ヨウ化エコチオパート
- 関
- echothiopate、echothiophate、echothiophate iodide、ecothiopate
WordNet
- a salt or ester of hydriodic acid
PrepTutorEJDIC
- ヨウ化物
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/09/04 13:51:26」(JST)
[Wiki en表示]
Echothiophate
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| Clinical data |
| Trade names |
Phospholine |
Routes of
administration |
Topical (eye drops) |
| ATC code |
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| Identifiers |
IUPAC name
- 2-(Diethoxyphosphorylsulfanyl)ethyl-N,N,N-trimethylazanium iodide
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| CAS Number |
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| PubChem CID |
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| DrugBank |
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| ChemSpider |
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| UNII |
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| KEGG |
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| ChEBI |
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| ChEMBL |
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| Chemical and physical data |
| Formula |
C9H23INO3PS |
| Molar mass |
383.228 g/mol |
| 3D model (JSmol) |
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SMILES
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[I-].O=P(OCC)(OCC)SCC[N+](C)(C)C
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InChI
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InChI=1S/C9H23NO3PS.HI/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5;/h6-9H2,1-5H3;1H/q+1;/p-1 Y
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Key:OVXQHPWHMXOFRD-UHFFFAOYSA-M Y
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| NY (what is this?) (verify) |
Echothiophate (Phospholine) is an irreversible acetylcholinesterase inhibitor.[1]
Contents
- 1 Uses
- 2 Mechanism of action
- 3 Shortage
- 4 Chemistry
- 5 References
Uses
It is used as an ocular antihypertensive in the treatment of chronic glaucoma and, in some cases, accommodative esotropia. It is available under several trade names such as Phospholine Iodide (Wyeth-Ayerst).
Echothiophate binds irreversibly to cholinesterase. Because of the very slow rate at which echothiophate is hydrolyzed by cholinesterase, its effects can last a week or more. Adverse effects include muscle spasm and other systemic effects.
Mechanism of action
It covalently binds by its phosphate group to serine group at the active site of the cholinesterase. Once bound, the enzyme is permanently inactive and the cell has to make new enzymes.
Shortage
Wyeth Pharmaceuticals stopped manufacturing echothiophate iodide in the US in 2003. After contacting the American Academy of Ophthalmology (AAO), Wyeth rescinded their decision and, according to AAO public relations representative Michelle Stephens, the AAO and Wyeth were in talks for about a year about manufacturing it.[2]
In the meantime, a worldwide shortage of the drug has occurred.
Chemistry
Echothiophate is made by reacting diethylchlorophosphoric acid with 2-dimethylaminoethylmercaptan, giving S-(2-dimethylaminoethyl)-O,O-diethylthiophosphate, which is alkylated by methyl iodide, forming echothiophate.[3]
References
- ^ Gabelt BT, Hennes EA, Seeman JL, Tian B, Kaufman PL (August 2004). "H-7 effect on outflow facility after trabecular obstruction following long-term echothiophate treatment in monkeys". Invest. Ophthalmol. Vis. Sci. 45 (8): 2732–6. PMID 15277498. doi:10.1167/iovs.04-0083.
