Clonidine

Identification

Summary

Clonidine is an alpha-2 adrenergic agonist used to treat hypertension and severe cancer pain, among other conditions, and to treat withdrawal symptoms from various substances. It is also used to aid in the diagnosis of pheochromocytoma and to prevent migraines.

Brand Names

Catapres, Catapres-TTS, Catapres-tts-1, Duraclon, Kapvay, Nexiclon XR

Generic Name

Clonidine

DrugBank Accession Number

DB00575

Background

Clonidine is an imidazole derivate that acts as an agonist of alpha-2 adrenoceptors.² This activity is useful for the treatment of hypertension, severe pain, and ADHD.^8,9,10,11

Clonidine was granted FDA approval on 3 September 1974.⁸

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 230.094
Monoisotopic: 229.017352717
Chemical Formula: C₉H₉Cl₂N₃

Synonyms

2-((2,6-Dichlorophenyl)imino)imidazolidine
2,6-Dichloro-N-2-imidazolidinylidenebenzenamine
Chlofazoline
Clonidin
Clonidina
Clonidine
Clonidinum

External IDs

M-5041T
SKF 34427
ST 155
ST 155-BS

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Pharmacology

Indication

Clonidine tablets and transdermal systems are indicated for the treatment of hypertension alone or in combination with other medications.^8,9 A clonidine injection is indicated for use with opiates in the treatment of severe cancer pain where opiates alone are insufficient.¹⁰ An extended release tablet of clonidine is indicated for the treatment of ADHD either alone or in combination with other medications.¹¹

Clonidine is also used for the diagnosis of pheochromocytoma,³ treatment of nicotine dependance,⁴ and opiate withdrawal.⁵

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Associated Conditions

Indication Type	Indication	Approval Level	Dose Form
Management of	Adhd	••••••••••••	••• ••••••••••• •••••••• •••••••• •••••• •••••••• •••••••• ••••••• •••••••• •••••••
Diagnostic agent	Growth hormone deficiency	••• •••••
Management of	Hot flashes	••• •••••
Management of	Hypertension	••••••••••••	••••••• •••••
Symptomatic treatment of	Opioid withdrawal	••• •••••

Associated Therapies

Smoking, Cessation

Contraindications & Blackbox Warnings

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Pharmacodynamics

Clonidine functions through agonism of alpha-2 adrenoceptors which have effects such as lowering blood pressure, sedation, and hyperpolarization of nerves.² It has a long duration of action as it is given twice daily and the therapeutic window is between 0.1mg and 2.4mg daily.^8,9,10,11

Mechanism of action

Clonidine is primarily an alpha-2 adrenoceptor agonist which causes central hypotensive and anti-arrhythmogenic effects.² The alpha-2 adrenoceptor is coupled to the G-proteins G_o and G_i.² G_i inhibits adenylyl cyclase and activates opening of a potassium channel that causes hyperpolarization.² Clonidine binding to the alpha-2 adrenoceptor causes structural changes in the alpha subunit of the G-protein, reducing its affinity for GDP.² Magnesium catalyzes the replacement of GDP with GTP.² The alpha subunit dissociates from the other subunits and associates with an effector.²

The stimulation of alpha-2 adrenoceptors in the locus coeruleus may be responsible for the hypnotic effects of clonidine as this region of the brain helps regulate wakefulness.² Clonidine can also decrease transmission of pain signals at the spine.² Finally clonidine can affect regulators of blood pressure in the ventromedial and rostral-ventrolateral areas of the medulla.²

Target	Actions	Organism
AAlpha-2B adrenergic receptor	agonist	Humans
AAlpha-2C adrenergic receptor	agonist	Humans
AAlpha-2A adrenergic receptor	agonist	Humans
UAlpha-1A adrenergic receptor	agonist	Humans
UAlpha-1B adrenergic receptor	agonist	Humans
UAlpha-1D adrenergic receptor	agonist	Humans

Absorption

Clonidine reaches maximum concentration in 60-90 minutes after oral administration.^2,6 Race and fasting status do not influence pharmacokinetics of clonidine.⁸

A 100µg oral clonidine tablet reaches a C_max of 400.72pg/mL with an AUC of 5606.78h*pg/mL and a bioavailability of 55-87%.⁶

Volume of distribution

The volume of distribution of clonidine has been reported as 1.7-2.5L/kg², 2.9L/kg⁹, or 2.1±0.4L/kg¹⁰ depending on the source.

