Echothiophate - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Carriers (1)

Targets (1)Carriers (1)Biointeractions (1)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide

Echothiophate

Ecothiopate

Ecothiopatum

Phospholine

External IDs

MI 217

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Echothiophate iodide	BA9QH3P00T	513-10-0	OVXQHPWHMXOFRD-UHFFFAOYSA-M	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Phospholine Iodide - Liq Pws 3mg/5ml	Liquid; Powder, for solution	3 mg	Ophthalmic	Storz, Division Of Wyeth Ayerst Canada Inc.	1997-04-29	1999-08-12	Canada
Phospholine Iodide - Pws 12.5mg/5ml	Powder, for solution	12.5 mg	Ophthalmic	Storz, Division Of Wyeth Ayerst Canada Inc.	1997-08-29	1999-08-12	Canada
Phospholine Iodide - Pws 6.25mg/5ml	Powder, for solution	6.25 mg	Ophthalmic	Storz, Division Of Wyeth Ayerst Canada Inc.	1997-04-29	2000-08-02	Canada
Phospholine Iodide 12.5mg/5ml	Powder, for solution	12.5 mg	Ophthalmic	Wyeth Ayerst Canada Inc.	1994-12-31	2001-08-30	Canada
Phospholine Iodide 3mg/5ml	Powder, for solution	3 mg	Ophthalmic	Wyeth Ayerst Canada Inc.	1998-12-02	2001-05-07	Canada
Phospholine Iodide 6.25mg/5ml	Powder, for solution	6.25 mg	Ophthalmic	Wyeth Ayerst Canada Inc.	1999-10-06	2001-08-03	Canada
Phospholine Iodide Ophthalmic	Kit			Wyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.	1959-12-04	Not applicable	US
Phospholine Iodide Pws 6.25mg/5ml	Powder, for solution	6.25 mg	Ophthalmic	Wyeth Ayerst Canada Inc.	1994-12-31	1997-08-14	Canada

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Echodide	Alcon
Phospholine Iodide	Wyeth-Ayerst

Brand mixtures

Not Available

Categories

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.

Structured Indications

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Cholinesterase	Protein	yes	inhibitor	Human	P06276	details