- ^ Eurotimes article: "Echothiophate iodide shortage leaves US specialists struggling to find alternative for acute cases"
- ^ H.M. Fitch, U.S. Patent 2,911,430 (1959)
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Drugs used for glaucoma preparations and miosis (S01E)
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| Sympathomimetics |
- Apraclonidine
- Brimonidine (+timolol)
- Clonidine
- Dipivefrine
- Epinephrine
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| Parasympathomimetics |
| muscarinic |
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| muscarinic/nicotinic |
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| acetylcholinesterase inhibitors |
- Demecarium
- Ecothiopate
- Stigmine (Fluostigmine
- Neostigmine
- Physostigmine)
- Paraoxon
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Carbonic anhydrase inhibitors/
(sulfonamides) |
- Acetazolamide
- Brinzolamide (+timolol)
- Diclofenamide
- Dorzolamide (+timolol)
- Methazolamide
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| Beta blocking agents |
- Befunolol
- Betaxolol
- Carteolol
- Levobunolol
- Metipranolol
- Timolol
- Mepindolol
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| Prostaglandin analogues (F2α) |
- Bimatoprost (+timolol)
- Latanoprost (+timolol)
- Tafluprost
- Travoprost (+timolol)
- Unoprostone
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| Other agents |
- Dapiprazole
- Guanethidine
- Ripasudil
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Acetylcholine metabolism and transport modulators
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Enzyme
(modulators) |
| ChAT |
- Inhibitors: 1-(-Benzoylethyl)pyridinium
- 2-(α-Naphthoyl)ethyltrimethylammonium
- 3-Chloro-4-stillbazole
- 4-(1-Naphthylvinyl)pyridine
- Acetylseco hemicholinium-3
- Acryloylcholine
- AF64A
- B115
- BETA
- CM-54,903
- N,N-Dimethylaminoethylacrylate
- N,N-Dimethylaminoethylchloroacetate
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| AChE |
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| BChE |
- Inhibitors: Affinine
- Affinisine
- Conodurine
- Cymserine
- Ladostigil
- Profenamine (ethopropazine)
- Rivastigmine
- Tacrine
- ZINC-12613047
- Many of the other AChE inhibitors listed above
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Transporter
(modulators) |
| CHT |
- Inhibitors: Hemicholinium-3 (hemicholine)
- Triethylcholine
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| VAChT |
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Release
(modulators) |
| Inhibitors |
- SNAP-25 inactivators: Botulinum toxin (A, C, E)
- VAMP inactivators: Botulinum toxin (B, D, F, G)
- Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
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| Enhancers |
- LPHN agonists: α-Latrotoxin
- Others: Atracotoxin (e.g., robustoxin, versutoxin)
- Crotoxin
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See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Nicotinic acetylcholine receptor modulators
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UpToDate Contents
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English Journal
- α7-Containing and non-α7-containing nicotinic receptors respond differently to spillover of acetylcholine.
- Stanchev D, Sargent PB.SourceDepartment of Cell and Tissue Biology and Neuroscience Graduate Program, University of California, San Francisco, California 94143, USA.
- The Journal of neuroscience : the official journal of the Society for Neuroscience.J Neurosci.2011 Oct 19;31(42):14920-30.
- We explored whether nicotinic acetylcholine receptors (nAChRs) might participate in paracrine transmission by asking if they respond to spillover of ACh at a model synapse in the chick ciliary ganglion, where ACh activates diffusely distributed α7- and α3-containing nAChRs (α7-nAChRs and α3*-nAC
- PMID 22016525
- X-ray crystallographic snapshots of reaction intermediates in the G117H mutant of human butyrylcholinesterase, a nerve agent target engineered into a catalytic bioscavenger.
- Nachon F, Carletti E, Wandhammer M, Nicolet Y, Schopfer LM, Masson P, Lockridge O.SourceCellule Enzymologie, Département de Toxicologie, Institut de Recherche Biomédicale des Armées-CRSSA, 24 avenue des Maquis du Grésivaudan, La Tronche, France. florian@nachon.net
- The Biochemical journal.Biochem J.2011 Feb 15;434(1):73-82.
- OPs (organophosphylates) exert their acute toxicity through inhibition of acetylcholinesterase, by phosphylation of the catalytic serine residue. Engineering of human butyrylcholinesterase, by substitution of a histidine residue for the glycine residue at position 117, led to the creation of OP hydr
- PMID 21091433
Related Links
- Ecothiopate Iodide is a medicine available in a number of countries worldwide. A list of US medications equivalent to Ecothiopate Iodide is available on the Drugs.com website. ... Drugs.com provides accurate and independent ...
- Structure, properties, spectra, suppliers and links for: ecothiopate iodide, 6736-03-4, Echothiophate Iodide. ... No predicted properties have been calculated for this compound.
★リンクテーブル★
[★]
- 英
- echothiophate、((欧州))ecothiopate、echothiopate、echothiophate iodide、ecothiopate iodide
- 関
- エコチオファート、ヨウ化エコチオファート、ヨウ化エコチオパート
[★]
ヨウ化エコチオパート、ヨウ化エコチオファート
- 関
- echothiopate、echothiophate、ecothiopate、ecothiopate iodide
[★]
エコチオパート、エコチオファート
- 関
- echothiopate、echothiophate iodide、ecothiopate、ecothiopate iodide
[★]
- 英
- echothiophate iodide、ecothiopate iodide
- 関
- エコチオパート、ヨウ化エコチオファート
[★]
- 関
- echothiophate、echothiophate iodide、ecothiopate、ecothiopate iodide
[★]
エコチオパート
- 関
- echothiopate、echothiophate、echothiophate iodide、ecothiopate iodide
[★]
- 関
- I、I2、iodine、iodo