| Revision as of 14:05, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 459416960 of page Triethylenetetramine for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 17:50, 19 December 2024 edit Brandmeister (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers38,034 edits →top: wlinks |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 410157990 |
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| verifiedrevid = 470614378 |
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| ImageFile = N1,N1'-(ethane-1,2-diyl)bis(ethane-1,2-diamine) 200.svg |
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|ImageFile=Triethylene tetramine.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageSize=200px |
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| ImageSize = 220 |
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|ImageName=Chemical structure of triethylenetetramine |
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| ImageName = Skeletal formula of triethylenetetramine |
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|IUPACName=''N'',''N'''-bis(2-aminoethyl)ethane-1,2-diamine |
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| ImageFile1 = Triethylenetetramine-3D-balls.png |
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|OtherNames=Trientine |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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|Section1= {{Chembox Identifiers |
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| ImageSize1 = 220 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ImageName1 = Ball and stick model of triethylenetetramine |
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| ImageFile2 = Triethylenetetramine-3D-spacefill.png |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageSize2 = 220 |
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| ImageName2 = Spacefill model of triethylenetetramine |
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| PIN = ''N''<sup>1</sup>,''N''<sup>1′</sup>-(Ethane-1,2-diyl)di(ethane-1,2-diamine) |
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| OtherNames = {{Unbulleted list| |
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''N'',''N'''-Bis(2-aminoethyl)ethane-1,2-diamine |
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| TETA |
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| trien |
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| trientine (]) |
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| trientine dihydrochloride |
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| MK-0681 |
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}} |
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|Section1={{Chembox Identifiers |
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| index1_label = hydrochloride |
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| CASNo = 112-24-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 38260-01-4 |
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| PubChem = 5565 |
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| PubChem1 = 71433 |
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| ChemSpiderID = 21106175 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1 = 64521 |
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| UNII = SJ76Y07H5F |
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| UNII = SJ76Y07H5F |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = HC3NX54582 |
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| EINECS = 203-950-6 |
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| UNNumber = 2259 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C07166 |
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| KEGG = C07166 |
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| MeSHName = Trientine |
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| InChI = 1/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 |
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| ChEBI = 39501 |
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| InChIKey = VILCJCGEZXAXTO-UHFFFAOYAI |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI1 = 9706 |
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| ChEMBL = 609 |
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| ChEMBL = 609 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL1 = 3989777 |
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| DrugBank = DB06824 |
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| RTECS = YE6650000 |
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| Beilstein = 605448 |
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| Gmelin = 27008 |
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| SMILES = NCCNCCNCCN |
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| StdInChI = 1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 |
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| StdInChI = 1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VILCJCGEZXAXTO-UHFFFAOYSA-N |
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| StdInChIKey = VILCJCGEZXAXTO-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo=112-24-3 |
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|Section2={{Chembox Properties |
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| PubChem=5565 |
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| C=6 | H=18 | N=4 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Appearance = Colorless liquid |
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| ChemSpiderID=21106175 |
