1046
| AHFS_Codes | - |
| ATC_Codes | Not Available |
| Absorption | Not Available |
| Biotransformation | Not Available |
| Brand_Mixtures | Phospholine Iodide PWS 3mg/5ml (Diluent + Echothiophate Iodide) |
| Brand_Names | Echodide<br />Phospholine Iodide |
| CAS_Registry_Number | 6736-03-4 |
| ChEBI_ID | 4753 |
| Chemical_Formula | C9H23NO3PS |
| Chemical_IUPAC_Name | diethyl {[2-(trimethylazaniumyl)ethyl]sulfanyl}phosphonate |
| Chemical_Structure | Not Available |
| Creation_Date | 2005-06-13 07:24:05 -0600 |
| DPD_Drug_ID_Number | 2238076 |
| Description | A potent, long-acting irreversible cholinesterase inhibitor used as an ocular hypertensive in the treatment of glaucoma. Occasionally used for accomodative esotropia. |
| Dosage_Forms | Solution / drops Ophthalmic |
| Drug_Category | Cholinesterase Inhibitors<br />Miotics<br />Parasympathomimetics |
| Drug_Interactions | Succinylcholine Echothiophate iodide may increase the effect of succinylcholine. |
| Drug_Reference | 20673046 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.<br />7166393 Reddy RH: Echothiophate iodide: its use in accommodative esotropia (high Ac/A ratio). Indian J Ophthalmol. 1982 Jul;30(4):225. |
| Drug_Type | Approved<br />Small Molecule |
| Experimental_Caco2_Permeability | Not Available |
| Experimental_LogP_Hydrophobicity | -2.25 |
| Experimental_Logs | Not Available |
| Experimental_Water_Solubility | Soluble |
| Food_Interactions | Not Available |
| GenBank_ID | Not Available |
| Generic_Name | Echothiophate |
| HET_ID | Not Available |
| Half_Life | Not Available |
| InChI_Identifier | InChI=1S/C9H23NO3PS/c1-6-12-14(11,13-7-2)15-9-8-10(3,4)5/h6-9H2,1-5H3/q+1 |
| InChI_Key | InChIKey=BJOLKYGKSZKIGU-UHFFFAOYSA-N |
| Indication | For use in the treatment of subacute or chronic angle-closure glaucoma after iridectomy or where surgery is refused or contraindicated. |
| KEGG_Compound_ID | Not Available |
| KEGG_Drug_ID | D02193 |
| LIMS_Drug_ID | 1057 |
| 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. |
| Melting_Point | 138 oC |
| Molecular_Weight_Avg | 256.323 |
| Molecular_Weight_Mono | 256.113625809 |
| Organisms_Affected | Humans and other mammals |
| PDB_Experimental_ID | Not Available |
| PDB_Homology_ID | Not Available |
| PDRhealth_Link | Not Available |
| Pathways | Not Available |
| PharmGKB_ID | PA449429 |
| Pharmacology | 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. |
| Predicted_LogP_Hydrophobicity | -2.15 |
| Predicted_LogS | -2.99 |
| Predicted_Water_Solubility | 2.97e-01 g/l |
| Primary_Accession_No | DB01057 |
| Protein_Binding | Not Available |
| PubChem_Compound_ID | 10547 |
| PubChem_Substance_ID | 46505944 |
| RxList_Link | <a href="http://www.rxlist.com/cgi/generic2/phospholine.htm" target="_blank">http://www.rxlist.com/cgi/generic2/phospholine.htm</a> |
| Secondary_Accession_No | APRD00942 |
| Smiles_String_canonical | Not Available |
| Smiles_String_isomeric | CCOP(=O)(OCC)SCC[N+](C)(C)C |
| State | solid |
| Structure | true |
| SwissProt_ID | Not Available |
