypertensive activities of Midodrine.Investigational
MetipranololMetipranolol may increase the bradycardic activities of Midodrine.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Midodrine.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Midodrine.Approved
MinaprineMinaprine may increase the hypertensive activities of Midodrine.Approved
MirtazapineMirtazapine may increase the vasopressor activities of Midodrine.Approved
MoclobemideMoclobemide may increase the hypertensive activities of Midodrine.Approved
NabiloneNabilone may increase the tachycardic activities of Midodrine.Approved, Investigational
NadololNadolol may increase the bradycardic activities of Midodrine.Approved
NialamideNialamide may increase the hypertensive activities of Midodrine.Withdrawn
NorepinephrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Norepinephrine.Approved
NortriptylineNortriptyline may increase the vasopressor activities of Midodrine.Approved
NylidrinThe risk or severity of adverse effects can be increased when Midodrine is combined with Nylidrin.Approved
OctamoxinOctamoxin may increase the hypertensive activities of Midodrine.Withdrawn
OpipramolOpipramol may increase the vasopressor activities of Midodrine.Investigational
OrciprenalineThe risk or severity of adverse effects can be increased when Midodrine is combined with Orciprenaline.Approved
OuabainOuabain may increase the bradycardic activities of Midodrine.Approved
OxprenololOxprenolol may increase the bradycardic activities of Midodrine.Approved
OxymetazolineThe risk or severity of adverse effects can be increased when Midodrine is combined with Oxymetazoline.Approved
PargylinePargyline may increase the hypertensive activities of Midodrine.Approved
PenbutololPenbutolol may increase the bradycardic activities of Midodrine.Approved, Investigational
PhenelzinePhenelzine may increase the hypertensive activities of Midodrine.Approved
PheniprazinePheniprazine may increase the hypertensive activities of Midodrine.Withdrawn
PhenmetrazineThe risk or severity of adverse effects can be increased when Midodrine is combined with Phenmetrazine.Approved, Illicit
PhenoxypropazinePhenoxypropazine may increase the hypertensive activities of Midodrine.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Midodrine.Approved, Illicit
PhenylephrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Phenylephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Midodrine is combined with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PindololPindolol may increase the bradycardic activities of Midodrine.Approved
PirlindolePirlindole may increase the hypertensive activities of Midodrine.Approved
PivhydrazinePivhydrazine may increase the hypertensive activities of Midodrine.Withdrawn
PractololPractolol may increase the bradycardic activities of Midodrine.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Midodrine.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Midodrine is combined with Procaterol.Approved
PropranololPropranolol may increase the bradycardic activities of Midodrine.Approved, Investigational
ProtriptylineProtriptyline may increase the vasopressor activities of Midodrine.Approved
PseudoephedrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Pseudoephedrine.Approved
RacepinephrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Racepinephrine.Approved
RasagilineRasagiline may increase the hypertensive activities of Midodrine.Approved
RitodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Ritodrine.Approved
SafrazineSafrazine may increase the hypertensive activities of Midodrine.Withdrawn
SelegilineSelegiline may increase the hypertensive activities of Midodrine.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Midodrine.Approved
SotalolSotalol may increase the bradycardic activities of Midodrine.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Midodrine.Approved
SynephrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Synephrine.Experimental
TamsulosinTamsulosin may decrease the vasoconstricting activities of Midodrine.Approved, Investigational
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Midodrine.Approved
TerazosinTerazosin may decrease the vasoconstricting activities of Midodrine.Approved
TerbutalineThe risk or severity of adverse effects can be increased when Midodrine is combined with Terbutaline.Approved
TetryzolineThe risk or severity of adverse effects can be increased when Midodrine is combined with Tetryzoline.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Midodrine.Approved
TianeptineTianeptine may increase the vasopressor activities of Midodrine.Approved
TimololTimolol may increase the bradycardic activities of Midodrine.Approved
ToloxatoneToloxatone may increase the hypertensive activities of Midodrine.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Midodrine.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Midodrine.Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Midodrine.Experimental
TrimipramineTrimipramine may increase the vasopressor activities of Midodrine.Approved
TyramineThe risk or severity of adverse effects can be increased when Midodrine is combined with Tyramine.Investigational, Nutraceutical
VenlafaxineVenlafaxine may increase the tachycardic activities of Midodrine.Approved
VerapamilVerapamil may increase the bradycardic activities of Midodrine.Approved
Food Interactions
  • Take without regard to meals.
