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Cyclopentolate

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Cyclopentolate
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  • C
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ATC code
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Identifiers
  • (RS)-2-(dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate
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ECHA InfoCard100.007.398Edit this at Wikidata
Chemical and physical data
FormulaC17H25NO3
Molar mass291.391g·mol−1
3D model (JSmol)
  • O=C(OCCN(C)C)C(c1ccccc1)C2(O)CCCC2
  • InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3checkY
  • Key:SKYSRIRYMSLOIN-UHFFFAOYSA-NcheckY
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Cyclopentolateis amuscarinic antagonist.[2]It is commonly used as an eye drop duringpediatriceye examinationsto dilate the eye (mydriatic) and prevent the eye from focusing/accommodating(cycloplegic). Cyclopentolate[citation needed]oratropinecan also be administered to reverse muscarinic and central nervous system effects of indirectcholinomimetic(anti-AChase) administration.

It is on theWorld Health Organization's List of Essential Medicines.[3]

After instillation of cyclopentolate, pupil dilation (mydriasis) typically lasts up to 24 hours, while paralysis of theciliary muscle(cycloplegia) typically lasts 6-24 hours.[4]During this time, patients may be more light sensitive than normal and may notice close objects blurred (and possibly distant objects blurred, depending on the patient's visual system). Cyclopentolate is often chosen as a milder, shorter-lasting, cycloplegic alternative toatropine,another cycloplegic agent which lasts much longer.Tropicamideis an even shorter-lasting cycloplegic than cyclopentolate, but is less reliable for finding latent hyperopia. Cyclopentolate drops act rapidly to dilate the pupil.[5]

The side and adverse effects of cyclopentolate are similar to the side and adverse effects of otheranticholinergicmedications. Because of that, extra caution should be taken when prescribing cyclopentolate to patients who are already taking other anticholinergic drugs. A possible ocular (eye-related) side effect is increase in pressure inside the eye, which is of particular concern when there is a predisposition toward or a presence ofglaucoma.Other ocular side effects can include burning sensations, discomfort with bright light (photophobia), blurred vision, irritation, inflammation of the eye mucous membranes (conjunctivitis), inflammation of the cornea of the eye (keratitis), and other issues. Nonocular (not eye-related) side and adverse effects can include neuropsychiatric symptoms.[6]like subtleconcentrationandmemoryproblems, subtledecision-makingproblems,drowsiness,and more pronounceddisorientationto time and place,confusion,disturbances ofspeechand movement,hyperactivity,restlessness,andseizures.Temporarypsychosis[7]can develop that includeshallucinations,particularly when higher doses are used in children or older adults[8]on other anticholinergic medications.[9]Patients withdementiaof the Alzheimer's type can experience worsening of their dementia symptoms. Additional side and adverse effects can include skin flushing, skin rashes, gastrointestinal problems, increased heart beat (tachycardia), increased body temperature (hyperpyrexia), blood vessel dilation,urinary retention,dry mouthand reducedsweating,and reducedbronchial secretions.Severe poisoning with cyclopentolate may result incoma,paralysisof breathing, anddeath.Cyclopentolate derivatives can be used as an antidote fororganophosphatepoisoning.[10][11] [12][13][14]

Lethality of cyclopentolate has been studied in rodents. The LD50 (the dose at which 50% of animals die from the drug) is approximately 4000 mg/kg in rats and 960 mg/kg in mice. Readily recognizable symptoms of overdose includetachycardia,dizziness,dry mouth,behavioral disturbances,uncoordination,anddrowsiness.

Cycloplegiais necessary in cases of suspected latenthyperopia(or "over-focusing" ) so that anophthalmologistoroptometristcan accurately measure how much a person has to flex theirfocusing muscle(accommodation) in order to see in the distance and up-close. Correction of latent hyperopia in children can often prevent, or sometimes correct, unwanted eye turns (strabismus), some forms of refractiveamblyopia,and may alleviate eye strain or frontal headaches caused by prolonged near-work. Cycloplegia is also helpful in relievingaccommodative spasm.

