U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H20N2O2
Molecular Weight 284.3535
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROPICAMIDE

SMILES

CCN(Cc1ccncc1)C(=O)C(CO)c2ccccc2

InChI

InChIKey=BGDKAVGWHJFAGW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/tropicamide.html

Tropicamide (Mydriacyl) is an anticholinergic used as a mydriatic.Tropicamide belongs to the group of medicines called anti-muscarinics. Tropicamide blocks the receptors in the muscles of the eye (muscarinic receptors). These receptors are involved controlling the pupil size and the shape of the lens. By blocking these receptors, tropicamide produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia). Tropicamide is given as eye drops to dilate the pupil and relax the lens so that eye examinations can be carried out thoroughly.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
MYDRIACYL

Approved Use

For mydriasis and cycloplegia for diagnostic procedures.

Launch Date

-3.11126393E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28.9 ng/mL
0.5 % single, ocular
dose: 0.5 %
route of administration: Ocular
experiment type: SINGLE
co-administered: PHENYLEPHRINE
TROPICAMIDE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
2.8 ng/mL
400 μg single, ocular
dose: 400 μg
route of administration: Ocular
experiment type: SINGLE
co-administered:
TROPICAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
25.1 μg × h/mL
0.5 % single, ocular
dose: 0.5 %
route of administration: Ocular
experiment type: SINGLE
co-administered: PHENYLEPHRINE
TROPICAMIDE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30 min
unknown
TROPICAMIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
TROPICAMIDE unknown
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Ocular hypertension induced by tropicamide after treatment of the angle with argon laser].
1985
Muscarinic binding sites of the pig intravesical ureter.
1995 Oct
Pupil dilatation assay by tropicamide is modulated by apolipoprotein E epsilon 4 allele dosage in Alzheimer's disease.
1996 Mar 22
Apolipoprotein E epsilon 4 allele and pupillary response to tropicamide.
1997 May
Identification of muscarinic receptor subtypes in RINm5F cells by means of polymerase chain reaction, subcloning, and DNA sequencing.
1997 Sep
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.
1998 Nov
The effect of pupil dilation with tropicamide on vision and driving simulator performance.
2000 Jun
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.
2001 May
Design, pharmacokinetic, and pharmacodynamic evaluation of soft anticholinergics based on tropyl alpha-phenylcyclopentylacetate.
2002 Feb
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics.
2003 Oct
Parameters of drug antagonism: re-examination of two modes of functional competitive drug antagonism on intraocular muscles.
2004 Aug
Activation of muscarinic acetylcholine receptors elicits pigment granule dispersion in retinal pigment epithelium isolated from bluegill.
2004 Jul 13
A double-blind study comparing 0.5% and 1% tropicamide for annual retinal screening in diabetic adolescents.
2004 May
Neuronal nitric oxide synthase activity in rat urinary bladder detrusor: participation in M3 and M4 muscarinic receptor function.
2005 Jul
Why patients with Alzheimer's disease may show increased sensitivity to tropicamide eye drops: role of locus coeruleus.
2006 Jan
Activation of muscarinic cholinergic receptors inhibits giant neurones in the caudal pontine reticular nucleus.
2006 Oct
Messenger RNA levels and binding sites of muscarinic acetylcholine receptors in gastrointestinal muscle layers from healthy dairy cows.
2007
Corticotropin-releasing factor inhibition of sheep fetal colonic contractility: mechanisms to prevent meconium passage in utero.
2007 Apr
Segment-dependent expression of muscarinic acetylcholine receptors and G-protein coupling in the equine respiratory tract.
2007 Feb
Transcriptional up-regulation of nitric oxide synthase II by nuclear factor-kappaB at rostral ventrolateral medulla in a rat mevinphos intoxication model of brain stem death.
2007 Jun 15
Muscarinic receptor-independent activation of cyclic adenosine monophosphate-dependent protein kinase in rostral ventrolateral medulla underlies the sympathoexcitatory phase of cardiovascular responses during mevinphos intoxication in the rat.
2007 May
The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors.
2007 Oct
Impact of Intravitreal Injection of Bevacizumab (Avastin) on Rabbit's Choroid and Retina.
2008 Apr
A novel assay of Gi/o-linked G protein-coupled receptor coupling to potassium channels provides new insights into the pharmacology of the group III metabotropic glutamate receptors.
2008 Apr
Temporal evolution of intraocular pressure elevation after pupillary dilation in pigment dispersion syndrome.
2009 Mar
Effects of the adenosine A 2A antagonist KW 6002 (istradefylline) on pimozide-induced oral tremor and striatal c-Fos expression: comparisons with the muscarinic antagonist tropicamide.
2009 Sep 29
Efficacy assessment of various anticholinergic agents against topical sarin-induced miosis and visual impairment in rats.
2012 Apr
Synergism Between Anticholinergic and Oxime Treatments Against Sarin-Induced Ocular Insult in Rats.
2015 Aug
Patents

