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
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

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 TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAdhd••••••••••••••• ••••••••••• •••••••• •••••••• •••••• •••••••• •••••••• ••••••• •••••••• •••••••
Diagnostic agentGrowth hormone deficiency••• •••••
Management ofHot flashes••• •••••
Management ofHypertension••••••••••••••••••• •••••
Symptomatic treatment ofOpioid withdrawal••• •••••
Associated Therapies
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 Go and Gi.2 Gi 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

TargetActionsOrganism
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 Cmax 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

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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of sedation can be increased when Clonidine is combined with 1,2-Benzodiazepine.
AbaloparatideThe risk or severity of adverse effects can be increased when Clonidine is combined with Abaloparatide.
AbametapirThe serum concentration of Clonidine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Clonidine can be increased when combined with Abatacept.
AbirateroneThe 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
IngredientUNIICASInChI Key
Clonidine hydrochlorideW76I6XXF064205-91-8ZNIFSRGNXRYGHF-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CatapresPatch, extended release0.3 mg/24hTransdermalPhysicians Total Care, Inc.2004-07-082012-06-30US flag
CatapresTablet0.100 mg/1OralBoehringer Ingelheim Pharmaceuticals Inc.1999-05-01Not applicableUS flag
CatapresTablet0.100 mg/1OralBoehringer Ingelheim Promeco s.a. De c.v.1999-05-012013-03-25US flag
CatapresPatch, extended release0.1 mg/24hTransdermalRebel Distributors1985-10-01Not applicableUS flag
CatapresPatch, extended release0.2 mg/24hTransdermalPhysicians Total Care, Inc.1994-10-112011-06-30US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-clonidineTablet0.025 mgOralApotex Corporation2004-07-13Not applicableCanada flag
Apo-clonidine Tab 0.1mgTablet0.1 mgOralApotex Corporation1990-12-31Not applicableCanada flag
Apo-clonidine Tab 0.2mgTablet0.2 mgOralApotex Corporation1990-12-31Not applicableCanada flag
ClonidinePatch0.2 mg/1dTransdermalPhysicians Total Care, Inc.2010-12-14Not applicableUS flag
ClonidinePatch, extended release0.3 mg/24hTransdermalDr. Reddy's Labratories Inc.2024-02-10Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClorpresClonidine hydrochloride (0.1 mg/1) + Chlorthalidone (15 mg/1)TabletOralMylan Pharmaceuticals1998-03-132018-02-28US flag
ClorpresClonidine hydrochloride (0.1 mg/1) + Chlorthalidone (15 mg/1)TabletOralMylan Bertek Pharmaceuticals2015-11-012015-11-19US flag
ClorpresClonidine hydrochloride (0.3 mg/1) + Chlorthalidone (15 mg/1)TabletOralMylan Pharmaceuticals1998-03-132018-02-28US flag
ClorpresClonidine hydrochloride (0.2 mg/1) + Chlorthalidone (15 mg/1)TabletOralPhysicians Total Care, Inc.2005-04-152011-06-30US flag
ClorpresClonidine hydrochloride (0.3 mg/1) + Chlorthalidone (15 mg/1)TabletOralMylan Bertek Pharmaceuticals2015-11-012015-11-19US flag

Categories

ATC Codes
S01EA04 — ClonidineC02LC01 — Clonidine and diureticsC02AC01 — ClonidineN02CX02 — ClonidineC02LC51 — Clonidine and diuretics, combinations with other drugs
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Dichlorobenzenes
Alternative Parents
Aniline and substituted anilines / Aryl chlorides / Imidazolines / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,3-dichlorobenzene / 2-imidazoline / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Carboximidamide / Guanidine / Hydrocarbon derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
clonidine (CHEBI:3757)
Affected organisms
  • Humans and other mammals

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
  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. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. FDA Approved Drug Products: Catapres Clonidine Hydrochloride Oral Tablets [Link]
  9. FDA Approved Drug Products: Catapres Clonidine Transdermal System [Link]
  10. FDA Approved Drug Products: Duraclon Clonidine Hydrochloride Injection Solution [Link]
  11. FDA Approved Drug Products: Kapvay (clonidine hydrochloride) Oral Extended Release Tablets [Link]
  12. Cayman Chemicals: Clonidine MSDS [Link]
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