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

Interactions

Drug Interactions

Drug	Interaction	Drug group
16-Bromoepiandrosterone	The risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Echothiophate.	Investigational
19-norandrostenedione	The risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Echothiophate.	Experimental, Illicit
5-androstenedione	The risk or severity of adverse effects can be increased when 5-androstenedione is combined with Echothiophate.	Experimental, Illicit
Acebutolol	Echothiophate may increase the bradycardic activities of Acebutolol.	Approved
Acetylcholine	The risk or severity of adverse effects can be increased when Echothiophate is combined with Acetylcholine.	Approved
Aclidinium	The therapeutic efficacy of Aclidinium can be decreased when used in combination with Echothiophate.	Approved
Alclometasone	The risk or severity of adverse effects can be increased when Alclometasone is combined with Echothiophate.	Approved
Aldosterone	The risk or severity of adverse effects can be increased when Aldosterone is combined with Echothiophate.	Experimental
Alprenolol	Echothiophate may increase the bradycardic activities of Alprenolol.	Approved, Withdrawn
Amcinonide	The risk or severity of adverse effects can be increased when Amcinonide is combined with Echothiophate.	Approved
Androstenedione	The risk or severity of adverse effects can be increased when 4-Androstenedione is combined with Echothiophate.	Experimental, Illicit
Anecortave	The risk or severity of adverse effects can be increased when Anecortave is combined with Echothiophate.	Investigational
Anisotropine Methylbromide	The therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Echothiophate.	Approved
Arecoline	The risk or severity of adverse effects can be increased when Echothiophate is combined with Arecoline.	Experimental
Arotinolol	Echothiophate may increase the bradycardic activities of Arotinolol.	Approved
Atenolol	Echothiophate may increase the bradycardic activities of Atenolol.	Approved
Atracurium besylate	The therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Echothiophate.	Approved
Atropine	The therapeutic efficacy of Atropine can be decreased when used in combination with Echothiophate.	Approved, Vet Approved
Beclomethasone dipropionate	The risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Echothiophate.	Approved, Investigational
Befunolol	Echothiophate may increase the bradycardic activities of Befunolol.	Experimental
Benactyzine	The therapeutic efficacy of Benactyzine can be decreased when used in combination with Echothiophate.	Withdrawn
Benzatropine	The therapeutic efficacy of Benzatropine can be decreased when used in combination with Echothiophate.	Approved
Betamethasone	The risk or severity of adverse effects can be increased when Betamethasone is combined with Echothiophate.	Approved, Vet Approved
Betaxolol	Echothiophate may increase the bradycardic activities of Betaxolol.	Approved
Bethanechol	The risk or severity of adverse effects can be increased when Echothiophate is combined with Bethanechol.	Approved
Bevantolol	Echothiophate may increase the bradycardic activities of Bevantolol.	Approved
Biperiden	The therapeutic efficacy of Biperiden can be decreased when used in combination with Echothiophate.	Approved
Bisoprolol	Echothiophate may increase the bradycardic activities of Bisoprolol.	Approved
Bopindolol	Echothiophate may increase the bradycardic activities of Bopindolol.	Approved
Bucindolol	Echothiophate may increase the bradycardic activities of Bucindolol.	Investigational
Budesonide	The risk or severity of adverse effects can be increased when Budesonide is combined with Echothiophate.	Approved
Bufuralol	Echothiophate may increase the bradycardic activities of Bufuralol.	Experimental, Investigational
Bupranolol	Echothiophate may increase the bradycardic activities of Bupranolol.	Approved
Carbachol	The risk or severity of adverse effects can be increased when Echothiophate is combined with Carbachol.	Approved
Carteolol	Echothiophate may increase the bradycardic activities of Carteolol.	Approved
Carvedilol	Echothiophate may increase the bradycardic activities of Carvedilol.	Approved, Investigational
Celiprolol	Echothiophate may increase the bradycardic activities of Celiprolol.	Approved, Investigational
Cevimeline	The risk or severity of adverse effects can be increased when Echothiophate is combined with Cevimeline.	Approved
Chlorphenoxamine	The therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Echothiophate.	Withdrawn
Ciclesonide	The risk or severity of adverse effects can be increased when Ciclesonide is combined with Echothiophate.	Approved, Investigational
Clobetasol	The risk or severity of adverse effects can be increased when Clobetasol is combined with Echothiophate.	Investigational
Clobetasol propionate	The risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Echothiophate.	Approved
Clocortolone	The risk or severity of adverse effects can be increased when Clocortolone is combined with Echothiophate.	Approved
Cortisone acetate	The risk or severity of adverse effects can be increased when Cortisone acetate is combined with Echothiophate.	Approved
Cyclopentolate	The therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Echothiophate.	Approved
Darifenacin	The therapeutic efficacy of Darifenacin can be decreased when used in combination with Echothiophate.	Approved, Investigational
Desloratadine	The therapeutic efficacy of Desloratadine can be decreased when used in combination with Echothiophate.	Approved, Investigational
Desoximetasone	The risk or severity of adverse effects can be increased when Desoximetasone is combined with Echothiophate.	Approved
Desoxycorticosterone acetate	The risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Echothiophate.	Approved
Desoxycorticosterone Pivalate	The risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Echothiophate.	Experimental, Vet Approved
Dexamethasone	The risk or severity of adverse effects can be increased when Dexamethasone is combined with Echothiophate.	Approved, Investigational, Vet Approved
Dexamethasone isonicotinate	The risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Echothiophate.	Vet Approved
