Details of the Drug

General Information of Drug (ID: DMD2WPG)

Drug Name
TRIENTINE
Synonyms
Trientine HCl; 21121-06-2; triethylenetetramine HCl; SMR000058543; AC1NUQ0M; MLS000069683; SCHEMBL205201; CHEMBL1200783; CTK0I9735; DTXSID80419994; XPVOJYDIBHYVFL-UHFFFAOYSA-N; Pharmakon1600-01505675; NSC759164; NSC158271; AKOS027276425; NSC-158271; NSC-759164; 1, N,N'-bis(2-aminoethyl)-, tetrahydrochloride; 1,2-Ethanediamine, N,N'-bis(2-aminoethyl)-, hydrochloride; N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine hydrochloride
Indication
Disease Entry ICD 11 Status REF
Inborn error of metabolism 5C50-5C59 Approved [1]
Wilson disease 5C64.00 Investigative [2]
Affected Organisms
Humans and other mammals
ATC Code
A16AX12: TRIENTINE
A16AX: Various alimentary tract and metabolism products
A16A: OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS
A16: OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS
A: ALIMENTARY TRACT AND METABOLISM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 146.23
Logarithm of the Partition Coefficient (xlogp) -2.5
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.4-4.8 h [3]
Bioavailability
The bioavailability of drug is 12% [3]
Elimination
About 1% of the administered trientine and about 8% of the biotransformed trientine metabolite, acetyltrien, ultimately appear in the urine [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.3 - 4 hours [5]
Metabolism
The drug is metabolized via the acetylation []
Vd
The volume of distribution (Vd) of drug is 393 L [6]
Chemical Identifiers
Formula
C6H18N4
IUPAC Name
N'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine
Canonical SMILES
C(CNCCNCCN)N
InChI
InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2
InChIKey
VILCJCGEZXAXTO-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5565
ChEBI ID
CHEBI:39501
CAS Number
112-24-3
UNII
SJ76Y07H5F
DrugBank ID
DB06824
TTD ID
D09VAZ
ACDINA ID
D00702
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Carbonic anhydrase XIV (CA-XIV) TTEYTKG CAH14_HUMAN Inhibitor [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Advanced glycosylation end product-specific receptor (AGER) OTPY0IH7 RAGE_HUMAN Gene/Protein Processing [8]
Amyloid-beta precursor protein (APP) OTKFD7R4 A4_HUMAN Gene/Protein Processing [8]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [9]
Beta-secretase 1 (BACE1) OTCA7B6A BACE1_HUMAN Gene/Protein Processing [8]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [9]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [10]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Post-Translational Modifications [9]
High affinity copper uptake protein 1 (SLC31A1) OTXLRTUB COPT1_HUMAN Gene/Protein Processing [11]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [12]
Superoxide dismutase (SOD1) OT39TA1L SODC_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Inborn error of metabolism
ICD Disease Classification 5C50-5C59
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Carbonic anhydrase XIV (CA-XIV) DTT CA14 5.79E-07 -0.09 -0.16
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
FD&C blue no. 2 E00446 2723854 Colorant
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Food blue 1 aluminum lake E00512 11979396 Colorant
Ferric oxide black E00522 16211978 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Gelatin E00630 Not Available Other agent
Potassium hydroxide E00233 14797 Alkalizing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
FD&C yellow 5 aluminum lake E00684 56843209 Colorant
Shellac E00695 Not Available Coating agent; Film/membrane-forming agent; Microencapsulating agent; Modified-release agent
⏷ Show the Full List of 11 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Trientine 250 mg capsule 250 mg Oral Capsule Oral
Trientine Hydrochloride 250mg capsule 250mg Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trientine FDA Label
3 Lisciani R, Baldini A, Benedetti D, Campana A, Barcellona PS: Acute cardiovascular toxicity of trazodone, etoperidone and imipramine in rats. Toxicology. 1978 Jun;10(2):151-8.
4 Authors unspecified: EASL Clinical Practice Guidelines: Wilson's disease. J Hepatol. 2012 Mar;56(3):671-85. doi: 10.1016/j.jhep.2011.11.007.
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Lu J: Triethylenetetramine pharmacology and its clinical applications. Mol Cancer Ther. 2010 Sep;9(9):2458-67. doi: 10.1158/1535-7163.MCT-10-0523. Epub 2010 Jul 26.
7 Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem. 2010 Aug 12;53(15):5511-22.
8 Trientine reduces BACE1 activity and mitigates amyloidosis via the AGE/RAGE/NF-B pathway in a transgenic mouse model of Alzheimer's disease. Antioxid Redox Signal. 2013 Dec 10;19(17):2024-39. doi: 10.1089/ars.2012.5158. Epub 2013 May 3.
9 Increased susceptibility of copper-deficient neuroblastoma cells to oxidative stress-mediated apoptosis. Free Radic Biol Med. 2001 May 15;30(10):1177-87.
10 Prolonged copper depletion induces expression of antioxidants and triggers apoptosis in SH-SY5Y neuroblastoma cells. Cell Mol Life Sci. 2003 Aug;60(8):1733-43.
11 Mechanistic basis for overcoming platinum resistance using copper chelating agents. Mol Cancer Ther. 2012 Nov;11(11):2483-94. doi: 10.1158/1535-7163.MCT-12-0580. Epub 2012 Aug 21.
12 The copper chelator trientine has an antiangiogenic effect against hepatocellular carcinoma, possibly through inhibition of interleukin-8 production. Int J Cancer. 2002 Dec 10;102(5):445-52. doi: 10.1002/ijc.10740.