| SwissProt_Name | Not Available |
| Synonyms | Echothiophate Iodide<br />Phospholine<br />Phospholine Iodide |
| Synthesis_Reference | Not Available |
| Toxicity | Side effects include blurred vision or change in near or distant vision and eye pain. |
| Update_Date | 2011-04-19 15:08:10 -0600 |
| Wikipedia_Link | <a href="http://en.wikipedia.org/wiki/Echothiophate" target="_blank">http://en.wikipedia.org/wiki/Echothiophate</a> |
| pKa_Isoelectric_Point | Not Available |
| Drug_Target_1_Cellular_Location | Cytoplasmic |
| Drug_Target_1_Chromosome_Location | Not Available |
| Drug_Target_1_Drug_References | 11752352 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.<br />2481033 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. |
| Drug_Target_1_Essentiality | Non-Essential |
| Drug_Target_1_GenAtlas_ID | BCHE |
| Drug_Target_1_GenBank_ID_Gene | M32391 |
| Drug_Target_1_GenBank_ID_Protein | 1311630 |
| Drug_Target_1_GeneCard_ID | BCHE |
| Drug_Target_1_Gene_Name | BCHE |
| Drug_Target_1_Gene_Sequence | >1809 bp<br />ATGCATAGCAAAGTCACAATCATATGCATCAGATTTCTCTTTTGGTTTCTTTTGCTCTGC<br />ATGCTTATTGGGAAGTCACATACTGAAGATGACATCATAATTGCAACAAAGAATGGAAAA<br />GTCAGAGGGATGAACTTGACAGTTTTTGGTGGCACGGTAACAGCCTTTCTTGGAATTCCC<br />TATGCACAGCCACCTCTTGGTAGACTTCGATTCAAAAAGCCACAGTCTCTGACCAAGTGG<br />TCTGATATTTGGAATGCCACAAAATATGCAAATTCTTGCTGTCAGAACATAGATCAAAGT<br />TTTCCAGGCTTCCATGGATCAGAGATGTGGAACCCAAACACTGACCTCAGTGAAGACTGT<br />TTATATCTAAATGTATGGATTCCAGCACCTAAACCAAAAAATGCCACTGTATTGATATGG<br />ATTTATGGTGGTGGTTTTCAAACTGGAACATCATCTTTACATGTTTATGATGGCAAGTTT<br />CTGGCTCGGGTTGAAAGAGTTATTGTAGTGTCAATGAACTATAGGGTGGGTGCCCTAGGA<br />TTCTTAGCTTTGCCAGGAAATCCTGAGGCTCCAGGGAACATGGGTTTATTTGATCAACAG<br />TTGGCTCTTCAGTGGGTTCAAAAAAATATAGCAGCCTTTGGTGGAAATCCTAAAAGTGTA<br />ACTCTCTTTGGAGAAAGTGCAGGAGCAGCTTCAGTTAGCCTGCATTTGCTTTCTCCTGGA<br />AGCCATTCATTGTTCACCAGAGCCATTCTGCAAAGTGGATCCTTTAATGCTCCTTGGGCG<br />GTAACATCTCTTTATGAAGCTAGGAACAGAACGTTGAACTTAGCTAAATTGACTGGTTGC<br />TCTAGAGAGAATGAGACTGAAATAATCAAGTGTCTTAGAAATAAAGATCCCCAAGAAATT<br />CTTCTGAATGAAGCATTTGTTGTCCCCTATGGGACTCCTTTGTCAGTAAACTTTGGTCCG<br />ACCGTGGATGGTGATTTTCTCACTGACATGCCAGACATATTACTTGAACTTGGACAATTT<br />AAAAAAACCCAGATTTTGGTGGGTGTTAATAAAGATGAAGGGACAGCTTTTTTAGTCTAT<br />GGTGCTCCTGGCTTCAGCAAAGATAACAATAGTATCATAACTAGAAAAGAATTTCAGGAA<br />GGTTTAAAAATATTTTTTCCAGGAGTGAGTGAGTTTGGAAAGGAATCCATCCTTTTTCAT<br />TACACAGACTGGGTAGATGATCAGAGACCTGAAAACTACCGTGAGGCCTTGGGTGATGTT<br />GTTGGGGATTATAATTTCATATGCCCTGCCTTGGAGTTCACCAAGAAGTTCTCAGAATGG<br />GGAAATAATGCCTTTTTCTACTATTTTGAACACCGATCCTCCAAACTTCCGTGGCCAGAA<br />TGGATGGGAGTGATGCATGGCTATGAAATTGAATTTGTCTTTGGTTTACCTCTGGAAAGA<br />AGAGATAATTACACAAAAGCCGAGGAAATTTTGAGTAGATCCATAGTGAAACGTTGGGCA<br />AATTTTGCAAAATATGGGAATCCAAATGAGACTCAGAACAATAGCACAAGCTGGCCTGTC<br />TTCAAAAGCACTGAACAAAAATATCTAACCTTGAATACAGAGTCAACAAGAATAATGACG<br />AAACTACGTGCTCAACAATGTCGATTCTGGACATCATTTTTTCCAAAAGTCTTGGAAATG<br />ACAGGAAATATTGATGAAGCAGAATGGGAGTGGAAAGCAGGATTCCATCGCTGGAACAAT<br />TACATGATGGACTGGAAAAATCAATTTAACGATTACACTAGCAAGAAAGAAAGTTGTGTG<br />GGTCTCTAA |
