Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB14007
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 5
- Phase 2
- 20
- Phase 3
- 42
- Phase 4
- 9
- Mechanism of Action
- Transuranium elementsChelator
- Transuranium elements
Identification
- Generic Name
- Pentetic acid
- DrugBank Accession Number
- DB14007
- Background
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.1 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.6 DPTA was developed by the pharmaceutical company CIS US and FDA approved on April 14, 2004.8
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pentetic acid (DB14007)
- Weight
- Average: 393.349
Monoisotopic: 393.138343953 - Chemical Formula
- C14H23N3O10
- Synonyms
- Diethylene triamine pentaacetic acid
- Diethylenetriamine pentaacetic acid
- Diethylenetriaminepentaacetate
- Diethylenetriaminepentaacetic acid
- DTP-A
- DTPA
- Pentetate
- Pentetic acid
Pharmacology
- Indication
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.1 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.7
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.4
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Internal contamination with americium •••••••••••• Treatment of Internal contamination with curium •••••••••••• Treatment of Internal contamination with plutonium •••••••••••• - Contraindications & Blackbox Warnings
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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.5 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.3
- Mechanism of action
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.1
Target Actions Organism ATransuranium elements chelatorHumans - Absorption
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.1 When inhaled, the absorption is of about 20% of the administered dose.3
- Volume of distribution
The volume of distribution of DPTA is 17 L.4
- Protein binding
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.2 It is reported that DPTA is negligibly bound to alpha1-antitrypsin.4
- Metabolism
Pentetic acid and its derivatives present a very minimal metabolism in the body.3
- Route of elimination
DTPA metal complexes are quickly excreted in the urine.7It is predominantly excreted by the kidney and it is not excreted by non-renal routes to any significant extent.4
- Half-life
In preclinical studies, DTPA has been shown to present a very short half-life of 18.5-31.8 min after intravenous administration.
- Clearance
Pentetic acid presents a very rapid blood clearance which explains for the short half-life.2 The reported clearance rate in patients with normal renal function is 80-120ml/min.4
- Adverse Effects
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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.2
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Pentetic acid which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Pentetic acid which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Pentetic acid which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Pentetic acid which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Pentetic acid which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pentetate calcium trisodium G79YN26H5B 12111-24-9 AYFCVLSUPGCQKD-UHFFFAOYSA-I Pentetate zinc trisodium NXU65IC8PG 11082-38-5 HVASDHJNLYRZEA-UHFFFAOYSA-I - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Draximage Dtpa Injection, powder, lyophilized, for solution 20 mg/1 Intravenous; Respiratory (inhalation) Jubilant DraxImage Inc., dba Jubilant Radiopharma 1989-12-29 Not applicable US 
Kit for the Preparation of Technetium Tc 99m Pentetate Injection Injection 20.6 mg/10mL Intravenous Pharmalucence, Inc. 1976-11-16 2010-08-02 US Pentetate calcium trisodium Injection, solution, concentrate 1000 mg/5mL Intravenous; Respiratory (inhalation) hameln pharma gmbh 2004-08-11 2026-05-31 US Pentetate Calcium Trisodium Injection, solution, concentrate 200 mg/1mL Intravenous; Respiratory (inhalation) hameln pharma gmbh 2006-12-18 Not applicable US Pentetate Zinc Trisodium Injection, solution, concentrate 200 mg/1mL Intravenous; Respiratory (inhalation) hameln pharma gmbh 2006-12-18 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image INDIO (111IN) DTPA CURIUM NETHERLANDS Pentetic acid (0.1 mg/ml) + Indium In-111 chloride (37 MBQ/ML) Injection, solution Intrathecal Curium Netherlands B.V. 2019-05-23 Not applicable Italy 
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Pentacarboxylic acids and derivatives
- Direct Parent
- Pentacarboxylic acids and derivatives
- Alternative Parents
- Alpha amino acids / Trialkylamines / Amino acids / Carboxylic acids / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / Organic nitrogen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- pentacarboxylic acid (CHEBI:35739)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7A314HQM0I
- CAS number
- 67-43-6
- InChI Key
- QPCDCPDFJACHGM-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H23N3O10/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27)
- IUPAC Name
- 2-[bis({2-[bis(carboxymethyl)amino]ethyl})amino]acetic acid
- SMILES
- OC(=O)CN(CCN(CC(O)=O)CC(O)=O)CCN(CC(O)=O)CC(O)=O
References
- General References
- Yang YT, Di Pasqua AJ, Zhang Y, Sueda K, Jay M: Solid dispersions of the penta-ethyl ester prodrug of diethylenetriaminepentaacetic acid (DTPA): formulation design and optimization studies. Pharm Dev Technol. 2014 Nov;19(7):806-12. doi: 10.3109/10837450.2013.836216. Epub 2013 Sep 19. [Article]
- Harrington KJ, Rowlinson-Busza G, Syrigos KN, Uster PS, Abra RM, Stewart JS: Biodistribution and pharmacokinetics of 111In-DTPA-labelled pegylated liposomes in a human tumour xenograft model: implications for novel targeting strategies. Br J Cancer. 2000 Jul;83(2):232-8. doi: 10.1054/bjoc.1999.1232. [Article]
- Abe T: [Pharmacological properties and clinical efficacy of pentetate calcium trisodium and pentetate zinc trisodium, antidotes for transuranium elements]. Nihon Yakurigaku Zasshi. 2012 Jan;139(1):33-8. [Article]
- Reilly R. (2013). The fundamental principles of compartmental pharmacokinetics illustrated by radiopharmaceuticals commonly used in nuclear medicine. ACPE.
