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Tropicamid

Tropicamide

HCID 5593
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Grundinformationen

CAS
1508-75-4
Standard-SMILES
CCN(Cc1ccncc1)C(=O)C(CO)c1ccccc1
InChIKey
BGDKAVGWHJFAGW-UHFFFAOYSA-N
Summenformel
C17H20N2O2
Durchschnittliche Molmasse
284,35 g/mol
Monoisotopische Masse
284,15247789

Überblick

Tropicamide is a member of acetamides.

Namen und Bezeichner

Bevorzugter Name
Tropicamide
IUPAC
N-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
Lokaler Name
Tropicamid
Englischer Name
Tropicamide
Summenformel
C17H20N2O2
Molmasse
284.35

Namen und Synonyme

tropicamide1508-75-4MydriacylBistropamideTropicacylN-ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamideMydriafairVisumidriaticTropicamidumTropicamidaTropimilRo 1-7683
Weitere Namen anzeigen
Tropicamidropicamidemydrinmydrummydriatro1-7683Mydrapid
N-Ethyl-2-phenyl-N-(4-pyridylmethyl)hydracrylamideDTXSID8045220N-Ethyl-N-(4-pyridylmethyl)tropamideN-Ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)benzeneacetamideN0A3Z5XTC6NSC-757372Benzeneacetamide, N-ethyl-alpha-(hydroxymethyl)-N-(4-pyridinylmethyl)-RO-1-7683

Datenbank-Bezeichner

CAS
1508-75-4
PubChem CID
5593
DTXSID
DTXSID8045220
ChEMBL
CHEMBL1200604
ChEBI
CHEBI:9757
UNII
N0A3Z5XTC6
EC Number
216-140-2
Nikkaji
J3.670F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,5
Polarare Oberfläche (TPSA)
53,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
6
Schwere Atome
21
Formalladung
0
Komplexität
310

Experimentelle und physikochemische Eigenschaften

LogP1.3
Solubility · 2 Einträge

3.75e-01 g/L

>42.7 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 5 Einträge

Breast Feeding; Lactation; Mydriatics; Muscarinic Antagonists; Parasympatholytics

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Diagnostic agents > Ophthalmic medicines

Melting Point96.5 °C
Physical DescriptionSolid
Collision Cross Section · 2 Einträge

170.4 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

169.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
98 °C · 98 °C
Siedepunkt
492.8 · 492.8±45.0 °C(Predicted)
Dichte
1.161 · 1.161±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 4.3 mg/mL
Aggregatzustand
solid
pka
5.3 · pKa 5.3 (Uncertain)
Farbe
white
Wasserlöslichkeit
0.2 g/L · 0.2g/L(25 ºC)
Merck
14 · 14,9780
Major Application
pharmaceutical (small molecule)
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
InChIKey
BGDKAVGWHJFAGW-UHFFFAOYSA-N
SMILES
C(CO)(C(=O)N(CC)CC1=CC=NC=C1)C1C=CC=CC=1
CAS Datenbank
1508 · 1508-75-4(CAS DataBase Reference)
NIST chemische Informationen
Tropicamide(1508-75-4)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (98.4%)

Toxikologische Informationen

Adverse EffectsOcular adverse events include transient stinging, photophobia, superficial punctate keratitis, blurred vision, and a rise in intraocular pressure.
Toxicity Summary · 1 Eintrag

Although tropicamide is a short-acting drug, and the frequency of associated adverse events is rare, there are certain instances when reversal of mydriasis is necessary, including decreasing the risk of angle-closure glaucoma, improving blurry vision, and decreasing recovery time for patient comfort. Presumably, a cholinergic agent like pilocarpine should be able to undo the effects of an anticholinergic drug. However, several studies have reported conflicting pupillary responses. At times, only a partial reversal was observed.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
hs_code
29333990
RTECS-Nr.
CY1487860
risk_code
20/21/22-36/37/38-42/43-41-37/38-22
hazard_code
Xn,Xi
safety_code
22-26-36-36/37/39
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

