TETRAETHYLENEPENTAMINE

First approved in 1977

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H23N5
Molecular Weight	189.3017
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCNCCNCCNCCN

InChI

InChIKey=FAGUFWYHJQFNRV-UHFFFAOYSA-N

InChI=1S/C8H23N5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h11-13H,1-10H2

HIDE SMILES / InChI

Description
Sources: http://www.google.com/patents/WO1993000915A1?cl=enhttp://www.huntsman.com/performance_products/Media%20Library/a_MC348531CFA3EA9A2E040EBCD2B6B7B06/Products_MC348531D0B9FA9A2E040EBCD2B6B7B06/Amines_MC348531D0BECA9A2E040EBCD2B6B7B06/Ethyleneamines_MC348531D0CD3A9A2E040EBCD2B6B7B06/files/tetraethylenepentamine_tepa.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26581493 | http://pubs.acs.org/doi/abs/10.1021/ic50099a028?journalCode=inocaj | http://pubs.acs.org/doi/abs/10.1021/ic50048a017?journalCode=inocaj | https://clinicaltrials.gov/ct2/show/NCT01484470 | https://www.ncbi.nlm.nih.gov/pubmed/18209724 | https://www.ncbi.nlm.nih.gov/pubmed/16219531

Tetraethylenepentamine (TEPA) is a low-molecular-weight linear polyamine exerting metal-chelating properties. TEPA is widely used in industrial applications. The principal hazards that arise in working with TEPA are those associated with similar organic amines; namely, a corrosive action on skin and eyes. TEPA biological activity was attributed to its effect on cellular Cu levels as (a) treatment with TEPA resulted in reduction of cellular Cu, and (b) excess of Cu reversed TEPA's activity and accelerated differentiation. TEPA was shown to attenuate the differentiation of ex vivo cultured hematopoietic cells resulting in preferential expansion of early progenitors. A phase I/II trial was performed to test the feasibility and safety of transplantation of CD133+ cord blood (CB) hematopoietic progenitors cultured in media containing stem cell factor, FLT-3 ligand, interleukin-6, thrombopoietin and TEPA. Transplanting a population of CD133+ CB cells which were expanded ex vivo for 21 days using SCF, FLT3, IL-6, TPO and the copper chelator TEPA (StemEx) was feasible. The expanded cells were well tolerated, with no infusion-related adverse events observed.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18047399	Inhibitor 8504
Copper 17 Target ID: CHEMBL2363057 Sources: http://pubs.acs.org/doi/abs/10.1021/ic50099a028?journalCode=inocaj	Chelating Agent 139
Bile acids 3 Target ID: CHEMBL2364175 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017563s023,020222s005lbl.pdf	Binding Agent 1076

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hematologic malignancies 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18209724 http://www.bloodjournal.org/content/122/21/295?sso-checked=true https://clinicaltrials.gov/ct2/show/NCT01484470	Primary		Phase II 1147	StemEx Approved Use Unknown
Primary hypercholesterolemia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017563s023,020222s005lbl.pdf	Palliative		Approved 8583	COLESTID Approved Use COLESTID Granules and FLAVORED COLESTID Granules are indicated as adjunctive therapy to diet for the reduction of elevated serum total and low-density lipoprotein (LDL) cholesterol in patients with primary hypercholesterolemia (elevated low density lipoproteins [LDL] cholesterol) who do not respond adequately to diet. Generally, COLESTID and FLAVORED COLESTID have no clinically significant effect on serum triglycerides, but with its use triglyceride levels may be raised in some patients. Launch Date 1977

