Clonidine

Title: Clonidine
CAS Registry Number: 4205-90-7
CAS Name: N-(2,6-Dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
Additional Names: 2-(2,6-dichloroanilino)-2-imidazoline; 2,6-dichloro-N-2-imidazolidinylidenebenzenamine; 2-(2,6-dichloroanilino)-1,3-diazacyclopentene-(2); 2-[(2,6-dichlorophenyl)imino]-2-imidazoline
Molecular Formula: C9H9Cl2N3
Molecular Weight: 230.09
Percent Composition: C 46.98%, H 3.94%, Cl 30.82%, N 18.26%
Literature References: a2-Adrenergic agonist. Prepn: Zeile et al., US 3202660 (1965 to Boehringer, Ing.). Use in shaving soap formulations: eidem, US 3190802 (1965 to Boehringer, Ing.). Pharmacology: Bolme, Fuxe, Eur. J. Pharmacol. 13, 168 (1971). Revised structure: L. M. Jackman, T. Jen, J. Am. Chem. Soc. 97, 2811 (1975). GC determn in plasma: P. O. Edlund, J. Chromatogr. 187, 161 (1980). Preliminary studies on potential antidepressant activity: D. C. Jimerson et al., Biol. Psychiatry 15, 45 (1980); J. B. Malick, Prog. Clin. Biol. Res. 71, 165 (1981). Exptl use in drug rehabilitation: M. S. Gold, A. C. Pottash, Ann. N.Y. Acad. Sci. 362, 191-202 (1981). Activity as a-adrenoceptor agonist: A. G. Roach et al., J. Pharmacol. Exp. Ther. 227, 421 (1983). Symposium on cardiovascular and psychotropic pharmacology and clinical experience: Central Blood Pressure Regulation: The Role of a2-Receptor Stimulation, K. Hayduk, K. B. Bock, Eds. (Steinkopff Verlag, Darmstadt, 1983) 284 pp. Effects in acute smoking withdrawal syndrome: A. H. Glassman et al., Science 226, 864 (1984); in alcoholism withdrawal: Z. Jraidi et al., Therapie 42, 21 (1987). Clinical trial in Tourette's syndrome: J. F. Leckman et al., Neurology 35, 343 (1985); in cigarette smoking cessation: R. Davison et al., Clin. Pharmacol. Ther. 44, 265 (1988). Clinical trial for intractable cancer pain: J. C. Eisenach et al., Pain 61, 391 (1995). Reviews: A. Walland in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, D.C., 1977) pp 67-107; H. Schmitt, Handb. Exp. Pharmacol. 39, 299-396 (1977); M. C. Houston, Prog. Cardiovasc. Dis. 23, 337-350 (1981). Comprehensive description: M. A. Abounassif et al., Anal. Profiles Drug Subs. Excip. 21, 109-147 (1992).
Properties: Crystals, mp 130°.
Melting point: mp 130°
Derivative Type: Hydrochloride
CAS Registry Number: 4205-91-8
Manufacturers' Codes: ST-155
Trademarks: Catapres (Boehringer, Ing.); Catapresan (Boehringer, Ing.); Clonistada (Stadapharm); Dixarit (Boehringer, Ing.); Duraclon (Roxane); Isoglaucon (Boehringer, Ing.); Tenso-Timelets
Molecular Formula: C9H9Cl2N3.HCl
Molecular Weight: 266.55
Percent Composition: C 40.55%, H 3.78%, Cl 39.90%, N 15.76%
Properties: Crystals, mp 305°. Sol in abs. ethanol; slightly sol in chloroform. Practically insol in ether. One gram is sol in 6 mls water (60°C); about 13 mls water (20°C); about 5.8 mls methanol; about 25 mls ethanol; about 5000 mls chloroform. uv max (water): 213, 271, 302 nm (e 8290.327, 713.074, 339.876). LD50 in mice, rats (mg/kg): 328, 270 orally; 18, 29 i.v. (Walland).
Melting point: mp 305°
Absorption maximum: uv max (water): 213, 271, 302 nm (e 8290.327, 713.074, 339.876)
Toxicity data: LD50 in mice, rats (mg/kg): 328, 270 orally; 18, 29 i.v. (Walland)
Use: In shaving soaps.
Therap-Cat: Antihypertensive; analgesic for neuropathic pain.
Keywords: a-Adrenergic Agonist; Antidyskinetic; Antihypertensive; Imidazole Derivatives.
Clonitazene Clonitrate Clonixin Clopamide Clopenthixol

Clonidine
Clonidine2DACS3.svg
Clonidine3DanBS.gif
Systematic (IUPAC) name
N-(2,6-dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
Clinical data
Trade names Catapres, Kapvay, Nexiclon
AHFS/Drugs.com monograph
MedlinePlus a682243
Licence data US FDA:link
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes oral, epidural, IV, transdermal, topical
Pharmacokinetic data
Bioavailability 75-85% (IR), 89% (XR)[1]
Protein binding 20-40%[1]
Metabolism Hepatic to inactive metabolites[1]
Half-life 12-16 hours[1]
Excretion urine (72%)[1]
Identifiers
CAS number 4205-90-7 YesY
ATC code C02AC01 N02CX02, S01EA04
PubChem CID 2803
IUPHAR ligand 516
DrugBank DB00575
ChemSpider 2701 YesY
UNII MN3L5RMN02 YesY
KEGG D00281 YesY
ChEBI CHEBI:3757 YesY
ChEMBL CHEMBL134 YesY
Chemical data
Formula C9H9Cl2N3 
Mol. mass 230.093 g/mol
 YesY (what is this?)  (verify)

Clonidine (trade names Catapres, Kapvay, Nexiclon and others) is a sympatholytic medication used to treat high blood pressure, ADHD, anxiety/panic disorder, and certain pain conditions. It is classified as a centrally acting α2 adrenergic agonist. An alternative hypothesis that has been proposed is that clonidine acts centrally as an imidazoline receptor agonist.