TROPICAMIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H20N2O2
Molecular Weight	284.3529
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC1=CC=NC=C1)C(=O)C(CO)C2=CC=CC=C2

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

Molecular Formula	C17H20N2O2
Molecular Weight	284.3529
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.drugbank.ca/drugs/DB00809
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Melanocortin receptor 4 5 Target ID: CHEMBL259 Sources: https://www.drugbank.ca/drugs/DB00809 \| https://www.ncbi.nlm.nih.gov/pubmed/27085897 \| https://www.ncbi.nlm.nih.gov/pubmed/17594079	Antagonist 2778		6.86 null [pKi]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.drugbank.ca/drugs/DB00809 \| https://www.ncbi.nlm.nih.gov/pubmed/27085897	Antagonist 2778		6.99 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Eye diseases 25 Sources: https://www.drugs.com/pro/tropicamide.html	Diagnostic		Approved 8429	MYDRIACYL Approved Use For mydriasis and cycloplegia for diagnostic procedures. Launch Date 1960

C_max

Value	Dose	Co-administered	Analyte	Population
28.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32320311	0.5 % single, ocular dose: 0.5 % route of administration: Ocular experiment type: SINGLE co-administered: PHENYLEPHRINE	PHENYLEPHRINE	TROPICAMIDE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
2.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8083562	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

Value	Dose	Co-administered	Analyte	Population
25.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32320311	0.5 % single, ocular dose: 0.5 % route of administration: Ocular experiment type: SINGLE co-administered: PHENYLEPHRINE	PHENYLEPHRINE	TROPICAMIDE plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
30 min EXPERIMENT https://www.tandfonline.com/doi/full/10.1080/24750573.2017.1347601	unknown		TROPICAMIDE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
55% OTHER https://go.drugbank.com/drugs/DB00809			TROPICAMIDE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-5180	http://www.3bsc.com/index/pro_info.php?id=83219
AA Blocks	AA007XBN	http://www.aablocks.com/goods/Goods/detail?id=AA007XBN
AK Scientific, Inc. (AKSCI)	69107	http://www.aksci.com/item_detail.php?cat=69107
Aaron Chemicals	AR007Y3F	http://www.aaronchem.com/1508-75-4
AbMole Bioscience	M6040	http://www.abmole.com/products/tropicamide.html
Achemo Scientific Limited	AC-62351	http://www.achemo.com/search/?Keyword= 1508-75-4
Achemtek	0104-008811	http://www.achemtek.com/1508-75-4
Acorn PharmaTech	ACN-036667	http://www.acornpharmatech.com/
Alfa Chemistry	AP1508754-A	https://reagents.alfa-chemistry.com/product/tropicamide-cas-1508-75-4-5436.html
Alfa Chemistry	AP1508754-B	https://reagents.alfa-chemistry.com/product/tropicamide-cas-1508-75-4-5437.html
Ark Pharm	AK164485	http://www.arkpharminc.com/products/1508-75-4.html
Aurora Fine Chemicals LLC	K02.118.488	http://online.aurorafinechemicals.com/info?ID=K02.118.488
Aurum Pharmatech LLC	K-4793	http://www.Aurumpharmatech.com/Product/ProductDetails/K_4793
BLD Pharm	BD156008	http://www.bldpharm.com/products/1508-75-4.html
BioChemPartner	BCP13504	http://www.biochempartner.com/1508-75-4-BCP13504
BioCrick	BCC4574	http://www.biocrick.com/Tropicamide-BCC4574.html
BioSynth	Q-201902	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201902.html
CSNpharm	CSN12156	https://www.csnpharm.com/products/tropicamide.html
Chem Scene	CS-2362	http://www.chemscene.com/1508-75-4.html
ChemMol	30102335	http://www.chemmol.com/chemmol/30102335.html
ChemMol	44001969	http://www.chemmol.com/chemmol/44001969.html
ChemMol	49409310	http://www.chemmol.com/chemmol/49409310.html
ChemMol	97900361	http://www.chemmol.com/chemmol/97900361.html
ChemMol	99043186	http://www.chemmol.com/chemmol/99043186.html
Chemspace	CSSB00016993650	https://chem-space.com/CSSB00016993650
Clearsynth	CS-O-02428	https://www.clearsynth.com/en/CSO02428.html
DC Chemicals	DC31906	http://www.dcchemicals.com//product_show-Tropicamide.html
Finetech	FT-0657590	http://www.finetechnology-ind.com/prod/detail/pub/1508-75-4.html
Glentham Life Sciences	GP3255	http://www.glentham.com/products/product/GP3255/
Hello Bio	HB1510	http://www.hellobio.com/tropicamide.html
LGC Standards	LGCFOR0601.00	https://www.lgcstandards.com/US/en/p/LGCFOR0601.00
LGC Standards	MM0601.00	https://www.lgcstandards.com/US/en/p/MM0601.00
Lab Network	LN00873077	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00873077
MedChem Express	HY-B0321	https://www.medchemexpress.com/Tropicamide.html
MuseChem	A001220	https://www.musechem.com/product/A001220.html
OChem	9720	http://www.ocheminc.com/index.php?act=psearch&pid=508T754
Renno Tech	RP29909	http://www.rennotech.com/product_show.asp?id=35514
Sigma-Aldrich	T2580000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/t2580000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	Y0001316_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/y0001316?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T9778_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/t9778?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1699005_USP	https://www.sigmaaldrich.com/catalog/product/usp/1699005?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S545978	http://www.smolecule.com/products/s545978
Smolecule	S772622	https://www.smolecule.com/products/s772622
TCI (Tokyo Chemical Industry)	T1470	http://www.tcichemicals.com/eshop/en/us/commodity/T1470/index.html
THE BioTek	bt-284357	https://www.thebiotek.com/product/inhibitors/bt-284357
Tocris	909	https://www.tocris.com/products/tropicamide_0909
VladaChem	VL273850-10G	https://www.vladachem.com/product.php?products=1508-75-4
Yuhao Chemical	CJ3064	http://www.chemyuhao.com/1508-75-4.html
abcr GmbH	AB251831	http://www.abcr.com/shop/en/AB251831
eNovation Chemicals	D673690	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673690
eNovation Chemicals	D762946	https://www.enovationchem.com/ProductDetails.asp?ProductID=D762946
iChemical	EBD22886	http://www.ichemical.com/chemicals/cas-1508-75-4
mcule	MCULE-4102613027	https://mcule.com/MCULE-4102613027/

