Clonidine

Clonidine
Clinical data
Pronunciation/ˈklɒnədiːn/
Trade namesCatapres, others
AHFS/Drugs.comMonograph
MedlinePlusa682243
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, epidural, intravenous, transdermal, topical
Drug classα2A-adrenergic receptor agonist
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability70–80% (oral),[3][4] 60–70% (transdermal)[5]
Protein binding20–40%[6]
MetabolismLiver to inactive metabolites,[6] 2/3 CYP2D6[10]
Onset of actionIR: 30–60 minutes after an oral dose[7]
Elimination half-lifeIR: 12–16 hours; 41 hours in kidney failure,[8][9] 48 hours for repeated dosing[5]
Duration of actionBlood pressure:
  • ≤ 8 hours
ExcretionUrine (72%)[6]
Identifiers
IUPAC name
  • N-(2,6-Dichlorophenyl)-4,5--1H-imidazol-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.021.928
Chemical and physical data
FormulaC9H9Cl2N3
Molar mass230.09 g·mol−1
3D model (JSmol)
SMILES
  • Clc1cccc(Cl)c1N/C2=N/CCN2
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) Y
  • Key:GJSURZIOUXUGAL-UHFFFAOYSA-N Y
  (verify)

Clonidine, sold under the brand name Catapres among others, is an α2A-adrenergic receptor agonist[11] medication used to treat high blood pressure, attention deficit hyperactivity disorder (ADHD), drug withdrawal (e.g., alcohol, opioids, or nicotine), menopausal flushing, diarrhea, spasticity, and certain pain conditions.[12] The drug is often prescribed off-label for tics. It is used orally (by mouth), by injection, or as a transdermal skin patch.[12] Onset of action is typically within an hour with the effects on blood pressure lasting for up to eight hours.[12]

Common side effects include dry mouth, dizziness, headaches, hypotension, and sleepiness.[12] Severe side effects may include hallucinations, heart arrhythmias, and confusion.[13] If rapidly stopped, withdrawal effects may occur, such as a dangerous rise in blood pressure.[12] Use during pregnancy or breastfeeding is not recommended.[13] Clonidine lowers blood pressure by stimulating α2-adrenergic receptors in the brain, which results in relaxation of many arteries.[12]

Clonidine was patented in 1961 and came into medical use in 1966.[14][15][16] It is available as a generic medication.[12] In 2022, it was the 71st most commonly prescribed medication in the United States, with more than 9 million prescriptions.[17][18]

  1. ^ "Catapres-TTS-1- clonidine transdermal system patch; Catapres-TTS-2- clonidine transdermal system patch; Catapres-TTS-3- clonidine transdermal system patch". DailyMed. 25 March 2023. Retrieved 5 September 2024.
  2. ^ "Onyda XR- clonidine hydrochloride suspension, extended release". DailyMed. 7 June 2024. Retrieved 5 September 2024.
  3. ^ Cite error: The named reference davies was invoked but never defined (see the help page).
  4. ^ "Catapres- clonidine hydrochloride tablet". DailyMed. 6 September 2016. Archived from the original on 4 August 2020. Retrieved 21 December 2019. The pharmacokinetics of clonidine is dose-proportional in the range of 100 to 600 µg.The absolute bioavailability of clonidine on oral administration is 70% to 80%. Peak plasma clonidine levels are attained in approximately 1 to 3 hours.
  5. ^ a b Lowenthal DT, Matzek KM, MacGregor TR (May 1988). "Clinical pharmacokinetics of clonidine". Clinical Pharmacokinetics. 14 (5): 287–310. doi:10.2165/00003088-198814050-00002. PMID 3293868. S2CID 24783447.
  6. ^ a b c "clonidine (Rx) - Catapres, Catapres-TTS, more." Medscape Reference. WebMD. Archived from the original on 4 December 2020. Retrieved 10 November 2013.
  7. ^ "Catapres- clonidine hydrochloride tablet". DailyMed. 6 September 2016. Archived from the original on 4 August 2020. Retrieved 21 December 2019. Catapres tablets act relatively rapidly. The patient's blood pressure declines within 30 to 60 minutes after an oral dose, the maximum decrease occurring within 2 to 4 hours.
  8. ^ "Catapres- clonidine hydrochloride tablet". DailyMed. 6 September 2016. Archived from the original on 4 August 2020. Retrieved 21 December 2019. Following intravenous administration, clonidine displays biphasic disposition with a distribution half-life of about 20 minutes and an elimination half-life ranging from 12 to 16 hours. The half-life increases up to 41 hours in patients with severe impairment of renal function. Clonidine crosses the placental barrier. It has been shown to cross the blood–brain barrier in rats.
  9. ^ "Kapvay". RxList. Archived from the original on 12 October 2017. Retrieved 30 October 2014.
  10. ^ Claessens AJ, Risler LJ, Eyal S, Shen DD, Easterling TR, Hebert MF (September 2010). "CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance". Drug Metabolism and Disposition. 38 (9): 1393–1396. doi:10.1124/dmd.110.033878. PMC 2939473. PMID 20570945.
  11. ^ Westfall TC, Macarthur H, Westfall DP (2017). "Chapter 12:Adrenergic Agonists and Antagonists". In Brunton L, Knollmann B, Hilal-Dandan R (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics (13th ed.). McGraw-Hill Education / Medical. ISBN 9781259584732.
  12. ^ a b c d e f g "Clonidine Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 3 February 2019. Retrieved 2 February 2019.
  13. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 144. ISBN 9780857113382.
  14. ^ Neil MJ (November 2011). "Clonidine: clinical pharmacology and therapeutic use in pain management". Current Clinical Pharmacology. 6 (4): 280–287. doi:10.2174/157488411798375886. PMID 21827389. S2CID 40756251.
  15. ^ Stähle H (June 2000). "A historical perspective: development of clonidine". Best Practice & Research Clinical Anaesthesiology. 14 (2): 237–246. doi:10.1053/bean.2000.0079.
  16. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 550. ISBN 9783527607495. Archived from the original on 29 April 2023. Retrieved 12 September 2020.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Clonidine Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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