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| Odor = Fishy, ammoniacal |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| Density = 982 mg mL<sup>−1</sup> |
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| ChEBI = 39501 |
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| MeltingPtK = 238.5 |
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| SMILES=C(CNCCNCCN)N |
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| BoilingPtK = 539.7 |
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}} |
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| Solubility = Miscible |
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|Section2= {{Chembox Properties |
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| LogP = 1.985 |
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| Formula=C<sub>6</sub>H<sub>18</sub>N<sub>4</sub> |
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| VaporPressure = <1 Pa (at 20 °C) |
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| MolarMass=146.23392 |
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| RefractIndex = 1.496 |
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| Appearance= |
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}} |
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| Density= |
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|Section3={{Chembox Thermochemistry |
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| MeltingPtC=12 |
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| HeatCapacity = 376 J K<sup>−1</sup> mol<sup>−1</sup> (at 60 °C) |
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| BoilingPtCL=266 | BoilingPtCH=267 |
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}} |
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| Solubility=Miscible |
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|Section5={{Chembox Hazards |
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}} |
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| GHSPictograms = {{gHS corrosion}} {{gHS exclamation mark}} |
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|Section3= {{Chembox Hazards |
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| GHSSignalWord = '''DANGER''' |
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| MainHazards= |
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| HPhrases = {{h-phrases|312|314|317|412}} |
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| FlashPt= |
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| PPhrases = {{p-phrases|273|280|305+351+338|310}} |
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| Autoignition= |
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| FlashPtC = 129 |
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| LD50 = {{unbulleted list|550 mg kg<sup>−1</sup> <small>(dermal, rabbit)</small>|2.5 g kg<sup>−1</sup> <small>(oral, rat)</small>}} |
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}} |
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| Section6 = {{Chembox Pharmacology |
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| Legal_AU_comment = |
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| Legal_CA = Rx-only |
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| Legal_CA_comment = <ref>{{cite web | title=Health product highlights 2021: Annexes of products approved in 2021 | website=] | date=3 August 2022 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-product-highlights-2021/appendices.html | access-date=25 March 2024}}</ref><ref>{{cite web | title=Regulatory Decision Summary for Waymade-Trientine | website=] | date=20 April 2021 | url=https://dhpp.hpfb-dgpsa.ca/review-documents/resource/RDS00834 | access-date=25 March 2024}}</ref> |
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|Section9={{Chembox Related |
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| OtherFunction_label = amines |
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| OtherFunction = {{unbulleted list|]|]|]}} |
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| OtherCompounds = {{unbulleted list|]}} |
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'''Triethylenetetramine''' ('''TETA''' and '''trien'''), also known as '''trientine''' (]) when used medically, is an ] with the ] <sub>2</sub>. The pure ] is a colorless oily liquid, but, like many ]s, older samples assume a yellowish color due to impurities resulting from air ]. It is soluble in polar solvents. The branched ] ] and ] derivatives may also be present in commercial samples of TETA.<ref>{{cite web | url = http://www.huntsman.com/performance_products/Media%20Library/a_MC348531CFA3EA9A2E040EBCD2B6B7B06/Products_MC348531D0B9FA9A2E040EBCD2B6B7B06/Amines_MC348531D0BECA9A2E040EBCD2B6B7B06/Ethyleneamines_MC348531D0CD3A9A2E040EBCD2B6B7B06/files/ethyleneamines_brochure_huntsman_ethyleneamines.pdf | title = Ethyleneamines | publisher = Huntsman | year = 2007 | access-date = 2016-07-10 | archive-date = 2019-03-06 | archive-url = https://web.archive.org/web/20190306111337/http://www.huntsman.com/performance_products/Media%20Library/a_MC348531CFA3EA9A2E040EBCD2B6B7B06/Products_MC348531D0B9FA9A2E040EBCD2B6B7B06/Amines_MC348531D0BECA9A2E040EBCD2B6B7B06/Ethyleneamines_MC348531D0CD3A9A2E040EBCD2B6B7B06/files/ethyleneamines_brochure_huntsman_ethyleneamines.pdf | url-status = dead }}</ref> |
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The ] salts are used medically as a treatment for ]. |
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==Uses== |
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===Epoxy uses=== |
