- Procyclidine
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Procyclidine Systematic (IUPAC) name 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride Clinical data AHFS/Drugs.com monograph MedlinePlus a605037 Pregnancy cat. ? Legal status ? Routes oral, im, iv Pharmacokinetic data Protein binding ~100%-albumin Half-life ~12 h Identifiers CAS number 77-37-2
77-37-2 (free base)ATC code N04AA04 PubChem CID 207841 DrugBank APRD00383 ChemSpider 4750 UNII C6QE1Q1TKR ChEMBL CHEMBL1761 Chemical data Formula C19H30ClNO Mol. mass 323.9 g/mol (what is this?) (verify) Not to be confused with Phencyclidine.Procyclidine is an anticholinergic drug principally used for the treatment of:
- Drug-induced parkinsonism, akathisia and acute dystonia;
- Parkinson disease; and
- Idiopathic or secondary dystonia.
Contents
Uses
It is used in patients with parkinsonism and akathisia and to reduce the side effects of antipsychotic treatment given for schizophrenia. Procyclidine is also a second-line drug for the treatment of Parkinson's disease. It improves tremor but not rigidity or bradykinesia.
Procyclidine is also sometimes used for the treatment of dystonia (but not tardive dyskinesia), a rare disorder that causes abnormal muscle contraction, resulting in twisting postures of limbs, trunk, or face.
Overdose
Signs of procyclidine overdose are those of an anticholinergic and include confusion, agitation and sleeplessness that can last up to or more than 24 hours. Pupils become dilated and unreactive to light. Tachycardia (fast heart beat), as well as auditory and visual hallucinations have also been reported.
Other known symptoms of overdose are: clumsiness or unsteadiness, being severely drowsy, having a severely dry mouth, nose, or throat, having an altered mood or other mental changes, seizures, being short of breath or having troubled breathing, a dry and warm, flushed skin.
A suspected overdose with severe life-threatening symptoms should immediately be brought to medical attention, where reversal can be attempted with physostigmine administered intravenously or subcutaneously.
Chemistry
Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in the exact same manner as was seen for trihexyphenidyl, except this time the linear synthesis begins with the preparation of 3-(1-pyrrolidino)propiophenone.
- E. Jassmann, H. Pfanz, DE 1084734 (1960).
- E.M. Boffort, U.S. Patent 2,826,590 (1958).
- D.W. Adamson, P.A. Barrett, S. Wilkinson, J. Chem. Soc., 52(1951).
References
- British National Formulary (45 ed.). March 2003.
Antiparkinson agents (N04) Dopaminergics DA receptor agonistsAplindore • Apomorphine • Bromocriptine • Cabergoline • Ciladopa • Dihydroergocryptine • Lisuride • Pardoprunox • Pergolide • Piribedil • Pramipexole • Ropinirole • RotigotineAnticholinergics Benzatropine • Biperiden# • Bornaprine • Chlorphenoxamine • Cyrimine • Dexetimide • Dimenhydrinate • Diphenhydramine • Etanautine • Etybenzatropine • Mazaticol • Metixene • Orphenadrine • Phenglutarimide • Piroheptine • Procyclidine • Profenamine • Trihexyphenidyl • TropatepineOthers Cholinergics Receptor ligands Agonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine • Suberylcholine • Talsaclidine • Tazomeline • Thiopilocarpine • Vedaclidine • VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide • Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate • Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine (Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium bromide • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID • PD-102,807 • PD-0298029 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium bromide • Tolterodine • Trihexyphenidyl • Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Xanomeline • Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine/pyrilamine, phenindamine, pheniramine, tripelennamine, triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, doxepin, trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, maprotiline, etc) • Typical Antipsychotics (Chlorpromazine, thioridazine, etc) • Atypical Antipsychotics (Clozapine, olanzapine, quetiapine, etc)Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • Anatoxin-a • AR-R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium • Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y • SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 • TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • WAY-317,538 • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion (Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine (Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic acid • Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan • Tropeinium • Tubocurarine • Vecuronium • XenonReuptake inhibitors PlasmalemmalCHT InhibitorsHemicholinium-3 (Hemicholine; HC3) • TriethylcholineVAChT InhibitorsEnzyme inhibitors ChAT inhibitors1-(-Benzoylethyl)pyridinium • 2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole • 4-(1-Naphthylvinyl)pyridine • Acetylseco hemicholinium-3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 • CatabolismAChE inhibitorsReversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb • Carbaryl • Carbendazim • Carbetamide • Carbofuran • Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb • Fenobucarb • Fenoxycarb • Formetanate • Furadan • Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl • Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb • Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine • Phenserine • Physostigmine • Pyridostigmine • Rivastigmine; Others: Acotiamide • Ambenonium • Donepezil • Edrophonium • Galantamine • Huperzine A • Minaprine • Tacrine • Zanapezil
Irreversible: Organophosphates: Acephate • Azinphos-methyl • Bensulide • Cadusafos • Chlorethoxyfos • Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl • Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl fluorophosphate (Guthion) • Diisopropylphosphate • Dimethoate • Dioxathion • Disulfoton • EA-3148 • Echothiophate • Ethion • Ethoprop • Fenamiphos • Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate • Isoxathion • Malaoxon • Malathion • Methamidophos • Methidathion • Metrifonate • Mevinphos • Monocrotophos • Naled • Novichok agent • Omethoate • Oxydemeton-Methyl • Paraoxon • Parathion • Parathion-Methyl • Phorate • Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos • Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE • VG • VM • VR • VX; Others: Demecarium • Onchidal (Onchidella binneyi)BChE inhibitorsCymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.Others Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE, deanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) • Phosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine • PirisudanolOthersAcetylcholine releasing agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime • Obidoxime • PralidoximeCategories:- Muscarinic antagonists
- Tardive dyskinesia
- Alcohols
- Pyrrolidines
- Chlorides
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Procyclidine hydrochloride — drugbox IUPAC name = 1 cyclohexyl 1 phenyl 3 pyrrolidin 1 yl propan 1 ol hydrochloride width= CAS number = 77 37 2 ATC prefix = N04 ATC suffix = AA04 PubChem = 207841 DrugBank = APRD00383 C=19 | H=30 | Cl=1 | N=1 | O=1 molecular weight = 323.9… … Wikipedia
procyclidine — noun An anticholinergic drug mainly used to treat drug induced parkinsonism, akathisia and acute dystonia … Wiktionary
procyclidine — n. an anticholinergic drug used to reduce muscle tremor and rigidity in parkinsonism. It is administered by mouth; common side effects include dry mouth, blurred vision, and giddiness. Trade names: Arpicolin, Kemadrin … Medical dictionary
procyclidine — n. an antimuscarinic drug used to reduce muscle tremor and rigidity in parkinsonism. It is administered by mouth or injection; common side effects include dry mouth, blurred vision, and giddiness. Trade names: Arpicolin, Kemadrin … The new mediacal dictionary
procyclidine — noun drug (trade name Kemadrin) used to reduce tremors in Parkinsonism • Syn: ↑Kemadrin • Usage Domain: ↑trade name (for: ↑Kemadrin) • Hypernyms: ↑muscle relaxant … Useful english dictionary
procyclidine hydrochloride — An anticholinergic agent used in the treatment of paralysis agitans and drug induced parkinsonism. * * * pro·cy·cli·dine hy·dro·chlo·ride (pro siґklĭ dēn) [USP] a synthetic anticholinergic with a direct antispasmodic effect on smooth… … Medical dictionary
procyclidine methochloride — An anticholinergic drug used in the treatment of functional gastrointestinal spasm. SYN: tricyclamol chloride … Medical dictionary
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ПРОЦИКЛИДИН — (procyclidine) лекарственное вещество, сходное по своему действию с атропином; применяется для уменьшения тремора и ригидности мышц при паркинсонизме. Может назначаться внутрь или в инъекциях; возможные побочные эффекты: сухость во рту, нарушение … Толковый словарь по медицине
Muscarinic antagonist — In neurochemistry, a muscarinic receptor antagonist is an agent that reduces the activity of the muscarinic acetylcholine receptor. Acetylcholine (often abbreviated ACh) is a neurotransmitter, whose receptor is a protein found in synapses and… … Wikipedia