TETRAXETAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H28N4O8
Molecular Weight	404.4155
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1

InChI

InChIKey=WDLRUFUQRNWCPK-UHFFFAOYSA-N

InChI=1S/C16H28N4O8/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28)

HIDE SMILES / InChI

Molecular Formula	C16H28N4O8
Molecular Weight	404.4155
Charge	0
Count

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

Description
Sources: http://www.nbcnews.com/id/42859142/ns/business-press_releases/t/results-single-dose-escalation-study-y--clivatuzumab-tetraxetan-advanced-pancreatic-cancer-published/
Curator's Comment: description was created based on several sources, including http://www.immunomedics.com/clivatuzumab-demo.shtml http://www.ncbi.nlm.nih.gov/pubmed/21527562 https://www.ncbi.nlm.nih.gov/pubmed/10717908

Tetraxetan (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (also known as DOTA) is used as a complexing agent. Its complexes have medical applications as contrast agents and cancer treatments. DOTA can be conjugated to monoclonal antibodies by attachment of one of the four-carboxyl groups as an amide. The modified antibody accumulates in the tumour cells, concentrating the effects of the radioactivity of 90Y. DOTA can also be linked to molecules that have an affinity for various structures. The resulting compounds are used with a number of radioisotopes in cancer therapy and diagnosis. Clivatuzumab tetraxetan is a humanized monoclonal antibody targeting a mucin antigen expressed in most pancreatic cancers, but not pancreatitis, normal pancreas or most other normal tissues. Preclinical studies in mice with human pancreatic cancer xenografts given the murine version of 90Y-clivatuzumab tetraxetan demonstrated favourable tumour responses, which could be further improved when given in combination with gemcitabine. (64)Cu-DOTA-trastuzumab PET (positron emission tomography) could be a potential noninvasive procedure for serial identification of metastatic brain lesions in patients with HER2-positive breast cancer. 90Y-DOTA-biotin may have the application of pre-targeted radioimmunotherapy for the treatment of advanced colorectal cancer in humans.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
mucin antigen of pancreatic cancers 1 Target ID: mucin antigen of pancreatic cancers Sources: http://www.nbcnews.com/id/42859142/ns/business-press_releases/t/results-single-dose-escalation-study-y--clivatuzumab-tetraxetan-advanced-pancreatic-cancer-published/	Binding Agent 1076

Conditions

Condition	Modality	Highest Phase	Product
Pancreatic cancer 98 Sources: http://www.immunomedics.com/clivatuzumab-demo.shtml	Diagnostic	Phase III 665	90Y Clivatuzumab Tetraxetan Approved Use Unknown
Breast cancer 432 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25853014	Diagnostic	Phase I 438	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10717908	Diagnostic	Basic research	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00E9AT	https://www.1pchem.com/search?query=1P00E9AT
A2B Chem	AG64437	http://a2bchem.com/prod/AG64437
AK Scientific	9614AL	https://aksci.com/item_detail.php?cat=9614AL
AK Scientific	Y0481	https://aksci.com/item_detail.php?cat=Y0481
Ambeed	A349340	http://www.ambeed.com/search/Search.html?keyword=A349340
AstaTech	F16414	http://astatechinc.com/CPSResult.php?CRNO=F16414
BioSynth	J-650232	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-650232
BOC Sciences	60239-18-1	http://www.bocsci.com/description.asp?cas=60239-18-1
Chem Scene	CS-0046228	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0046228
Chemik	CHO0208	http://www.chemik.com/cgi/search-en.cgi?f=product_en+product_en1+company_en_1_&t=product_en7&w=product_en&terms=CHO0208
ChemShuttle	185795	https://www.chemshuttle.com/catalogsearch/result/?q=185795
Combi-Blocks	QJ-1739	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-1739
Creative Peptides	M34140617H	https://www.creative-peptides.com/search?q=M34140617H
eMolecules	110010545	https://orderbb.emolecules.com/search/#?query=110010545
eMolecules	260152308	https://orderbb.emolecules.com/search/#?query=260152308
eMolecules	46008203	https://orderbb.emolecules.com/search/#?query=46008203
eMolecules	531948	https://orderbb.emolecules.com/search/#?query=531948
eNovation Chemicals	D660861	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D660861&searchbtn.x=0&searchbtn.y=0
Hairui	HR114495	http://www.hairuichem.com/en/product/search.do?q=HR114495
KeyOrganics	AS-19566	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-19566
Lab Seeker	SC-73832	http://www.labseeker.com/search.php?keywords=SC-73832&category=0
Lab Seeker	SC-97988	http://www.labseeker.com/search.php?keywords=SC-97988&category=0
LabSeeker	SC-73832	http://www.labseeker.com/search.php?keywords=SC-73832&category=0
mcule	MCULE-9183319653	https://mcule.com/MCULE-9183319653/
MolPort	MolPort-003-939-477	https://www.molport.com/shop/molecule-link/MolPort-003-939-477
MuseChem	M009883	https://www.musechem.com/product/M009883.html
MuseChem	M136656	https://www.musechem.com/product/M136656.html
MuseChem	R016824	https://www.musechem.com/product/R016824.html
MuseChem	R043795	https://www.musechem.com/product/R043795.html
PI Chemicals	PI-39541	http://www.pipharm.com/catalog_products/PI-39541.html
Princeton BioMolecular Research	PBMR121272	http://www.princetonbio.com/order_online?common_id=PBMR121272
ShangHai Biochempartner	BCP13075	http://www.biochempartner.com/search_BCP13075
Synthonix	T61786	https://synthonix.com/catalogsearch/result/?q=T61786
Tetrahedron	TS69406	http://www.thsci.com/search.do?q=TS69406
Toronto Research Chemicals	D535500	https://www.trc-canada.com/product-detail/?CatNum=D535500
Toronto Research Chemicals	I775000	https://www.trc-canada.com/product-detail/?CatNum=I775000
W&J PharmaChem	50C489226	http://wjpharmachem.com/new/searcht.php?keyword=50C489226
Wonderchem	WD03SJM	http://www.wonder-chem.com/search.html?text=WD03SJM

