Chemistry:Cyclopentolate
 | |
| Clinical data | |
|---|---|
| Pregnancy category |
|
| Routes of administration | Topic |
| ATC code | |
| Legal status | |
| Legal status |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| Chemical and physical data | |
| Formula | C17H25NO3 |
| Molar mass | 291.391 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
Cyclopentolate is a muscarinic antagonist.[1] 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[citation needed] 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.[2]
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.[3] 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.[4]
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.[5] 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[6] can develop that includes hallucinations, particularly when higher doses are used in children or older adults[7] on other anticholinergic medications.[8] 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.[9][10] [11][12][13]
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."[14]
Brand names for cyclopentolate include Cyclogyl, Cylate, Mydrilate, and Pentolair.[15]
References
- ↑ "Cyclopentolate". Drug Bank. http://www.drugbank.ca/drugs/DB00979.
- ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02.
- ↑ "Chapter 9: Cycloplegics. Table 9-1: Mydriatic and Cycloplegic Properties of Anticholinergic Agents". Clinical Ocular Pharmacology (5th ed.). Saint Louis: Butterworth Heinemann - Elsevier. 2008. pp. 127. ISBN 978-0-7506-7576-5.
- ↑ "Cyclogyl Eye Drops Medsafe data sheet New Zealand". 11 January 2017. http://www.medsafe.govt.nz/profs/Datasheet/c/Cyclogyleyedrop.pdf.
- ↑ "Inability to walk, disequilibrium, incoherent speech, disorientation following the instillation of 1% cyclopentolate eyedrops: case report". Pediatric Emergency Care 28 (1): 59–60. January 2012. doi:10.1097/PEC.0b013e3182417a63. PMID 22217890.
- ↑ "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. January 2014. doi:10.4103/0975-2870.122789.
- ↑ "The potential for mental status changes associated with systemic absorption of anticholinergic ophthalmic medications: concerns in the elderly". Dicp 24 (9): 847–850. September 1990. doi:10.1177/106002809002400911. PMID 2260344.
- ↑ "Precipitous mental deterioration following cycloplegia with 0.2 percent cyclopentolate HCl". Archives of Ophthalmology 78 (4): 445–447. October 1967. doi:10.1001/archopht.1967.00980030447006. PMID 6046837.
- ↑ "Parenteral ophthalmic tropicamide or cyclopentolate protects rats from lethal organophosphate poisoning". American Journal of Therapeutics 16 (3): 231–234. 2009. doi:10.1097/MJT.0b013e318182254b. PMID 19454862.
- ↑ "Systemic cyclopentolate (Cyclogyl) toxicity in the newborn infant". The Journal of Pediatrics 82 (3): 501–505. March 1973. doi:10.1016/s0022-3476(73)80134-9. PMID 4698940.
- ↑ "Seizures associated with 1% cyclopentolate eyedrops". Journal of Paediatrics and Child Health 26 (2): 106–107. April 1990. doi:10.1111/j.1440-1754.1990.tb02399.x. PMID 2113819.
- ↑ "Systemic toxicity with cyclopentolate eye drops". Indian Pediatrics 37 (3): 329–331. March 2000. PMID 10750080.
- ↑ "Fatal necrotising enterocolitis due to mydriatic eye drops". Journal of the College of Physicians and Surgeons--Pakistan 24 (Suppl 2): S147–S149. May 2014. PMID 24906272.
- ↑ "Basic Esters and Quaternary Derivatives of β-Hydroxy Acids as Antispasmodics1". Journal of the American Chemical Society 74 (1): 46–48. 1952. doi:10.1021/ja01121a012. ISSN 0002-7863.
- ↑ "cyclopentolate hydrochloride solution - ophthalmic, Cyclogyl, Cylate, Pentolair". http://www.medicinenet.com/cyclopentolate_hydrochloride-eye_drops/article.htm.
Further reading
- Vaughan & Asbury's general ophthalmology (17th ed.). McGraw-Hill Medical. 2007-10-18. p. 63. ISBN 978-0071443142.
 |  |