- Zhou H. and Theil F. (2016). ADME amd translational pharmacokinetics/pharmacodynamics of therapeutic proteins. John Wiley & Sons.
- FDA Inactive ingredient search [Link]
- FDA guidelines [Link]
- FDA orphan list [Link]
- External Links
- FDA label
- Download (204 KB)
- MSDS
- Download (232 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Diagnostic Hepatic Metastases / Hepatocellular Carcinoma / Liver and Intrahepatic Bile Duct Disorder / Primary Malignant Liver Neoplasm 1 somestatus stop reason just information to hide Not Available Completed Not Available Acellular Pertussis / Diphtheria / Poliomyelitis / Tetanus / Viral Hepatitis B 1 somestatus stop reason just information to hide Not Available Completed Not Available Acellular Pertussis / Diphtheria / Tetanus 1 somestatus stop reason just information to hide Not Available Completed Not Available Diphtheria-Tetanus-acellular Pertussis Vaccines 1 somestatus stop reason just information to hide Not Available Completed Not Available Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intravenous; Respiratory (inhalation) 20 mg/1 Injection, solution Intrathecal Injection Intravenous 20.6 mg/10mL Injection, powder, lyophilized, for solution Intravenous 7.8 mg Injection, powder, lyophilized, for solution Intravenous; Oral; Respiratory (inhalation) 9.1 mg Injection, solution, concentrate Intravenous; Respiratory (inhalation) 1000 mg/5mL Injection, solution, concentrate Intravenous; Respiratory (inhalation) 200 mg/1mL Injection Intravenous 20 mg/1 Injection, powder, lyophilized, for solution Intravenous 10 mg Pellet Intravenous; Oral; Respiratory (inhalation) Injection, solution Intravenous 20.8 mg Injection, powder, for solution Intravenous 20.8 mg Injection, powder, lyophilized, for solution Intravenous 20.8 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 219-220 ºC Zhang, et al. AAPS J. (2013) boiling point (°C) Decomposes 'MSDS' water solubility Highly soluble Zhang, et al. AAPS J. (2013) logP -4.90 Zhang, et al. AAPS J. (2013) pKa pentabasic (1.5-10.6) BASF techinical information - Predicted Properties
Property Value Source Water Solubility 4.18 mg/mL ALOGPS logP -1.3 ALOGPS logP -6.3 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 1.95 Chemaxon pKa (Strongest Basic) 8.82 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 196.22 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 86.45 m3·mol-1 Chemaxon Polarizability 36.41 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002f-0009000000-b74955a728239ccd85df Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001r-0495000000-a5bf8c7ef981d61cfcf2 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0955000000-9b5f74405a6673ac169e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f8a-1119000000-d363fd27de378da6d77c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ik9-1900000000-81faf714f168ca9e84b3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a59-0900000000-8521e3bfad9bcc2355eb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.80211 predictedDeepCCS 1.0 (2019) [M+H]+ 185.16011 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.50816 predictedDeepCCS 1.0 (2019)
Targets
References
- Yang YT, Di Pasqua AJ, Zhang Y, Sueda K, Jay M: Solid dispersions of the penta-ethyl ester prodrug of diethylenetriaminepentaacetic acid (DTPA): formulation design and optimization studies. Pharm Dev Technol. 2014 Nov;19(7):806-12. doi: 10.3109/10837450.2013.836216. Epub 2013 Sep 19. [Article]
- FDA guidelines [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Inhibitor of serine proteases. Its primary target is elastase, but it also has a moderate affinity for plasmin and thrombin. Irreversibly inhibits trypsin, chymotrypsin and plasminogen activator. The aberrant form inhibits insulin-induced NO synthesis in platelets, decreases coagulation time and has proteolytic activity against insulin and plasmin
- Specific Function
- identical protein binding
- Gene Name
- SERPINA1
- Uniprot ID
- P01009
- Uniprot Name
- Alpha-1-antitrypsin
- Molecular Weight
- 46736.195 Da
References
- Reilly R. (2013). The fundamental principles of compartmental pharmacokinetics illustrated by radiopharmaceuticals commonly used in nuclear medicine. ACPE.
Drug created at April 10, 2018 16:42 / Updated at February 21, 2021 18:54