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Record Information
Version3.6
Creation Date2013-06-15 16:49:36 UTC
Update Date2016-02-11 08:08:17 UTC
HMDB IDHMDB60558
Secondary Accession NumbersNone
Metabolite Identification
Common NameDesglymidodrine
DescriptionDesglymidodrine is a metabolite of midodrine. Midodrine (brand names Amatine, ProAmatine, Gutron) is a vasopressor/antihypotensive agent. Midodrine was approved in the United States by the Food and Drug Administration (FDA) in 1996 for the treatment of dysautonomia and orthostatic hypotension. In August 2010, the FDA proposed withdrawing this approval because the manufacturer, Shire plc, has failed to complete required studies after the medicine reached the market. (Wikipedia) Midodrine, a prodrug, is converted after oral administration into its active drug, desglymidodrine, which acts as an alpha(1)-adrenoceptor stimulant. (PMID: 17901021 ) Through selective alpha(1)-adrenergic receptor-binding, desglymidodrine, the active metabolite of midodrine, raises blood pressure by enhancing venous and arterial tone. (PMID: 12904123 )
Structure
Thumb
Synonyms
ValueSource
(+-)-2-amino-1-(2,5-Dimethoxyphenyl)ethanolChEBI
(+/-)-2-amino-1-(2,5-dimethoxyphenyl)ethanolChEBI
1-(2',5'-Dimethoxyphenyl)aminoethanolChEBI
alpha-(Aminomethyl)-2,5-dimethoxybenzenemethanolChEBI
De-glymidodrineChEBI
ST-1059ChEBI
Chemical FormulaC10H15NO3
Average Molecular Weight197.231
Monoisotopic Molecular Weight197.105193351
IUPAC Name2-amino-1-(2,5-dimethoxyphenyl)ethan-1-ol
Traditional Name2-amino-1-(2,5-dimethoxyphenyl)ethanol
CAS Registry NumberNot Available
SMILES
COC1=CC(C(O)CN)=C(OC)C=C1
InChI Identifier
InChI=1/C10H15NO3/c1-13-7-3-4-10(14-2)8(5-7)9(12)6-11/h3-5,9,12H,6,11H2,1-2H3
InChI KeyInChIKey=VFRCNXKYZVQYLX-UHFFFAOYNA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.9 mg/mLALOGPS
logP-0.01ALOGPS
logP0.15ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.71 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.42 m3·mol-1ChemAxon
Polarizability20.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00829
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60558
Metagene LinkHMDB60558
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vaidyanathan S, Soni BM, Hughes PL: Midodrine: insidious development of urologic adverse effects in patients with spinal cord injury: a report of 2 cases. Adv Ther. 2007 Jul-Aug;24(4):712-20. [17901021 ]
  2. Perazella MA: Efficacy and safety of midodrine in the treatment of dialysis-associated hypotension. Expert Opin Drug Saf. 2003 Jan;2(1):37-47. [12904123 ]