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Diethylenetriaminepentaacetic acid

HCID 3053
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
67-43-6
Standard SMILES
O=C(O)CN(CCN(CC(=O)O)CC(=O)O)CCN(CC(=O)O)CC(=O)O
InChIKey
QPCDCPDFJACHGM-UHFFFAOYSA-N
Molecular formula
C14H23N3O10
Average molar mass
393.35 g/mol
Monoisotopic mass
393.13834394

Overview

Pentetic acid is a pentacarboxylic acid. It has a role as a copper chelator. It is a conjugate acid of a pentetate(1-).

Names & identifiers

Preferred name
Diethylenetriaminepentaacetic acid
IUPAC
2-[bis[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid
English name
DTPA
Molecular formula
C14H23N3O10
Molecular weight
393.35

Names & synonyms

Pentetic aciddiethylenetriaminepentaacetic acid67-43-6DTPADetapacDetarexTitriplex VMonaquest CAIPerma kleerDabeersen 503CHEL 330 acidPenthanil
Show more names
Diethylenetriamine Pentaacetic AcidPenthamilChel DTPADissolvine DPentacarboxymethyldiethylenetriamineAcido penteticoAcide pentetique(Diethylenetrinitrilo)pentaacetic acid

Database identifiers

CAS
67-43-6
PubChem CID
3053
DTXSID
DTXSID2023434
ChEMBL
CHEMBL780
ChEBI
CHEBI:35739
UNII
7A314HQM0I
EC Number
200-652-8
Nikkaji
J2.813D、J479.816C

Properties

Computed structural propertiesFilling in

XLogP
-8.5
Topological polar surface area
196 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
13
Rotatable bonds
16
Heavy atoms
27
Formal charge
0
Complexity
481

Experimental & physicochemical properties

Chemical ClassesOther Uses -> Chelating Agents
Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Cosmetics · 2 items

Cosmetic ingredients (Pentetic Acid) -> CIR (Cosmetic Ingredient Review)

Chelating

SolubilityHighly soluble
Boiling PointDecomposes
Melting Point · 2 items

219-220 ºC

219 °C

Physical Description · 2 items

CBI; Dry Powder

White to off-white solid; [Acros Organics MSDS]

Dissociation Constantspentabasic (1.5-10.6)
Collision Cross Section180.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Boiling point
721.1 · 721.1±60.0 °C(Predicted)
Density
1.545 · 1.545±0.06 g/cm3(Predicted)
pka
1.48 · 1.48±0.10(Predicted)
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
319 · H319-H332-H361fd-H373
Precautionary statements
202 · P202-P260-P264-P304+P340+P312-P305+P351+P338-P308+P313

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P203, P260, P261, P264+P265, P271, P280, P304+P340, P305+P351+P338, P317, P318, P319, P337+P317, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.3% (7 of 530) of reports.

Danger

H319 (98.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Hazard information

Regulatory Information · 5 items

Chemical: Glycine, N,N-bis[2-[bis(carboxymethyl)amino]ethyl]-

Hazard Traits - Reproductive Toxicity

Glycine, N,N-bis[2-[bis(carboxymethyl)amino]ethyl]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Glycine, N,N-bis[2-[bis(carboxymethyl)amino]ethyl]- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: N-carboxymethyliminobis(ethylenenitrilo)tetra(acetic acid) (EC: 200-652-8)

Pentetic acid: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

The calcium salt causes fetal death and teratogenic effects in mice (thought to be associated with the chelation of essential divalent cations such as zinc); [REPROTOX] Causes convulsions and chronic pulmonary edema in intraperitoneal lethal-dose studies of rats (LD50 = 587 mg/kg); [RTECS] An eye irritant; [Acros Organics MSDS] See Edetic acid.

