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Tropicamide

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tropicamide
Clinical data
Trade namesMydriacyl, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • C
Routes of
administration
Topicaleye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding45%
Identifiers
  • (RS)-N-Ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.014.673Edit this at Wikidata
Chemical and physical data
FormulaC17H20N2O2
Molar mass284.359 g·mol−1
3D model (JSmol)
  • CCN(Cc1ccncc1)C(=O)C(CO)c1ccccc1
  • InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3
  • Key:BGDKAVGWHJFAGW-UHFFFAOYSA-N
 ☒NcheckY (what is this?)  (verify)

Tropicamide, sold under the brand nameMydriacyl among others, is a medication used todilate the pupil and help with theexamination of the eye.[3] Specifically it is used to help examine theback of the eye.[4] It is applied aseye drops.[3] Effects occur within 40 minutes and last for up to a day.[3]

Common side effects includeblurry vision,increased intraocular pressure, andsensitivity to light.[3] Another rare but severe side effect ispsychosis, particularly in children.[3] It is unclear if use duringpregnancy is safe for the fetus.[5] Tropicamide is in theantimuscarinic part of theanticholinergic family of medications.[3] It works by making the muscles within the eye unable to respond to nerve signals.[3]

Tropicamide was approved for medical use in the United States in 1960.[3] It is on theWorld Health Organization's List of Essential Medicines.[6]

Medical use

[edit]
Right eye was instilled with tropicamide, leading to mydriasis and therefore anisocoria (unequal pupil size)
Anisocoria caused by tropicamide instilled into the subject's right eye only.

Tropicamide is anantimuscarinic drug that produces short actingmydriasis (dilation of thepupil) andcycloplegia[7] when applied aseye drops. It is used to allow better examination of thelens,vitreous humor, andretina. Due to its relatively short duration of effect (4–8 hours), it is typically used duringeye examinations such as thedilated fundus examination, but it may also be used before or aftereye surgery. Cycloplegic drops are often also used to treat anterioruveitis, decreasing the risk of posteriorsynechiae and decreasing inflammation in the anterior chamber of the eye.

Tropicamide is occasionally administered in combination withp-hydroxyamphetamine (brand nameParemyd), which is asympathomimetic. The use of the sympathomimetic drug causes the iris dilator muscle to be directly stimulated, causing increased dilation. In the United States, the sympathomimetic drop most commonly used along with tropicamide, is 2.5%phenylephrine hydrochloride (brand name AK-Dilate).

Side effects

[edit]

Tropicamide induces transient stinging and a slight and transient rise inintraocular pressure in the majority of patients. It may cause redness orconjunctivitis (inflammation) and alsoblurs near vision for a short while after instillation (care must be taken, and the patient must only drive when vision returns to normal). Tropicamide may, in very rare cases,[8] cause an attack ofacute angle-closure glaucoma. This tends to be in patients with narrowanterior chamberangles, and closure risk must be assessed by the practitioner prior to instillation.

Tropicamide is often preferred toatropine because atropine has a longerhalf-life, causing prolonged dilation and blurry vision for up to a week. Atropine has lesssting effect, but can be toxic or fatal if ingested in large quantities by children or adults.

Witheye drops,systemic effects are minimal to nonexistent due to very low absorption into the bloodstream.[9]

Pharmacology

[edit]

Pharmacodynamics

[edit]

Tropicamide is ananticholinergic.[10] It is specifically anantimuscarinic, acting as aselectivemuscarinic acetylcholineM1 andM4 receptorantagonist.[10] However, it has also been reported to be a non-selective antagonist of all five muscarinic acetylcholine receptors.[11] As with other antimuscarinics, tropicamide can producedeliriant effects.[10]

Recreational use

[edit]

Tropicamide is sometimes abused (injected intravenously e.g. byinsulin syringe) as an inexpensive recreationaldeliriant drug (along withnaphazoline). This was initially reported in Russia, but has subsequently spread to various other countries in the former Soviet Union and around Europe, and later in the United States.[12][13][14]

Tropicamide severely destroys internal organs when injected.[15][16]

Stereochemistry

[edit]

Tropicamide has achiral center and twoenantiomers. Medications areracemates.[17]