Protein binding

Clonidine is 20-40% bound to plasma proteins, especially albumin.^2,10

Metabolism

The metabolism of clonidine is poorly understood.⁷ The main reaction in clonidine metabolism is the 4-hydroxylation of clonidine by CYP2D6, CYP1A2, CYP3A4, CYP1A1, and CYP3A5.⁷

Clonidine is <50% metabolized in the liver to inactive metabolites.^2,8,9,10,11

Hover over products below to view reaction partners

Clonidine
- 4-Hydroxyclonidine

Route of elimination

Approximately 50% of a clonidine dose is excreted in the urine as the unchanged drug and 20% is eliminated in the feces.^2,8

Half-life

The elimination half life after epidural administration is 30 minutes but otherwise can range from 6-23h.²

Clearance

The clearance of clonidine is 1.9-4.3mL/min/kg.²

Adverse Effects

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Toxicity

Oral LD₅₀ is 126 mg/kg in rats.¹² The TDLO is 70µg/kg in children, 126µg/kg in women, and 69µg/kg in men.¹²

Symptoms of overdose include hypertension followed by hypotension, bradycardia, respiratory depression, hypothermia, drowsiness, decreased reflexes, weakness, irritability, and miosis.^8,9,10,11 Severe overdoses can cause reversible cardiac conduction defects or dysrhythmias, apnea, coma, and seizures.^8,9,10,11 Induction of vomiting is not recommended due to CNS depression but gastric lavage or activated charcoal may be useful in recent ingestion.^8,9,10,11 Dialysis is also unlikely to be beneficial.^8,9,10,11 Overdose can be treated with supportive measures such as atropine sulfate for bradycardia, intravenous fluids or vasopressors for hypotension, vasodilators for hypertension, naloxone for respiratory depression, and blood pressure monitoring.^8,9,10,11

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of sedation can be increased when Clonidine is combined with 1,2-Benzodiazepine.
Abaloparatide	The risk or severity of adverse effects can be increased when Clonidine is combined with Abaloparatide.
Abametapir	The serum concentration of Clonidine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Clonidine can be increased when combined with Abatacept.
Abiraterone	The metabolism of Clonidine can be decreased when combined with Abiraterone.

Food Interactions

Avoid alcohol.
Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Clonidine hydrochloride	W76I6XXF06	4205-91-8	ZNIFSRGNXRYGHF-UHFFFAOYSA-N

Product Images

International/Other Brands

Catapresan (Boehringer Ingelheim) / Catapressan (Boehringer Ingelheim) / Catarpres-TTS / Dixarit (Boehringer Ingelheim) / Isoglaucon (Agepha) / Run Rui (Bausch & Lomb) / Velaril (Roemmers) / Winpress (Winston)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Catapres	Tablet	0.100 mg/1	Oral	Boehringer Ingelheim Pharmaceuticals Inc.	1999-05-01	Not applicable
Catapres	Tablet	.300 mg/1	Oral	Boehringer Ingelheim Promeco s.a. De c.v.	1999-05-01	2013-03-25
Catapres	Patch, extended release	0.1 mg/24h	Transdermal	Rebel Distributors	1985-10-01	Not applicable
Catapres	Tablet	0.100 mg/1	Oral	Physicians Total Care, Inc.	1974-09-03	2011-06-30
Catapres	Tablet	0.300 mg/1	Oral	Boehringer Ingelheim Pharmaceuticals Inc.	1999-05-01	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-clonidine	Tablet	0.025 mg	Oral	Apotex Corporation	2004-07-13	Not applicable
Apo-clonidine Tab 0.1mg	Tablet	0.1 mg	Oral	Apotex Corporation	1990-12-31	Not applicable
Apo-clonidine Tab 0.2mg	Tablet	0.2 mg	Oral	Apotex Corporation	1990-12-31	Not applicable
Clonidine	Patch, extended release	0.3 mg/24h	Transdermal	Mayne Pharma Inc.	2016-08-03	Not applicable
Clonidine	Patch	0.3 mg/1d	Transdermal	Mylan Pharmaceuticals Inc.	2013-03-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Clorpres	Clonidine hydrochloride (0.2 mg/1) + Chlorthalidone (15 mg/1)	Tablet	Oral	Mylan Pharmaceuticals	1998-03-13	2018-02-28
Clorpres	Clonidine hydrochloride (0.2 mg/1) + Chlorthalidone (15 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	2005-04-15	2011-06-30
Clorpres	Clonidine hydrochloride (0.2 mg/1) + Chlorthalidone (15 mg/1)	Tablet	Oral	Mylan Bertek Pharmaceuticals	2015-11-01	2015-11-19
Clorpres	Clonidine hydrochloride (0.1 mg/1) + Chlorthalidone (15 mg/1)	Tablet	Oral	Mylan Pharmaceuticals	1998-03-13	2018-02-28
Clorpres	Clonidine hydrochloride (0.1 mg/1) + Chlorthalidone (15 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	2005-01-26	2011-06-30

