PENTETATE ZINC

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H18N3O10.Zn.3H
Molecular Weight	456.74
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H+].[H+].[H+].[Zn++].[O-]C(=O)CN(CCN(CC([O-])=O)CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O

InChI

InChIKey=UVJDUBUJJFBKLD-UHFFFAOYSA-L

InChI=1S/C14H23N3O10.Zn/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);/q;+2/p-2

HIDE SMILES / InChI

Molecular Formula	Zn
Molecular Weight	65.409
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H
Molecular Weight	1.0079
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C14H18N3O10
Molecular Weight	388.3068
Charge	-5
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18830865 | https://www.truthinaging.com/ingredients/pentasodium-pentetatehttp://www.accessdata.fda.gov/drugsatfda_docs/label/2004/021749lbl.pdf
Curator's Comment: description was created based on several sources, including: https://www.federalregister.gov/articles/2011/08/19/2011-21227/determination-that-pentetate-calcium-trisodium-trisodium-calcium-diethylenetriaminepentaacetate

Pentetate calcium trisodium is also known as trisodium calcium diethylenetriaminepentaacetate and is commonly referred to as Ca-DTPA is indicated for treatment of individuals with known or suspected internal contamination with plutonium, americium, or curium to increase the rates of elimination. It is a white, water-soluble solid. It has a molecular formula of Na3CaC14H18N3O10 and a molecular weight of 497.4 Daltons. Ca-DTPA is supplied as a clear, colorless, hyperosmolar (1260 mOsmol/kg) solution in a colorless ampoule containing 5 mL. The ampoule contents are sterile, non-pyrogenic and suitable for intravenous administration. Each mL of solution contains the equivalent of 200 mg pentetate calcium trisodium (obtained from 158.17 mg pentetic acid, 40.24 mg calcium carbonate and NaOH) in water for injection, USP. The pH of the solution is adjusted with NaOH and is between 7.3 - 8.3. Ca-DTPA forms stable chelates with metal ions by exchanging calcium for a metal of greater binding capacity. The radioactive chelates are then excreted by glomerular filtration into the urine. In animal studies, Ca-DTPA forms less stable chelates with uranium and neptunium in vivo resulting in the deposition of these elements in tissues including the bone. The Food and Drug Administration (FDA) has determined that PENTETATE CALCIUM TRISODIUM (trisodium calcium diethylenetriaminepentaacetate (Ca-DTPA)) solution for intravenous or inhalation administration, equivalent to (EQ) 1 gram (g) base/5 milliliters (mL) (EQ 200 milligrams (mg) base/mL) was not withdrawn from sale for reasons of safety or effectiveness. This determination will allow FDA to approve abbreviated new drug applications (ANDAs) for PENTETATE CALCIUM TRISODIUM (Ca-DTPA) solution for intravenous or inhalation administration (EQ 1 g base/5 mL (EQ 200 mg base/mL)), if all other legal and regulatory requirements are met. Ca-DTPA treatments are not expected to be effective for uranium and neptunium. Radioactive iodine is not bound by DTPA

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metallic ions 7 Target ID: Metallic ions Sources: https://www.ncbi.nlm.nih.gov/pubmed/18830865	Chelating Agent 142
Radioactive metals 7 Target ID: CHEMBL2366037 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/021749lbl.pdf	Chelating Agent 142

Conditions

Condition	Modality	Highest Phase	Product
Acne 98 Sources: https://www.drugs.com/otc/110273/dermaklear-akne-treatment-with-sulfur.html	Inactive ingredient	Approved 8429	DermaKlear Akne Treatment with Sulfur Approved Use Uses for the treatment of acne. Dries acne blemishes and allows skin to heal. Helps prevent new acne blemishes from forming. Launch Date 1940
Contamination with plutonium, americium, or curium 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/021749lbl.pdf	Diagnostic	Withdrawn	PENTETATE CALCIUM TRISODIUM Approved Use Ca-DTPA is indicated for treatment of individuals with known or suspected internal contamination with plutonium, americium, or curium to increase the rates of elimination. Launch Date 2004
Internal contamination with plutonium, americium, or curium 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021751s008lbl.pdf	Palliative	Approved 8429	PENTETATE ZINC TRISODIUM Approved Use Pentetate zinc trisodium injection is a radiomitigation chelator indicated for treatment of individuals with known or suspected internal contamination with plutonium, americium, or curium to increase the rates of elimination. Launch Date 2004