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentInguinal Hernias / Spinal Anesthesia therapy1
4CompletedBasic ScienceHeart Failure1
4CompletedPreventionCardiovascular Disease (CVD)1
4CompletedPreventionDiabetic Nephropathy1
4CompletedPreventionHypertension1

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
FormRouteStrength
Injection
Patch, extended releaseTransdermal0.1 mg/24h
Patch, extended releaseTransdermal0.2 mg/24h
Patch, extended releaseTransdermal0.3 mg/24h
TabletOral.300 mg/1
TabletOral0.075 MG
Capsule0.25 MG
Injection, solution150 MICROGRAMMI/ML
TabletOral150 MICROGRAMMI
TabletOral300 MICROGRAMMI
Injection, solutionParenteral0.15 mg/ml
TabletOral0.15 mg/1
TabletOral0.075 mg/1
PatchTransdermal2.5 mg
PatchTransdermal5 mg
PatchTransdermal7.5 mg
TabletOral300 UG
Capsule, extended releaseOral0.25 mg/1
Injection, solution
TabletOral150 mcg
TabletOral15000000 mcg
PatchTransdermal0.1 mg/1d
PatchTransdermal0.2 mg/1d
PatchTransdermal0.3 mg/1d
TabletOral.2 mg
TabletOral
Injection, solutionEpidural0.5 mg/1mL
Injection, solutionEpidural100 ug/1mL
Injection, solutionEpidural500 ug/1mL
Injection, solutionIntravenous100 ug/1mL
Injection, solutionIntravenous500 ug/1mL
TabletOral.1 mg/1
TabletOral.2 mg/1
TabletOral.3 mg/1
TabletOral0.1 mg/1
TabletOral0.100 mg/1
TabletOral0.2 mg/1
TabletOral0.200 mg/1
TabletOral0.3 mg/1
TabletOral0.300 mg/1
Tablet, extended releaseOral25 mg/1
Capsule, extended releaseOral0.25 MG
TabletOral0.3 MG
TabletOral
Injection, solutionEpidural0.1 mg/1mL
Injection, solutionIntravenous0.1 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
SolutionParenteral150.00 mcg
Solution / dropsOphthalmic
KitOral
Tablet, extended releaseOral0.1 mg/1
Tablet, extended releaseOral0.2 mg/1
For suspension, extended releaseOral0.09 mg/1mL
Suspension, extended releaseOral0.09 mg/1mL
Tablet, extended releaseOral0.17 mg/1
Tablet, extended releaseOral0.26 mg/1
TabletOral.1 mg
TabletOral0.025 mg
TabletOral0.1 mg
TabletOral0.2 mg
TabletOral0.15 mg
Prices
Unit descriptionCostUnit
Catapres-TTS-3 4 0.3 mg/24hr Patches Box328.42USD box
CloNIDine HCl 4 0.3 mg/24hr Patches Box279.9USD box
Catapres-TTS-2 4 0.2 mg/24hr Patches Box236.75USD box
CloNIDine HCl 4 0.2 mg/24hr Patches Box201.75USD box
Catapres-TTS-1 4 0.1 mg/24hr Patches Box141.08USD box
CloNIDine HCl 4 0.1 mg/24hr Patches Box119.84USD box
Catapres-tts 3 patch78.95USD patch
Clonidine 0.3 mg/day patch67.28USD patch
Clonidine hcl powder53.09USD g
Clonidine 0.2 mg/day patch48.5USD patch
Duraclon 500 mcg/ml vial47.4USD ml
Catapres-tts 2 patch39.23USD patch
Clonidine 0.1 mg/day patch28.81USD patch
Catapres-tts 1 patch21.18USD patch
Clonidine 5000 mcg/10 ml vial21.0USD ml
Duraclon 0.1 mg/ml vial14.4USD ml
Clonidine 1000 mcg/10 ml vial5.04USD ml
Catapres 0.3 mg tablet2.98USD tablet
Catapres 0.2 mg tablet2.35USD tablet
Catapres 0.1 mg tablet1.57USD tablet
Clonidine hcl 0.3 mg tablet0.5USD tablet
Clonidine hcl 0.2 mg tablet0.35USD tablet
Catapres 0.2 mg Tablet0.35USD tablet
Apo-Clonidine 0.2 mg Tablet0.33USD tablet
Novo-Clonidine 0.2 mg Tablet0.33USD tablet
Nu-Clonidine 0.2 mg Tablet0.33USD tablet
Dixarit 0.025 mg Tablet0.28USD tablet
Clonidine hcl 0.1 mg tablet0.24USD tablet
Catapres 0.1 mg Tablet0.19USD tablet
Apo-Clonidine 0.1 mg Tablet0.18USD tablet
Novo-Clonidine 0.1 mg Tablet0.18USD tablet
Nu-Clonidine 0.1 mg Tablet0.18USD tablet
Apo-Clonidine 0.025 mg Tablet0.16USD tablet
Novo-Clonidine 0.025 mg Tablet0.16USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5869100No1999-02-092013-10-13US flag
US8623409No2014-01-072031-09-08US flag
US8337890No2012-12-252027-04-17US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)130http://www.chemspider.com/Chemical-Structure.2701.html?rid=816613e6-a54a-46f0-8152-4a93e09e4170
logP1.59HANSCH,C & LEO,AJ (1985)
Caco2 permeability-4.59ADME Research, USCD
pKa8.05 (at 25 °C)KONTTURI,K & MURTOMAKI,L (1992)
Predicted Properties
PropertyValueSource
Water Solubility0.48 mg/mLALOGPS
logP2.55ALOGPS
logP2.49Chemaxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.16Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area36.42 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity59.09 m3·mol-1Chemaxon
Polarizability21.7 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9632
Blood Brain Barrier+0.9402
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.6305
P-glycoprotein inhibitor INon-inhibitor0.9061
