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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:50 UTC
Update Date2019-07-23 07:15:29 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 one of the two major metabolites of tizanidine (PMID: 9929503 , 19961320 ). 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
Data?1563866128
Synonyms
ValueSource
2-[(5-Chloro-2,1,3-benzothiadiazol-4-yl)amino]-3,5-dihydro-4H-imidazol-4-oneHMDB
DS 200-717HMDB
5-Chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiazdiazoleHMDB
Chemical FormulaC9H6ClN5OS
Average Molecular Weight267.69
Monoisotopic Molecular Weight266.9981587
IUPAC Name2-[(5-chloro-2,1,3-benzothiadiazol-4-yl)amino]-4,5-dihydro-1H-imidazol-4-one
Traditional Name2-[(5-chloro-2,1,3-benzothiadiazol-4-yl)amino]-1,5-dihydroimidazol-4-one
CAS Registry Number125292-32-2
SMILES
ClC1=C(NC2=NC(=O)CN2)C2=NSN=C2C=C1
InChI Identifier
InChI=1S/C9H6ClN5OS/c10-4-1-2-5-8(15-17-14-5)7(4)13-9-11-3-6(16)12-9/h1-2H,3H2,(H2,11,12,13,16)
InChI KeyUAPHNYZODWBPMU-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Thiadiazole
  • Imidazole
  • Azole
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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
logP1.58ALOGPS
logP1.21ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-0.051ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.27 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.65 m³·mol⁻¹ChemAxon
Polarizability24.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FooDB 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 Compound125355057
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Kaddar N, Vigneault P, Pilote S, Patoine D, Simard C, Drolet B: Tizanidine (Zanaflex): a muscle relaxant that may prolong the QT interval by blocking IKr. J Cardiovasc Pharmacol Ther. 2012 Mar;17(1):102-9. doi: 10.1177/1074248410395020. Epub 2011 Feb 11. [PubMed:21317414 ]
      2. El-Hefnawy AS, Helmy T, El-Assmy MM, Sarhan O, Hafez AT, Dawaba M: Doxazosin versus tizanidine for treatment of dysfunctional voiding in children: a prospective randomized open-labeled trial. Urology. 2012 Feb;79(2):428-33. doi: 10.1016/j.urology.2011.10.043. Epub 2011 Dec 22. [PubMed:22196407 ]
      3. Shellenberger MK, Groves L, Shah J, Novack GD: A controlled pharmacokinetic evaluation of tizanidine and baclofen at steady state. Drug Metab Dispos. 1999 Feb;27(2):201-4. [PubMed:9929503 ]
      4. Zhou SF, Wang B, Yang LP, Liu JP: Structure, function, regulation and polymorphism and the clinical significance of human cytochrome P450 1A2. Drug Metab Rev. 2010 May;42(2):268-354. doi: 10.3109/03602530903286476. [PubMed:19961320 ]