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Cyclopentolate

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(Redirected from Cyclopentolate hydrochloride) Pair of enantiomers Pharmaceutical compound
Cyclopentolate
Clinical data
Pregnancy
category
  • C
Routes of
administration		Topic
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)
Identifiers
IUPAC name
  • (RS)-2-(dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate
CAS Number
PubChem CID
DrugBank
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KEGG
ChEBI
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ECHA InfoCard100.007.398 Edit this at Wikidata
Chemical and physical data
FormulaC17H25NO3
Molar mass291.391 g·mol
3D model (JSmol)
SMILES
  • O=C(OCCN(C)C)C(c1ccccc1)C2(O)CCCC2
InChI
  • 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,6-7,10-13H2,1-2H3
  • Key:SKYSRIRYMSLOIN-UHFFFAOYSA-N
  (what is this?)  (verify)

Cyclopentolate is a muscarinic antagonist. It is commonly used as an eye drop during pediatric eye examinations to dilate the eye (mydriatic) and prevent the eye from focusing/accommodating (cycloplegic). Cyclopentolate or atropine can also be administered to reverse muscarinic and central nervous system effects of indirect cholinomimetic (anti-AChase) administration.

It is on the World Health Organization's List of Essential Medicines.

After instillation of cyclopentolate, pupil dilation (mydriasis) typically lasts up to 24 hours, while paralysis of the ciliary muscle (cycloplegia) typically lasts 6-24 hours. 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 to atropine, another cycloplegic agent which lasts much longer. Tropicamide is an even shorter-lasting cycloplegic than cyclopentolate, but is less reliable for finding latent hyperopia. Cyclopentolate drops act rapidly to dilate the pupil.

The side and adverse effects of cyclopentolate are similar to the side and adverse effects of other anticholinergic medications. 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 of glaucoma. 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. like subtle concentration and memory problems, subtle decision-making problems, drowsiness, and more pronounced disorientation to time and place, confusion, disturbances of speech and movement, hyperactivity, restlessness, and seizures. Temporary psychosis can develop that includes hallucinations, particularly when higher doses are used in children or older adults on other anticholinergic medications. Patients with dementia of 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 mouth and reduced sweating, and reduced bronchial secretions. Severe poisoning with cyclopentolate may result in coma, paralysis of breathing, and death. Cyclopentolate derivatives can be used as an antidote for organophosphate poisoning.

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 include tachycardia, dizziness, dry mouth, behavioral disturbances, uncoordination, and drowsiness.

Cycloplegia is necessary in cases of suspected latent hyperopia (or "over-focusing") so that an ophthalmologist or optometrist can accurately measure how much a person has to flex their focusing 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 refractive amblyopia, and may alleviate eye strain or frontal headaches caused by prolonged near-work. Cycloplegia is also helpful in relieving accommodative spasm.

History

Cyclopentolate was first synthesized in 1952 as a chemical analogue of atropine. It was one of several derivatives of an analogue to tropic acid which were tested for pharmacological action "in a search for new and better antispasmodic agents."

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

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

References

  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). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. "Cyclopentolate". Drug Bank. Retrieved June 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. ISBN 978-0-7506-7576-5.
  5. "Cyclogyl Eye Drops Medsafe data sheet New Zealand" (PDF). 11 January 2017. Retrieved 3 June 2017.
  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. PMID 22217890.
  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. PMID 2260344. S2CID 6896684.
  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. PMID 6046837.
  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. PMID 19454862. S2CID 36599696.
  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. PMID 4698940.
  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. PMID 2113819. S2CID 20030473.
  13. Bhatia SS, Vidyashankar C, Sharma RK, Dubey AK (March 2000). "Systemic toxicity with cyclopentolate eye drops". Indian Pediatrics. 37 (3): 329–331. PMID 10750080.
  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. PMID 24906272.
  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. ISSN 0002-7863.
  16. "cyclopentolate hydrochloride solution - ophthalmic, Cyclogyl, Cylate, Pentolair". Retrieved June 15, 2012.

Further reading

  • Whitcher JP, Riordan-Eva P (2007-10-18). Vaughan & Asbury's general ophthalmology (17th ed.). McGraw-Hill Medical. p. 63. ISBN 978-0071443142.
Ophthalmologicals: mydriasis and cycloplegia (S01F)
Anticholinergics/antimuscarinics
Sympathomimetics
Muscarinic acetylcholine receptor modulators
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
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