Dexetimide	The therapeutic efficacy of Dexetimide can be decreased when used in combination with Echothiophate.	Withdrawn
Dicyclomine	The therapeutic efficacy of Dicyclomine can be decreased when used in combination with Echothiophate.	Approved
Diflorasone	The risk or severity of adverse effects can be increased when Diflorasone is combined with Echothiophate.	Approved
Difluocortolone	The risk or severity of adverse effects can be increased when Difluocortolone is combined with Echothiophate.	Approved
Difluprednate	The risk or severity of adverse effects can be increased when Difluprednate is combined with Echothiophate.	Approved
Dipyridamole	The therapeutic efficacy of Echothiophate can be decreased when used in combination with Dipyridamole.	Approved
Epibatidine	The risk or severity of adverse effects can be increased when Echothiophate is combined with EPIBATIDINE.	Experimental
Equilenin	The risk or severity of adverse effects can be increased when Equilenin is combined with Echothiophate.	Experimental
Equilin	The risk or severity of adverse effects can be increased when Equilin is combined with Echothiophate.	Approved
Esmolol	Echothiophate may increase the bradycardic activities of Esmolol.	Approved
Estrone	The risk or severity of adverse effects can be increased when Estrone is combined with Echothiophate.	Approved
Estrone sulfate	The risk or severity of adverse effects can be increased when Estrone sulfate is combined with Echothiophate.	Approved
Ethopropazine	The therapeutic efficacy of Ethopropazine can be decreased when used in combination with Echothiophate.	Approved
Fesoterodine	The therapeutic efficacy of Fesoterodine can be decreased when used in combination with Echothiophate.	Approved
fluasterone	The risk or severity of adverse effects can be increased when fluasterone is combined with Echothiophate.	Investigational
Fludrocortisone	The risk or severity of adverse effects can be increased when Fludrocortisone is combined with Echothiophate.	Approved
Flumethasone	The risk or severity of adverse effects can be increased when Flumethasone is combined with Echothiophate.	Approved, Vet Approved
Flunisolide	The risk or severity of adverse effects can be increased when Flunisolide is combined with Echothiophate.	Approved, Investigational
Fluocinolone Acetonide	The risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Echothiophate.	Approved, Investigational, Vet Approved
Fluocinonide	The risk or severity of adverse effects can be increased when Fluocinonide is combined with Echothiophate.	Approved, Investigational
Fluocortolone	The risk or severity of adverse effects can be increased when Fluocortolone is combined with Echothiophate.	Approved, Withdrawn
Fluorometholone	The risk or severity of adverse effects can be increased when Fluorometholone is combined with Echothiophate.	Approved
Fluprednidene	The risk or severity of adverse effects can be increased when Fluprednidene is combined with Echothiophate.	Approved, Withdrawn
Fluprednisolone	The risk or severity of adverse effects can be increased when Fluprednisolone is combined with Echothiophate.	Approved
Flurandrenolide	The risk or severity of adverse effects can be increased when Flurandrenolide is combined with Echothiophate.	Approved
Fluticasone furoate	The risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Echothiophate.	Approved
Fluticasone propionate	The risk or severity of adverse effects can be increased when Fluticasone Propionate is combined with Echothiophate.	Approved
Formestane	The risk or severity of adverse effects can be increased when Formestane is combined with Echothiophate.	Approved, Investigational, Withdrawn
Gallamine Triethiodide	The therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Echothiophate.	Approved
Glycopyrronium	The therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Echothiophate.	Approved, Investigational, Vet Approved
GTS-21	The risk or severity of adverse effects can be increased when Echothiophate is combined with GTS-21.	Investigational
HE3286	The risk or severity of adverse effects can be increased when HE3286 is combined with Echothiophate.	Investigational
Hexamethonium	The therapeutic efficacy of Hexamethonium can be decreased when used in combination with Echothiophate.	Experimental
Homatropine	The therapeutic efficacy of Homatropine can be decreased when used in combination with Echothiophate.	Approved
Hydrocortisone	The risk or severity of adverse effects can be increased when Hydrocortisone is combined with Echothiophate.	Approved, Vet Approved
Hyoscyamine	The therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Echothiophate.	Approved
Indenolol	Echothiophate may increase the bradycardic activities of Indenolol.	Withdrawn
Ipratropium bromide	The therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Echothiophate.	Approved
Istaroxime	The risk or severity of adverse effects can be increased when Istaroxime is combined with Echothiophate.	Investigational
Labetalol	Echothiophate may increase the bradycardic activities of Labetalol.	Approved
Landiolol	Echothiophate may increase the bradycardic activities of Aop200704.	Investigational
Levobunolol	Echothiophate may increase the bradycardic activities of Levobunolol.	Approved
Lobeline	The risk or severity of adverse effects can be increased when Echothiophate is combined with Lobeline.	Investigational
ME-609	The risk or severity of adverse effects can be increased when ME-609 is combined with Echothiophate.	Investigational
Mecamylamine	The therapeutic efficacy of Mecamylamine can be decreased when used in combination with Echothiophate.	Approved
Medrysone	The risk or severity of adverse effects can be increased when Medrysone is combined with Echothiophate.	Approved
Melengestrol	The risk or severity of adverse effects can be increased when Melengestrol is combined with Echothiophate.	Vet Approved
Methacholine	The risk or severity of adverse effects can be increased when Echothiophate is combined with Methacholine.	Approved
Methantheline	The therapeutic efficacy of Methantheline can be decreased when used in combination with Echothiophate.	Approved
Methylprednisolone	The risk or severity of adverse effects can be increased when Methylprednisolone is combined with Echothiophate.	Approved, Vet Approved
