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Record Information
Version3.6
Creation Date2013-06-15 16:49:36 UTC
Update Date2017-03-02 22:05:12 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
DesglymidodrineChEBI
ST-1059ChEBI
a-(Aminomethyl)-2,5-dimethoxybenzenemethanolGenerator
α-(aminomethyl)-2,5-dimethoxybenzenemethanolGenerator
ST 1059 HydrochlorideMeSH
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=1S/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 KeyVFRCNXKYZVQYLX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • P-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Ether
  • Organic nitrogen compound
  • Primary amine
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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 Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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. [PubMed: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. [PubMed:12904123 ]