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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyEchothiophate
Identification
- Name
- Echothiophate
- Accession Number
- DB01057 (APRD00942)
- Type
- Small Molecule
- Groups
- Approved
- Description
A potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia.
- Structure
Structure for Echothiophate (DB01057)
- Synonyms
- 2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
- Echothiophate
- Ecothiopate
- Ecothiopatum
- Phospholine
- External IDs
- MI 217
- Product Ingredients
Ingredient UNII CAS InChI Key Echothiophate iodide BA9QH3P00T 513-10-0 OVXQHPWHMXOFRD-UHFFFAOYSA-M - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataPhospholine Iodide Solution 3 mg/5mL Ophthalmic Wyeth Pharmaceuticals Inc. 2006-11-03 2006-11-03 US 
Phospholine Iodide Solution 1.5 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 Powder, for solution 6.25 mg/5mL Ophthalmic Cangene bioPharma Inc 2005-12-01 2010-02-25 US Phospholine Iodide Solution 12.5 mg/5mL Ophthalmic Wyeth Pharmaceuticals Inc. 2006-11-03 2006-11-03 US Phospholine Iodide - Liq Pws 3mg/5ml Liquid; Powder, for solution Ophthalmic Storz, Division Of Wyeth Ayerst Canada Inc. 1997-04-29 1999-08-12 Canada 
Phospholine Iodide - Pws 12.5mg/5ml Powder, for solution Ophthalmic Storz, Division Of Wyeth Ayerst Canada Inc. 1997-08-29 1999-08-12 Canada Phospholine Iodide - Pws 6.25mg/5ml Powder, for solution Ophthalmic Storz, Division Of Wyeth Ayerst Canada Inc. 1997-04-29 2000-08-02 Canada Phospholine Iodide 12.5mg/5ml Powder, for solution Ophthalmic Wyeth Ayerst Canada Inc. 1994-12-31 2001-08-30 Canada Phospholine Iodide 3mg/5ml Powder, for solution Ophthalmic Wyeth Ayerst Canada Inc. 1998-12-02 2001-05-07 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- International/Other Brands
- Echodide (Alcon)
- 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
- UNII
- 0F350BVT6S
- CAS number
- 6736-03-4
- Weight
- Average: 256.323
Monoisotopic: 256.113625809 - Chemical Formula
- C9H23NO3PS
- 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
Pharmacology
- Indication
For use in the treatment of subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated.
- Associated Conditions
- Pharmacodynamics
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
- Toxicity
Side effects include blurred vision or change in near or distant vision and eye pain. LD50: 174 mcg/kg in rats. (MSDS)
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
- 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 Unlock Additional DataDipyridamole The therapeutic efficacy of Echothiophate can be decreased when used in combination with Dipyridamole. Fluoxetine The risk or severity of QTc prolongation can be increased when Fluoxetine is combined with Echothiophate. Haloperidol The risk or severity of QTc prolongation can be increased when Echothiophate is combined with Haloperidol. Hydroxyzine The risk or severity of QTc prolongation can be increased when Echothiophate is combined with Hydroxyzine. Lefamulin Lefamulin may increase the QTc-prolonging activities of Echothiophate. Pitolisant Echothiophate may increase the QTc-prolonging activities of Pitolisant. Trazodone The risk or severity of QTc prolongation can be increased when Trazodone is combined with Echothiophate. Ziprasidone The risk or severity of QTc prolongation can be increased when Echothiophate is combined with Ziprasidone. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- No interactions found.
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. [PubMed:7166393]
- 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. [PubMed:20673046]
- External Links
- Human Metabolome Database
- HMDB0015190
- KEGG Drug
- D02193
- KEGG Compound
- C06975
- PubChem Compound
- 10548
- PubChem Substance
- 46505944
- ChemSpider
- 10108
- RxNav
- 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
- ATC Codes
- S01EB03 — Ecothiopate
- FDA label
- Download (45 KB)
- MSDS
- Download (87.9 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Wyeth Pharmaceuticals
- Dosage forms
Form Route Strength 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 Powder, for solution Ophthalmic - 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) Unlock Additional DataUS2911430 No 1958-01-15 1978-01-15 US Additional Data Available- Filed On
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 Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- 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
- Tetraalkylammonium salt / Sulfenyl compound / Organothiophosphorus compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organic salt / Organosulfur compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- quaternary ammonium ion, phosphocholines, organic thiophosphate (CHEBI:4753)
Targets
- 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. [PubMed:2481033]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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. [PubMed:15525694]
Drug created on June 13, 2005 07:24 / Updated on May 02, 2020 03:25
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