History

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Cyclopentolate was first synthesized in 1952 as a chemical analogue ofatropine.It was one of several derivatives of an analogue to tropic acid which were tested for pharmacological action "in a search for new and betterantispasmodicagents. "[15]

Brand names for cyclopentolate include Cyclogyl, Cylate, Mydrilate, and Pentolair.[16]

Both eyes instilled with cyclopentolate 1%, causing both mydriasis and cycloplegia
Pupil dilation (mydriasis) caused by cyclopentolate 1% instilled into both eyes

References

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  1. ^Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-16.
  2. ^"Cyclopentolate".Drug Bank.RetrievedJune 15,2012.
  3. ^World Health Organization(2021).World Health Organization model list of essential medicines: 22nd list (2021).Geneva: World Health Organization.hdl:10665/345533.WHO/MHP/HPS/EML/2021.02.
  4. ^Bartlett JD, Jaanus SD, eds. (2008). "Chapter 9: Cycloplegics. Table 9-1: Mydriatic and Cycloplegic Properties of Anticholinergic Agents".Clinical Ocular Pharmacology(5th ed.). Saint Louis: Butterworth Heinemann - Elsevier. p. 127.ISBN978-0-7506-7576-5.
  5. ^"Cyclogyl Eye Drops Medsafe data sheet New Zealand"(PDF).11 January 2017.Retrieved3 June2017.
  6. ^Derinoz O, Er A (January 2012). "Inability to walk, disequilibrium, incoherent speech, disorientation following the instillation of 1% cyclopentolate eyedrops: case report".Pediatric Emergency Care.28(1): 59–60.doi:10.1097/PEC.0b013e3182417a63.PMID22217890.
  7. ^Rajappa N, Patra S, Bhalsing S, Lune AA (January 2014)."A case of acute psychosis induced by topical cyclopentolate eye drops in an elderly patient".Medical Journal of Dr. D.Y. Patil University.7(1): 68–69.doi:10.4103/0975-2870.122789.
  8. ^Barker DB, Solomon DA (September 1990). "The potential for mental status changes associated with systemic absorption of anticholinergic ophthalmic medications: concerns in the elderly".DICP: The Annals of Pharmacotherapy.24(9): 847–850.doi:10.1177/106002809002400911.PMID2260344.S2CID6896684.
  9. ^Carpenter WT (October 1967). "Precipitous mental deterioration following cycloplegia with 0.2 percent cyclopentolate HCl".Archives of Ophthalmology.78(4): 445–447.doi:10.1001/archopht.1967.00980030447006.PMID6046837.
  10. ^Bryant SM, Rhee JW, Thompson TM, Lu JJ, Aks SE (2009). "Parenteral ophthalmic tropicamide or cyclopentolate protects rats from lethal organophosphate poisoning".American Journal of Therapeutics.16(3): 231–234.doi:10.1097/MJT.0b013e318182254b.PMID19454862.S2CID36599696.
  11. ^Bauer CR, Trottier MC, Stern L (March 1973). "Systemic cyclopentolate (Cyclogyl) toxicity in the newborn infant".The Journal of Pediatrics.82(3): 501–505.doi:10.1016/s0022-3476(73)80134-9.PMID4698940.
  12. ^Fitzgerald DA, Hanson RM, West C, Martin F, Brown J, Kilham HA (April 1990). "Seizures associated with 1% cyclopentolate eyedrops".Journal of Paediatrics and Child Health.26(2): 106–107.doi:10.1111/j.1440-1754.1990.tb02399.x.PMID2113819.S2CID20030473.
  13. ^Bhatia SS, Vidyashankar C, Sharma RK, Dubey AK (March 2000). "Systemic toxicity with cyclopentolate eye drops".Indian Pediatrics.37(3): 329–331.PMID10750080.
  14. ^Ozgun U, Demet T, Ozge KA, Zafer D, Murat S, Mehmet Y, Nilgun K (May 2014). "Fatal necrotising enterocolitis due to mydriatic eye drops".Journal of the College of Physicians and Surgeons--Pakistan.24(Suppl 2): S147–S149.PMID24906272.
  15. ^Treves GR, Testa FC (1952). "Basic Esters and Quaternary Derivatives of β-Hydroxy Acids as Antispasmodics1".Journal of the American Chemical Society.74(1): 46–48.doi:10.1021/ja01121a012.ISSN0002-7863.
  16. ^"cyclopentolate hydrochloride solution - ophthalmic, Cyclogyl, Cylate, Pentolair".RetrievedJune 15,2012.

Further reading

[edit]
  • Whitcher JP, Riordan-Eva P (2007-10-18).Vaughan & Asbury's general ophthalmology(17th ed.). McGraw-Hill Medical. p. 63.ISBN978-0071443142.
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