Metipranolol	Echothiophate may increase the bradycardic activities of Metipranolol.	Approved
Metixene	The therapeutic efficacy of Metixene can be decreased when used in combination with Echothiophate.	Approved
Metoprolol	Echothiophate may increase the bradycardic activities of Metoprolol.	Approved, Investigational
Mivacurium	Echothiophate may decrease the neuromuscular blocking activities of Mivacurium.	Approved
Mometasone	The risk or severity of adverse effects can be increased when Mometasone is combined with Echothiophate.	Approved, Vet Approved
Nadolol	Echothiophate may increase the bradycardic activities of Nadolol.	Approved
NCX 1022	The risk or severity of adverse effects can be increased when NCX 1022 is combined with Echothiophate.	Investigational
Nicotine	The risk or severity of adverse effects can be increased when Echothiophate is combined with Nicotine.	Approved
Oleoyl-estrone	The risk or severity of adverse effects can be increased when Oleoyl estrone is combined with Echothiophate.	Investigational
Orphenadrine	The therapeutic efficacy of Orphenadrine can be decreased when used in combination with Echothiophate.	Approved
Oxprenolol	Echothiophate may increase the bradycardic activities of Oxprenolol.	Approved
Oxybutynin	The therapeutic efficacy of Oxybutynin can be decreased when used in combination with Echothiophate.	Approved, Investigational
Oxyphenonium	The therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Echothiophate.	Approved
Pancuronium	The therapeutic efficacy of Pancuronium can be decreased when used in combination with Echothiophate.	Approved
Paramethasone	The risk or severity of adverse effects can be increased when Paramethasone is combined with Echothiophate.	Approved
Penbutolol	Echothiophate may increase the bradycardic activities of Penbutolol.	Approved, Investigational
Pentolinium	The therapeutic efficacy of Pentolinium can be decreased when used in combination with Echothiophate.	Approved
Pilocarpine	The risk or severity of adverse effects can be increased when Echothiophate is combined with Pilocarpine.	Approved
Pindolol	Echothiophate may increase the bradycardic activities of Pindolol.	Approved
Pipecuronium	The therapeutic efficacy of Pipecuronium can be decreased when used in combination with Echothiophate.	Approved
Pirenzepine	The therapeutic efficacy of Pirenzepine can be decreased when used in combination with Echothiophate.	Approved
Practolol	Echothiophate may increase the bradycardic activities of Practolol.	Approved
Prasterone	The risk or severity of adverse effects can be increased when Prasterone is combined with Echothiophate.	Approved, Nutraceutical
Prasterone sulfate	The risk or severity of adverse effects can be increased when dehydroepiandrosterone sulfate is combined with Echothiophate.	Investigational
Prednicarbate	The risk or severity of adverse effects can be increased when Prednicarbate is combined with Echothiophate.	Approved
Prednisolone	The risk or severity of adverse effects can be increased when Prednisolone is combined with Echothiophate.	Approved, Vet Approved
Prednisone	The risk or severity of adverse effects can be increased when Prednisone is combined with Echothiophate.	Approved, Vet Approved
Pregnenolone	The risk or severity of adverse effects can be increased when Pregnenolone is combined with Echothiophate.	Experimental
Procyclidine	The therapeutic efficacy of Procyclidine can be decreased when used in combination with Echothiophate.	Approved
Propantheline	The therapeutic efficacy of Propantheline can be decreased when used in combination with Echothiophate.	Approved
Propiverine	The therapeutic efficacy of Propiverine can be decreased when used in combination with Echothiophate.	Investigational
Propranolol	Echothiophate may increase the bradycardic activities of Propranolol.	Approved, Investigational
Quinidine	The therapeutic efficacy of Quinidine can be decreased when used in combination with Echothiophate.	Approved
Rapacuronium	Echothiophate may decrease the neuromuscular blocking activities of Rapacuronium.	Withdrawn
Rimexolone	The risk or severity of adverse effects can be increased when Rimexolone is combined with Echothiophate.	Approved
Scopolamine	The therapeutic efficacy of Scopolamine can be decreased when used in combination with Echothiophate.	Approved
Scopolamine butylbromide	The therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Echothiophate.	Approved, Vet Approved
Solifenacin	The therapeutic efficacy of Solifenacin can be decreased when used in combination with Echothiophate.	Approved
Sotalol	Echothiophate may increase the bradycardic activities of Sotalol.	Approved
Succinylcholine	The serum concentration of Succinylcholine can be increased when it is combined with Echothiophate.	Approved
Timolol	Echothiophate may increase the bradycardic activities of Timolol.	Approved
Tiotropium	The therapeutic efficacy of Tiotropium can be decreased when used in combination with Echothiophate.	Approved
Tixocortol	The risk or severity of adverse effects can be increased when Tixocortol is combined with Echothiophate.	Approved
Tolterodine	The therapeutic efficacy of Tolterodine can be decreased when used in combination with Echothiophate.	Approved, Investigational
Triamcinolone	The risk or severity of adverse effects can be increased when Triamcinolone is combined with Echothiophate.	Approved, Vet Approved
Trihexyphenidyl	The therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Echothiophate.	Approved
Trimethaphan	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Echothiophate.	Approved
Tropicamide	The therapeutic efficacy of Tropicamide can be decreased when used in combination with Echothiophate.	Approved
Trospium	The therapeutic efficacy of Trospium can be decreased when used in combination with Echothiophate.	Approved
Tubocurarine	The therapeutic efficacy of Tubocurarine can be decreased when used in combination with Echothiophate.	Approved
Umeclidinium	The therapeutic efficacy of Umeclidinium can be decreased when used in combination with Echothiophate.	Approved
Varenicline	The risk or severity of adverse effects can be increased when Echothiophate is combined with Varenicline.	Approved, Investigational
Vecuronium	The therapeutic efficacy of Vecuronium can be decreased when used in combination with Echothiophate.	Approved

