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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:09:48 UTC
HMDB IDHMDB0014714
Secondary Accession Numbers
  • HMDB14714
Metabolite Identification
Common NameClonidine
DescriptionClonidine, an imidazoline-derivative hypotensive agent is a centrally-acting α2-adrenergic agonist. It crosses the blood-brain barrier and acts in the hypothalamus to induce a decrease in blood pressure. It may also be administered as an epidural infusion as an adjunct treatment in the management of severe cancer pain that is not relieved by opiate analgesics alone. Clonidine may be used for differential diagnosis of pheochromocytoma in hypertensive patients. Other uses for clonidine include prophylaxis of vascular migraine headaches, treatment of severe dysmenorrhea, management of vasomotor symptoms associated with menopause, rapid detoxification in the management of opiate withdrawal, treatment of alcohol withdrawal used in conjunction with benzodiazepines, management of nicotine dependence, topical use to reduce intraocular pressure in the treatment of open-angle and secondary glaucoma and hemorrhagic glaucoma associated with hypertension, and in the treatment of attention-deficit hyperactivity disorder (ADHD). Clonidine also exhibits some peripheral activity.
Structure
Thumb
Synonyms
ValueSource
2,6-dichloro-N-2-ImidazolidinylidenebenzenamineChEBI
2-[(2,6-Dichlorophenyl)imino]imidazolineChEBI
ChlornidinumHMDB
ClonidinHMDB
ClonidinhydrochloridHMDB
ST 155BSHMDB
CatapresMeSH
ClofenilMeSH
Clonidine monohydrobromideMeSH
Clonidine monohydrochlorideMeSH
CatapresanMeSH
Clonidine hydrochlorideMeSH
Dihydrochloride, clonidineMeSH
DixaritMeSH
GemitonMeSH
KlofelinMeSH
Boehringer ingelheim brand OF clonidine hydrochlorideMeSH
ClofelinMeSH
Clonidine dihydrochlorideMeSH
ClophelineMeSH
Hydrochloride, clonidineMeSH
IsoglauconMeSH
CatapressanMeSH
ChlophazolinMeSH
HemitonMeSH
KlofenilMeSH
Monohydrobromide, clonidineMeSH
Monohydrochloride, clonidineMeSH
Chemical FormulaC9H9Cl2N3
Average Molecular Weight230.094
Monoisotopic Molecular Weight229.017352717
IUPAC NameN-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
Traditional Nameclonidine
CAS Registry Number4205-90-7
SMILES
ClC1=CC=CC(Cl)=C1NC1=NCCN1
InChI Identifier
InChI=1S/C9H9Cl2N3/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9/h1-3H,4-5H2,(H2,12,13,14)
InChI KeyGJSURZIOUXUGAL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Substituents
  • 1,3-dichlorobenzene
  • Aniline or substituted anilines
  • Aryl chloride
  • Aryl halide
  • 2-imidazoline
  • Guanidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.48 g/LNot Available
LogP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP2.55ALOGPS
logP2.49ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.42 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity59.09 m³·mol⁻¹ChemAxon
Polarizability21.7 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-02vi-8910000000-a3e51d12bf5d7c152fa8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dl-0279000000-5f6a2e746dea4ac42952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-2c051509a637beaafe73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-f1477af875c25c537ccbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-ccdeb1dfce0424b12c0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01po-6950000000-dd68628a46215027ef29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-6900000000-ce531320f1fda74d127eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03fr-2980000000-24b18e2a89a65b2b178fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0190000000-7cbbf9fb244993abe922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1090000000-9444e2a6ad340b2e0c4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2190000000-b31dc3277959bc7da1f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-9000000000-8f9953cf5ba876f810b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-1c3f1ad6c77da1103c66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1590000000-be2bbba9747b47393450View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-50e611f207ee7d674aacView in MoNA
MSMass Spectrum (Electron Ionization)splash10-003r-5970000000-33c27878b8b7ad9d5d75View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00575 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00575 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00575
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2701
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClonidine
METLIN IDNot Available
PubChem Compound2803
PDB IDCLU
ChEBI ID3757
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hossmann V, Maling TJ, Hamilton CA, Reid JL, Dollery CT: Sedative and cardiovascular effects of clonidine and nitrazepam. Clin Pharmacol Ther. 1980 Aug;28(2):167-76. [PubMed:7398184 ]
  2. Schapiro NA: "Dude, you don't have Tourette's:" Tourette's syndrome, beyond the tics. Pediatr Nurs. 2002 May-Jun;28(3):243-6, 249-53. [PubMed:12087644 ]