Identification
- Summary
Echothiophate is an acetylcholinesterase inhibitor used in ophthalmic preparations to increase the drainage of intraocular fluid; most commonly used for the treatment of glaucoma.
- Brand Names
- Phospholine Iodide
- Generic Name
- Echothiophate
- DrugBank Accession Number
- DB01057
- Background
A potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Echothiophate (DB01057)
- Weight
- Average: 256.323
Monoisotopic: 256.113625809 - Chemical Formula
- C9H23NO3PS
- Synonyms
- 2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
- Echothiophate
- Ecothiopate
- Ecothiopatum
- Phospholine
- External IDs
- MI 217
Pharmacology
- Indication
For use in the treatment of subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Chronic angle-closure glaucoma •••••••••••• Management of Open-angle glaucoma •••••••••••• Management of Secondary glaucoma •••••••••••• Management of Accomodative esotropia •••••••••••• Management of Nonuveitic secondary glaucoma •••••••••••• - Contraindications & Blackbox Warnings
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Echothiophate Iodide is a potent, long-acting cholinesterase inhibitor used as a miotic in the treatment of glaucoma. Echothiophate iodide will depress both plasma and erythrocyte cholinesterase levels in most patients after a few weeks of eyedrop therapy.
- Mechanism of action
Echothiophate Iodide is a long-acting cholinesterase inhibitor for topical use which enhances the effect of endogenously liberated acetylcholine in iris, ciliary muscle, and other parasympathetically innervated structures of the eye. Echothiophate iodide binds irreversibly to cholinesterase, and is long acting due to the slow rate of hydrolysis by cholinesterase. It causes miosis, increase in facility of outflow of aqueous humor, fall in intraocular pressure, and potentiation of accommodation.
Target Actions Organism ACholinesterase inhibitorHumans - Absorption
This ophthalmic medication may be systemically absorbed.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Side effects include blurred vision or change in near or distant vision and eye pain. LD50: 174 mcg/kg in rats. (MSDS)
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareBedaquiline The risk or severity of QTc prolongation can be increased when Echothiophate is combined with Bedaquiline. Citalopram The risk or severity of QTc prolongation can be increased when Echothiophate is combined with Citalopram. Clozapine The risk or severity of QTc prolongation can be increased when Echothiophate is combined with Clozapine. Dipyridamole The therapeutic efficacy of Echothiophate can be decreased when used in combination with Dipyridamole. Encorafenib The risk or severity of QTc prolongation can be increased when Encorafenib is combined with Echothiophate. - Food Interactions
- No interactions found.
Products
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Ingredient UNII CAS InChI Key Echothiophate iodide BA9QH3P00T 513-10-0 OVXQHPWHMXOFRD-UHFFFAOYSA-M - International/Other Brands
- Echodide (Alcon)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Phospholine Iodide Solution 1.5 mg/5mL Ophthalmic Wyeth Pharmaceuticals Inc. 2006-11-03 2006-11-03 US 
Phospholine Iodide Solution 3 mg/5mL Ophthalmic Wyeth Pharmaceuticals Inc. 2006-11-03 2006-11-03 US Phospholine Iodide Powder, for solution 6.25 mg/5mL Ophthalmic Cangene bioPharma Inc 2005-12-01 2010-02-25 US Phospholine Iodide Kit 6.25 mg/5mL Ophthalmic Fera Pharmaceuticals, LLC 2021-11-17 Not applicable US Phospholine Iodide Powder, for solution 6.25 mg/5mL Ophthalmic Cangene bioPharma Inc 2005-12-01 2010-02-25 US
Categories
- ATC Codes
- S01EB03 — Ecothiopate
- Drug Categories
- Antiglaucoma Preparations and Miotics
- Autonomic Agents
- Cholinergic Agents
- Cholinesterase Inhibitors
- Enzyme Inhibitors
- Miotics
- Neurotransmitter Agents
- Ophthalmologicals
- Organophosphates
- Organophosphorus Compounds
- Organothiophosphates
- Organothiophosphorus Compounds
- Parasympathomimetics
- Peripheral Nervous System Agents
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Sensory Organs
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Quaternary ammonium salts
- Direct Parent
- Tetraalkylammonium salts
- Alternative Parents
- Sulfenyl compounds / Organothiophosphorus compounds / Organopnictogen compounds / Organooxygen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Amines / Organic cations
- Substituents
- Aliphatic acyclic compound / Amine / Hydrocarbon derivative / Organic cation / Organic oxide / Organic oxygen compound / Organic salt / Organooxygen compound / Organopnictogen compound / Organosulfur compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- quaternary ammonium ion, phosphocholines, organic thiophosphate (CHEBI:4753)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0F350BVT6S
- CAS number
- 6736-03-4
- InChI Key
- BJOLKYGKSZKIGU-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1
- IUPAC Name
- diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate
- SMILES
- CCOP(=O)(OCC)SCC[N+](C)(C)C
References
- Synthesis Reference
Fitch, H.M.; U.S. Patent 2,911,430; November 3, 1959; assigned to Campbell Pharmaceuticals, Inc.
