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Home > Encyclopedia > Diethylenetriaminepentaacetic acid

Diethylenetriaminepentaacetic acid

pharmaceutical raw materials
Diethylenetriaminepentaacetic acid structure

Diethylenetriaminepentaacetic acid 

structure
  • CAS No:

    67-43-6

  • Formula:

    C14H23N3O10

  • Chemical Name:

    Diethylenetriaminepentaacetic acid

  • Synonyms:

    Glycine,N,N-bis[2-[bis(carboxymethyl)amino]ethyl]-;N,N-Bis[2-[bis(carboxymethyl)amino]ethyl]glycine;[[(Carboxymethyl)imino]bis(ethylenenitrilo)]tetraacetic acid;Chel 330 acid;1,1,4,7,7-Diethylenetriaminepentaacetic acid;Monaquest CAI;3,6,9-Triazaundecanedioic acid,3,6,9-tris(carboxymethyl)-;Acetic acid,2,2′,2′′,2′′′-[[(carboxymethyl)imino]bis(2,1-ethanediylnitrilo)]tetrakis-;Diethylenetriamine-N,N,N′,N′′,N′′-pentaacetic acid;DTPA;DETPA;Pentetic acid;Pentacarboxymethyl diethylenetriamine;Detarex;Diethylenetriaminepentaacetic acid;Hamp-Ex Acid;Complexon V;Dabeersen 503;DETP;Detapac;DPTA;Titriplex V;Clewat DA;Chel DTPA;Dissolvine D;NSC 7340;25: PN: WO2013046163 PAGE: 13 claimed sequence;Trilon CS;Chelest 3PA;Chelest PA;[(2-[[2-(Bis-carboxymethyl-amino)-ethyl]-carboxymethyl-amino]-ethyl)-carboxymethyl-amino]-acetic acid;2-[Bis[2-[bis(carboxymethyl)amino]ethyl]amino]acetic acid;Chelest PA-SD;D 1;6889-50-5;7575-40-8;13407-13-1;25737-54-6;49758-21-6;84932-15-0;573987-64-1;782415-12-7;803683-39-8

  • Categories:

    Cosmetic Ingredient  >  Chelating

Description

solid Pentetic acid occurs as a white crystalline solid and is almost odorless. Diethylenetriaminepentaacetic acid is a solid.


DryPowder


Pentetic acid is a pentacarboxylic acid. It has a role as a copper chelator. It is a conjugate acid of a pentetate(1-).|Pentetic acid, also known as diethylenetriaminepentaacetic acid (DTPA), is a synthetic polyamino carboxylic acid with eight coordinate bond forming sites that can sequester metal ions and form highly stable DTPA-metal ion complexes. DTPA, along with its calcium and zinc trisodium salts, are the only FDA approved agents for the treatment of internal contamination by transuranics. It is currently considered, in all the dosage forms, as a member of the list of approved inactive ingredients for drug products by the FDA. DPTA was developed by the pharmaceutical company CIS US and FDA approved on April 14, 2004.|Pentetic acid is a Lead Chelator. The mechanism of action of pentetic acid is as a Lead Chelating Activity.|Pentetic Acid is an edetate and a chelating agent used in preparing radiopharmaceuticals. Pentetic acid (DTPA) has strong affinity for iron but also shows affinities for other heavy metals, thereby is used in the treatment of iron-storage disease and poisoning from heavy and radioactive metals. DTPA may chelate metallic moieties of unbound, extracellular radioimmunotherapeutics, thereby aggregating radioimmunotherapeutics locally to higher concentrations, and improving tumor cell radiocytotoxicity, while sparing normal tissues from the radiocytotoxic effects. In addition, DTPA is used in radioimaing procedures when complexes with radioisotopes, ex., Tc 99m or In 111.|An iron chelating agent with properties like EDETIC ACID. DTPA has also been used as a chelator for other metals, such as plutonium.

Diethylenetriaminepentaacetic acid Basic Attributes

393.35

393.35

1810219

200-652-8

7A314HQM0I

759314|7340

DTXSID2023434

C460

2916190090

Characteristics

196

-8.5

White to almost white Crystalline Powder

1.56

219-220 °C(lit.)

Decomposes

200 °C

1.590

H2O: 5 g/L (20 ºC);0.1 M NaOH: 0.1 M at 20 °C, clear, colorless

-20°C

LD50 orally in Rabbit: > 2000 mg/kg

pentabasic (1.5-10.6)

pentabasic (1.5-10.6)

180.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

9

UN 3077 9/PG 3

2

36-51/53-36/37/38-20-63

26-36-61-37/39-36/37

MB8205000

Xi,N,Xn

Stable. Incompatible with strong oxidizing agents.

P281-P305 + P351 + P338

H319-H332-H361d

|Warning|H319 (99.77%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P260, P261, P264, P271, P280, P281, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P314, P337+P313, P405, and P501|Aggregated GHS information provided by 503 companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Some toxicity has been reported related to administration of pentetic acid including depletion of trace metals, kidney and liver vacuolization and small bowel hemorrhage lesions.

The 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.

Drug Information

DTPA is widely used in industry and medicine. As a medical agent, it is approved for its use in medical imaging and for the decorporation of internally deposited radionuclides. It is FDA approved for the treatment of individuals with known or suspected internal contamination with plutonium, americium or curium to increase the rates of elimination. Due to the pharmacokinetic elimination by the kidneys, pentetic acid conjugated with technetium Tc-99m is being used clinically to estimate physiological parameters such as glomerular filtration rat and effective renal plasma flow.|FDA Label

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.

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)|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. (See all compounds classified as Iron Chelating Agents.)|Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)

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.

Pentetic acid and its derivatives present a very minimal metabolism in the body.

In preclinical studies, DTPA has been shown to present a very short half-life of 18.5-31.8 min after intravenous administration.

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.

Ca-DTPA

Diethylenetriaminepentaacetic acid Use and Manufacturing

Uses

Diethylenetriaminepentaacetic Acid is a component of manganese and zinc fertilizers.


Fillers

All other basic organic chemical manufacturing|Glycine, N,N-bis[2-[bis(carboxymethyl)amino]ethyl]-: ACTIVE

Cosmetics -> Chelating

Computed Properties

Molecular Weight:393.35
XLogP3:-8.5
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:16
Exact Mass:393.13834394
Monoisotopic Mass:393.13834394
Topological Polar Surface Area:196
Heavy Atom Count:27
Complexity:481
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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