| Drug_Target_1_General_Function | Lipid transport and metabolism |
| Drug_Target_1_General_References | 2322535 Arpagaus M, Kott M, Vatsis KP, Bartels CF, La Du BN, Lockridge O: Structure of the gene for human butyrylcholinesterase. Evidence for a single copy. Biochemistry. 1990 Jan 9;29(1):124-31.<br />2915989 McGuire MC, Nogueira CP, Bartels CF, Lightstone H, Hajra A, Van der Spek AF, Lockridge O, La Du BN: Identification of the structural mutation responsible for the dibucaine-resistant (atypical) variant form of human serum cholinesterase. Proc Natl Acad Sci U S A. 1989 Feb;86(3):953-7.<br />3035536 Prody CA, Zevin-Sonkin D, Gnatt A, Goldberg O, Soreq H: Isolation and characterization of full-length cDNA clones coding for cholinesterase from fetal human tissues. Proc Natl Acad Sci U S A. 1987 Jun;84(11):3555-9.<br />3067729 Lockridge O: Structure of human serum cholinesterase. Bioessays. 1988 Oct;9(4):125-8.<br />3115973 Lockridge O, Adkins S, La Du BN: Location of disulfide bonds within the sequence of human serum cholinesterase. J Biol Chem. 1987 Sep 25;262(27):12945-52.<br />3477799 McTiernan C, Adkins S, Chatonnet A, Vaughan TA, Bartels CF, Kott M, Rosenberry TL, La Du BN, Lockridge O: Brain cDNA clone for human cholinesterase. Proc Natl Acad Sci U S A. 1987 Oct;84(19):6682-6.<br />3542989 Lockridge O, Bartels CF, Vaughan TA, Wong CK, Norton SE, Johnson LL: Complete amino acid sequence of human serum cholinesterase. J Biol Chem. 1987 Jan 15;262(2):549-57. |
| Drug_Target_1_HGNC_ID | HGNC:983 |
| Drug_Target_1_HPRD_ID | 01519 |
| Drug_Target_1_ID | 3923 |
| Drug_Target_1_Locus | 3q26.1-q26.2 |
| Drug_Target_1_Molecular_Weight | 68419 |
| Drug_Target_1_Name | Cholinesterase |
| Drug_Target_1_Number_of_Residues | 612 |
| Drug_Target_1_PDB_ID | 1P0Q |
| Drug_Target_1_Pathway | Heroin Pathway SMP00407<br />Irinotecan Pathway SMP00433 |
| Drug_Target_1_Pfam_Domain_Function | PF00135 COesterase<br />PF08674 AChE_tetra |
| Drug_Target_1_Protein_Sequence | >Cholinesterase<br />MHSKVTIICIRFLFWFLLLCMLIGKSHTEDDIIIATKNGKVRGMNLTVFGGTVTAFLGIP<br />YAQPPLGRLRFKKPQSLTKWSDIWNATKYANSCCQNIDQSFPGFHGSEMWNPNTDLSEDC<br />LYLNVWIPAPKPKNATVLIWIYGGGFQTGTSSLHVYDGKFLARVERVIVVSMNYRVGALG<br />FLALPGNPEAPGNMGLFDQQLALQWVQKNIAAFGGNPKSVTLFGESAGAASVSLHLLSPG<br />SHSLFTRAILQSGSFNAPWAVTSLYEARNRTLNLAKLTGCSRENETEIIKCLRNKDPQEI<br />LLNEAFVVPYGTPLSVNFGPTVDGDFLTDMPDILLELGQFKKTQILVGVNKDEGTAFLVY<br />GAPGFSKDNNSIITRKEFQEGLKIFFPGVSEFGKESILFHYTDWVDDQRPENYREALGDV<br />VGDYNFICPALEFTKKFSEWGNNAFFYYFEHRSSKLPWPEWMGVMHGYEIEFVFGLPLER<br />RDNYTKAEEILSRSIVKRWANFAKYGNPNETQNNSTSWPVFKSTEQKYLTLNTESTRIMT<br />KLRAQQCRFWTSFFPKVLEMTGNIDEAEWEWKAGFHRWNNYMMDWKNQFNDYTSKKESCV<br />GL |
| Drug_Target_1_Reaction | an acylcholine + H2O = choline + a carboxylate |
| Drug_Target_1_Signals | 1-28 |
| Drug_Target_1_Specific_Function | An acylcholine + H(2)O = choline + a carboxylate |
| Drug_Target_1_SwissProt_ID | P06276 |
| Drug_Target_1_SwissProt_Name | CHLE_HUMAN |
| Drug_Target_1_Synonyms | Acylcholine acylhydrolase<br />Butyrylcholine esterase<br />Choline esterase II<br />Cholinesterase precursor<br />EC 3.1.1.8<br />Pseudocholinesterase |
