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Record Information
Version4.0
Creation Date2013-07-09 16:09:50 UTC
Update Date2017-09-27 08:43:57 UTC
HMDB IDHMDB0060964
Secondary Accession Numbers
  • HMDB60964
Metabolite Identification
Common Name5-Chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiazdiazole
Description5-Chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiadiazole is a metabolite of tizanidine. Tizanidine (trade names Zanaflex, Sirdalud) is a drug that is used as a muscle relaxant. It is a centrally acting α2 adrenergic agonist. It is used to treat the spasms, cramping, and tightness of muscles caused by medical problems such as multiple sclerosis, spastic diplegia, back pain, or certain other injuries to the spine or central nervous system. It is also prescribed off-label for migraine headaches, as a sleep aid, and as an anticonvulsant. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
5-chloro-4-(2-Imidazolin-2-ylamino)-2,1,3-benzothiadiazoleChEBI
TizanidinaChEBI
TizanidinumChEBI
5-chloro-4-(2-Imidazolin-4-on-2-ylamino)-2,1,3-benzothiadiazoleHMDB
ZanaflexMeSH
Tizanidine monohydrochlorideMeSH
5-chloro-4-(2-Imidazolin-2-yl-amino)-2,1,3-benzothiadiazoleMeSH
Acorda brand OF tizanidine hydrochlorideMeSH
Novartis brand OF tizanidine hydrochlorideMeSH
Sanofi synthelabo brand OF tizanidine hydrochlorideMeSH
SirdaludMeSH
Tizanidine hydrochlorideMeSH
Chemical FormulaC9H8ClN5S
Average Molecular Weight253.711
Monoisotopic Molecular Weight253.018893678
IUPAC Name5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
Traditional Nametizanidine
CAS Registry NumberNot Available
SMILES
ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1
InChI Identifier
InChI=1S/C9H8ClN5S/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9/h1-2H,3-4H2,(H2,11,12,13)
InChI KeyXFYDIVBRZNQMJC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiadiazoles. These are heterocyclic aromatic compounds containing a benzene ring fused to a thiadiazole ring. Thiadiazole is a five-membered aromatic heterocycle made up of one sulfur atom and two nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiadiazoles
Sub ClassNot Available
Direct ParentBenzothiadiazoles
Alternative Parents
Substituents
  • 2,1,3-benzothiadiazole
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • 2-imidazoline
  • Thiadiazole
  • Guanidine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carboximidamide
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

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 Solubility0.13 g/LALOGPS
logP1.6ALOGPS
logP2.02ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)7.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.2 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.77 m³·mol⁻¹ChemAxon
Polarizability23.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3960000000-3aca4c577af73cfa3997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-03af7132e7796b671fd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2090000000-6ed6a84b177d1e4425adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9020000000-a1d6e32b00fde6ba39d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-9ebe0248119b57c01175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1390000000-5ba6bc72d04cb138d433View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2590000000-0e6b317aeab569aa3c97View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-5490000000-5ee0610f321160b63c82View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00274
      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
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available