C_max

Value	Dose	Co-administered	Analyte	Population
1.6 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16257469/	29.4 μmol/kg single, intravenous dose: 29.4 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PENTETIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
0.007 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16257469/	29.4 μmol/kg single, intravenous dose: 29.4 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PENTETIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.53 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16257469/	29.4 μmol/kg single, intravenous dose: 29.4 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PENTETIC ACID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.5 g 1 times / day multiple, subcutaneous (starting) Dose: 0.5 g, 1 times / day Route: subcutaneous Route: multiple Dose: 0.5 g, 1 times / day Co-administed with:: Zinc sulphate(200 mg two to five times daily) Sources: https://pubmed.ncbi.nlm.nih.gov/2923478	unhealthy, 5-20 years) n = 5 Health Status: unhealthy Condition: homozygous beta thalassaemia Age Group: 5-20 years) Sex: M+F Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/2923478	Sources: https://pubmed.ncbi.nlm.nih.gov/2923478
4 g 1 times / day multiple, intramuscular Overdose Dose: 4 g, 1 times / day Route: intramuscular Route: multiple Dose: 4 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021749s008lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021749s008lbl.pdf	Other AEs: Hemochromatosis... Other AEs: Hemochromatosis (grade 5, 3 patients) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021749s008lbl.pdf

AEs

AE	Significance	Dose	Population
Hemochromatosis	grade 5, 3 patients	4 g 1 times / day multiple, intramuscular Overdose Dose: 4 g, 1 times / day Route: intramuscular Route: multiple Dose: 4 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021749s008lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021749s008lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:35739	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:35739
ChemicalBook	CB5303977	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5303977
MolPort	MolPort-002-324-582	https://www.molport.com/shop/molecule-link/MolPort-002-324-582
ZINC	ZINC000019419017	http://zinc15.docking.org/substances/ZINC000019419017
eMolecules	497513	https://www.emolecules.com/cgi-bin/more?vid=497513

PubMed

Title	Date	PubMed
Towards the characterisation of heavy metals in dredged canal sediments and an appreciation of 'availability': two examples from the UK.	2001	11428147
Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone.	2001	11355772
Blood-pool scintigraphic diagnosis of fractured lumbar vertebral hemangioma.	2001 Apr	11392297
In vivo evaluation of bismuth-labeled monoclonal antibody comparing DTPA-derived bifunctional chelates.	2001 Apr	11385960
Mechanism of lipid peroxidation photosensitized by tiaprofenic acid: product studies using linoleic acid and 1,4-cyclohexadienes as model substrates.	2001 Apr	11332030
Diethylenetriaminopentaacetic acid is unsuitable for long-term preservation of RBCs.	2001 Apr	11316910
Decomposition of beta-alaninediacetic acid and diethylenetriamine-pentaacetic acid by hydrogen peroxide in alkaline conditions.	2001 Apr 1	11348070
Liver targeting of interferon-beta with a liver-affinity polysaccharide based on metal coordination in mice.	2001 Aug	11454945
Albumin thiolate anion is an intermediate in the formation of albumin-S-S-homocysteine.	2001 Aug 10	11371573
Bilaminar pattern of tibial condyle cartilage layer on the fat-suppressed 3D gradient echo images: artifact or structural and biochemical difference in composition of cartilage?	2001 Feb	11358656
Inhibitors of advanced glycation end product-associated protein cross-linking.	2001 Feb 14	11341999
Metal chelators inhibit S-nitrosation of Cys beta 93 in oxyhemoglobin.	2001 Feb 28	11456789
Chelated metal ions for therapeutic and diagnostic applications.	2001 Jul	11444098
Somatostatin receptor imaging: current status and future perspectives.	2001 Jul	11438628
Buttock granulomas: a consequence of intramuscular injection of Sandostatin detected by In-111 octreoscan.	2001 Jul	11416760
Detection of cerebrospinal fluid leak by dual-isotope spect with In-111 DTPA and Tc-99m HMDP.	2001 Jul	11416747
Effects of peroxynitrite on the reactivity of diabetic rat aorta.	2001 Jul	11408833
Dynamic micro-magnetic resonance imaging of liver micrometastasis in mice with a novel liver macromolecular magnetic resonance contrast agent DAB-Am64-(1B4M-Gd)(64).	2001 Jul 1	11431325
The effect of irradiation on the biodistribution of radiolabeled pegylated liposomes.	2001 Jul 1	11395251
Lanthanide chemistry with (bis[[bis(carboxymethyl)amino]methyl]phosphinate: what does an extra phosphinate group do to EDTA?	2001 Jul 16	11442371
Avidin-dendrimer-(1B4M-Gd)(254): a tumor-targeting therapeutic agent for gadolinium neutron capture therapy of intraperitoneal disseminated tumor which can be monitored by MRI.	2001 Jul-Aug	11459464
Poly(ethylene glycol)-conjugated anti-EGF receptor antibody C225 with radiometal chelator attached to the termini of polymer chains.	2001 Jul-Aug	11459459
In vivo evaluation of 111In-DTPA-N-TIMP-2 in Kaposi sarcoma associated with HIV infection.	2001 Jun	11440037
Gastric emptying is accelerated in obese type 2 diabetic patients without autonomic neuropathy.	2001 Jun	11431601
The use of a modified technique to reduce radioactive air contamination in aerosol lung ventilation imaging.	2001 Jun	11430516
Early responses to nonconjugated polyribosylribitol phosphate challenge as evidence of immune memory after combined diphtheria-tetanus-pertussis-polio-Haemophilus influenzae type b primary vaccination.	2001 Jun	11419500
A synthetic macromolecule for sentinel node detection: (99m)Tc-DTPA-mannosyl-dextran.	2001 Jun	11390562
Scintigraphy and Doppler ultrasonography for the evaluation of obstructive urinary calculi.	2001 Jun	11378662
Biodegradability of ethylenediamine-based complexing agents.	2001 Jun	11337848
Oxidation of metal-diethylenetriaminepentaacetate (DTPA)--complexes during drinking water ozonation.	2001 Jun	11337832
Specific localization, gamma camera imaging, and intracellular trafficking of radiolabelled chimeric anti-G(D3) ganglioside monoclonal antibody KM871 in SK-MEL-28 melanoma xenografts.	2001 Jun 1	11389078
Fluorometric determination of EDTA and EGTA using terbium-salicylate complex.	2001 Jun 1	11373087
Zinc-induced activation of the human cytomegalovirus major immediate-early promoter is mediated by metallothionein and nuclear factor-kappaB.	2001 Jun 15	11437636
Multi-level disruption of the spinal nerve root sleeves in spontaneous spinal cerebrospinal fluid leakage--two case reports.	2001 Mar	11372561
The kinetics and mechanisms of the reactions of aluminium(III) with gallic acid, gallic acid methyl ester and adrenaline.	2001 Mar	11330467
Magnetic resonance imaging of a benign Brenner tumor with an ipsilateral simple cyst.	2001 May	11409485
Significance of (111)In-DTPA chelate in renal radioactivity levels of (111)In-DTPA-conjugated peptides.	2001 May	11395320
Synthesis and evaluation of a macrocyclic bifunctional chelating agent for use with bismuth radionuclides.	2001 May	11395314
Cardiovascular effects caused by rapid administration of gadoversetamide injection in anesthetized dogs.	2001 May	11394361
Relationships between chromium biomagnification ratio, accumulation factor, and mycorrhizae in plants growing on tannery effluent-polluted soil.	2001 May	11392761
Contrast agents in acute myocardial infarction.	2001 May	11390263
Rapid imaging of human melanoma xenografts using an scFv fragment of the human monoclonal antibody H11 labelled with 111In.	2001 May	11388583
Direct MR arthrography of plica synovialis mediopatellaris.	2001 May	11350286
Dysprosium-bearing red cells as potential transverse relaxation agents for MRI.	2001 May	11323820
[Should school children receive pertussis vaccine?].	2001 May 10	11449768
Storage at -3 degrees C for 24 h alters the immunogenicity of pertussis vaccines.	2001 May 14	11348721
Negatively charged polymers protect antinuclear antibody against inactivation by acylating agents.	2001 May 15	11355857
Antitumor and antiangiogenic effects of somatostatin receptor-targeted in situ radiation with (111)In-DTPA-JIC 2DL.	2001 May 15	11341788
Quantitative assays of the amount of diethylenetriaminepentaacetic acid conjugated to water-soluble polymers using isothermal titration calorimetry and colorimetry.	2001 May-Jun	11353534
Final report on the safety assessment of pentasodium pentetate and pentetic acid as used in cosmetics.	2008	18830865