PubMed

Title	Date	PubMed
Relaxometric and solution NMR structural studies on ditopic lanthanide(III) complexes of a phosphinate analogue of DOTA with a fast rate of water exchange.	2006-05-21	16688320
Radiolanthanide-labeled monoclonal antibody CC49 for radioimmunotherapy of cancer: biological comparison of DOTA conjugates and 149Pm, 166Ho, and 177Lu.	2006-03-16	16536481
Internalization of sst2, sst3, and sst5 receptors: effects of somatostatin agonists and antagonists.	2006-03	16513620
Non-invasive temperature imaging with thulium 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethyl-1,4,7,10-tetraacetic acid (TmDOTMA-).	2006-02	16404728
Density-functional theory structures of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid complexes for ions across the lanthanide series.	2005-12-22	16396532
A bisphosphonate monoamide analogue of DOTA: a potential agent for bone targeting.	2005-11-30	16305234
Structural and chiroptical properties of the two coordination isomers of YbDOTA-type complexes.	2005-11-14	16270977
Regressive DOTA labelling performance with indium-111 and yttrium-90 over a week of use.	2005-11	16142470
Blood pharmacokinetics of various monoclonal antibodies labeled with a new trifunctional chelating reagent for simultaneous conjugation with 1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid and biotin before radiolabeling.	2005-10-01	16203818
Does paclitaxel (Taxol) given after (111)In-labeled monoclonal antibodies increase tumor-cumulated activity in epithelial cancers?	2005-10-01	16203816
Determining maximal tolerable dose of the monoclonal antibody BR96 labeled with 90Y or 177Lu in rats: establishment of a syngeneic tumor model to evaluate means to improve radioimmunotherapy.	2005-10-01	16203809
Development of tumor targeting bioprobes ((111)In-chimeric L6 monoclonal antibody nanoparticles) for alternating magnetic field cancer therapy.	2005-10-01	16203807
On-resonance low B1 pulses for imaging of the effects of PARACEST agents.	2005-09	15979362
Spectral properties of pro-multimodal imaging agents derived from a NIR dye and a metal chelator.	2005-08-27	16120005
Derivatization of phosphopeptides with mercapto- and amino-functionalized conjugate groups by phosphate elimination and subsequent Michael addition.	2005-08-21	16186937
High-dose radioimmunotherapy combined with fixed, low-dose paclitaxel in metastatic prostate and breast cancer by using a MUC-1 monoclonal antibody, m170, linked to indium-111/yttrium-90 via a cathepsin cleavable linker with cyclosporine to prevent human anti-mouse antibody.	2005-08-15	16115934
An estradiol-conjugate for radiolabelling with 177Lu: an attempt to prepare a radiotherapeutic agent.	2005-07-01	15927837
Are gadolinium contrast agents suitable for gadolinium neutron capture therapy?	2005-06	15949236
Dendrimeric Gd(III) complex of a monophosphinated DOTA analogue: optimizing relaxivity by reducing internal motion.	2005-05-14	15877138
Gallium-68-DOTA-albumin as a PET blood-pool marker: experimental evaluation in vivo.	2005-04	15820764
MicroPET imaging of MCF-7 tumors in mice via unr mRNA-targeted peptide nucleic acids.	2005-03-17	15769082
Noninvasive MR thermometry using paramagnetic lanthanide complexes of 1,4,7,10-tetraazacyclodoecane-alpha,alpha',alpha'',alpha'''-tetramethyl-1,4,7,10-tetraacetic acid (DOTMA4-).	2005-02	15678553
Synthesis of a bifunctional monophosphinic acid DOTA analogue ligand and its lanthanide(III) complexes. A gadolinium(III) complex endowed with an optimal water exchange rate for MRI applications.	2005-01-07	15602605
Medicinal chemistry of somatostatin analogs leading to the DTPA and DOTA conjugates of the multi-receptor-ligand SOM230.	2005	16625840
Synthesis of novel polydiamidopropanoate dendrimer PNA-peptide chimeras for non-invasive magnetic resonance imaging of cancer.	2005	16247963
Lanthanide(III) complexes of DOTA-glycoconjugates: a potential new class of lectin-mediated medical imaging agents.	2004-11-05	15472943
Quantitation and visualization of tumor-specific T cells in the secondary lymphoid organs during and after tumor elimination by PET.	2004-11	15607484