Food Interactions

Not Available

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

Resource	Link
Human Metabolome Database (HMDB)	HMDB15190
KEGG Drug	D02193
KEGG Compound	C06975
PubChem Compound	10548
PubChem Substance	46505944
ChemSpider	10108
ChEBI	4753
ChEMBL	CHEMBL1201341
Therapeutic Targets Database	DAP000962
PharmGKB	PA164743139
Drug Product Database	9719
RxList	http://www.rxlist.com/cgi/generic2/phospholine.htm
Drugs.com	http://www.drugs.com/cdi/echothiophate-eye-drops.html
Wikipedia	Echothiophate

ATC Codes

S01EB03 — Ecothiopate

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Download (45 KB)

MSDS

Download (87.9 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Not Yet Recruiting	Prevention	Myopia	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Wyeth Pharmaceuticals

Dosage forms

Form	Route	Strength
Liquid; powder, for solution	Ophthalmic	3 mg
Powder, for solution	Ophthalmic	12.5 mg
Powder, for solution	Ophthalmic	3 mg
Kit
Powder, for solution	Ophthalmic	6.25 mg

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)
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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organic nitrogen compounds

Sub Class

Organonitrogen compounds

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

Details

1. Cholinesterase

Kind: Protein
Organism: Human
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

Details

1. Serum albumin

Kind: Protein
Organism: Human
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
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 September 01, 2017 10:35

Structure for DB01057 (Echothiophate)

Targets

References

Carriers

References