Tropicamide

Tropicamide
Clinical data
Trade namesMydriacyl, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • C
Routes of
administration		Topical eye drops
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)[1]
  • UK: POM (Prescription only)[2]
  • US: ℞-only
Pharmacokinetic data
Protein binding45%
Identifiers
IUPAC name
  • (RS)-N-Ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.673
Chemical and physical data
FormulaC17H20N2O2
Molar mass284.359 g·mol−1
3D model (JSmol)
SMILES
  • CCN(Cc1ccncc1)C(=O)C(CO)c1ccccc1
InChI
  • 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 name Mydriacyl among others, is a medication used to dilate the pupil and help with the examination of the eye.[3] Specifically it is used to help examine the back of the eye.[4] It is applied as eye drops.[3] Effects occur within 40 minutes and last for up to a day.[3]

Common side effects include blurry vision, increased intraocular pressure, and sensitivity to light.[3] Another rare but severe side effect is psychosis, particularly in children.[3] It is unclear if use during pregnancy is safe for the fetus.[5] Tropicamide is in the antimuscarinic part of the anticholinergic 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 the World Health Organization's List of Essential Medicines.[6]

Medical use

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 an antimuscarinic drug that produces short acting mydriasis (dilation of the pupil) and cycloplegia[7] when applied as eye drops. It is used to allow better examination of the lens, vitreous humor, and retina. Due to its relatively short duration of effect (4–8 hours), it is typically used during eye examinations such as the dilated fundus examination, but it may also be used before or after eye surgery. Cycloplegic drops are often also used to treat anterior uveitis, decreasing the risk of posterior synechiae and decreasing inflammation in the anterior chamber of the eye.

Tropicamide is occasionally administered in combination with p-hydroxyamphetamine (brand name Paremyd), which is a sympathomimetic. 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

Tropicamide induces transient stinging and a slight and transient rise in intraocular pressure in the majority of patients. It may cause redness or conjunctivitis (inflammation) and also blurs 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 of acute angle-closure glaucoma. This tends to be in patients with narrow anterior chamber angles, and closure risk must be assessed by the practitioner prior to instillation.

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

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

Pharmacology

Pharmacodynamics

Tropicamide is an anticholinergic.[10] It is specifically an antimuscarinic, acting as a selective muscarinic acetylcholine M1 and M4 receptor antagonist.[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 produce deliriant effects.[10]

Recreational use

Tropicamide is sometimes abused (injected intravenously e.g. by insulin syringe) as an inexpensive recreational deliriant drug (along with naphazoline). 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

Tropicamide has a chiral center and two enantiomers. Medications are racemates.[17]

Enantiomers

(R)-Tropicamid
CAS: 92934-63-9
(S)-Tropicamid
CAS: 92934-64-0

References

  1. ^ "Summary for ARTG Entry: 25356 Mydriacyl tropicamide 0.5% eye drops bottle". Therapeutic Goods Administration. Archived from the original on 5 June 2023. Retrieved 5 June 2023.
  2. ^ "Mydriacyl 1% eye drops, solution - Summary of Product Characteristics (SmPC)". Electronic Medicines Compendium. 12 February 2020. Archived from the original on 27 June 2022. Retrieved 29 July 2020.
  3. ^ a b c d e f g h "Tropicamide". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  4. ^ Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. p. 314. hdl:10665/44053. ISBN 978-92-4-154765-9.
  5. ^ "Tropicamide ophthalmic Use During Pregnancy". Drugs.com. Archived from the original on 28 December 2016. Retrieved 28 December 2016.
  6. ^ World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06.
  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.{{cite journal}}: CS1 maint: deprecated archival service (link)
  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. ^ a b c Lakstygal 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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