Chemical Identifiers

UNII: MN3L5RMN02
CAS number: 4205-90-7
InChI Key: GJSURZIOUXUGAL-UHFFFAOYSA-N
InChI: 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)
IUPAC Name: N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
SMILES: ClC1=CC=CC(Cl)=C1NC1=NCCN1

References

Synthesis Reference

David R. Pierce, William D. Dean, Michael E. Deason, "Process for preparation of clonidine derivatives." U.S. Patent US5684156, issued October, 1968.

US5684156

General References

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. [Article]
Khan ZP, Ferguson CN, Jones RM: alpha-2 and imidazoline receptor agonists. Their pharmacology and therapeutic role. Anaesthesia. 1999 Feb;54(2):146-65. doi: 10.1046/j.1365-2044.1999.00659.x. [Article]
Sjoberg RJ, Simcic KJ, Kidd GS: The clonidine suppression test for pheochromocytoma. A review of its utility and pitfalls. Arch Intern Med. 1992 Jun;152(6):1193-7. [Article]
Sliwinska-Mosson M, Zielen I, Milnerowicz H: New trends in the treatment of nicotine addiction. Acta Pol Pharm. 2014 Jul-Aug;71(4):525-30. [Article]
Fresquez-Chavez KR, Fogger S: Reduction of opiate withdrawal symptoms with use of clonidine in a county jail. J Correct Health Care. 2015 Jan;21(1):27-34. doi: 10.1177/1078345814557630. Epub 2014 Nov 26. [Article]
Vasseur B, Dufour A, Houdas L, Goodwin H, Harries K, Emul NY, Hutchings S: Comparison of the Systemic and Local Pharmacokinetics of Clonidine Mucoadhesive Buccal Tablets with Reference Clonidine Oral Tablets in Healthy Volunteers: An Open-Label Randomised Cross-Over Trial. Adv Ther. 2017 Aug;34(8):2022-2032. doi: 10.1007/s12325-017-0585-9. Epub 2017 Jul 19. [Article]
Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF: CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6. doi: 10.1124/dmd.110.033878. Epub 2010 Jun 22. [Article]
FDA Approved Drug Products: Catapres Clonidine Hydrochloride Oral Tablets [Link]
FDA Approved Drug Products: Catapres Clonidine Transdermal System [Link]
FDA Approved Drug Products: Duraclon Clonidine Hydrochloride Injection Solution [Link]
FDA Approved Drug Products: Kapvay (clonidine hydrochloride) Oral Extended Release Tablets [Link]
Cayman Chemicals: Clonidine MSDS [Link]

External Links

Human Metabolome Database: HMDB0014714
KEGG Drug: D00281
PubChem Compound: 2803
PubChem Substance: 46508119
ChemSpider: 2701
BindingDB: 14062
RxNav: 2599
ChEBI: 46632
ChEMBL: CHEMBL134
ZINC: ZINC000000896484
Therapeutic Targets Database: DAP000231
PharmGKB: PA449051
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: CLU
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Clonidine