| Drug_Target_1_Theoretical_pI | 7.47 |
| Drug_Target_1_Transmembrane_Regions | None |
| Drug_Target_2_Cellular_Location | - |
| Drug_Target_2_Chromosome_Location | - |
| Drug_Target_2_Drug_References | - |
| Drug_Target_2_Essentiality | - |
| Drug_Target_2_GenAtlas_ID | - |
| Drug_Target_2_GenBank_ID_Gene | - |
| Drug_Target_2_GenBank_ID_Protein | - |
| Drug_Target_2_GeneCard_ID | - |
| Drug_Target_2_Gene_Name | - |
| Drug_Target_2_Gene_Sequence | - |
| Drug_Target_2_General_Function | - |
| Drug_Target_2_General_References | - |
| Drug_Target_2_HGNC_ID | - |
| Drug_Target_2_HPRD_ID | - |
| Drug_Target_2_ID | - |
| Drug_Target_2_Locus | - |
| Drug_Target_2_Molecular_Weight | - |
| Drug_Target_2_Name | - |
| Drug_Target_2_Number_of_Residues | - |
| Drug_Target_2_PDB_ID | - |
| Drug_Target_2_Pathway | - |
| Drug_Target_2_Pfam_Domain_Function | - |
| Drug_Target_2_Protein_Sequence | - |
| Drug_Target_2_Reaction | - |
| Drug_Target_2_Signals | - |
| Drug_Target_2_Specific_Function | - |
| Drug_Target_2_SwissProt_ID | - |
| Drug_Target_2_SwissProt_Name | - |
| Drug_Target_2_Synonyms | - |
| Drug_Target_2_Theoretical_pI | - |
| Drug_Target_2_Transmembrane_Regions | - |
| Drug_Target_3_Cellular_Location | - |
| Drug_Target_3_Chromosome_Location | - |
| Drug_Target_3_Drug_References | - |
| Drug_Target_3_Essentiality | - |
| Drug_Target_3_GenAtlas_ID | - |
| Drug_Target_3_GenBank_ID_Gene | - |
| Drug_Target_3_GenBank_ID_Protein | - |
| Drug_Target_3_GeneCard_ID | - |
| Drug_Target_3_Gene_Name | - |
| Drug_Target_3_Gene_Sequence | - |
| Drug_Target_3_General_Function | - |
| Drug_Target_3_General_References | - |
| Drug_Target_3_HGNC_ID | - |
| Drug_Target_3_HPRD_ID | - |
| Drug_Target_3_ID | - |
| Drug_Target_3_Locus | - |
| Drug_Target_3_Molecular_Weight | - |
| Drug_Target_3_Name | - |
| Drug_Target_3_Number_of_Residues | - |
| Drug_Target_3_PDB_ID | - |
| Drug_Target_3_Pathway | - |
| Drug_Target_3_Pfam_Domain_Function | - |
| Drug_Target_3_Protein_Sequence | - |
| Drug_Target_3_Reaction | - |
| Drug_Target_3_Signals | - |
| Drug_Target_3_Specific_Function | - |
| Drug_Target_3_SwissProt_ID | - |
| Drug_Target_3_SwissProt_Name | - |
| Drug_Target_3_Synonyms | - |
| Drug_Target_3_Theoretical_pI | - |
| Drug_Target_3_Transmembrane_Regions | - |
| Phase_1_Metabolizing_Enzyme_1_Gene_Name | - |
| Phase_1_Metabolizing_Enzyme_1_ID | - |
| Phase_1_Metabolizing_Enzyme_1_Name | - |
| Phase_1_Metabolizing_Enzyme_1_Protein_Sequence | - |
| Phase_1_Metabolizing_Enzyme_1_SwissProt_ID | - |
| Phase_1_Metabolizing_Enzyme_2_Gene_Name | - |
| Phase_1_Metabolizing_Enzyme_2_ID | - |
| Phase_1_Metabolizing_Enzyme_2_Name | - |
| Phase_1_Metabolizing_Enzyme_2_Protein_Sequence | - |
| Phase_1_Metabolizing_Enzyme_2_SwissProt_ID | - |
| Phase_1_Metabolizing_Enzyme_3_Gene_Name | - |
| Phase_1_Metabolizing_Enzyme_3_ID | - |
| Phase_1_Metabolizing_Enzyme_3_Name | - |
| Phase_1_Metabolizing_Enzyme_3_Protein_Sequence | - |
| Phase_1_Metabolizing_Enzyme_3_SwissProt_ID | - |