U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of TETRAETHYLENEPENTAMINE

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
StemEx
Palliative
COLESTID

PubMed

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
Record UNII
YZD1C9KQ28
Record Status Validated (UNII)
Record Version