PDB Entries

2pnc / 7aww

MSDS

Download (73.8 KB)

Clinical Trials

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Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Inguinal Hernias / Spinal Anesthesia therapy	1
4	Completed	Basic Science	Heart Failure	1
4	Completed	Prevention	Cardiovascular Disease (CVD)	1
4	Completed	Prevention	Diabetic Nephropathy	1
4	Completed	Prevention	Hypertension	1

Pharmacoeconomics

Manufacturers

Boehringer ingelheim
Aveva drug delivery systems inc
Mylan technologies inc
Tris pharma inc
Pharmaforce inc
Bioniche pharma usa llc
Actavis elizabeth llc
American therapeutics inc
Dava pharmaceuticals inc
Duramed pharmaceuticals inc sub barr laboratories inc
Impax laboratories inc
Interpharm inc
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Par pharmaceutical inc
Sandoz inc
Teva pharmaceuticals usa inc
Unichem laboratories ltd
Vintage pharmaceuticals llc
Warner chilcott div warner lambert co
Watson laboratories inc
Shionogi pharma inc

Packagers

AAIPharma Inc.
Actavis Group
Advanced Pharmaceutical Services Inc.
Alza Corp.
American Regent
Amerisource Health Services Corp.
Apotheca Inc.
APP Pharmaceuticals
A-S Medication Solutions LLC
Bioniche Pharma
Blenheim Pharmacal
Boehringer Ingelheim Ltd.
Bryant Ranch Prepack
Cardinal Health
Central Texas Community Health Centers
Comprehensive Consultant Services Inc.
Coupler Enterprises Inc.
DAVA Pharmaceuticals
Dept Health Central Pharmacy
Direct Dispensing Inc.
Dispensing Solutions
Diversified Healthcare Services Inc.
Global Pharmaceuticals
Heartland Repack Services LLC
Innoviant Pharmacy Inc.
Lake Erie Medical and Surgical Supply
Liberty Pharmaceuticals
Major Pharmaceuticals
Mckesson Corp.
Medisca Inc.
Murfreesboro Pharmaceutical Nursing Supply
Mutual Pharmaceutical Co.
Mylan
Neighborcare Repackaging Inc.
Neuman Distributors Inc.
Nucare Pharmaceuticals Inc.
Palmetto Pharmaceuticals Inc.
Par Pharmaceuticals
PCA LLC
PD-Rx Pharmaceuticals Inc.
Pharmaceutical Utilization Management Program VA Inc.
Pharmaforce Inc.
Pharmedix
Physicians Total Care Inc.
Preferred Pharmaceuticals Inc.
Prepackage Specialists
Prepak Systems Inc.
Qualitest
Rebel Distributors Corp.
Redpharm Drug
Remedy Repack
Richmond Pharmacy
Sandhills Packaging Inc.
Southwood Pharmaceuticals
Stat Rx Usa
Tya Pharmaceuticals
UDL Laboratories
Unichem Laboratories Ltd.
United Research Laboratories Inc.
Vangard Labs Inc.
Vintage Pharmaceuticals Inc.
West-Ward Pharmaceuticals
Xanodyne Pharmaceuticals Inc.

