Details of the Drug

General Information of Drug (ID: DMA8LM5)

Drug Name

Cyclopentolate

Synonyms

Ciclopentolato; Cyclopentoiate; Cyclopentolatum; Cyclopentylate; Cylate; Diopentolate; Mydrilate; Bell Pentolate; Minims Cyclopentolate; Bell Pentolate (TN); Ciclopentolato [INN-Spanish]; Cyclopentolate (INN); Cyclopentolate [INN:BAN]; Cyclopentolatum [INN-Latin]; Ocu-Pentolate; B-dimethylaminoethyl(1-hydroxycyclopentyl)phenylacetate; Beta-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate; Beta-(Dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetate; Alpha-(1-hydroxycyclopentyl)benzeneacetic acid 2-(dimethylamino)ethyl ester; Benzeneacetic acid, alpha-(1-hydroxycyclopentyl)-, 2-(dimethylamino)ethyl ester; Benzeneacetic acid, .alpha.-(1-hydroxycyclopentyl)-, 2-(dimethylamino)ethyl ester; (+-)-cyclopentolate; 1-hydroxy-alpha-phenylcyclopentaneacetic acid 2-(dimethylamino)ethyl ester; 2-(Dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate; 2-(Dimethylamino)ethyl 1-hydroxy-alpha-phenylcyclopentaneacetate; 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate; 2-Dimethylaminoethyl 2-(1-hydroxycyclopentyl)-2-phenylacetat; 2-dimethylaminoethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate; 2-phenyl-2-(1-hydroxycyclopentyl)ethanoic acid beta-(dimethylamino)ethyl ester

Indication

Disease Entry	ICD 11	Status	REF
Examination of eyes or vision	QA00.6	Approved	[1]

Therapeutic Class

Parasympatholytics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

291.4

Topological Polar Surface Area (xlogp)

2.7

Rotatable Bond Count (rotbonds)

7

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

4

ADMET Property

Absorption: The drug is absorbed following ophthalmic administration [2]

Chemical Identifiers

Formula: C17H25NO3
IUPAC Name: 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
Canonical SMILES: CN(C)CCOC(=O)C(C1=CC=CC=C1)C2(CCCC2)O
InChI: InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
InChIKey: SKYSRIRYMSLOIN-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2905
ChEBI ID: CHEBI:4024
CAS Number: 512-15-2
DrugBank ID: DB00979
TTD ID: D0B1EV

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Muscarinic acetylcholine receptor M5 (CHRM5)	TTH18TF	ACM5_HUMAN	Antagonist	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Cyclopentolate (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Bethanechol	DMCLHO0	Moderate	Antagonize the effect of Cyclopentolate when combined with Bethanechol.	Abnormal micturition [MF50]	[14]
Rivastigmine	DMG629M	Moderate	Antagonize the effect of Cyclopentolate when combined with Rivastigmine.	Alzheimer disease [8A20]	[15]
Acetylcholine	DMDF79Z	Moderate	Antagonize the effect of Cyclopentolate when combined with Acetylcholine.	Cataract [9B10]	[16]
Pilocarpine	DMV9ADG	Moderate	Antagonize the effect of Cyclopentolate when combined with Pilocarpine.	Glaucoma [9C61]	[14]
Physostigmine	DM2N0TO	Moderate	Antagonize the effect of Cyclopentolate when combined with Physostigmine.	Lips/oral mucosa miscellaneous disorder [DA02]	[15]
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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
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3	High spatial resolution studies of muscarinic neuroeffector junctions in mouse isolated vas deferens. Neuroscience. 2009 Sep 15;162(4):1366-76.
4	Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12.
5	Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4- oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists. J Med Chem. 1993 Apr 2;36(7):842-7.
6	Retinoic acid prevents virus-induced airway hyperreactivity and M2 receptor dysfunction via anti-inflammatory and antiviral effects. Am J Physiol Lung Cell Mol Physiol. 2009 Aug;297(2):L340-6.
7	Medicinal plants in therapy. Bull World Health Organ. 1985;63(6):965-81.
8	Additive protective effects of donepezil and nicotine against salsolinol-induced cytotoxicity in SH-SY5Y cells. Neurotox Res. 2009 Oct;16(3):194-204.
9	Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8.
10	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7354).
11	Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
12	Comparison of pharmacological effects of L- and DL-n-butyl-scopolamine in rat uterus. Yao Xue Xue Bao. 1994;29(1):24-7.
13	Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
14	Benjamin KW "Toxicity of ocular medications." Int Ophthalmol Clin 19 (1979): 199-255. [PMID: 376469]
15	Katz IR, Sands LP, Bilker W, DiFilippo S, Boyce A, D'Angelo K "Identification of medications that cause cognitive impairment in older people: the case of oxybutynin chloride." J Am Geriatr Soc 46 (1998): 8-13. [PMID: 9434659]
16	Multum Information Services, Inc. Expert Review Panel.