S01FA06

S - Sensory organs

QS - Sensory organs

S01FA06

Protein BindingThe extent of protein binding has not been established. Tropicamide binds to albumin.
Pharmacodynamics · 1 Eintrag

Tropicamide is an anticholinergic drug and that works by non‐selectively blocking muscarinic receptors to cause mydriasis and cycloplegia. It relaxes the pupillary sphincter to dilate the pupil. The onset of tropicamide‐induced mydriasis is about 10 to 15 minutes, with optimal effect occurring 25 to 30 minutes post-administration. Mydriasis caused by tropicamide wears off within four to eight hours, but it was seen up to 24 hours in some individuals. Tropicamide hinders accommodation by causing the contraction of the ciliary muscle. The cycloplegic effect occurs within 20 to minutes following administration, with a duration of action of four to 10 hours. Tropicamide can elevate intraocular pressure. The ophthalmic use of tropicamide is not typically associated with serious systemic adverse events. One randomized pilot study showed that oral tropicamide alleviated perceived symptoms of sialorrhea in patients with Parkinson's Disease: anticholinergics are believed to restore the dopaminergic to cholinergic activity imbalance in neurodegenerative diseases. Similarly in one case report, tropicamide administered via ophthalmic solution relieved clozapine-induced sialorrhea. Interestingly, in rodent models, tropicamide suppressed drug-induced tremulous jaw movements which are often used as a model of parkinsonian tremor: the significance of this finding requires further investigations.

Mechanism of Action · 1 Eintrag

Muscarinic acetylcholine receptors are involved in numerous ocular functions. The M<sub>3</sub> subtype is predominantly expressed by smooth muscle cells of the sphincter pupillae, which is a circular muscle of the iris, and ciliary muscles. In response to light or binding of acetylcholine, M<sub>3</sub> receptor signalling leads to contraction of the sphincter pupillae and pupil constriction. Contraction of the ciliary muscle via M<sub>3</sub> receptor signalling also leads to accommodation, adjusting the lens for near vision. The eye is also innervated by parasympathetic nerves: ciliary ganglion neurons project to the ciliary body and the sphincter pupillae muscle of the iris to control ocular accommodation and pupil constriction. Tropicamide is a non-selective muscarinic antagonist that binds to all subtypes of muscarinic receptors. By binding to muscarinic receptors, tropicamide relaxes the pupillary sphincter muscle and causes pupil dilation. By blocking the muscarinic receptors of the ciliary body, tropicamide also prevents accommodation. Like other muscarinic antagonists, tropicamide inhibits the parasympathetic drive, allowing the sympathetic nervous system responses to dominate. Tropicamide is thought to ameliorate sialorrhea by blocking M<sub>4</sub> receptors expressed on salivary glands and reducing hypersalivation.

Biological Half-LifeTropicamide has a plasma half-life of 30 minutes.
Metabolism/MetabolitesNo information can be found.
FDA Pharmacological Classification · 6 Einträge

N0A3Z5XTC6

TROPICAMIDE

Established Pharmacologic Class [EPC] - Anticholinergic

Mechanisms of Action [MoA] - Cholinergic Antagonists

Tropicamide is an Anticholinergic. The mechanism of action of tropicamide is as a Cholinergic Antagonist.

TROPICAMIDE

MeSH Pharmacological Classification · 2 Einträge

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.

Absorption, Distribution and Excretion · 4 Einträge

Following ocular administration of 40 μL drops of 0.5% tropicamide in female subjects, tropicamide reached its mean peak concentration in plasma of 2.8 ± 1.7 ng/mL (mean ± SD) at five minutes.

No information can be found.

No information can be found.

No information can be found.

Cellular LocationsMembrane

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals

Anwendungen

VerwendenTropicamide, like cyclopentolate, is used in ophthalmoscopy for reaching pre-operational mydraises and for testing narrow-angle glaucoma.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

EthylaminHydrogenchloridEthanamine, N-(4-pyridinylmethylene)-Acetyltropylic chloride2-Phenyl-malonic acid monoethyl esterN-Ethylpyridin-4-methylaminTropasureDiethylphenylmalonatPyridin-4-carbaldehyd

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