Medication for motion sickness or vertigo
Pharmaceutical compound
Cyclizine , sold under a number of brand names, is a medication used to treat and preventnausea ,vomiting anddizziness due tomotion sickness orvertigo .[ 2] general anaesthesia or that which developed fromopioid use.[ 2] [ 3] by mouth , in therectum , orinjected into a vein .[ 3] [ 4]
Common side effects include sleepiness, dry mouth,constipation , and trouble with vision.[ 5] low blood pressure andurinary retention .[ 5] glaucoma .[ 2] [ 6] pregnancy but has not been well studied.[ 7] anticholinergic andantihistamine family of medications.[ 3] [ 6]
Cyclizine was discovered in 1947.[ 8] World Health Organization's List of Essential Medicines .[ 9] over the counter .[ 6]
Primary uses includenausea ,vomiting anddizziness associated withmotion sickness ,vertigo and post-operatively following administration ofgeneral anesthesia andopioids . It is sometimes given inhyperemesis gravidarum , although the manufacturer advises that it be avoided in pregnancy. Off-license use often occurs with specialists in hospitals to treat inpatients who have become severely dehydrated in pregnancy. An off-label use is as an opioid/opiate potentiator.[ 10]
The drug Diconal is a combination of cyclizine and the opioiddipipanone .[ 11] schedule I controlled substance in the US.[ 12]
Its antimuscarinic action warrants caution in patients withprostatic hypertrophy , urinary retention, or angle-closureglaucoma . Liver disease exacerbates itssedative effects.[ 10]
Common (over 10%) —Drowsiness ,dry mouth .
Uncommon (1% to 10%) — Headache, psychomotor impairment, dermatitis, andantimuscarinic effects such as diplopia (double vision),tachycardia ,constipation ,urinary retention and gastro-intestinal disturbances.
Rare (less than 1%) — Hypersensitivity reactions (bronchospasm ,angioedema ,anaphylaxis , rashes andphotosensitivity reactions),extrapyramidal effects, dizziness, confusion, depression, sleep disturbances,tremor , liver dysfunction, andhallucinations .
Cyclizine is apiperazine derivative with histamine H1 -receptor antagonist (antihistamine ) activity. The precise mechanism of action in inhibiting the symptoms of motion sickness is not well understood. It may have effects directly on thevestibular system and on thechemoreceptor trigger zone . Cyclizine exerts a centralanticholinergic (antimuscarinic ) action.[ 10]
Cyclizine may be prepared by theEschweiler–Clarke methylation ofdiphenylmethylpiperazine or by reaction of benzhydryl bromide with1-methylpiperazine in acetonitrile to form the hydrobromide salt of the drug.
Cyclizine was developed in the American division of pharmacy companyBurroughs Wellcome (todayGlaxoSmithKline ) during a research study involving many drugs of the antihistamine group. Cyclizine was quickly clinically found as a potent and long-acting antiemetic. The company named the substance – or more precisely cyclizine'shydrochloride form which it usually appears in – "marezine hydrochloride" and started to sell it in the United States under trade nameMarezine . Selling was begun inFrance under trade nameMarzine in 1965.[ 13] [ 14]
The substance received more credit whenNASA chose it as a space antiemetic for thefirst crewed Moon flight . Cyclizine was introduced to many countries as a common antiemetic. It is an over-the-counter drug in many countries because it has been well tolerated, although it has not been studied much.[ 13] [ 15]
Society and culture [ edit ] Some people using methadone recreationally combine cyclizine with theirmethadone dose, a combination that is known to produce strongpsychoactive effects.[ 16] anticholinergic effects to induce hallucinations.[ 17]
