QuickView for Clonidine (compound)

Summary
General Info

PubChem

PubChem Compound 20179

Name:	Clonidine
PubChem Compound ID:	20179
Description:	An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.
Molecular formula:	C₉H₁₀Cl₃N₃
Molecular weight:	266.554 g/mol
Synonyms:	2-((2,6-Dichlorophenyl)imino)imidazolidine monohydrochloride; Benzenamine, 2,6-dichloro-N-2-imidazolidinylidene-, hydrochloride; Catapres (TN); 57665-50-6; Clonidine hydrochloride; Catapresan; 2-Imidazoline, 2-(2,6-dichloroanilino)-, monohydrochloride; 1H-Imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, monohydrochloride (9CI); Dixarit; Capresin. show more » 2-((2,6-Dichlorophenyl)imino)imidazolidine monohydrochloride; Benzenamine, 2,6-dichloro-N-2-imidazolidinylidene-, hydrochloride; Catapres (TN); 57665-50-6; Clonidine hydrochloride; Catapresan; 2-Imidazoline, 2-(2,6-dichloroanilino)-, monohydrochloride; 1H-Imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, monohydrochloride (9CI); Dixarit; Capresin; Clonidine monohydrochloride; 4205-90-7; Benzenamine, 2,6-dichloro-N-2-imidazolidinylidene-, monohydrochloride; Edolglau; 66009-47-0; Nu-Clonidine; Clonistada; EINECS 224-121-5; Isaglaucon; Prestwick_73; Catanidin; Chlophazolin; D00604; Dispaclonidin; Catapres; Clonid-Ophal; 2-((2,6-Dichlorophenyl)amino)-2-imidazoline hydrochloride; Novo-Clonidine; Duraclon; 7555-15-9; Apo-Clonidine; Glausine; Clonilou; Isoglaucon; Katapresan; Clonidine hydrochloride [USAN:BAN:JAN]; Clonidil-Riker; Clonisin; 73121-65-0; Combipres; Haemitom; Haemiton; Atensina; 66073-52-7; 4205-91-8; Clonidine hydrochloride (JP15/USP); Iporel; EU-0100268; Clofelin; Barclyd; Hemiton; ST-155; Klophelin; Caprysin; DCAI; Normopresan; 64638-22-8; 2-(2,6-Dichloroanilino)-2-imidazoline hydrochloride; 2-(2,6-Dichlorophenylamino)-2-imidazolin hydrochlorid [German] show less «

DrugBank

Identification

Name:	Clonidine
Name (isomeric):	DB00575
Drug Type:	small molecule
Description:	An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.
Synonyms:	ST 155BS; Clonidin; Clonidinum [INN-Latin]; Clonidinhydrochlorid; Clonidine HCl; Chlornidinum
Brand:	Catapressan, Clonistada, Tenso-Timelets, Duraclont, Ipotensium, Catapres, Catapres-TTS, Duraclon, Adesipress, Dixarit, Catarpresan, Isoglaucon, Catarpres, Catapresan
Brand name mixture:	Combipres 0.1/15 Tab(Chlorthalidone + Clonidine Hydrochloride)
Category:	Central Alpha-Agonists, Sympatholytics, Adrenergic alpha-Agonists, Analgesics, Antihypertensive Agents
CAS number:	4205-90-7