Complexing mechanism of the lanthanide cations Eu3+, Gd3+, and Tb3+ with 1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane (dota)-characterization of three successive complexing phases: study of the thermodynamic and structural properties of the complexes by potentiometry, luminescence spectroscopy, and EXAFS.	2004-10-11	15372580
177Lu-DOTA-lanreotide: a novel tracer as a targeted agent for tumor therapy.	2004-08	15246366
68Ga-labelled DOTA-derivatised peptide ligands.	2004-08	15029459
Conjugates of gadolinium complexes to bile acids as hepatocyte-directed contrast agents for magnetic resonance imaging.	2004-07-01	15214790
An image worth a thousand lives?	2004-06	15175685
Imaging the pharmacodynamics of HER2 degradation in response to Hsp90 inhibitors.	2004-06	15133471
Microwave-supported preparation of (68)Ga bioconjugates with high specific radioactivity.	2004-05-20	15149183
Solution dynamics and stability of lanthanide(III) (S)-2-(p-nitrobenzyl)DOTA complexes.	2004-05-03	15106971
Novel gadolinium(III) polyaminocarboxylate macrocyclic complexes as potential magnetic resonance imaging contrast agents.	2004-05	15134912
90Y and 111In complexes of a DOTA-conjugated integrin alpha v beta 3 receptor antagonist: different but biologically equivalent.	2004-03-18	15025518
Radioimmunotherapy of prostate cancer in human xenografts using monoclonal antibodies specific to prostate specific membrane antigen (PSMA): studies in nude mice.	2004-02-01	14716739
Conformation and structure of polymeric contrast agents for medical imaging.	2004-01-13	14715008
Generation of DOTA-conjugated antibody fragments for radioimmunoimaging.	2004	15120256
Production and applications of copper-64 radiopharmaceuticals.	2004	15120255
Synthesis, characterization, and X-ray crystal structure of In(DOTA-AA) (AA = p-aminoanilide): a model for 111In-labeled DOTA-biomolecule conjugates.	2003-12-29	14686864
Radioimmunotherapy of non-Hodgkin's lymphoma with 90Y-DOTA humanized anti-CD22 IgG (90Y-Epratuzumab): do tumor targeting and dosimetry predict therapeutic response?	2003-12	14660727
Synthesis of radiometal-labeled and fluorescent cell-permeating peptide-PNA conjugates for targeting the bcl-2 proto-oncogene.	2003-11-20	14624621
pH-sensitive modulation of the second hydration sphere in lanthanide(III) tetraamide-DOTA complexes: a novel approach to smart MR contrast media.	2003-10-06	14566868
Radiolabeled alpha-melanocyte-stimulating hormone analogs for receptor-mediated targeting of melanoma: from tritium to indium.	2003-10-03	14523936
PARACEST agents: modulating MRI contrast via water proton exchange.	2003-10	14567712
Enhanced therapeutic index of radioimmunotherapy (RIT) in prostate cancer patients: comparison of radiation dosimetry for 1,4,7,10-tetraazacyclododecane-N,N',N",N"'-tetraacetic acid (DOTA)-peptide versus 2IT-DOTA monoclonal antibody linkage for RIT.	2003-09-01	14506192
Synthesis and visualization of a membrane-permeable MRI contrast agent.	2003-09	14505078
Towards the rational design of magnetic resonance imaging contrast agents: isolation of the two coordination isomers of lanthanide DOTA-type complexes.	2003	14673928

Patents

Sample Use Guides

In Vivo Use Guide

Gd-DOTA: was injected intravenously at 0.1 mmol/kg over approximately 2 minutes 90Y-Clivatuzumab Tetraxetan: 15, 20, and 25 mCi/m(2)

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:12 GMT 2025`
Record UNII	1HTE449DGZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAXETAN

Official Name

English

DOT-A

Preferred Name

English

DOTA

Code

English

2,2',2'',2'''-(1,4,7,10-TETRAAZACYCLODODECANE-1,4,7,10-TETRYL)TETRAACETIC ACID

Systematic Name

English

TETRAXETAN [USP MONOGRAPH]

Common Name

English

NSC-681107

Code

English

DOTA [MI]

Common Name

English

TETRAXETAN [USP-RS]

Common Name

English

DOTA ACID

Common Name

English

1,4,7,10-TETRAAZACYCLODODECANE-1,4,7,10-TETRAACETIC ACID

Systematic Name

English

tetraxetan [INN]

Common Name

English

1,4,7,10-TETRAAZACYCLODODECANE-N,N',N'',N'''-TETRAACETIC ACID

Systematic Name

English

TETRAXETAN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C360