It has been used illegally ingreyhound racing to sabotage a dog's performance.[ 18]
As cyclizine hydrochloride tablets and cyclizine lactate solution for intramuscular or intravenous injection (brand names: Valoid[ 10] [ 19]
Cyclizine derivatives [ edit ] ^ "DrugBank: Cyclizine. Pharmacology: metabolism" .DrugBank Database .Archived from the original on 30 January 2016. Retrieved5 January 2016 .^a b c "Cyclizine 50mg Tablets - Summary of Product Characteristics (SPC) - (eMC)" .www.medicines.org.uk . 27 March 2015.Archived from the original on 20 December 2016. Retrieved13 December 2016 .^a b c Feldman M, Friedman LS, Brandt LJ (2015).Sleisenger and Fordtran's Gastrointestinal and Liver Disease: Pathophysiology, Diagnosis, Management ISBN 9781455749898 Archived from the original on 20 December 2016. ^ World Health Organization (2019).World Health Organization model list of essential medicines: 21st list 2019 . Geneva: World Health Organization.hdl :10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.^a b "Cyclizine Side Effects in Detail - Drugs.com" .www.drugs.com .Archived from the original on 21 December 2016. Retrieved13 December 2016 .^a b c "Cyclizine: Indications, Side Effects, Warnings - Drugs.com" .www.drugs.com .Archived from the original on 21 December 2016. Retrieved13 December 2016 .^ "Cyclizine Use During Pregnancy | Drugs.com" .www.drugs.com .Archived from the original on 21 December 2016. Retrieved13 December 2016 .^ Williams P (2010).The story of the Wellcome Trust : unlocking Sir Henry's legacy to medical research ISBN 9781899163922 Archived from the original on 20 December 2016. ^ World Health Organization (2021).World Health Organization model list of essential medicines: 22nd list (2021) . Geneva: World Health Organization.hdl :10665/345533 ^a b c d "Valoid Tablets by Amdipharm" .Electronic Medicines Compendium . Datapharm. Archived fromthe original on 4 March 2016. Retrieved1 October 2011 .^ "Diconal Tablets by Amdipharm" .Electronic Medicines Compendium . Datapharm. Archived fromthe original on 1 April 2008. Retrieved5 August 2008 .^ "Conversion Factors for Controlled Substances" .DEA Diversion Control Division . Retrieved26 March 2020 .^a b Sneader W (2005).Drug discovery: a history ISBN 0-471-89979-8 Archived from the original on 10 September 2017. ^ Sittig M (1988).Pharmaceutical manufacturing encyclopedia ISBN 0-8155-1144-2 Archived from the original on 10 September 2017. ^ Rajoo SG."Introduction" . In Lobo M (ed.).Anti-emetics - Metoclopramide, Domperidone, Ondansetron, Cyclizine .Archived from the original on 2 April 2015. Retrieved9 March 2015 . {{cite book }}:|work= ignored (help )^ Ruben SM, McLean PC, Melville J (August 1989). "Cyclizine abuse among a group of opiate dependents receiving methadone".British Journal of Addiction .84 (8):929– 34.doi :10.1111/j.1360-0443.1989.tb00766.x .PMID 2775912 . ^ Bassett KE, Schunk JE, Crouch BI (September 1996). "Cyclizine abuse by teenagers in Utah".The American Journal of Emergency Medicine .14 (5):472– 4.doi :10.1016/S0735-6757(96)90156-4 .PMID 8765114 . ^ Conor Ryan for The Independent. June 20, 2013IGB left with €250k bill after dog doping case Archived 2016-03-04 at theWayback Machine ^ "Bonine for Kids" . Insight Pharmaceuticals. Archived fromthe original on 17 September 2010.^ Lemke TL, Williams DA, Roche VF, Zito SW (2013).Foye's Principles of Medicinal Chemistry (7th ed.). Philadelphia: Wolters Kluwer Health / Lippincott Williams & Wilkins. p. 1056.ISBN 978-1-60913-345-0 "Cyclizine" .Drug Information Portal . U.S. National Library of Medicine. Archived fromthe original on 4 January 2020.
