ContaminantDB: Clonidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:11 UTC

Update Date

2026-05-14 16:42:49 UTC

Accession Number

CHEM002223

Identification

Common Name

Clonidine

Class

Small Molecule

Description

Clonidine, 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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Adrenergic alpha-2 Receptor Agonist
Adrenergic alpha-Agonist
Amide
Amine
Analgesic
Antihypertensive Agent
Central alpha-Agonist
Drug
Human Neurotoxin
Metabolite
Organic Compound
Organochloride
Sympatholytic
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6-Dichloro-N-2-imidazolidinylidenebenzenamine	ChEBI
2-[(2,6-Dichlorophenyl)imino]imidazoline	ChEBI
Catarpres-TTS	HMDB
Chlornidinum	HMDB
Clonidin	HMDB
Clonidinhydrochlorid	HMDB
ST 155BS	HMDB
Catapres	HMDB
Clofenil	HMDB
Clonidine monohydrobromide	HMDB
Clonidine monohydrochloride	HMDB
Catapresan	HMDB
Clonidine hydrochloride	HMDB
Dihydrochloride, clonidine	HMDB
Dixarit	HMDB
Gemiton	HMDB
Klofelin	HMDB
Boehringer ingelheim brand OF clonidine hydrochloride	HMDB
Clofelin	HMDB
Clonidine dihydrochloride	HMDB
Clopheline	HMDB
Hydrochloride, clonidine	HMDB
Isoglaucon	HMDB
Catapressan	HMDB
Chlophazolin	HMDB
Hemiton	HMDB
Klofenil	HMDB
Monohydrobromide, clonidine	HMDB
Monohydrochloride, clonidine	HMDB
Clonidine	MeSH

Chemical Formula

C₉H₉Cl₂N₃

Average Molecular Mass

230.094 g/mol

Monoisotopic Mass

229.017 g/mol

CAS Registry Number

4205-90-7

IUPAC Name

N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine

Traditional Name

clonidine

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 Key

GJSURZIOUXUGAL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

clonidine (CHEBI:3757 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	305°C
Boiling Point	Not Available
Solubility	Appreciable

Predicted Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.49	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	8.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.42 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	59.09 m³·mol⁻¹	ChemAxon
Polarizability	21.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02vi-8910000000-a3e51d12bf5d7c152fa8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03dl-0279000000-5f6a2e746dea4ac42952	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0090000000-2c051509a637beaafe73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0090000000-f1477af875c25c537ccb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0090000000-ccdeb1dfce0424b12c0c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01po-6950000000-dd68628a46215027ef29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-6900000000-ce531320f1fda74d127e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-03fr-2980000000-24b18e2a89a65b2b178f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0190000000-7cbbf9fb244993abe922	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-285a93c6077b8174b42b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0090000000-2fa5eb2717a38b5ddc53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-fff41c3a9a890a8402d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-3190000000-a3308b4d4c0c2eaa7e1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03l0-0920000000-7827fba3068267e11fd7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-05gi-0900000000-7e2ad60d7fd425ea536c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03l0-0920000000-31421af1384e151ca804	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1090000000-9444e2a6ad340b2e0c4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2190000000-b31dc3277959bc7da1f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-015c-9000000000-8f9953cf5ba876f810b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-1c3f1ad6c77da1103c66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1590000000-be2bbba9747b47393450	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900000000-50e611f207ee7d674aac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-f2dc8cf311bd04067c45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-f2dc8cf311bd04067c45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9410000000-64bf1288d1fd79f1dd33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-939fc90511af10b4320a	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-003r-5970000000-33c27878b8b7ad9d5d75	Spectrum

Toxicity Profile

Route of Exposure

Well absorbed following oral administration. Bioavailability following chronic administration is approximately 65%.

Mechanism of Toxicity

Clonidine acts as an agonist at presynaptic alpha(2)-receptors in the nucleus tractus solitarius of the medulla oblongata. Stimulation of these receptors results in the supression of efferent sympathetic pathways and the subsequent decrease in blood pressure and vascular tone in the heart, kidneys, and peripheral vasculature. Clonidine is also a partial agonist at presynaptic alpha(2)-adrenergic receptors of peripheral nerves in vascular smooth muscle.

Metabolism

Hepatic. Metabolized via minor pathways. The major metabolite, p-hydroxyclonidine, is present in concentrations less than 10% of those of unchanged clonidine in urine. Four metabolites have been detected, but only p-hydroxyclonidine has been identified. Half Life: 6-20 hours; 40-60% is excreted in urine unchanged, 20% is excreted in feces. Less than 10% is excreted by p-hydroxyclonidine.

Toxicity Values

LD50: 150 mg/kg (oral, rat) LD50: 30 mg/kg (oral, dog)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

May be used as an adjunct in the treatment of hypertension, as an epidural infusion as an adjunct treatment in the management of severe cancer pain that is not relieved by opiate analgesics alone, for differential diagnosis of pheochromocytoma in hypertensive patients, 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).

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include constriction of pupils of the eye, drowsiness, high blood pressure followed by a drop in pressure, irritability, low body temperature, slowed breathing, slowed heartbeat, slowed reflexes, and weakness.

Treatment

There is no specific antidote for clonidine overdosage. Clonidine overdosage may result in the rapid development of CNS depression; therefore, induction of vomiting with ipecac syrup is not recommended. Gastric lavage may be indicated following recent and/or large ingestions. Administration of activated charcoal and/or a cathartic may be beneficial. Supportive care may include atropine sulfate for bradycardia, intravenous fluids and/or vasopressor agents for hypotension and vasodilators for hypertension. Naloxone may be a useful adjunct for the management of clonidine-induced respiratory depression, hypotension and/or coma; blood pressure should be monitored since the administration of naloxone has occasionally resulted in paradoxical hypertension. Tolazoline administration has yielded inconsistent results and is not recommended as first-line therapy. (4)

Concentrations

Not Available

External Links

DrugBank ID

DB00575

HMDB ID

HMDB0014714

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID