Tropicamide

Structural formula
	Structural formula without stereochemistry
General
Non-proprietary name	Tropicamide
other names	( RS ) - N -Ethyl-3-hydroxy-2-phenyl- N - (4-pyridylmethyl) propanamide ( IUPAC ) ; (±) - N -ethyl-3-hydroxy-2-phenyl- N - (4-pyridylmethyl) propanamide;
Molecular formula	C 17 H 20 N 2 O 2
Brief description	White to almost white, crystalline powder
External identifiers / databases
EC number	216-140-2
ECHA InfoCard	100.014.673
PubChem	5593
ChemSpider	5391
DrugBank	DB00809
Wikidata	Q29310
Drug information
ATC code	S01 FA06
Drug class	Anticholinergic
properties
Molar mass	284.35 g · mol -1
Physical state	firmly
Melting point	95-98 ° C
solubility	Slightly soluble in water, easily soluble in dichloromethane and ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-315-317-319-332-335
	P: 261-280-305 + 351 + 338
Toxicological data	865 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tropicamide is a synthetic pupil-expanding drug ( mydriatic ) that is used in the form of eye drops for diagnostics in ophthalmology .

effect

Tropicamide inhibits the parasympathetic nervous system ( parasympatholytic ) by blocking muscarinic acetylcholine receptors. This relaxes the sphincter pupillae muscle that constricts the pupil , causing the pupil to widen ( mydriasis ).

Mydriasis of the right eye due to tropicamide

The pupil dilates after a few minutes and lasts for one to two hours. Resorption into the circulatory system is possible.

When side effects occur a distinct accommodation paralysis , burning eyes, an increase of intraocular pressure with a possible release of a glaucoma attack as well as a contact dermatitis on. Systemic side effects of an anticholinergic type may occur (dry mouth, reddening of the skin, increased temperature, urinary retention and tachycardia )

Primary forms of glaucoma, in particular narrow-angle glaucoma, as well as pregnancy and lactation are given as contraindications . Caution is advised in the case of tachycardia, heart failure , urinary flow disorders, narrowing of the gastrointestinal tract, hyperthyroidism , pulmonary edema and myasthenia gravis .

Stereochemistry

Tropicamide contains a stereocenter, so it is chiral . It is produced as a 1: 1 mixture ( racemate ) of ( R ) - N -ethyl-3-hydroxy-2-phenyl- N - (4-pyridylmethyl) propanamide and ( S ) - N -ethyl-3-hydroxy-2 -phenyl- N - (4-pyridylmethyl) propanamide used.

Enantiomers of tropicamide
CAS number: 92934-63-9	CAS number: 92934-64-0

Trade names

Mydrum (D), Mydriaticum Stulln (D), Mydriacyl

literature

Technical information Mydrum eye drops, as of May 2008

Tropicamid in WHO Model List of Essential Medicines (PDF file; 432 kB).

Individual evidence

↑ ^a ^b ^c ^d data sheet TROPICAMIDE CRS (PDF) at EDQM , accessed on November 26, 2009.

↑ ^a ^b Tropicamide data sheet from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).

↑ Rote Liste Service GmbH (Ed.): Rote Liste 2017 - drug directory for Germany (including EU approvals and certain medical devices) . Rote Liste Service GmbH, Frankfurt / Main, 2017, edition 57, ISBN 978-3-946057-10-9 , p. 224.

↑ ^a ^b ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 224.

[Ph._Eur.-1] ta sheet TROPICAMIDE CRS (PDF) at EDQM , accessed on November 26, 2009.