Dosage Forms

Form	Route	Strength
Injection
Patch, extended release	Transdermal	0.1 mg/24h
Patch, extended release	Transdermal	0.2 mg/24h
Patch, extended release	Transdermal	0.3 mg/24h
Tablet	Oral	.300 mg/1
Tablet	Oral	0.075 MG
Capsule		0.25 MG
Injection, solution		150 MICROGRAMMI/ML
Tablet	Oral	150 MICROGRAMMI
Tablet	Oral	300 MICROGRAMMI
Injection, solution	Parenteral	0.15 mg/ml
Tablet	Oral	0.15 mg/1
Tablet	Oral	0.075 mg/1
Patch	Transdermal	2.5 mg
Patch	Transdermal	5 mg
Patch	Transdermal	7.5 mg
Tablet	Oral	300 UG
Capsule, extended release	Oral	0.25 mg/1
Injection, solution
Tablet	Oral	150 mcg
Tablet	Oral	15000000 mcg
Patch	Transdermal	0.1 mg/1d
Patch	Transdermal	0.2 mg/1d
Patch	Transdermal	0.3 mg/1d
Tablet	Oral	.2 mg
Tablet	Oral
Injection, solution	Epidural	0.5 mg/1mL
Injection, solution	Epidural	100 ug/1mL
Injection, solution	Epidural	500 ug/1mL
Injection, solution	Intravenous	100 ug/1mL
Injection, solution	Intravenous	500 ug/1mL
Tablet	Oral	.1 mg/1
Tablet	Oral	.2 mg/1
Tablet	Oral	.3 mg/1
Tablet	Oral	0.1 mg/1
Tablet	Oral	0.100 mg/1
Tablet	Oral	0.2 mg/1
Tablet	Oral	0.200 mg/1
Tablet	Oral	0.3 mg/1
Tablet	Oral	0.300 mg/1
Tablet, extended release	Oral	25 mg/1
Capsule, extended release	Oral	0.25 MG
Tablet	Oral	0.3 MG
Tablet	Oral
Injection, solution	Epidural	0.1 mg/1mL
Injection, solution	Intravenous	0.1 mg/1mL
Injection, solution	Intravenous	0.5 mg/1mL
Solution	Parenteral	150.00 mcg
Solution / drops	Ophthalmic
Kit	Oral
Tablet, extended release	Oral	0.1 mg/1
Tablet, extended release	Oral	0.2 mg/1
For suspension, extended release	Oral	0.09 mg/1mL
Suspension, extended release	Oral	0.09 mg/1mL
Tablet, extended release	Oral	0.17 mg/1
Tablet, extended release	Oral	0.26 mg/1
Tablet	Oral	.1 mg
Tablet	Oral	0.025 mg
Tablet	Oral	0.1 mg
Tablet	Oral	0.2 mg
Tablet	Oral	0.15 mg

Prices

Unit description	Cost	Unit
Catapres-TTS-3 4 0.3 mg/24hr Patches Box	328.42USD	box
CloNIDine HCl 4 0.3 mg/24hr Patches Box	279.9USD	box
Catapres-TTS-2 4 0.2 mg/24hr Patches Box	236.75USD	box
CloNIDine HCl 4 0.2 mg/24hr Patches Box	201.75USD	box
Catapres-TTS-1 4 0.1 mg/24hr Patches Box	141.08USD	box
CloNIDine HCl 4 0.1 mg/24hr Patches Box	119.84USD	box
Catapres-tts 3 patch	78.95USD	patch
Clonidine 0.3 mg/day patch	67.28USD	patch
Clonidine hcl powder	53.09USD	g
Clonidine 0.2 mg/day patch	48.5USD	patch
Duraclon 500 mcg/ml vial	47.4USD	ml
Catapres-tts 2 patch	39.23USD	patch
Clonidine 0.1 mg/day patch	28.81USD	patch
Catapres-tts 1 patch	21.18USD	patch
Clonidine 5000 mcg/10 ml vial	21.0USD	ml
Duraclon 0.1 mg/ml vial	14.4USD	ml
Clonidine 1000 mcg/10 ml vial	5.04USD	ml
Catapres 0.3 mg tablet	2.98USD	tablet
Catapres 0.2 mg tablet	2.35USD	tablet
Catapres 0.1 mg tablet	1.57USD	tablet
Clonidine hcl 0.3 mg tablet	0.5USD	tablet
Clonidine hcl 0.2 mg tablet	0.35USD	tablet
Catapres 0.2 mg Tablet	0.35USD	tablet
Apo-Clonidine 0.2 mg Tablet	0.33USD	tablet
Novo-Clonidine 0.2 mg Tablet	0.33USD	tablet
Nu-Clonidine 0.2 mg Tablet	0.33USD	tablet
Dixarit 0.025 mg Tablet	0.28USD	tablet
Clonidine hcl 0.1 mg tablet	0.24USD	tablet
Catapres 0.1 mg Tablet	0.19USD	tablet
Apo-Clonidine 0.1 mg Tablet	0.18USD	tablet
Novo-Clonidine 0.1 mg Tablet	0.18USD	tablet
Nu-Clonidine 0.1 mg Tablet	0.18USD	tablet
Apo-Clonidine 0.025 mg Tablet	0.16USD	tablet
Novo-Clonidine 0.025 mg Tablet	0.16USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5869100	No	1999-02-09	2013-10-13
US8623409	No	2014-01-07	2031-09-08
US8337890	No	2012-12-25	2027-04-17