Patents

Sample Use Guides

In Vivo Use Guide

Rats: The acute oral LD(50) of Pentasodium Pentetate in rats was > 5 g/kg. The acute dermal LD(50) of Pentapotassium Pentetate using rats was reported to be > 2 g/kg. The intraperitonal LD(50) of Pentetic Acid was reported to be 585 mg/kg.

Route of Administration: Other

In Vitro Use Guide

Approximately 0.1 ml of solution of Ca-DTPA (pentetate calcium trisodium) was added to the test cultures (human lymphocytes) at 3 different concentrations: 0.77, 0.077, and 0.0077 mg/ml, resulting in a final concentration in the culture medium of 13.51, 1.351, and 0.135 ug/ml, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:20:37 GMT 2023` Edited by `admin` on `Fri Dec 15 15:20:37 GMT 2023`
Record UNII	828I5G7VJ6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTETATE ZINC

Common Name

English

ZINCATE(3-), (N,N-BIS(2-(((CARBOXY-.KAPPA.O)METHYL)(CARBOXYMETHYL)AMINO-.KAPPA.N)ETHYL)GLYCINATO(5-)-.KAPPA.N,.KAPPA.O)-, HYDROGEN (1:3)

Systematic Name

English

ZNDTPA

Common Name

English

ZINC, (((CARBOXYMETHYLIMINO)BIS(ETHYLENENITRILO))TETRAACETATO)-

Common Name

English

GLYCINE, N,N-BIS(2-(BIS(CARBOXYMETHYL)AMINO)ETHYL)-, ZINC COMPLEX

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C62357