Psychedelics (5-HT2A R agonists) Tryptamines (e.g.,DMT ,psilocin ,psilocybin ,bufotenin ,5-MeO-DMT ,AMT )Phenethylamines (e.g.,mescaline ,2C-B ,DOM ,MDA ,TMA ,2C-B-FLY ,25I-NBOMe )Lysergamides (e.g.,LSD ,ergine ,isoergine )Others (e.g.,quipazine ,efavirenz ) For a full list of serotonergic psychedelics, see the navboxhere and the listhere instead. Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) Cannabinoids (CB1 R agonists)
κOR agonists GABAA R agonists Inhalants (mixedMoA Tooltip mechanism of action )Others Aminochromes (e.g.,adrenochrome ,adrenolutin )Carbogen CertainGABAA receptor positive allosteric modulators (nonbenzodiazepines /Z-drugs ) (e.g.,eszopiclone ,zaleplon ,zolpidem ,zopiclone ) CI-966 Cryogenine Glaucine Hallucinogenic bolete mushrooms (e.g.,Lanmaoa asiatica Harmala alkaloidsβ-carbolines (e.g.,harmaline ,6-methoxyharmalan )Iboga alkaloidsazepinoindoles (e.g.,ibogaine )Isoaminile Noscapine Nutmeg (e.g.,myristicin ,elemicin )Oneirogens (e.g.,Calea zacatechichi galantamine ,nicotine ,Silene capensis Prenoxdiazine Pukateine
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g.,brompheniramine ,buclizine ,captodiame ,chlorphenamine (chlorpheniramine) ,cinnarizine ,clemastine ,cyproheptadine ,dimenhydrinate ,dimetindene ,diphenhydramine ,doxylamine ,meclizine ,mequitazine ,perlapine ,phenindamine ,pheniramine ,phenyltoloxamine ,promethazine ,propiomazine ,triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g.,clozapine ,fluperlapine ,olanzapine (+fluoxetine ),rilapine ,quetiapine ,tenilapine ,zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol ,+indacaterol ,+neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,femoxetine ,paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g.,amitriptyline (+perphenazine ),amitriptylinoxide ,butriptyline ,cidoxepin ,clomipramine ,desipramine ,desmethyldesipramine ,dibenzepin ,dosulepin (dothiepin) ,doxepin ,imipramine ,lofepramine ,nitroxazepine ,northiaden (desmethyldosulepin) ,nortriptyline ,protriptyline ,quinupramine ,trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Tropine benzilate Trospium chloride Typical antipsychotics (e.g.,chlorpromazine ,chlorprothixene ,cyamemazine (cyamepromazine) ,loxapine ,mesoridazine ,thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (andprodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists PAMs Tooltip positive allosteric modulators )5-HIAA 6-Chloronicotine A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatabine Anatoxin-a AR-R17779 Bephenium hydroxynaphthoate Butinoline Butyrylcholine Carbachol Choline Choline m-bromophenyl ether Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol (alcohol) Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin JNJ-39393406 Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco )NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Pyrantel Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) Suxethonium (succinyldicholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tribendimidine Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists NAMs Tooltip negative allosteric modulators )
Precursors (andprodrugs )
H1
Agonists Antagonists Others: Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,brexpiprazole ,brilaroxazine ,clozapine ,iloperidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,ziprasidone ,zotepine )Phenylpiperazine antidepressants (e.g.,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione )Tetracyclic antidepressants (e.g.,amoxapine ,loxapine ,maprotiline ,mianserin ,mirtazapine ,oxaprotiline )Tricyclic antidepressants (e.g.,amitriptyline ,butriptyline ,clomipramine ,desipramine ,dosulepin (dothiepin) ,doxepin ,imipramine ,iprindole ,lofepramine ,nortriptyline ,protriptyline ,trimipramine )Typical antipsychotics (e.g.,chlorpromazine ,flupenthixol ,fluphenazine ,loxapine ,perphenazine ,prochlorperazine ,thioridazine ,thiothixene )
H2
H3
H4
Phenylpiperazines 1-Phenylpiperazine (1-PP; PP) 3,4-CFP 2C-B-PP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-7625 EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635 Benzylpiperazines Naphthylpiperazines Quinolinylpiperazines Diphenylalkylpiperazines Pyrimidinylpiperazines Pyridinylpiperazines Benzo(iso)thiazolyl piperazines Tricyclic -linked piperazinesOthers/uncategorized