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	130	http://www.chemspider.com/Chemical-Structure.2701.html?rid=816613e6-a54a-46f0-8152-4a93e09e4170
logP	1.59	HANSCH,C & LEO,AJ (1985)
Caco2 permeability	-4.59	ADME Research, USCD
pKa	8.05 (at 25 °C)	KONTTURI,K & MURTOMAKI,L (1992)

Predicted Properties

Property	Value	Source
Water Solubility	0.48 mg/mL	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

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9632
Blood Brain Barrier	+	0.9402
Caco-2 permeable	+	0.8866
P-glycoprotein substrate	Substrate	0.6305
P-glycoprotein inhibitor I	Non-inhibitor	0.9061
P-glycoprotein inhibitor II	Non-inhibitor	0.8383
Renal organic cation transporter	Inhibitor	0.745
CYP450 2C9 substrate	Non-substrate	0.8219
CYP450 2D6 substrate	Non-substrate	0.6984
CYP450 3A4 substrate	Non-substrate	0.6353
CYP450 1A2 substrate	Non-inhibitor	0.8998
CYP450 2C9 inhibitor	Non-inhibitor	0.7681
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Non-inhibitor	0.8732
CYP450 3A4 inhibitor	Non-inhibitor	0.8332
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.803
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.9303
Biodegradation	Not ready biodegradable	0.9949
Rat acute toxicity	3.5030 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7232
hERG inhibition (predictor II)	Non-inhibitor	0.8905

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-02vi-8910000000-a3e51d12bf5d7c152fa8
Mass Spectrum (Electron Ionization)	MS	splash10-003r-5970000000-33c27878b8b7ad9d5d75
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-03dl-0279000000-5f6a2e746dea4ac42952
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-0090000000-2c051509a637beaafe73
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-0090000000-f1477af875c25c537ccb
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-001i-0090000000-ccdeb1dfce0424b12c0c
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-01po-6950000000-dd68628a46215027ef29
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-6900000000-ce531320f1fda74d127e
LC-MS/MS Spectrum - LC-ESI-IT , positive	LC-MS/MS	splash10-03fr-2980000000-24b18e2a89a65b2b178f
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0190000000-7cbbf9fb244993abe922
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0090000000-c9f28b79d315b0909617
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-0090000000-2d1c9a107773e5467e9c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0090000000-de40bcc4aa4e5e4f2f1d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004l-2980000000-10e7fb22d63fbe3d13fe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01ox-7910000000-57baadf52de240629467
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9800000000-ae51141f009a5c7eabd9
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	141.5208735	predicted	DarkChem Lite v0.1.0
[M-H]-	138.30542	predicted	DeepCCS 1.0 (2019)
[M+H]+	142.1236735	predicted	DarkChem Lite v0.1.0
[M+H]+	141.04381	predicted	DeepCCS 1.0 (2019)
[M+Na]+	141.6042735	predicted	DarkChem Lite v0.1.0
[M+Na]+	149.7396	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	1174.9	N/A	N/A	A28619
Ki (nM)	69.18	N/A	N/A	A28266
Ki (nM)	309.0295	N/A	N/A	A28618
Ki (nM)	39.8107	N/A	N/A	A28618
Ki (nM)	31.62	N/A	N/A	A28620

Details1. Alpha-2B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Epinephrine binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name: ADRA2B
Uniprot ID: P18089
Uniprot Name: Alpha-2B adrenergic receptor
Molecular Weight: 49565.8 Da