Hazard Classes and Categories · 4 items

Eye Irrit. 2 (98.7%)

Acute toxicity (inhalation) - category 4

Acute toxicity (Inhalation: Dusts and mists) - Category 4

Repr. 1B

Safety & protection

Protective Action Criteria (PAC) · 3 items

3.5 [mg/m3]

39 [mg/m3]

230 [mg/m3]

Toxicology

Adverse Effects · 1 item

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pentetic acid

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Safety data

Signal word
Warning
Symbol(GHS)
GHS07,GHS08
Hazard statements
H319-H332-H361fd-H373
Precautionary statements
P202-P260-P264-P304+P340+P312-P305+P351+P338-P308+P313

Chemistry & industry

Pharmacology

Protein BindingThe fast clearance and very short half-life of pentetic acid suggest that this compound is very unlikely to become bound to serum proteins to any significant extent. It is reported that DPTA is negligibly bound to alpha1-antitrypsin.
Pharmacodynamics · 1 item

There are reports in vivo of low stability of complexes of DPTA with uranium and neptunium which is being reported to cause deposition of the radionuclides into the tissues. In the case of plutonium, some preclinical studies have shown a very high urine elimination efficacy 1 hour after initial contamination. This efficacy is conserved for approximately 24 hours while the radiocontaminant is circulating. When the radionuclide is inhaled, it has been reported a DPTA-induced reduction of even 98% of the lung deposits. It is important to consider that pentetic acid can bind directly to other trace metals in the body which can cause deficiencies.

Mechanism of Action · 1 item

The calcium and zinc trisodium salts of DTPA achieve the therapeutical potential by exchanging calcium and zinc cations with transuranic radionuclides to form higher affinity complexes and then promote their elimination by glomerular filtration into the urine. DTPA as an acid acts in a very similar way by sequestering ions with its eight coordinate bond forming sites.

Biological Half-LifeIn preclinical studies, DTPA has been shown to present a very short half-life of 18.5-31.8 min after intravenous administration.
Metabolism/MetabolitesPentetic acid and its derivatives present a very minimal metabolism in the body.
FDA Pharmacological Classification · 6 items

7A314HQM0I

PENTETIC ACID

Mechanisms of Action [MoA] - Lead Chelating Activity

Established Pharmacologic Class [EPC] - Lead Chelator

Pentetic acid is a Lead Chelator. The mechanism of action of pentetic acid is as a Lead Chelating Activity.

KIT FOR THE PREPARATION OF TECHNETIUM TC 99M PENTETATE

MeSH Pharmacological Classification · 3 items

Agents counteracting or neutralizing the action of POISONS.

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.

Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems.

Absorption, Distribution and Excretion · 4 items

DTPA and its trisodium salts present a very poor bioavailability after oral administration. Therefore, the normal administration of DTPA is done by slow intravenous infusion or inhalation with a nebulizer. When inhaled, the absorption is of about 20% of the administered dose.

DTPA metal complexes are quickly excreted in the urine.It is predominantly excreted by the kidney and it is not excreted by non-renal routes to any significant extent.

The volume of distribution of DPTA is 17 L.

Pentetic acid presents a very rapid blood clearance which explains for the short half-life. The reported clearance rate in patients with normal renal function is 80-120ml/min.

Uses & manufacturing

Uses · 3 items

CIR ingredient: Pentetic Acid

Used as a chelating agent; [Merck Index] An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium. [ChemIDplus] Used in cosmetic products, in industrial metal extraction, and therapeutically; [ExPub: TERIS]

Metal Extraction and Refining [Category: Industry]

U.S. Production2023: 100,000 - <250,000 lb
Consumer UsesIon exchange agent
Industry UsesIon exchange agent
Household ProductsInformation on 55 consumer products that contain Diethylenetriaminepentaacetic acid (DTPA) in the following categories is provided:
Use ClassificationCosmetics -> Chelating
General Manufacturing Information · 2 items

CBI

Glycine, N,N-bis[2-[bis(carboxymethyl)amino]ethyl]-: ACTIVE

Related reactions

33 records
New reaction record
HRID 5299 reaction equation
HRID 5299As reactantuspto-grants-1993_09
HRID 41801 reaction equation
HRID 41801As reactantuspto-grants-2013_09
HRID 344976 reaction equation
HRID 344976As reactantuspto-grants-1991_10
HRID 375990 reaction equation
HRID 375990As reactantuspto-grants-1996_01
HRID 486811 reaction equation
HRID 486811As reactantuspto-grants-1994_03
HRID 727479 reaction equation
HRID 727479As reactantuspto-grants-1998_01
HRID 990030 reaction equation
HRID 990030As reactantuspto-grants-2002_10
HRID 992579 reaction equation
HRID 992579As reactantuspto-grants-2002_10
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Compound notes

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