PubMed

Title	Date	PubMed
Functional polycarbonates and their self-assemblies as promising non-viral vectors.	2009-10-01	19470398
Primary biliary cirrhosis.	2009-09	19603170
Removal of Reactive Black 5 from aqueous solutions using magnetic chitosan resins.	2009-08-15	19272711
Chitosan based oligoamine polymers: synthesis, characterization, and gene delivery.	2009-07-01	19303039
Molecular nanocluster with a [Sn(4)Ga(4)Zn(2)Se(20)](8-) t3 supertetrahedral core.	2009-06-01	19466797
Role for copper in the cellular and regulatory effects of heme-hemopexin.	2009-06	19039664
Dyslipidemia treatment of patients with diabetes mellitus in a US managed care plan: a retrospective database analysis.	2009-05-18	19450274
Polyaspartamide-based oligo-ethylenimine brushes with high buffer capacity and low cytotoxicity for highly efficient gene delivery.	2009-03-18	19206529
Does nicotinic acid (niacin) lower blood pressure?	2009-01	19054161
Copper regulation of hypoxia-inducible factor-1 activity.	2009-01	18842833
Copper modulates the differentiation of mouse hematopoietic progenitor cells in culture.	2009	19520051
Management of complex lipid abnormalities with a fixed dose combination of simvastatin and extended release niacin.	2009	19436666
Preparation of polyurea capsules using electrocapillary emulsification.	2008-10-15	18768303
New advances in the treatment of Clostridium difficile infection (CDI).	2008-10	19209277
A capillary electrophoretic method for fingerprinting low molecular weight heparins.	2008-09-15	18572011
Bile acid sequestrants as a therapeutic option for glucose lowering in type 2 diabetes mellitus.	2008-08-30	18753111
Colesevelam HCl improves glycemic control and reduces LDL cholesterol in patients with inadequately controlled type 2 diabetes on sulfonylurea-based therapy.	2008-08	18458145
Synthesis of magnetic chelating resins functionalized with tetraethylenepentamine for adsorption of molybdate anions from aqueous solutions.	2008-06-30	18177999
Plasma PCSK9 levels are significantly modified by statins and fibrates in humans.	2008-06-11	18547436
Absorption spectroscopic and FTIR studies on EDA complexes between TNT (2,4,6-trinitrotoluene) with amines in DMSO and determination of the vertical electron affinity of TNT.	2008-06	17765603
Transplantation of ex vivo expanded cord blood cells using the copper chelator tetraethylenepentamine: a phase I/II clinical trial.	2008-05	18209724
Liver transplantation in a subject with familial hypercholesterolemia carrying the homozygous p.W577R LDL-receptor gene mutation.	2008-03-15	18339137
Thermodynamic and spectroscopic studies of lanthanides(III) complexation with polyamines in dimethyl sulfoxide.	2008-02-04	18166040
Pathogenesis and treatment of pruritus in cholestasis.	2008	18840005
Tetraethylenepentamine-directed controllable synthesis of wurtzite ZnSe nanostructures with tunable morphology.	2008	18792043
Efficient CO2 capturer derived from as-synthesized MCM-41 modified with amine.	2008	18283702
The 'forgotten' bile acid sequestrants: is now a good time to remember?	2007-12-20	18090882
The effect of the copper chelator tetraethylenepentamine on reactive oxygen species generation by human hematopoietic progenitor cells.	2007-12	18047399
In situ ligand reactions under hydrothermal conditions afford a novel zinc-substituted polyoxovanadate dimer.	2007-10-29	17915859
Fish-oil esters of plant sterols differ from vegetable-oil sterol esters in triglycerides lowering, carotenoid bioavailability and impact on plasminogen activator inhibitor-1 (PAI-1) concentrations in hypercholesterolemic subjects.	2007-10-25	17961204
Telmisartan/hydrochlorothiazide versus valsartan/hydrochlorothiazide in obese hypertensive patients with type 2 diabetes: the SMOOTH study.	2007-10-02	17910747
The use of colesevelam hydrochloride in the treatment of dyslipidemia: a review.	2007-10	17931091
One-dimensional indium sulfides with transition metal complexes of polyamines.	2007-08-06	17622136
Profiling recombinant major birch pollen allergen Bet v 1a and carbamylated variants with CZE and CIEF.	2007-07	17538926
Safety considerations with gastrointestinally active lipid-lowering drugs.	2007-03-19	17368279
Synthesis of a selenidostannate(IV), [Mn(tepa).Sn3Se7]n, demonstrating the transformation from achiral to chiral and dimeric to polymeric structure.	2007-03-05	17269765
Estimating the impact of adding C-reactive protein as a criterion for lipid lowering treatment in the United States.	2007-02	17356986
Colesevelam hydrochloride: reducing atherosclerotic coronary heart disease risk factors.	2007	18078024
Regression or reduction in progression of atherosclerosis, and avoidance of coronary events, with lovastatin in patients with or at high risk of cardiovascular disease: a review.	2007	17705568
Is the fixed-dose combination of telmisartan and hydrochlorothiazide a good approach to treat hypertension?	2007	17703634
Bile acid sequestrants and the treatment of type 2 diabetes mellitus.	2007	17600387
A preconcentration system using polyamine Metalfix-Chelamine resin for the on-line determination of palladium(II) and platinum(IV) by inductively coupled plasma optical emission spectrometry.	2006-12-15	18970884
Past, present, and future therapies for Clostridium difficile-associated disease.	2006-12	17148650
Complementary therapy to target LDL cholesterol: the role of the ezetimibe/simvastatin combination.	2006	17319467
Optimal lipid modification: the rationale for combination therapy.	2005	17315604
Effects of prolonged intensive lipid-lowering therapy on the characteristics of carotid atherosclerotic plaques in vivo by MRI: a case-control study.	2001-10	11597936
Interaction of l-malic acid with alkaline metals and open chain polyammonium cations in aqueous solution.	2001-03-30	18968222
Currently available hypolipidaemic drugs and future therapeutic developments.	1995-10	8593127
Inhibitors of hydroxymethylglutaryl coenzyme A reductase for treating hypercholesterolaemia.	1990-09-29	2224231
Treatment of heterozygous familial hypercholesterolemia with lipid-lowering drugs.	1989-01-01	2492189

