| Revision as of 17:48, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456502318 of page 3-Aminopyridine-2-carboxaldehyde_thiosemicarbazone for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 22:15, 1 November 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:2-Aminopyridines; added Category:3-Aminopyridines using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 456501177 |
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| verifiedrevid = 477218187 |
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|ImageFile=3-Aminopyridine-2-carboxaldehyde thiosemicarbazone.svg |
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| ImageFile=Triapine.svg |
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|ImageSize= |
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| ImageSize= |
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|IUPACName=3-aminopyridine-2-carbaldehyde thiosemicarbazone |
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| IUPACName=3-aminopyridine-2-carbaldehyde thiosemicarbazone |
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|OtherNames= |
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| OtherNames= 3AP, Triapine, OCX-0191 |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7846300 |
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| ChemSpiderID = 7846300 |
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| InChI = 1/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+ |
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| InChI = 1/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XMYKNCNAZKMVQN-NYYWCZLTSA-N |
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| StdInChIKey = XMYKNCNAZKMVQN-NYYWCZLTSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 236392-56-6 --> |
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| CASNo=236392-56-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=9571836 |
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| UNII = U4XIL4091C |
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| PubChem=9571836 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 231616 |
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| ChEMBL = 231616 |
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| ChEBI = 231347 |
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| SMILES=C1=CC(=C(N=C1)C=NNC(=S)N)N |
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| SMILES=C1=CC(=C(N=C1)C=NNC(=S)N)N |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 7 | H = 9 | N = 5 | S = 1 |
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| Formula=C<sub>7</sub>H<sub>9</sub>N<sub>5</sub>S |
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| MolarMass=195.25 g/mol |
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|Section3= {{Chembox Hazards |
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'''3-Aminopyridine-2-carboxaldehyde thiosemicarbazone''' ('''3-AP''', also called '''Triapine''') is substance of interest for the treatment of ]. It is a ] derivative of 3-]-2-carboxaldehyde. It presents an N-N-S array of donor sites that strongly bind iron, robbing iron-containing enzymes of their prosthetic group.<ref>{{cite journal |doi=10.1021/jm900528d |title=Impact of Metal Coordination on Cytotoxicity of 3-Aminopyridine-2-carboxaldehyde Thiosemicarbazone (Triapine) and Novel Insights into Terminal Dimethylation |date=2009 |last1=Kowol |first1=Christian R. |last2=Trondl |first2=Robert |last3=Heffeter |first3=Petra |last4=Arion |first4=Vladimir B. |last5=Jakupec |first5=Michael A. |last6=Roller |first6=Alexander |last7=Galanski |first7=Mathea Sophia |last8=Berger |first8=Walter |last9=Keppler |first9=Bernhard K. |journal=Journal of Medicinal Chemistry |volume=52 |issue=16 |pages=5032–5043 |pmid=19637923 }}</ref> |
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It belongs to the family of drugs called ]s.<ref name="pmid12647987">{{cite journal |author =Tsimberidou AM |author2 =Alvarado Y |author3 =Giles FJ |title=Evolving role of ribonucleoside reductase inhibitors in hematologic malignancies |journal=Expert Rev Anticancer Ther |volume=2 |issue=4 |pages=437–48 |date=August 2002 |pmid=12647987 |doi=10.1586/14737140.2.4.437 |s2cid =30047759 |url=http://www.future-drugs.com/doi/abs/10.1586/14737140.2.4.437?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dncbi.nlm.nih.gov}}</ref> |
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3AP is a potent inhibitor of ribonucleotide reductase, the rate determining enzyme in the supply of deoxynucleotides (DNA building blocks) for ]. DNA synthesis is required for cellular proliferation and ]. It is a very strong iron chelator and in the body it is likely that the iron chelate is the active species that quenches the active site tyrosyl radical required by ribonucleotide reductase for its enzymatic activity. The 3AP iron chelate is redox active and there have been several reports in the literature ascribing this property to some of the biological activities of 3AP. 3AP was chosen, based on the results of studying and the screening these products, as the candidate inhibitor most likely to express activity in the setting of human neoplastic disease. Vion Pharmaceuticals has also filed several use patents concerning the antiviral and antifungal activity of 3AP. |
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3AP was initially developed by ] until company declared bankruptcy in December 2009. Nanotherapeutics, Inc. acquired the product from bankruptcy in 2010 and supported trials at NCI until 2018 when the product was transferred to Nanoshift, LLC. Nanoshift LLC and Nanopharmaceutics, Inc. continue to support clinical studies with the NCI. |
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==References== |
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{{reflist}} |
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==External links== |
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{{DEFAULTSORT:Aminopyridine-2-carboxaldehyde thiosemicarbazone, 3-}} |
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