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

Molecular Formula	C8H23N5
Molecular Weight	189.3017
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18047399	Inhibitor 8297
Copper 16 Target ID: CHEMBL2363057 Sources: http://pubs.acs.org/doi/abs/10.1021/ic50099a028?journalCode=inocaj	Chelating Agent 142
Bile acids 3 Target ID: CHEMBL2364175 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017563s023,020222s005lbl.pdf	Binding Agent 1064

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 1132	StemEx Approved Use Unknown
Primary hypercholesterolemia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017563s023,020222s005lbl.pdf	Palliative		Approved 8429	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
Treatment of heterozygous familial hypercholesterolemia with lipid-lowering drugs.	1989 Jan-Feb	2492189
Inhibitors of hydroxymethylglutaryl coenzyme A reductase for treating hypercholesterolaemia.	1990 Sep 29	2224231
Colestipol-induced hepatotoxicity.	2001 Apr	11310528
Application of capillary electrophoresis for organic acid analysis in herbal studies.	2001 Jul	11504059
Effect of concomitant colestipol hydrochloride administration on the bioavailability of diltiazem from immediate- and sustained-release formulations.	2002 Dec	12469330
Aluminum accumulation and membrane fluidity alteration in synaptosomes isolated from rat brain cortex following aluminum ingestion: effect of cholesterol.	2002 Oct	12354633
Purification, bacteriolytic activity, and specificity of beta-lytic protease from Lysobacter sp. IB-9374.	2003	16233362
Differential effects of lipid-lowering therapies on stroke prevention: a meta-analysis of randomized trials.	2003 Mar 24	12639199
Analysis of organic acids and inorganic anions in beverage drinks by capillary electrophoresis.	2003 Sep	14518049
Mevinolin and colestipol stimulate receptor-mediated clearance of low density lipoprotein from plasma in familial hypercholeserolemia heterozygotes. 1983.	2004 Oct	15531277
Effectiveness and tolerability of ezetimibe add-on therapy to a bile acid resin-based regimen for hypercholesterolemia.	2004 Sep 15	15374793
Sodium monofluoroacetate (Compound 1080) poisoning in dogs.	2005 Aug	16119418
A highly efficient preparative-scale generic immunoaffinity chromatography method for the purification of antibodies to hydrophobic haptens: purification procedure and monitoring tests.	2005 Dec 5	16202669
Profiling preparations of recombinant birch pollen allergen Bet v 1a with capillary zone electrophoresis in pentamine modified fused-silica capillaries.	2006 Jul 24	16504605
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
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
One-dimensional indium sulfides with transition metal complexes of polyamines.	2007 Aug 6	17622136
Synthesis of a selenidostannate(IV), [Mn(tepa).Sn3Se7]n, demonstrating the transformation from achiral to chiral and dimeric to polymeric structure.	2007 Mar 5	17269765
The use of colesevelam hydrochloride in the treatment of dyslipidemia: a review.	2007 Oct	17931091
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 Oct 25	17961204
Transplantation of ex vivo expanded cord blood cells using the copper chelator tetraethylenepentamine: a phase I/II clinical trial.	2008 May	18209724

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:59:13 GMT 2023` Edited by `admin` on `Fri Dec 15 17:59:13 GMT 2023`
Record UNII	YZD1C9KQ28
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAETHYLENEPENTAMINE

Systematic 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

ANCAMINE TEPA

Brand 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