PubMed

Title	Date	PubMed
[Ocular hypertension induced by tropicamide after treatment of the angle with argon laser].	1985	3833883
Muscarinic binding sites of the pig intravesical ureter.	1995 Oct	8744975
Pupil dilatation assay by tropicamide is modulated by apolipoprotein E epsilon 4 allele dosage in Alzheimer's disease.	1996 Mar 22	8724673
Interaction of neuromuscular blocking drugs with recombinant human m1-m5 muscarinic receptors expressed in Chinese hamster ovary cells.	1998 Nov	9846649
M3 muscarinic receptor activation of a delayed rectifier potassium current in canine atrial myocytes.	1999	10353596
The effect of pupil dilation with tropicamide on vision and driving simulator performance.	2000 Jun	11026989
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.	2001 May	11306684
Design, pharmacokinetic, and pharmacodynamic evaluation of soft anticholinergics based on tropyl alpha-phenylcyclopentylacetate.	2002 Feb	11878186
Search of antimicrobial activity of selected non-antibiotic drugs.	2002 Nov-Dec	12669766
Design, pharmacokinetic, and pharmacodynamic evaluation of a new class of soft anticholinergics.	2003 Oct	14620526
Parameters of drug antagonism: re-examination of two modes of functional competitive drug antagonism on intraocular muscles.	2004 Aug	15285850
Activation of muscarinic acetylcholine receptors elicits pigment granule dispersion in retinal pigment epithelium isolated from bluegill.	2004 Jul 13	15251036
A double-blind study comparing 0.5% and 1% tropicamide for annual retinal screening in diabetic adolescents.	2004 May	15089787
Neuronal nitric oxide synthase activity in rat urinary bladder detrusor: participation in M3 and M4 muscarinic receptor function.	2005 Jul	15955028
Why patients with Alzheimer's disease may show increased sensitivity to tropicamide eye drops: role of locus coeruleus.	2006 Jan	16308726
Activation of muscarinic cholinergic receptors inhibits giant neurones in the caudal pontine reticular nucleus.	2006 Oct	17040474
Messenger RNA levels and binding sites of muscarinic acetylcholine receptors in gastrointestinal muscle layers from healthy dairy cows.	2007	17613726
Corticotropin-releasing factor inhibition of sheep fetal colonic contractility: mechanisms to prevent meconium passage in utero.	2007 Apr	17403421
Segment-dependent expression of muscarinic acetylcholine receptors and G-protein coupling in the equine respiratory tract.	2007 Feb	17180451
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	17395621
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	17438462
The muscarinic receptor antagonist tropicamide suppresses tremulous jaw movements in a rodent model of parkinsonian tremor: possible role of M4 receptors.	2007 Oct	17594079
Impact of Intravitreal Injection of Bevacizumab (Avastin) on Rabbit's Choroid and Retina.	2008 Apr	21346840
Functional expression of M3, a muscarinic acetylcholine receptor subtype, in taste bud cells of mouse fungiform papillae.	2008 Jan	17872906
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	19467297
Efficacy assessment of various anticholinergic agents against topical sarin-induced miosis and visual impairment in rats.	2012 Apr	22247005

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

The muscarine action on GABAergic mIPSC frequency was completely blocked by 1 uM tropicamide in rat tuberomammillary nucleus neurons.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:59:09 GMT 2023` Edited by `admin` on `Fri Dec 15 14:59:09 GMT 2023`
Record UNII	N0A3Z5XTC6
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TROPICAMIDE

Official Name

English

tropicamide [INN]

Common Name

English

Tropicamide [WHO-DD]

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 COMPONENT OF MYDCOMBI

Brand Name

English

TROPICAMIDE [ORANGE BOOK]

Common Name

English

TROPICAMIDE [JAN]

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

MYDCOMBI COMPONENT TROPICAMIDE

Brand 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