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The reactivity and uses of TETA are similar to those for the related polyamines ] and ]. It is primarily used as a crosslinker ("hardener") in ] curing.<ref name=Ullmann/><ref>{{Cite web |title=Triethylenetetramine |url=https://webbook.nist.gov/cgi/cbook.cgi?ID=C39421777&Mask=8 |access-date=2022-07-20 |website=webbook.nist.gov |language=en}}</ref> TETA, like other aliphatic amines, react quicker and at lower temperatures than aromatic amines due to less negative ] since the linear nature of the molecule provides it the ability to rotate and twist. |
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=== Medical uses === |
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{{Infobox drug |
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| drug_name = Trientine |
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<!-- Clinical data --> |
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| pronounce = |
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| tradename = Syprine, Cuprior, Cufence, others |
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| Drugs.com = {{drugs.com|monograph|trientine-hydrochloride}} |
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| MedlinePlus = |
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| DailyMedID = Trientine |
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| ATC_prefix = A16 |
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| ATC_suffix = AX12 |
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| ATC_supplemental = |
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| legal_AU = S4 |
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| legal_AU_comment = <ref name="Trientine APM summary">{{cite web | title=Trientine Waymade | website=Therapeutic Goods Administration (TGA) | date=25 January 2021 | url=https://www.tga.gov.au/apm-summary/trientine-waymade | access-date=8 September 2021}}</ref><ref name="AusPAR: Trientine dihydrochloride">{{cite web | title=AusPAR: Trientine dihydrochloride | website=Therapeutic Goods Administration (TGA) | date=3 May 2021 | url=https://www.tga.gov.au/auspar/auspar-trientine-dihydrochloride | access-date=8 September 2021}}</ref> |
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| legal_CA = Rx-only |
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| legal_CA_comment = <ref>{{cite web | title=Summary Basis of Decision (SBD) for Mar-Trientine | website=Health Canada | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00505&lang=en | access-date=29 May 2022}}</ref> |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = POM |
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| legal_UK_comment = <ref>{{cite web | title=Cuprior 150 mg film-coated tablets - Summary of Product Characteristics (SmPC) | website=(emc) | url=https://www.medicines.org.uk/emc/product/10100/smpc | access-date=21 September 2020}}</ref><ref>{{cite web | title=Trientine dihydrochloride Tillomed 250 mg capsules, hard - Summary of Product Characteristics (SmPC) | website=(emc) | url=https://www.medicines.org.uk/emc/product/11626/smpc | access-date=21 September 2020}}</ref> |
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| legal_US = Rx-only |
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| legal_US_comment = <ref name="Syprine FDA label">{{cite web | title=Syprine- trientine hydrochloride capsule | website=DailyMed | date=22 December 2016 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c34f77a7-996b-4470-b5df-d946a7fe5dbe | access-date=21 September 2020}}</ref><ref>{{cite web | title=Trientine hydrochloride capsule | website=DailyMed | date=28 February 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a7cf5608-6446-4965-a855-5a0c0b7afddc | access-date=21 September 2020}}</ref><ref>{{cite web | title=Cuvrior- trientine tetrahydrochloride tablet, film coated | website=DailyMed | date=20 May 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f73feeae-62ad-401e-b9f7-5cb269127750 | access-date=21 January 2023}}</ref> |
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| legal_EU = Rx-only |
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| legal_EU_comment = <ref name="Cuprior EPAR " /><ref name="Cufence EPAR" /> |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = <!-- For countries not listed above --> |
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| pregnancy_category = |
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| pregnancy_AU = D |
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| pregnancy_AU_comment = <ref name="Trientine APM summary" /><ref name="AusPAR: Trientine dihydrochloride" /> |
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| routes_of_administration = ] |
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<!-- Identifiers --> |
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| IUPHAR_ligand = |
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| DrugBank_Ref = |
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| DrugBank = DB06824 |
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| DrugBank2 = DBSALT001269 |
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| KEGG_Ref = |
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| NIAID_ChemDB = |
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| PDB_ligand = 104 |
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| synonyms = |
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<!-- Chemical and physical data --> |
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| IUPAC_name = (2-aminoethyl)({2-ethyl})amine |