Enantiomers

(R)-Tropicamid
CAS: 92934-63-9

(S)-Tropicamid
CAS: 92934-64-0

References

[edit]
  1. ^"Summary for ARTG Entry: 25356 Mydriacyl tropicamide 0.5% eye drops bottle".Therapeutic Goods Administration. Archived fromthe original on 5 June 2023. Retrieved5 June 2023.
  2. ^"Mydriacyl 1% eye drops, solution - Summary of Product Characteristics (SmPC)".Electronic Medicines Compendium. 12 February 2020. Archived fromthe original on 27 June 2022. Retrieved29 July 2020.
  3. ^abcdefgh"Tropicamide".Drugs.com.American Society of Health-System Pharmacists.Archived from the original on 28 December 2016. Retrieved8 December 2016.
  4. ^World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.).WHO Model Formulary 2008. World Health Organization. p. 314.hdl:10665/44053.ISBN 9789241547659.
  5. ^"Tropicamide ophthalmic Use During Pregnancy".Drugs.com.Archived from the original on 28 December 2016. Retrieved28 December 2016.
  6. ^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.
  7. ^Manny RE, Hussein M, Scheiman M, Kurtz D, Niemann K, Zinzer K (July 2001)."Tropicamide (1%): an effective cycloplegic agent for myopic children".Investigative Ophthalmology & Visual Science.42 (8):1728–35.PMID 11431435. Archived fromthe original on 2013-01-12.
  8. ^Liew G, Mitchell P, Wang JJ, Wong TY (January 2006)."Fundoscopy: to dilate or not to dilate?".BMJ.332 (7532): 3.doi:10.1136/bmj.332.7532.3.PMC 1325111.PMID 16399709.
  9. ^Vuori ML, Kaila T, Iisalo E, Saari KM (1994-01-01). "Systemic absorption and anticholinergic activity of topically applied tropicamide".Journal of Ocular Pharmacology.10 (2):431–437.doi:10.1089/jop.1994.10.431.PMID 8083562.
  10. ^abcLakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV (May 2019). "DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens".ACS Chem Neurosci.10 (5):2144–2159.doi:10.1021/acschemneuro.8b00615.PMID 30566832.
  11. ^Lavrador M, Cabral AC, Veríssimo MT, Fernandez-Llimos F, Figueiredo IV, Castel-Branco MM (January 2023)."A Universal Pharmacological-Based List of Drugs with Anticholinergic Activity".Pharmaceutics.15 (1): 230.doi:10.3390/pharmaceutics15010230.PMC 9863833.PMID 36678858.
  12. ^Bersani FS, Corazza O, Simonato P, Mylokosta A, Levari E, Lovaste R, Schifano F (2013). "Drops of madness? Recreational misuse of tropicamide collyrium; early warning alerts from Russia and Italy".General Hospital Psychiatry.35 (5):571–3.doi:10.1016/j.genhosppsych.2013.04.013.PMID 23706777.
  13. ^Bersani FS, Imperatori C, Prilutskaya M, Kuliev R, Corazza O (July 2015). "Injecting eye-drops: a mini-review on the non-clinical use of tropicamide".Hum Psychopharmacol.30 (4):262–4.doi:10.1002/hup.2481.PMID 26216560.S2CID 190289.
  14. ^Bellman V, Ukolova A, Erovichenkova E, Lam S, Srivastava HK, Bruce J, Burgess DM (November 2022)."Abuse of tropicamide eye drops: review of clinical data".Braz J Psychiatry.44 (5):522–531.doi:10.47626/1516-4446-2021-2446.PMC 9561840.PMID 35739063.
  15. ^"Bellman, V., Ukolova, A., Erovichenkova, E., Lam, S., Srivastava, H. K., Bruce, J., & Burgess, D. M. (2022). Abuse of tropicamide eye drops: review of clinical data. Revista brasileira de psiquiatria (Sao Paulo, Brazil : 1999)".Braz J Psychiatry.44. 2 Nov 2022.
  16. ^"Krokodil: Russia's Deadliest Drug (NSFW)".YouTube. 17 May 2012.
  17. ^Rote Liste (in German). Vol. 57. Frankfurt/Main: Rote Liste Service GmbH. 2017. p. 224.ISBN 978-3-946057-10-9.Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte)

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