References

Millan MJ, Dekeyne A, Newman-Tancredi A, Cussac D, Audinot V, Milligan G, Duqueyroix D, Girardon S, Mullot J, Boutin JA, Nicolas JP, Renouard-Try A, Lacoste JM, Cordi A: S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine. J Pharmacol Exp Ther. 2000 Dec;295(3):1192-205. [Article]
Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	57.54	N/A	N/A	A28619
Ki (nM)	30	N/A	N/A	A27956 / A28616
Ki (nM)	134.9	N/A	N/A	A28266
Ki (nM)	160	N/A	N/A	A28617
Ki (nM)	501.1872	N/A	N/A	A28618
Ki (nM)	63.0957	N/A	N/A	A28618
Ki (nM)	9.33	N/A	N/A	A28620

Details2. Alpha-2C adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name: ADRA2C
Uniprot ID: P18825
Uniprot Name: Alpha-2C adrenergic receptor
Molecular Weight: 49521.585 Da

References

Millan MJ, Dekeyne A, Newman-Tancredi A, Cussac D, Audinot V, Milligan G, Duqueyroix D, Girardon S, Mullot J, Boutin JA, Nicolas JP, Renouard-Try A, Lacoste JM, Cordi A: S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine. J Pharmacol Exp Ther. 2000 Dec;295(3):1192-205. [Article]
Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	8.32	N/A	N/A	A28619
EC 50 (nM)	28	N/A	N/A	A27959
EC 50 (nM)	30	N/A	N/A	A27960
Ki (nM)	3.8	N/A	N/A	A27956 / A28616
Ki (nM)	61.66	N/A	N/A	A28266
Ki (nM)	853	N/A	N/A	A28617
Ki (nM)	35.4813	N/A	N/A	A28618
Ki (nM)	50.1187	N/A	N/A	A28618
Ki (nM)	31.6228	N/A	N/A	A28618
Ki (nM)	8.71	N/A	N/A	A28620

Details3. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Thioesterase binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name: ADRA2A
Uniprot ID: P08913
Uniprot Name: Alpha-2A adrenergic receptor
Molecular Weight: 48956.275 Da

References

Fairbanks CA, Stone LS, Kitto KF, Nguyen HO, Posthumus IJ, Wilcox GL: alpha(2C)-Adrenergic receptors mediate spinal analgesia and adrenergic-opioid synergy. J Pharmacol Exp Ther. 2002 Jan;300(1):282-90. [Article]
Lavand'homme PM, Ma W, De Kock M, Eisenach JC: Perineural alpha(2A)-adrenoceptor activation inhibits spinal cord neuroplasticity and tactile allodynia after nerve injury. Anesthesiology. 2002 Oct;97(4):972-80. [Article]
Ozdogan UK, Lahdesmaki J, Hakala K, Scheinin M: The involvement of alpha 2A-adrenoceptors in morphine analgesia, tolerance and withdrawal in mice. Eur J Pharmacol. 2004 Aug 23;497(2):161-71. [Article]
Ozdogan UK, Lahdesmaki J, Mansikka H, Scheinin M: Loss of amitriptyline analgesia in alpha 2A-adrenoceptor deficient mice. Eur J Pharmacol. 2004 Feb 6;485(1-3):193-6. [Article]
Wang XM, Zhang ZJ, Bains R, Mokha SS: Effect of antisense knock-down of alpha(2a)- and alpha(2c)-adrenoceptors on the antinociceptive action of clonidine on trigeminal nociception in the rat. Pain. 2002 Jul;98(1-2):27-35. [Article]
Millan MJ, Dekeyne A, Newman-Tancredi A, Cussac D, Audinot V, Milligan G, Duqueyroix D, Girardon S, Mullot J, Boutin JA, Nicolas JP, Renouard-Try A, Lacoste JM, Cordi A: S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine. J Pharmacol Exp Ther. 2000 Dec;295(3):1192-205. [Article]
Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]