References
Synthesis Reference

Anup K. Ray, Hiren Patel, Mahendra R. Patel, “Synthesis of midodrine HCI from a novel intermediate 1-(2’,5’-dimethoxyphenyl)-2-azidoethanone.” U.S. Patent US6201153, issued July, 1965.

US6201153
General References
  1. Hebenstreit G: [Treatment of hypotension caused by psychopharmacological drugs (author's transl)]. Wien Med Wochenschr. 1981 Feb 28;131(4):109-12. [PubMed:6165144 ]
  2. Tsuda M, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K: Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60. Epub 2006 Apr 5. [PubMed:16597710 ]
External Links
ATC CodesC01CA17
AHFS Codes
  • 12:12.00
  • 12:12.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7686
Blood Brain Barrier-0.856
Caco-2 permeable-0.7382
P-glycoprotein substrateSubstrate0.784
P-glycoprotein inhibitor INon-inhibitor0.9781
P-glycoprotein inhibitor IINon-inhibitor0.9866
Renal organic cation transporterNon-inhibitor0.8896
CYP450 2C9 substrateNon-substrate0.8519
CYP450 2D6 substrateNon-substrate0.7593
CYP450 3A4 substrateNon-substrate0.5595
CYP450 1A2 substrateInhibitor0.8848
CYP450 2C9 inhibitorNon-inhibitor0.9385
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.867
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9316
Ames testNon AMES toxic0.774
CarcinogenicityNon-carcinogens0.8613
BiodegradationNot ready biodegradable0.9595
Rat acute toxicity2.3137 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9772
hERG inhibition (predictor II)Non-inhibitor0.8604
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Apotex inc etobicoke site
  • Impax pharmaceuticals
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Upsher smith laboratories inc
  • Shire development inc
Packagers
Dosage forms
FormRouteStrength
TabletOral5 mg
TabletOral2.5 mg
TabletOral5.0 mg
TabletOral10 mg/1
TabletOral2.5 mg/1
TabletOral5 mg/1
Prices
Unit descriptionCostUnit
Proamatine 10 mg tablet5.91USD tablet
Midodrine hcl 10 mg tablet4.93USD tablet
Proamatine 5 mg tablet3.08USD tablet
Midodrine hcl 5 mg tablet2.47USD tablet
Proamatine 2.5 mg tablet1.53USD tablet
Midodrine hcl 2.5 mg tablet1.23USD tablet
Apo-Midodrine 5 mg Tablet0.59USD tablet
Apo-Midodrine 2.5 mg Tablet0.35USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point200 to 203°CNot Available
water solubilitySolubleNot Available
logP-0.5Not Available
pKa7.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.45 mg/mLALOGPS
logP-0.49ALOGPS
logP-0.95ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.77ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area93.81 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity66.22 m3·mol-1ChemAxon
Polarizability26.65 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • P-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Ether
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Buckner SA, Milicic I, Daza AV, Meyer MD, Altenbach RJ, Williams M, Sullivan JP, Brioni JD: ABT-866, a novel alpha(1A)-adrenoceptor agonist with antagonist properties at the alpha(1B)- and alpha(1D)-adrenoceptor subtypes. Eur J Pharmacol. 2002 Aug 2;449(1-2):159-65. [PubMed:12163120 ]
  2. Taniguchi N, Hamada K, Ogasawara T, Ukai Y, Yoshikuni Y, Kimura K: NS-49, an alpha 1A-adrenoceptor agonist, selectively increases intraurethral pressure in dogs. Eur J Pharmacol. 1996 Dec 27;318(1):117-22. [PubMed:9007522 ]
  3. Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O'Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP: 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. J Med Chem. 2004 Jun 3;47(12):3220-35. [PubMed:15163201 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O'Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP: 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. J Med Chem. 2004 Jun 3;47(12):3220-35. [PubMed:15163201 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Altenbach RJ, Khilevich A, Meyer MD, Buckner SA, Milicic I, Daza AV, Brune ME, O'Neill AB, Gauvin DM, Cain JC, Nakane M, Holladay MW, Williams M, Brioni JD, Sullivan JP: 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. J Med Chem. 2002 Sep 26;45(20):4395-7. [PubMed:12238918 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Tsuda M, Terada T, Irie M, Katsura T, Niida A, Tomita K, Fujii N, Inui K: Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives. J Pharmacol Exp Ther. 2006 Jul;318(1):455-60. Epub 2006 Apr 5. [PubMed:16597710 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23