- General References
- Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. [Article]
- Schmidt KG, Horowitz Y, Buckman G, Segev E, Levinger E, Geyer O: Lowering of IOP by echothiophate iodide in pseudophakic eyes with glaucoma. Curr Eye Res. 2010 Aug;35(8):698-702. doi: 10.3109/02713681003794076. [Article]
- External Links
- Human Metabolome Database
- HMDB0015190
- KEGG Drug
- D02193
- KEGG Compound
- C06975
- PubChem Compound
- 10548
- PubChem Substance
- 46505944
- ChemSpider
- 10108
- 89778
- ChEBI
- 4753
- ChEMBL
- CHEMBL1201341
- ZINC
- ZINC000001530628
- Therapeutic Targets Database
- DAP000962
- PharmGKB
- PA164743139
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Echothiophate
- FDA label
- Download (45 KB)
- MSDS
- Download (87.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Unknown Status Prevention Myopia (Disorder) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Wyeth Pharmaceuticals
- Dosage Forms
Form Route Strength Kit Ophthalmic 6.25 mg/5mL Powder, for solution Ophthalmic 6.25 mg/5mL Solution Ophthalmic 1.5 mg/5mL Solution Ophthalmic 12.5 mg/5mL Solution Ophthalmic 3 mg/5mL Liquid; powder, for solution Ophthalmic 3 mg / 5 mL Powder, for solution Ophthalmic 12.5 mg / 5 mL Powder, for solution Ophthalmic 3 mg / 5 mL Kit; powder, for solution Ophthalmic 6.25 mg/5mL Powder, for solution Ophthalmic 6.25 mg / 5 mL - Prices
Unit description Cost Unit Phospholine iodide 0.125% 16.09USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US2911430 No 1958-01-15 1978-01-15 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 124-124.5 Fitch, H.M.; U.S. Patent 2,911,430; November 3, 1959; assigned to Campbell Pharmaceuticals, Inc. water solubility Soluble Not Available logP -2.25 Not Available - Predicted Properties
Property Value Source Water Solubility 0.297 mg/mL ALOGPS logP -2.2 ALOGPS logP -3.1 Chemaxon logS -3 ALOGPS pKa (Strongest Basic) -8.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 35.53 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 78.14 m3·mol-1 Chemaxon Polarizability 27.65 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7708 Blood Brain Barrier + 0.91 Caco-2 permeable + 0.5098 P-glycoprotein substrate Non-substrate 0.6063 P-glycoprotein inhibitor I Non-inhibitor 0.8482 P-glycoprotein inhibitor II Non-inhibitor 0.962 Renal organic cation transporter Non-inhibitor 0.7835 CYP450 2C9 substrate Non-substrate 0.8237 CYP450 2D6 substrate Non-substrate 0.7603 CYP450 3A4 substrate Non-substrate 0.5252 CYP450 1A2 substrate Non-inhibitor 0.8317 CYP450 2C9 inhibitor Non-inhibitor 0.7972 CYP450 2D6 inhibitor Non-inhibitor 0.8991 CYP450 2C19 inhibitor Non-inhibitor 0.8013 CYP450 3A4 inhibitor Non-inhibitor 0.9093 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9377 Ames test Non AMES toxic 0.8524 Carcinogenicity Carcinogens 0.7021 Biodegradation Ready biodegradable 0.9528 Rat acute toxicity 4.3595 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5816 hERG inhibition (predictor II) Non-inhibitor 0.7263
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0bti-9430000000-9a12a7daa0bdce2c4cbf Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 156.93001 predictedDeepCCS 1.0 (2019) [M+H]+ 159.28798 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.57785 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Henderson EG, Post-Munson DJ, Reynolds LS, Epstein PM: Echothiophate and cogeners decrease the voltage dependence of end-plate current decay in frog skeletal muscle. J Pharmacol Exp Ther. 1989 Dec;251(3):810-6. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Peeples ES, Schopfer LM, Duysen EG, Spaulding R, Voelker T, Thompson CM, Lockridge O: Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicol Sci. 2005 Feb;83(2):303-12. Epub 2004 Nov 3. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:01