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The hydrochloride salt of TETA, referred to as ''trientine hydrochloride'', is a ] that is used to bind and remove ] in the body to treat ], particularly in those who are intolerant to ].<ref name="Syprine FDA label" /> Some recommend trientine as first-line treatment, but experience with penicillamine is more extensive.<ref name=Roberts>{{cite journal | vauthors = Roberts EA, Schilsky ML | title = A practice guideline on Wilson disease | journal = Hepatology | volume = 37 | issue = 6 | pages = 1475–92 | date = June 2003 | pmid = 12774027 | doi = 10.1053/jhep.2003.50252 | url = http://www3.interscience.wiley.com/cgi-bin/fulltext/106595824/PDFSTART | format = pdf | s2cid = 263620 | doi-access = free }}{{dead link|date=February 2019|bot=medic}}{{cbignore|bot=medic}}</ref> |
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Trientine hydrochloride (brand name Syprine) was approved for medical use in the United States in November 1985.<ref name="Syprine FDA label" /> |
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Trientine tetrahydrochloride (brand name Cuprior) was approved for medical use in the European Union in September 2017.<ref name="Cuprior EPAR ">{{cite web | title=Cuprior EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/cuprior | access-date=21 September 2020}} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> It is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy.<ref name="Cuprior EPAR " /> |
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Trientine dihydrochloride (brand name Cufence) was approved for medical use in the European Union in July 2019.<ref name="Cufence EPAR">{{cite web | title=Cufence EPAR | website=] (EMA) | date=24 May 2019 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/cufence | access-date=21 September 2020}} Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</ref> It is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy.<ref name="Cufence EPAR" /> |
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The most common side effects include ], especially when starting treatment, ], ] (inflammation of the duodenum, the part of the gut leading out of the stomach), and severe ] (inflammation in the large bowel causing pain and ]).<ref name="Cufence EPAR" /> |
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== Society and culture == |
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=== Controversies === |
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In the United States, ] raised the price of its Syprine brand of TETA from $625 to $21,267 for 100 pills over five years.<ref name="NYT 20180223" /> '']'' said that this "egregious" price increase caused public outrage.<ref name="NYT 20180223" /> ] developed a generic, which patients and doctors expected to be cheaper, but when it was introduced in February 2018, Teva's price was $18,375 for 100 pills.<ref name="NYT 20180223" /> ], who studies drug pricing at Harvard Medical School, said that drug companies price the product at what they think the market will bear.<ref name="NYT 20180223">{{cite news | first=Katie | last=Thomas | title=Patients Eagerly Awaited a Generic Drug. Then They Saw the Price. | website=] | date=23 February 2018 | url=https://www.nytimes.com/2018/02/23/health/valeant-drug-price-syprine.html | access-date=21 September 2020 | name-list-style=vanc }}</ref> |
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==Production== |
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TETA is prepared by heating ethylenediamine or ]/] mixtures over an oxide ]. This process gives a variety of amines, especially ethylene amines which are separated by distillation and sublimation.<ref name=Ullmann>{{cite encyclopedia | vauthors = Eller K, Henkes E, Rossbacher R, Höke H | chapter = Amines, Aliphatic | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | year = 2005 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a02_001 |isbn=3527306730 }}</ref><ref>{{cite book| vauthors = Brydson JA |title=Plastics Materials|url=https://archive.org/details/plasticsmaterial00bryd|url-access=limited|pages=–777|chapter=Epoxide Resins| veditors = Brydson JA |year=1999|publisher=Butterworth-Heinemann |location=Oxford|doi=10.1016/B978-075064132-6/50067-X|isbn=9780750641326|edition=Seventh}}</ref> |
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==Coordination chemistry== |
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TETA is a tetradentate ] in ], where it is referred to as trien.<ref>{{cite book | vauthors = von Zelewsky A | title = Stereochemistry of Coordination Compounds | publisher = John Wiley | location = Chichester | year = 1995 | isbn = 047195599X | url-access = registration | url = https://archive.org/details/stereochemistryo0000zele }}</ref> Octahedral complexes of the type M(trien)L<sub>2</sub> can adopt several diastereomeric structures.<ref>{{cite book | vauthors = Utsuno S, Sakai Y, Yoshikawa Y, Yamatera H | title = Three Isomers of the ''trans''-Diammine--Cobalt(III) Complex Cation | chapter = Three Isomers of the Trans -Diammine-[N,N′-bis(2-Aminoethyl)-1,2-Ethanediamine]-Cobalt(III) Complex Cation | series = Inorganic Syntheses | year = 1985 | volume = 23 | pages = 79–82 | doi = 10.1002/9780470132548.ch16 | isbn = 9780470132548 }}</ref> |
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== References == |
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{{reflist}} |
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{{Portal bar | Medicine}} |
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