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterInhibitor0.745
CYP450 2C9 substrateNon-substrate0.8219
CYP450 2D6 substrateNon-substrate0.6984
CYP450 3A4 substrateNon-substrate0.6353
CYP450 1A2 substrateNon-inhibitor0.8998
CYP450 2C9 inhibitorNon-inhibitor0.7681
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.8732
CYP450 3A4 inhibitorNon-inhibitor0.8332
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.803
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9303
BiodegradationNot ready biodegradable0.9949
Rat acute toxicity3.5030 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7232
hERG inhibition (predictor II)Non-inhibitor0.8905
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-02vi-8910000000-a3e51d12bf5d7c152fa8
Mass Spectrum (Electron Ionization)MSsplash10-003r-5970000000-33c27878b8b7ad9d5d75
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03dl-0279000000-5f6a2e746dea4ac42952
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0090000000-2c051509a637beaafe73
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0090000000-f1477af875c25c537ccb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-0090000000-ccdeb1dfce0424b12c0c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01po-6950000000-dd68628a46215027ef29
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-6900000000-ce531320f1fda74d127e
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03fr-2980000000-24b18e2a89a65b2b178f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0190000000-7cbbf9fb244993abe922
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-c9f28b79d315b0909617
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-2d1c9a107773e5467e9c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-de40bcc4aa4e5e4f2f1d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-2980000000-10e7fb22d63fbe3d13fe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-7910000000-57baadf52de240629467
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9800000000-ae51141f009a5c7eabd9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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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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
  1. 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]
  2. Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]
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
  1. 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]
  2. Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. Hein, L. (2004). alpha-Adrenergic system. In Encyclopedic reference of molecular pharmacology (pp. 27-30). Berlin: Springer. [ISBN:9783540298328]
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
  1. 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]
  2. PDSP Ki Database [Link]
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
  1. 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]
  2. PDSP Ki Database [Link]
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
  1. 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]
  2. PDSP Ki Database [Link]

Enzymes

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
  1. 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]
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
  1. 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]
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
  1. 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]
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
  1. 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]
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
  1. 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

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
  1. 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]
  2. FDA Approved Drug Products: Duraclon Clonidine Hydrochloride Injection Solution [Link]

Transporters

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
  1. 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]
  2. 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]
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
  1. 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]
  2. 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]
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
  1. 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 March 18, 2024 16:48