Patents

Sample Use Guides

In Vivo Use Guide

The recommended daily adult dose is 5-30 g (granules) or 2-16 g (tablets) given once or in divided doses.

Route of Administration: Oral

In Vitro Use Guide

In vitro binding capacity is 1 mequiv cholic acid/g.

Name

Type

Language

TETRAETHYLENEPENTAMINE

Systematic Name

English

ANCAMINE TEPA

Preferred Name

English

1,4,7,10,13-PENTAAZATRIDECANE

Systematic Name

English

3,6,9-TRIAZA-1,11-DIAMINOUNDECANE

Common Name

English

BIS(2-(2-AMINOETHYLAMINO)ETHYL)AMINE

Systematic Name

English

TETREN

Common Name

English

ETHOXYLATED TETRAETHYLENEPENTAMINE

Common Name

English

NSC-88603

Code

English

INSULCURE 9

Brand Name

English

TH 160

Code

English

3,6,9-TRIAZAUNDECANE-1,11-DIAMINE

Systematic Name

English

1,2-ETHANEDIAMINE, N1-(2-AMINOETHYL)-N2-(2-((2-AMINOETHYL)AMINO)ETHYL)-

Systematic Name

English

DEH 26

Brand Name

English

T-11509

Code

English

1,2-ETHANEDIAMINE, N-(2-AMINOETHYL)-N'-(2-((2-AMINOETHYL)AMINO)ETHYL)-

Systematic Name

English

1,11-DIAMINO-3,6,9-TRIAZAUNDECANE

Systematic Name

English

N-(2-AMINOETHYL)-N'-(2-((2-AMINOETHYL)AMINO)ETHYL)-1,2-ETHANEDIAMINE

Systematic Name

English

TETRAETHYLENEPENTAMINE [HSDB]

Common Name

English

Classification Tree Code System Code

Food Contact Sustance Notif, (FCN No.)

FCN NO. 361