Sample Use Guides

Usual Adult Dose for Refraction Cycloplegic Refraction: -Instill 1 or 2 drops of the 1% solution into eye(s); repeat in 5 minutes. Comment: -An additional drop may be given if the examination is not done within 20 to 30 minutes. Usual Adult Dose for Pupillary Dilation Fundoscopy: -Instill 1 or 2 drops of 0.5% solution into eye(s) 15 or 20 minutes prior to examination. Comments: -Heavily pigmented irides may require higher strength or more doses. Usual Pediatric Dose for Refraction Cycloplegic Refraction: -Instill 1 or 2 drops of the 1% solution into eye(s); repeat in 5 minutes.
Route of Administration: Topical
The muscarine action on GABAergic mIPSC frequency was completely blocked by 1 uM tropicamide in rat tuberomammillary nucleus neurons.
Name Type Language
TROPICAMIDE
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
TROPICAMIDE [WHO-DD]
Common Name English
TROPICAMIDE [INN]
Common Name English
RO-1-7683
Code English
NSC-757372
Code English
TROPICAMIDE [MART.]
Common Name English
MYDRIACYL
Brand Name English
TROPICAMIDE [USP-RS]
Common Name English
TROPICAMIDE [EP MONOGRAPH]
Common Name English
TROPICAMIDE [VANDF]
Common Name English
TROPICAMIDE [ORANGE BOOK]
Common Name English
BENZENEACETAMIDE, N-ETHYL-.ALPHA.-(HYDROXYMETHYL)-N-(4-PYRIDINYLMETHYL)-, (+/-)-
Systematic Name English
TROPICAMIDUM [WHO-IP LATIN]
Common Name English
TROPICAMIDE [MI]
Common Name English
TROPICACYL
Brand Name English
TROPICAMIDE [USP MONOGRAPH]
Common Name English
TROPICAMIDE [USAN]
Common Name English
TROPICAMIDE COMPONENT OF PAREMYD
Common Name English
PAREMYD COMPONENT TROPICAMIDE
Common Name English
(+/-)-N-ETHYL-2-PHENYL-N-(4-PYRIDYLMETHYL)HYDRACRYLAMIDE
Systematic Name English
VISUMIDRIATIC
Common Name English
BISTROPAMIDE
Common Name English
TROPICAMIDE [WHO-IP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1937
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
WHO-VATC QS01FA06
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 14.1
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
NDF-RT N0000175574
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
WHO-ATC S01FA56
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
WHO-ATC S01BB01
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
NDF-RT N0000175370
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
WHO-ATC S01FA06
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
TROPICAMIDE
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder. Solubility: Slightly soluble in water; freely soluble in dichloromethane R and ethanol (~750 g/l) TS. Category: Mydriatic. Storage: Tropicamide should be kept in a tightly closed container, protected from light. Labelling: The designation Tropicamide for sterile non-injectable use indicates that the substance complies with the additional requirement and may be used for sterile applications. Expiry date. Requirement: Tropicamide contains not less than 99.0% and not more than 101.0% of C17H20N2O2, calculated with reference to the dried substance.
ECHA (EC/EINECS)
216-140-2
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
DRUG CENTRAL
2774
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
USP_CATALOG
1699005
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY USP-RS
INN
1059
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
FDA UNII
N0A3Z5XTC6
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
WIKIPEDIA
Tropicamide
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
RXCUI
10869
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C47776
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
MERCK INDEX
M11229
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00809
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
EVMPD
SUB11342MIG
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
EPA CompTox
1508-75-4
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
LACTMED
Tropicamide
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
PUBCHEM
5593
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200604
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
MESH
D014331
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
IUPHAR
7319
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY
CAS
1508-75-4
Created by admin on Fri Jun 25 21:04:34 UTC 2021 , Edited by admin on Fri Jun 25 21:04:34 UTC 2021
PRIMARY