トリエンチン
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- trientine hydrochloride、triethylenetetramine
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/04/14 11:18:51」(JST)
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Triethylenetetramine
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| Names |
| Other names
N,N'-Bis(2-aminoethyl)ethane-1,2-diamine; TETA; Trien; Trientine (INN); Syprine (brand name)
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| Identifiers |
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CAS Number
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3D model (JSmol)
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Beilstein Reference
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605448 |
| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard |
100.003.591 |
| EC Number |
203-950-6 |
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Gmelin Reference
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27008 |
| KEGG |
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| MeSH |
Trientine |
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| RTECS number |
YE6650000 |
| UNII |
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| UN number |
2259 |
InChI
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InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 Y
Key: VILCJCGEZXAXTO-UHFFFAOYSA-N Y
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| Properties |
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Chemical formula
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C6H18N4 |
| Molar mass |
146.24 g·mol−1 |
| Appearance |
Colorless liquid |
| Odor |
Fishy, ammoniacal |
| Density |
982 mg mL−1 |
| Melting point |
−34.6 °C; −30.4 °F; 238.5 K |
| Boiling point |
266.6 °C; 511.8 °F; 539.7 K |
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Solubility in water
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Miscible |
| log P |
1.985 |
| Vapor pressure |
<1 Pa (at 20 °C) |
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Refractive index (nD)
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1.496 |
| Thermochemistry |
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Specific
heat capacity (C)
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376 J K−1 mol−1 (at 60 °C) |
| Pharmacology |
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ATC code
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A16AX12 (WHO) |
| Hazards |
| GHS pictograms |
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| GHS signal word |
DANGER |
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GHS hazard statements
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H312, H314, H317, H412 |
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GHS precautionary statements
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P273, P280, P305+351+338, P310 |
| Flash point |
129 °C (264 °F; 402 K) |
| Lethal dose or concentration (LD, LC): |
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LD50 (median dose)
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- 550 mg kg−1 (dermal, rabbit)
- 2.5 g kg−1 (oral, rat)
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| Related compounds |
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Related amines
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- Ethylenediamine
- Diethylenetriamine
- Cyclam
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Related compounds
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- Ethylenediaminetetraacetic acid
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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Triethylenetetramine, abbreviated TETA and trien and also called trientine (INN), is an organic compound with the formula [CH2NHCH2CH2NH2]2. This oily liquid is colorless but, like many amines, assumes a yellowish color due to impurities resulting from air-oxidation. It is soluble in polar solvents. The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of TETA.[1]
Contents
- 1 Production
- 2 Uses
- 3 Coordination chemistry
- 4 References
Production
TETA is prepared by heating ethylenediamine or ethanolamine/ammonia mixtures over an oxide catalyst. This process gives a variety of amines, which are separated by distillation and sublimation.[2]
Uses
The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine. It was primarily used as a crosslinker ("hardener") in epoxy curing.[2]
The hydrochloride salt of TETA, referred to as trientine hydrochloride, is a chelating agent that is used to bind and remove copper in the body to treat Wilson's disease, particularly in those who are intolerant to penicillamine. Some recommend trientine as first-line treatment, but experience with penicillamine is more extensive.[3]
In the United States, Valeant Pharmaceuticals International raised the price of its Syprine brand of TETA from $625 to $21,267 for 100 pills over five years. The New York Times said that this "egregious" price increase caused public outrage. Teva Pharmaceuticals 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. Aaron S. Kesselheim, who studies drug pricing at Harvard Medical School, said that drug companies price the product at what they think the market will bear.[4]
Coordination chemistry
TETA is a tetradentate ligand in coordination chemistry, where it is referred to as trien.[5] Octahedral complexes of the type M(trien)Cl3 can adopt several diastereomeric structures, most of which are chiral.[6]
References
- ^ "Ethyleneamines" (PDF). Huntsman. 2007.
- ^ a b Eller, K.; Henkes, E.; Rossbacher, R.; Höke, H. (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
- ^ Roberts, E. A.; Schilsky, M. L. (2003). "A practice guideline on Wilson disease" (pdf). Hepatology. 37 (6): 1475–1492. doi:10.1053/jhep.2003.50252. PMID 12774027.
- ^ Patients Eagerly Awaited a Generic Drug. Then They Saw the Price. By KATIE THOMAS. New York Times. FEB. 23, 2018
- ^ von Zelewsky, A. (1995). Stereochemistry of Coordination Compounds. Chichester: John Wiley. ISBN 047195599X.
- ^ Utsuno, S.; Sakai, Y.; Yoshikawa, Y.; Yamatera, H. (1985). "Three Isomers of the Trans-Diammine-[N,N′-bis(2-Aminoethyl)-1,2-Ethanediamine]-Cobalt(III) Complex Cation". Inorganic Syntheses. 23: 79–82. doi:10.1002/9780470132548.ch16.
UpToDate Contents
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English Journal
- Atypical neuroimaging in Wilson's disease.
- Patell R1, Dosi R1, Joshi HK1, Storz D2.
- BMJ case reports.BMJ Case Rep.2014 Jun 6;2014. pii: bcr2013200100. doi: 10.1136/bcr-2013-200100.
- Wilson's disease is a rare metabolic disease involving copper metabolism. Neuroimaging plays an important part in evaluation of patients with a neuropsychiatric presentation. We present a case of a 14-year-old girl with atypical confluent white matter disease and cystic degeneration on MRI, with a r
- PMID 24907221
- Exploratory study of carboplatin plus the copper-lowering agent trientine in patients with advanced malignancies.
- Fu S1, Hou MM, Wheler J, Hong D, Naing A, Tsimberidou A, Janku F, Zinner R, Piha-Paul S, Falchook G, Kuo MT, Kurzrock R.
- Investigational new drugs.Invest New Drugs.2014 Jun;32(3):465-72. doi: 10.1007/s10637-013-0051-8. Epub 2013 Dec 5.
- PURPOSE: Preclinical data showed that trientine, a copper-lowering agent, re-sensitized cancer cells to carboplatin through enhanced human copper transporter 1 (hCtr1) -mediated platinum uptake.EXPERIMENTAL DESIGN: We studied carboplatin and trientine in patients (n = 55; 45 who had failed plati
- PMID 24306314
- Clinical considerations for an effective medical therapy in Wilson's disease.
- Weiss KH1, Stremmel W.
- Annals of the New York Academy of Sciences.Ann N Y Acad Sci.2014 May;1315:81-5. doi: 10.1111/nyas.12437. Epub 2014 Apr 22.
- Wilson's disease is an autosomal recessively inherited copper overload disorder that leads to hepatic and/or neurologic symptoms. More than a century after the first description of Wilson's disease, the available medical treatment options have not been standardized. The efficacy of the commonly used
- PMID 24754532
Japanese Journal
- 症例報告 塩酸トリエンチンと酢酸亜鉛内服治療によるウィルソン病の頭部MRI所見の推移
- 長期にわたり統合失調症として加療されたウイルソン病の1例
- Trientine and renin-angiotensin system blockade ameliorate progression of glomerular morphology in hypertensive experimental diabetic nephropathy
Related Links
- The goal of drug therapy in individuals with Wilson Disease is to remove excess copper from the body and prevent ongoing copper accumulation. Drug therapy therefore must be life long. Trientine Dihydrochloride, also referred to as ...
- Univar has been manufacturing and supplying Trientine dihydrochloride for the treatment of Wilson Disease patients since 1985. This website is intended for information purposes only. Each patient is strongly advised to consult ...
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