Pharmacology

Indication:	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).
Pharmacology:	Clonidine is an α-adrenergic agent that acts specifically on α₂-receptors. α₂-receptors regulate a number of signaling pathways mediated by multiple G_i proteins, Gα_i1, Gα_i2, and G&alpha_i3. Stimulation of α₂-receptors mediates effects suc... show more » Clonidine is an α-adrenergic agent that acts specifically on α₂-receptors. α₂-receptors regulate a number of signaling pathways mediated by multiple G_i proteins, Gα_i1, Gα_i2, and G&alpha_i3. Stimulation of α₂-receptors mediates effects such as inhibition of adenylyl cyclase, stimulation fo phospholipase D, stimulation of mitogen-activated protein kinases, stimulation of K⁺ currents and inhibition of Ca²⁺ currents. Three G-protein coupled α₂-receptor subtypes have been identified: α_2A, α_2B, and α_2C. Each subtype has a unique pattern of tissue distribution in the central nervous system and peripheral tissues. The α_2A-receptor is widely distributed throughout the central nervous system; it is found in the locus coeruleus, brain stem nuclei, cerebral cortex, septum, hypothalamus, and hippocampus. α_2A-receptors are also expressed in the kidneys, spleen, thymus, lung and salivary glands. The α_2C-receptor is primarily expressed in the central nervous system, including the striatum, olfactory tubercle, hippocampus and cerebral cortex. Low levels of the α_2C-subtype are also found in the kidneys. The α_2B-receptor is located primarily in the periphery (kidney, liver, lung and heart) with low levels of expression in the thalamic nuclei of the central nervous system. The α_2A- and α_2C-receptors are located presynaptically and inhibit the released of noradrenaline from sympathetic nerves. Stimulation of these receptors decreases sympathetic tone, resulting in decreases in blood pressure and heart rate. Sedation and analgesia is mediated by centrally located α_2A-receptors, while peripheral α_2B-receptors mediate constriction of vascular smooth muscle. α_2A-Receptors also mediate essential components of the analgesic effect of nitrous oxide in the spinal cord. Clonidine stimulates all three α₂-receptor subtypes with similar potency. Its actions in the nervous system decreases blood pressure in patients with hypertension and decreases sympathetic overactivity in patients undergoing opioid withdrawal. Clonidine is also a potent sedative and analgesic and can prevent post-operative shivering in intensive and post-operative care. Its use in differential diagnosis of pheochromocytoma owes to the fact that hypertension in patients with pheochromocytoma is refractory to antihypertensive treatment with clonidine. show less «
Mechanism of Action:	See Pharmacology section above.
Absorption:	Well absorbed following oral administration. Bioavailability following chronic administration is approximately 65%.
Protein binding:	20-40%, primarily to albumin
Biotransformation:	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:	Oral LD₅₀ is 150 mg/kg in rat and 30 mg/kg in dog. 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.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol.

Take without regard to meals.

Drug interaction:

Imipramine	The tricyclic antidepressant, imipramine, decreases the effect of clonidine.
Bevantolol	Increased hypertension when clonidine stopped
Esmolol	Increased hypertension when clonidine stopped
Practolol	Increased hypertension when clonidine stopped
Desipramine	The tricyclic antidepressant, desipramine, decreases the effect of clonidine.

Imipramine	The tricyclic antidepressant, imipramine, decreases the effect of clonidine.
Bevantolol	Increased hypertension when clonidine stopped
Esmolol	Increased hypertension when clonidine stopped
Practolol	Increased hypertension when clonidine stopped
Desipramine	The tricyclic antidepressant, desipramine, decreases the effect of clonidine.
Doxepin	The tricyclic antidepressant, doxepin, decreases the effect of clonidine.
Carteolol	Increased hypertension when clonidine stopped
Oxprenolol	Increased hypertension when clonidine stopped
Amoxapine	The tricyclic antidepressant, amoxapine, decreases the effect of clonidine.
Propranolol	Increased hypertension when clonidine stopped
Labetalol	Increased hypertension when clonidine stopped
Bisoprolol	Increased hypertension when clonidine stopped
Atenolol	Increased hypertension when clonidine stopped
Treprostinil	Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Clomipramine	The tricyclic antidepressant, clomipramine, may decrease the effect of clonidine.
Amitriptyline	The tricyclic antidepressant, amitriptyline, decreases the effect of clonidine.
Carvedilol	Increased hypertension when clonidine stopped
Protriptyline	The tricyclic antidepressant, protriptyline, decreases the effect of clonidine.
Mirtazapine	Possible hypertensive crisis
Nadolol	Increased hypertension when clonidine stopped
Pindolol	Increased hypertension when clonidine stopped
Acebutolol	Increased hypertension when clonidine stopped
Sotalol	Increased hypertension when clonidine stopped
Timolol	Increased hypertension when clonidine stopped
Metoprolol	Increased hypertension when clonidine stopped
Trimipramine	Trimipramine may reduce the antihypertensive effect of the alpha2-agonist, Clonidine. Trimipramine may also increase the rebound hypertensive effect of Clonidine. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Clonidine if Trimipramine is initiated, discontinued or dose changed. Clonidine should be withdrawn very gradually to reduce the risk of hypertensive crisis.
Betaxolol	Increased hypertension when clonidine stopped
Nortriptyline	The tricyclic antidepressant, nortriptyline, decreases the effect of clonidine.
Penbutolol	Increased hypertension when clonidine stopped

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Targets

Alpha-2A adrenergic receptor

Alpha-2B adrenergic receptor

Alpha-2C adrenergic receptor

Enzymes

Transporters

Solute carrier family 22 member 1

Solute carrier family 22 member 3

Organic cation/carnitine transporter 2

Organic cation/carnitine transporter 1

Multidrug resistance protein 1