Details4. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

Millan MJ, Dekeyne A, Newman-Tancredi A, Cussac D, Audinot V, Milligan G, Duqueyroix D, Girardon S, Mullot J, Boutin JA, Nicolas JP, Renouard-Try A, Lacoste JM, Cordi A: S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine. J Pharmacol Exp Ther. 2000 Dec;295(3):1192-205. [Article]
PDSP Ki Database [Link]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	316.2278	N/A	N/A	A28618

Details5. Alpha-1B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1B
Uniprot ID: P35368
Uniprot Name: Alpha-1B adrenergic receptor
Molecular Weight: 56835.375 Da

References

Millan MJ, Dekeyne A, Newman-Tancredi A, Cussac D, Audinot V, Milligan G, Duqueyroix D, Girardon S, Mullot J, Boutin JA, Nicolas JP, Renouard-Try A, Lacoste JM, Cordi A: S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine. J Pharmacol Exp Ther. 2000 Dec;295(3):1192-205. [Article]
PDSP Ki Database [Link]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	125.8925	N/A	N/A	A28618

Details6. Alpha-1D adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Alpha1-adrenergic receptor activity
Specific Function: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name: ADRA1D
Uniprot ID: P25100
Uniprot Name: Alpha-1D adrenergic receptor
Molecular Weight: 60462.205 Da

References

Millan MJ, Dekeyne A, Newman-Tancredi A, Cussac D, Audinot V, Milligan G, Duqueyroix D, Girardon S, Mullot J, Boutin JA, Nicolas JP, Renouard-Try A, Lacoste JM, Cordi A: S18616, a highly potent, spiroimidazoline agonist at alpha(2)-adrenoceptors: I. Receptor profile, antinociceptive and hypothermic actions in comparison with dexmedetomidine and clonidine. J Pharmacol Exp Ther. 2000 Dec;295(3):1192-205. [Article]
PDSP Ki Database [Link]

Enzymes

Details1. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Curator comments: Data is limited to an in vitro study.

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF: CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6. doi: 10.1124/dmd.110.033878. Epub 2010 Jun 22. [Article]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF: CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6. doi: 10.1124/dmd.110.033878. Epub 2010 Jun 22. [Article]

Details3. Cytochrome P450 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d 24-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A1
Uniprot ID: P04798
Uniprot Name: Cytochrome P450 1A1
Molecular Weight: 58164.815 Da

References

Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF: CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6. doi: 10.1124/dmd.110.033878. Epub 2010 Jun 22. [Article]

Details4. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF: CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6. doi: 10.1124/dmd.110.033878. Epub 2010 Jun 22. [Article]

Details5. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF: CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6. doi: 10.1124/dmd.110.033878. Epub 2010 Jun 22. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Khan ZP, Ferguson CN, Jones RM: alpha-2 and imidazoline receptor agonists. Their pharmacology and therapeutic role. Anaesthesia. 1999 Feb;54(2):146-65. doi: 10.1046/j.1365-2044.1999.00659.x. [Article]
FDA Approved Drug Products: Duraclon Clonidine Hydrochloride Injection Solution [Link]

Transporters

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	79300	N/A	N/A	A16100

Details1. Solute carrier family 22 member 3

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Toxin transporter activity
Specific Function: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name: SLC22A3
Uniprot ID: O75751
Uniprot Name: Solute carrier family 22 member 3
Molecular Weight: 61279.485 Da

References

Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [Article]
Martel F, Grundemann D, Calhau C, Schomig E: Apical uptake of organic cations by human intestinal Caco-2 cells: putative involvement of ASF transporters. Naunyn Schmiedebergs Arch Pharmacol. 2001 Jan;363(1):40-9. [Article]

Details2. Solute carrier family 22 member 5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [Article]

Details3. Solute carrier family 22 member 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Symporter activity
Specific Function: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name: SLC22A4
Uniprot ID: Q9H015
Uniprot Name: Solute carrier family 22 member 4
Molecular Weight: 62154.48 Da

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Clonidine

Identification

Structure for Clonidine (DB00575)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

References

References

Enzymes

References

References

References

References

References

Carriers

References

Transporters

References

References

References